Next Issue
Volume 2022, June
Previous Issue
Volume 2021, December
 
 

Molbank, Volume 2022, Issue 1 (March 2022) – 48 articles

Cover Story (view full-size image): Metal phosphido compounds can facilitate the formation of phosphorous-element bonds and have become important synthetic intermediates in organophosphorus chemistry. We have been studying copper phosphido compounds as intermediates in copper catalyzed hydrophosphination. In this work, the copper phosphido compound Cu4(μ-PPh2)4(PtBu3)2 was synthesized by three methods and structurally characterized by X-ray diffraction and 1H, 31P, 13C, and 31P HMBC NMR spectroscopy. Cu4(μ-PPh2)4(PtBu3)2 was then demonstrated to be an active hydrophosphination pre-catalyst under photocatalytic conditions. View this paper
  • Issues are regarded as officially published after their release is announced to the table of contents alert mailing list.
  • You may sign up for e-mail alerts to receive table of contents of newly released issues.
  • PDF is the official format for papers published in both, html and pdf forms. To view the papers in pdf format, click on the "PDF Full-text" link, and use the free Adobe Reader to open them.
Order results
Result details
Section
Select all
Export citation of selected articles as:
4 pages, 758 KiB  
Short Note
(Z)-2-{[(4-Chloro-5H-1,2,3-dithiazol-5-ylidene)amino](methylthio)methylene}malononitrile
by Andreas S. Kalogirou and Panayiotis A. Koutentis
Molbank 2022, 2022(1), M1354; https://doi.org/10.3390/M1354 - 13 Mar 2022
Viewed by 1842
Abstract
Reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with 2-[amino(methylthio)methylene])malononitrile (1 equiv) in the presence of pyridine (2 equiv) gave (Z)-2-{[(4-chloro-5H-1,2,3-dithiazol-5-ylidene)amino](methylthio)methylene}malononitrile in 20% yield. The compound was fully characterized. Full article
(This article belongs to the Section Organic Synthesis)
Show Figures

Scheme 1

10 pages, 2339 KiB  
Communication
Design, Synthesis and 5-HT1A Binding Affinity of N-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl)tricyclo[3.3.1.13,7]decan-1-amine and N-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl)-3,5-dimethyl-tricylo[3.3.1.13,7]decan-1-amine
by Grigoris Zoidis, María Isabel Loza and Marco Catto
Molbank 2022, 2022(1), M1353; https://doi.org/10.3390/M1353 - 10 Mar 2022
Viewed by 2085
Abstract
Based on previously highlighted structural features, the development of highly selective 5-HT1A receptor inhibitors is closely linked to the incorporation of a 4-alkyl-1-arylpiperazine scaffold on them. In this paper, we present the synthesis of two new compounds bearing the 2-MeO-Ph-piperazine moiety linked [...] Read more.
Based on previously highlighted structural features, the development of highly selective 5-HT1A receptor inhibitors is closely linked to the incorporation of a 4-alkyl-1-arylpiperazine scaffold on them. In this paper, we present the synthesis of two new compounds bearing the 2-MeO-Ph-piperazine moiety linked via a three carbon atom linker to the amine group of 1-adamantanamine and memantine, respectively. Both were tested for their binding affinity against 5-HT1A receptor. N-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)tricyclo[3.3.1.13,7]decan-1-amine fumarate (8) and N-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-3,5-dimethyl-tricylo[3.3.1.13,7]decan-1-amine fumarate (10) proved to be highly selective ligands towards 5-HT1A receptor with a binding constant of 1.2 nM and 21.3 nM, respectively, while 5-carboxamidotriptamine (5-CT) (2) was used as an internal standard for this assay with a measured Ki = 0.5 nM. Full article
Show Figures

Graphical abstract

10 pages, 2491 KiB  
Communication
In Silico Evaluation of a Promising Key Intermediate Thieno [2,3-d] Pyrimidine Derivative with Expected JAK2 Kinase Inhibitory Activity
by Elshaymaa I. Elmongy and Hanan Ali Henidi
Molbank 2022, 2022(1), M1352; https://doi.org/10.3390/M1352 - 9 Mar 2022
Cited by 6 | Viewed by 2248
Abstract
This work describes the synthesis and the cytotoxic evaluation of thiophene and thienopyrimidine derivatives. The investigated compound was subjected to target prediction that indicated its high affinity to kinases and to Janus kinase 2 (JAK2) specifically. Molecular docking screening was performed on three [...] Read more.
This work describes the synthesis and the cytotoxic evaluation of thiophene and thienopyrimidine derivatives. The investigated compound was subjected to target prediction that indicated its high affinity to kinases and to Janus kinase 2 (JAK2) specifically. Molecular docking screening was performed on three different JAK2 proteins downloaded from the Protein Data Bank (PDB: 5AEP, 4C62 and 3ZMM). In vitro kinase inhibitory activity was evaluated and then compound cytotoxicity was performed on three different cancerous cell lines (HT-29, HepG-2, and MCF-7). Marked cytotoxic activity of the thienopyrimidine derivative against the HepG-2 cell line was demonstrated, reflected by its IC50 value of 8.001 ± 0.0445 μM, which is better than that of the reference standard (IC50 13.91 ± 2.170 μM). Pharmacokinetic studies revealed good well permeability and GI absorption with no violations against Lipinski’s rule. Full article
Show Figures

Figure 1

7 pages, 877 KiB  
Short Note
2-Bromo-3-((1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)-methoxy)-benzaldehyde
by Xiaoyun Yun, Yuhan Xie, Jerome P. L. Ng, Betty Yuen Kwan Law, Vincent Kam Wai Wong and Paolo Coghi
Molbank 2022, 2022(1), M1351; https://doi.org/10.3390/M1351 - 9 Mar 2022
Cited by 2 | Viewed by 2439
Abstract
The 1,2,3-triazole ring system can be easily obtained by copper-catalyzed click reaction of azides with alkynes. 1,2,3-Triazole exhibits a myriad of biological activities, including antimalarial, antibacterial, and antiviral activities. We herein reported the synthesis of quinoline-based [1,2,3]-triazole [...] Read more.
The 1,2,3-triazole ring system can be easily obtained by copper-catalyzed click reaction of azides with alkynes. 1,2,3-Triazole exhibits a myriad of biological activities, including antimalarial, antibacterial, and antiviral activities. We herein reported the synthesis of quinoline-based [1,2,3]-triazole hybrid via Cu(I)-catalyzed click reaction of 4-azido-7-chloroquinoline with alkyne derivative of 2-bromobenzaldehyde. The compound was fully characterized by proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), ultraviolet (UV), and high-resolution mass spectroscopies (HRMS). This compound was screened in vitro against two different normal cell lines. Preliminary studies attempted to evaluate its interaction with Delta RBD of spike protein of SARS-CoV-2 by bio-layer interferometry. Finally, the drug-likeness of the compound was also investigated by predicting its pharmacokinetic properties. Full article
(This article belongs to the Section Organic Synthesis)
Show Figures

Graphical abstract

12 pages, 1759 KiB  
Communication
Synthesis of New 1,2,3,4-Tetrahydroquinoline Hybrid of Ibuprofen and Its Biological Evaluation
by Stanimir Manolov, Iliyan Ivanov and Dimitar Bojilov
Molbank 2022, 2022(1), M1350; https://doi.org/10.3390/M1350 - 7 Mar 2022
Cited by 6 | Viewed by 2985
Abstract
Herein we report the obtaining of 1-(3,4-dihydroquinolin-1(2H)-yl)-2- (4-isobutylphenyl)propan-1-one and its characterization. The newly obtained hybrid and its derivatives (hybrids of ibuprofen with 1,2,3,4-tetrahydroisoquinoline, and piperidine) were screened for their in vitro antioxidant, antitryptic, and inhibition of albumin denaturation activity. The lipophilicity was established [...] Read more.
Herein we report the obtaining of 1-(3,4-dihydroquinolin-1(2H)-yl)-2- (4-isobutylphenyl)propan-1-one and its characterization. The newly obtained hybrid and its derivatives (hybrids of ibuprofen with 1,2,3,4-tetrahydroisoquinoline, and piperidine) were screened for their in vitro antioxidant, antitryptic, and inhibition of albumin denaturation activity. The lipophilicity was established using both reversed-phase thin layer chromatography and in silico calculations. Full article
(This article belongs to the Special Issue Quinoline, Derivatives and Applications)
Show Figures

Graphical abstract

4 pages, 605 KiB  
Short Note
(±)-((2S,5R)-5-(Acetoxymethyl)tetrahydrofuran-2-yl)methyl Benzoate
by Vincenzo Piccialli
Molbank 2022, 2022(1), M1349; https://doi.org/10.3390/M1349 - 4 Mar 2022
Viewed by 2085
Abstract
In this note we report the synthesis of a doubly acylated cis-THF-diol product synthesised in three steps by the stereoselective RuO4-catalysed oxidative cyclisation of 1,5-hexadiene, followed by benzoylation and acetylation. This substance is one of the substrates chosen to probe [...] Read more.
In this note we report the synthesis of a doubly acylated cis-THF-diol product synthesised in three steps by the stereoselective RuO4-catalysed oxidative cyclisation of 1,5-hexadiene, followed by benzoylation and acetylation. This substance is one of the substrates chosen to probe a new developed oxidative procedure to transform bis-acylated THF-diols into bis-acylated 1,4-diketones. This new derivative was fully characterised by spectroscopic methods. Full article
(This article belongs to the Collection Molecules from Catalytic Processes)
Show Figures

Graphical abstract

6 pages, 878 KiB  
Short Note
6-(2′-(4″-Oxabutyloxy)phenyl)-1,6,11-triaza-3,9,14,17,22,25-hexaoxa-2(1,2)(4-methylbenzena)-10(1,2)(5-methylbenzena)bicyclo(9.8.8)heptacosaphane Sodium Bromide Dichloromethane
by Matthias Jochem, Dieter Schollmeyer and Heiner Detert
Molbank 2022, 2022(1), M1348; https://doi.org/10.3390/M1348 - 3 Mar 2022
Viewed by 1996
Abstract
Potassium ion sensors are important for the study of concentration profiles in tissues. The synthesis of a cryptand suited for potassium ions and the crystal structure of it with a chelated sodium ion are presented. Full article
(This article belongs to the Section Structure Determination)
Show Figures

Graphical abstract

7 pages, 865 KiB  
Communication
Synthesis and Crystal Structure of 9,12-Dibromo-ortho-Carborane
by Olga B. Zhidkova, Anna A. Druzina, Sergey A. Anufriev, Kyrill Yu. Suponitsky, Igor B. Sivaev and Vladimir I. Bregadze
Molbank 2022, 2022(1), M1347; https://doi.org/10.3390/M1347 - 1 Mar 2022
Cited by 5 | Viewed by 2539
Abstract
Synthesis, NMR spectral data and crystal structure of 9,12-dibromo derivative of ortho-carborane are reported. Full article
(This article belongs to the Section Structure Determination)
Show Figures

Figure 1

5 pages, 823 KiB  
Short Note
O-((Ferrocenyl)(3-fluorophenyl)methyl)hydroxylamine
by Angeliki S. Foscolos, Maria Georgiou, Minas S. Papadopoulos and Aristeidis Chiotellis
Molbank 2022, 2022(1), M1346; https://doi.org/10.3390/M1346 - 1 Mar 2022
Viewed by 1900
Abstract
Based on the diaryl hydroxylamine scaffold, which exhibits the potential to inhibit all three enzymes of the first step of the kynurenine pathway, the main tryptophan degradation pathway in mammals, which is often activated in cancer, we report herein the synthesis of a [...] Read more.
Based on the diaryl hydroxylamine scaffold, which exhibits the potential to inhibit all three enzymes of the first step of the kynurenine pathway, the main tryptophan degradation pathway in mammals, which is often activated in cancer, we report herein the synthesis of a ferrocenyl analogue as an attempt to improve the scaffold’s pan-inhibitory potency through the isosteric replacement of a phenyl group with the ferrocenyl moiety. The synthetic methodology followed gives access to O-((ferrocenyl)(aryl)methyl)hydroxylamines, a class of compounds not yet reported in the literature. Full article
(This article belongs to the Section Organic Synthesis)
Show Figures

Figure 1

7 pages, 673 KiB  
Short Note
O6-[(2″,3″-O-Isopropylidene-5″-O-tbutyldimethylsilyl)pentyl]-5′-O-tbutyldiphenylsilyl-2′,3′-O-isopropylideneinosine
by Maria Marzano, Monica Terracciano, Vincenzo Piccialli, Ahmed Mahal, Roberto Nilo and Stefano D’Errico
Molbank 2022, 2022(1), M1345; https://doi.org/10.3390/M1345 - 1 Mar 2022
Cited by 3 | Viewed by 2665
Abstract
Cyclic adenosine diphosphate ribose (cADPR) is a cyclic nucleotide involved in the Ca2+ homeostasis. In its structure, the northern ribose, bonded to adenosine through an N1 glycosidic bond, is connected to the southern ribose through a pyrophosphate bridge. Due to the chemical [...] Read more.
Cyclic adenosine diphosphate ribose (cADPR) is a cyclic nucleotide involved in the Ca2+ homeostasis. In its structure, the northern ribose, bonded to adenosine through an N1 glycosidic bond, is connected to the southern ribose through a pyrophosphate bridge. Due to the chemical instability at the N1 glycosidic bond, new bioactive cADPR derivatives have been synthesized. One of the most interesting analogues is the cyclic inosine diphosphate ribose (cIDPR), in which the hypoxanthine replaced adenosine. The efforts for synthesizing new linear and cyclic northern ribose modified cIDPR analogues led us to study in detail the inosine N1 alkylation reaction. In the last few years, we have produced new flexible cIDPR analogues, where the northern ribose has been replaced by alkyl chains. With the aim to obtain the closest flexible cIDPR analogue, we have attached to the inosine N1 position a 2″,3″-dihydroxypentyl chain, possessing the two OH groups in a ribose-like fashion. The inosine alkylation reaction afforded also the O6-alkylated regioisomer, which could be a useful intermediate for the construction of new kinds of cADPR mimics. Full article
(This article belongs to the Collection Molecules from Side Reactions)
Show Figures

Graphical abstract

8 pages, 1367 KiB  
Communication
Charge-Transfer Adducts of Chalcogenourea Derivatives of N-Heterocyclic Carbenes with Iodine Monochloride
by Marina Saab, Fady Nahra and Kristof Van Hecke
Molbank 2022, 2022(1), M1344; https://doi.org/10.3390/M1344 - 23 Feb 2022
Cited by 1 | Viewed by 2205
Abstract
In this communication, we investigate the reaction between seleno- and thiourea, derived from N-heterocyclic carbenes, with the interhalogen iodine monochloride. The formation of all three products was confirmed by NMR spectroscopy, while single-crystal X-ray analyses were able to establish a charge-transfer coordination [...] Read more.
In this communication, we investigate the reaction between seleno- and thiourea, derived from N-heterocyclic carbenes, with the interhalogen iodine monochloride. The formation of all three products was confirmed by NMR spectroscopy, while single-crystal X-ray analyses were able to establish a charge-transfer coordination type, which showed a linear Se/S-I-Cl arrangement, for all adducts formed. Based on a detailed crystallographic analysis, we can deduce the zwitterionic character of these compounds. Full article
(This article belongs to the Section Structure Determination)
Show Figures

Figure 1

11 pages, 1882 KiB  
Communication
Synthesis of Novel Pyrazolo[3,4-b]pyridines with Affinity for β-Amyloid Plaques
by Veroniki P. Vidali, Georgia Nigianni, Georgia D. Athanassopoulou, Aleksander Canko, Barbara Mavroidi, Dimitris Matiadis, Maria Pelecanou and Marina Sagnou
Molbank 2022, 2022(1), M1343; https://doi.org/10.3390/M1343 - 22 Feb 2022
Cited by 2 | Viewed by 2895
Abstract
Three novel pyrazolo[3,4-b]pyridines were synthesized via the cyclization of 5-amino-1-phenylpyrazole with the corresponding unsaturated ketone in the catalytic presence of ZrCl4. The ketones were afforded by modifying a stabilized ylide facilitated Wittig reaction in fairly high yields. The novel [...] Read more.
Three novel pyrazolo[3,4-b]pyridines were synthesized via the cyclization of 5-amino-1-phenylpyrazole with the corresponding unsaturated ketone in the catalytic presence of ZrCl4. The ketones were afforded by modifying a stabilized ylide facilitated Wittig reaction in fairly high yields. The novel compounds exhibited exciting photophysical properties with the dimethylamine phenyl-bearing pyrazolopyridine showing exceptionally large Stoke’s shifts. Finally, both the dimethylamino- and the pyrene-substituted compounds demonstrated high and selective binding to amyloid plaques of Alzheimer’s disease (AD) patient brain slices upon fluorescent confocal microscopy observation. These results reveal the potential application of pyrazolo[3,4-b]pyridines in the development of AD amyloid plaque probes of various modalities for AD diagnosis. Full article
Show Figures

Graphical abstract

12 pages, 2492 KiB  
Communication
A Simple and Efficient Approach to the Synthesis of 4-Aryl-2-dialkylphosphonomethyl-4-oxobutanenitrile
by Ferid Yaccoubi, Hitham Elleuch, Hussein S. Mohamed, Zeinab S. Hamza and Yasser H. Zaki
Molbank 2022, 2022(1), M1342; https://doi.org/10.3390/M1342 - 15 Feb 2022
Cited by 3 | Viewed by 2151
Abstract
In this work, we describe a simple and easy synthetic approach to variously 4-aryl-2-alkylphosphonomethyl-4-oxobutanenitrile based on the reaction of aromatic aldehydes with phosphorylated Michael’s acceptors in good yields. A general mechanism for the reactions was also proposed. Characterization of the products was carried [...] Read more.
In this work, we describe a simple and easy synthetic approach to variously 4-aryl-2-alkylphosphonomethyl-4-oxobutanenitrile based on the reaction of aromatic aldehydes with phosphorylated Michael’s acceptors in good yields. A general mechanism for the reactions was also proposed. Characterization of the products was carried out by several spectroscopic tools, including Infrared and Nuclear Magnetic Resonance Spectroscopies (1H, 13C, and 31P-NMR). Molecular docking studies were conducted on the synthesized materials against (1UK4) the crystal structure of the SARS Coronavirus Main Proteinase (3CLpro) to study the antiviral activity of these compounds and against (1E3K) the Human Progesterone Receptor to study the anticancer activity of these compounds. We found that compound (5i) was the best one in both antiviral and anticancer activity (according to the binding energy values). Full article
Show Figures

Figure 1

7 pages, 929 KiB  
Communication
Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method
by Jorge Trilleras, Jairo Quiroga and Angelina Hormaza
Molbank 2022, 2022(1), M1341; https://doi.org/10.3390/M1341 - 15 Feb 2022
Cited by 1 | Viewed by 2203
Abstract
The synthesis and structural diversification of N-heterocycles systems have attracted much attention because of their potential applications. Three 6-aryl-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde 4 derivatives, in reaction with acetophenones 5, via conventional Claisen–Schmidt condensation reactions, generated the respective enones. The enones [...] Read more.
The synthesis and structural diversification of N-heterocycles systems have attracted much attention because of their potential applications. Three 6-aryl-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde 4 derivatives, in reaction with acetophenones 5, via conventional Claisen–Schmidt condensation reactions, generated the respective enones. The enones were used as electron-deficient olefins in a “formal” [2+3] cycloaddition reaction using p-tosylmethyl isocyanide—TosMIC 7. This protocol allows access to 3-(substituted aroyl)-4-heteroaryl pyrrole derivatives by the Van Leusen method. Full article
(This article belongs to the Section Organic Synthesis)
Show Figures

Scheme 1

10 pages, 2448 KiB  
Communication
Ethyl 5-Formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, and DFT Calculation
by Nazariy T. Pokhodylo, Yuriy I. Slyvka, Evgeny A. Goreshnik and Mykola D. Obushak
Molbank 2022, 2022(1), M1340; https://doi.org/10.3390/M1340 - 15 Feb 2022
Cited by 1 | Viewed by 2077
Abstract
For the first time, 5-formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate was synthesized via a two-step scheme. The molecular structure of the compound was determined by a single-crystal X-ray diffraction analysis. The Hirshfeld surface analysis was used to study various intermolecular interactions. The crystalline structure is marked [...] Read more.
For the first time, 5-formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate was synthesized via a two-step scheme. The molecular structure of the compound was determined by a single-crystal X-ray diffraction analysis. The Hirshfeld surface analysis was used to study various intermolecular interactions. The crystalline structure is marked by the presence of three types of π-interactions (n→π*, lp···π, and π···π) between the -C(H)=O group and triazole rings. The compound is a versatile polyfunctional building block for construction of annulated 1,2,3-triazoles. Full article
(This article belongs to the Section Organic Synthesis)
Show Figures

Graphical abstract

8 pages, 1493 KiB  
Short Note
6-Chloro-3H-benzo[d][1,2,3]dithiazol-2-ium Chloride
by Alexander J. Nicholls and Ian R. Baxendale
Molbank 2022, 2022(1), M1339; https://doi.org/10.3390/M1339 - 11 Feb 2022
Viewed by 1747
Abstract
This short note describes the synthesis of an amorphous benzo[1,2,3]dithiazole chloride salt (commonly known as a ‘Herz salt’) by use of the Herz reaction. Hetero- and homolytic transformations of this species to a variety of useful adducts in medicinal and materials chemistry are [...] Read more.
This short note describes the synthesis of an amorphous benzo[1,2,3]dithiazole chloride salt (commonly known as a ‘Herz salt’) by use of the Herz reaction. Hetero- and homolytic transformations of this species to a variety of useful adducts in medicinal and materials chemistry are well established, although there are limited examples of isolation in the literature, and characterisation data is even harder find. While several studies have confirmed the structure of the benzodithiazole ring beyond doubt, (having generated suitably crystalline salts with large counterions for XRD-analysis), there remains value in understanding and optimising the synthesis of the simple, amorphous polymorphs. For the first time, MS data is provided for this compound and a new mechanism of its formation is proposed based upon new experimental observations and data. Full article
Show Figures

Graphical abstract

6 pages, 1414 KiB  
Short Note
Ethyl 7-Acetyl-8a-methyl-3-(1-phenyl-1H-tetrazol-5-yl)-1,4,4a,5,6,8a-hexahydro-7H-pyrano[2,3-c]pyridazine-1-carboxylate
by Susana M. M. Lopes, Américo Lemos, José A. Paixão and Teresa M. V. D. Pinho e Melo
Molbank 2022, 2022(1), M1338; https://doi.org/10.3390/M1338 - 10 Feb 2022
Cited by 1 | Viewed by 1883
Abstract
The Diels–Alder reaction of ethyl 3-(1-phenyl-1H-tetrazol-5-yl-1,2-diaza-1,3-butadiene-1-carboxylate with 2-acetyl-6-methyl-2,3-dihydro-4H-pyran (methyl vinyl ketone dimer) regioselectively afforded the corresponding 3-(tetrazol-5-yl)-hexahydro-7H-pyrano[2,3-c]pyridazine in quantitative yield. An X-ray crystal structure of this cycloadduct is reported. Full article
Show Figures

Graphical abstract

4 pages, 1094 KiB  
Short Note
(1R,2R,3S,4R)-1-(Acetylamino)-2,4,5-tris(acetyloxy)-1-((2S)-4-(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)pentan-3-yl Acetate
by Liam S. Fitzgerald, Ciaran O’Malley and Paul V. Murphy
Molbank 2022, 2022(1), M1337; https://doi.org/10.3390/M1337 - 10 Feb 2022
Viewed by 2007
Abstract
Treatment of N-acetylneuraminic acid with excess base in the presence of benzyl bromide gives a polyhydroxylated 1,4 lactone which after acetylation gave the title compound in 20% overall yield. The structure of the product was confirmed by single crystal X-ray diffraction analysis, [...] Read more.
Treatment of N-acetylneuraminic acid with excess base in the presence of benzyl bromide gives a polyhydroxylated 1,4 lactone which after acetylation gave the title compound in 20% overall yield. The structure of the product was confirmed by single crystal X-ray diffraction analysis, as well as FT-IR, NMR spectroscopic and HRMS analysis. Full article
(This article belongs to the Section Organic Synthesis)
Show Figures

Figure 1

4 pages, 480 KiB  
Short Note
Barium 5-(tert-butyl)-2,3-dihydroxybenzenesulfonate
by Lyubov G. Rubicheva and Daniil A. Lukyanov
Molbank 2022, 2022(1), M1336; https://doi.org/10.3390/M1336 - 9 Feb 2022
Viewed by 1790
Abstract
Catechols and their derivatives attract great scientific interest due to the broad spectrum of their functional properties, including complexation, redox behavior, association ability and antioxidant activity. Because of the low molecular mass and two-electron redox process, they are considered to be a promising [...] Read more.
Catechols and their derivatives attract great scientific interest due to the broad spectrum of their functional properties, including complexation, redox behavior, association ability and antioxidant activity. Because of the low molecular mass and two-electron redox process, they are considered to be a promising energy storage compound in different types of electrochemical power sources, such as metal-ion batteries or redox flow batteries. Herein, we report a preparation of the sterically hindered sulfonated catechol, namely the barium salt of 5-(tert-butyl)-2,3-dihydroxybenzenesulfonic acid, by the direct sulfonation of 4-tert-butylcatechol, by concentrated sulfuric acid. The proposed procedure is green and atom-economic, providing the desired product in high yield after simple purification. The solvent-free procedure is inexpensive and highly scalable, which enables direct industrial production of the title product. The resulting product was characterized by the 1H and 13C nuclear magnetic resonance (NMR) and ESI-high resolution mass spectrometry (ESI-HRMS). Full article
(This article belongs to the Section Organic Synthesis)
Show Figures

Graphical abstract

6 pages, 1195 KiB  
Communication
Crystal Structure of a Chiral Sec-Amine, 4-Chloro-N-(1-(pyridin-2-yl)ethyl)aniline
by Adesola A. Adeleke and Bernard Omondi
Molbank 2022, 2022(1), M1335; https://doi.org/10.3390/M1335 - 9 Feb 2022
Cited by 1 | Viewed by 2052
Abstract
In this communication, we present the crystal structure of a secondary amine: 4-chloro-N-(1-(pyridin-2-yl)ethyl)aniline (Lb) obtained from a stepwise reduction of an imine, (E)-N-(4-chlorophenyl)-1-(pyridin-2-yl)ethan-1-imine (La) with sodium borohydride. The structure was characterized by FT-IR, 1H and 13C NMR, Mass Spectroscopy and X-ray diffraction. Full article
Show Figures

Figure 1

6 pages, 978 KiB  
Short Note
Cyclo-Tetrakis(μ-diphenylphosphido)-1,5-bis(tri-tert-butylphosphine)-Tetracopper
by Steven G. Dannenberg and Rory Waterman
Molbank 2022, 2022(1), M1334; https://doi.org/10.3390/M1334 - 9 Feb 2022
Cited by 3 | Viewed by 2226
Abstract
Copper phosphido compound Cu4(μ-PPh2)4(PtBu3)2 was synthesized by three synthetic methods and structurally characterized by X-ray diffraction and 1H, 31P, 13C and 31P HMBC NMR spectroscopy. Cu4(μ-PPh2)4(PtBu3)2 was also demonstrated to be a hydrophosphination pre-catalyst. Full article
(This article belongs to the Section Structure Determination)
Show Figures

Graphical abstract

7 pages, 859 KiB  
Communication
Synthesis, Crystal Structure and Anti-Leukemic Activity of 1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one
by Jean Guillon, Solène Savrimoutou, Sandra Albenque-Rubio, Noël Pinaud, Stéphane Moreau and Vanessa Desplat
Molbank 2022, 2022(1), M1333; https://doi.org/10.3390/M1333 - 9 Feb 2022
Cited by 4 | Viewed by 1998
Abstract
1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one has been synthesized through a multi-step pathway starting from commercially available 2-nitroaniline. A structure characterization of this new substituted pyrrolo[1,2-a]quinoxaline compound was achieved by using FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This [...] Read more.
1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one has been synthesized through a multi-step pathway starting from commercially available 2-nitroaniline. A structure characterization of this new substituted pyrrolo[1,2-a]quinoxaline compound was achieved by using FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This new pyrroloquinoxaline derivative shows an interesting cytotoxic potential against several human leukemia cell lines (HL60, K562 and U937 cells). Full article
(This article belongs to the Collection Heterocycle Reactions)
Show Figures

Graphical abstract

5 pages, 366 KiB  
Short Note
4,7-Bis(5-(9-hexyl-9H-carbazol-3-yl)thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine
by Timofey N. Chmovzh, Vladislav M. Korshunov, Ilya V. Taydakov and Oleg A. Rakitin
Molbank 2022, 2022(1), M1332; https://doi.org/10.3390/M1332 - 8 Feb 2022
Viewed by 2033
Abstract
Donor molecules of the D-π-A-π-D type structure are often used for applications in organic photovoltaics. In this communication, bromination of 4,7-di(thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine followed by Suzuki cross-coupling with carbazoleboronic acid gave 4,7-bis( 5-(9-hexyl-9H-carbazol-3-yl)thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine. The structure of the newly synthesized [...] Read more.
Donor molecules of the D-π-A-π-D type structure are often used for applications in organic photovoltaics. In this communication, bromination of 4,7-di(thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine followed by Suzuki cross-coupling with carbazoleboronic acid gave 4,7-bis( 5-(9-hexyl-9H-carbazol-3-yl)thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine. The structure of the newly synthesized compounds was established by high resolution mass-spectrometry, 1H, 13C NMR, IR, and UV spectroscopy and mass-spectrometry. A study of the luminescent properties of the dye showed that it exhibits fluorescence in the near infrared region of the spectrum, which makes it a promising compound for use as an active emitting layer in NIR OLED as well as for other possible applications as an IR luminophore. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
Show Figures

Graphical abstract

9 pages, 1406 KiB  
Communication
Synthesis and Antimicrobial Evaluation of 2-(6-Imidazo[1,2-a]pyridin-2-yl-5-methyl-2,4-dioxo-3-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)-N-arylacetamide Derivatives
by Sergiy V. Vlasov, Hanna I. Severina, Oleksandr V. Borysov, Konstantin Yu. Krolenko, Pavlo E. Shynkarenko, Narzullo B. Saidov, Vitaliy S. Vlasov and Victoriya A. Georgiyants
Molbank 2022, 2022(1), M1331; https://doi.org/10.3390/M1331 - 7 Feb 2022
Cited by 2 | Viewed by 2263
Abstract
6-Heteryl-5-methylthieno[2,3-d]pyrimidin-2,4(1H,3H)-diones are of great interest as the promising objects for the search of antibacterials. In this communication, we obtained 6-(imidazo[1,2-a]pyridin-2-yl)-5-methyl-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione by interaction of 6-(bromoacetyl)-5-methyl-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H [...] Read more.
6-Heteryl-5-methylthieno[2,3-d]pyrimidin-2,4(1H,3H)-diones are of great interest as the promising objects for the search of antibacterials. In this communication, we obtained 6-(imidazo[1,2-a]pyridin-2-yl)-5-methyl-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione by interaction of 6-(bromoacetyl)-5-methyl-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione with 2-aminopyridine. The obtained heterocyclic hybrid was further modified by alkylation with 2-chloroarylacetamides. Antimicrobial activity studies for the synthesized compounds using the agar well diffusion method revealed their moderate activity against S. aureus, E. coli and B. subtilis. According to the double dilution assay MIC value results for 6-(imidazo[1,2-a]pyridin-2-yl)-5-methyl-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneagainst P. aeruginosa was less than the value determined for the reference drug streptomycin. The docking study of the synthesized compounds to the active site of TrmD isolated from P. aeruginosa did not show their effective inhibitory activity. Full article
Show Figures

Figure 1

8 pages, 5776 KiB  
Short Note
3-Isobutyl-5,5,7-tris(3-methylbut-2-en-1-yl)-1-phenyl-1,7-dihydro-4H-indazole-4,6(5H)-dione
by José Edmilson Ribeiro do Nascimento, Daniela Hartwig, Raquel Guimarães Jacob and Márcio Santos Silva
Molbank 2022, 2022(1), M1330; https://doi.org/10.3390/M1330 - 1 Feb 2022
Viewed by 1780
Abstract
Here we describe the functionalization of lupulone natural compound in obtaining 3-isobutyl-5,5,7-tris(3-methylbut-2-en-1-yl)-1-phenyl-1,7-dihydro-4H-indazole-4,6(5H)-dione. The lupulone-H-indazole derivative was prepared with 75% yield through the reaction between lupulone and phenyl-hydrazine employing SiO2/ZnCl2 (30% m/m) [...] Read more.
Here we describe the functionalization of lupulone natural compound in obtaining 3-isobutyl-5,5,7-tris(3-methylbut-2-en-1-yl)-1-phenyl-1,7-dihydro-4H-indazole-4,6(5H)-dione. The lupulone-H-indazole derivative was prepared with 75% yield through the reaction between lupulone and phenyl-hydrazine employing SiO2/ZnCl2 (30% m/m) as a support solid in a solvent-free condition. Based on the possibilities of products, a complete NMR structural characterization of this lupulone-H-indazole was performed by 1H, 13C{1H}, COSY, HSQC and HMBC NMR experiments, showing an important contribution in producing the first results related to lupulone reactivity. Full article
(This article belongs to the Collection Molecules from Side Reactions)
Show Figures

Figure 1

8 pages, 634 KiB  
Communication
Quercetin Hybrids—Synthesis, Spectral Characterization and Radical Scavenging Potential
by Desislava Kirkova, Yordan Stremski, Stela Statkova-Abeghe and Margarita Docheva
Molbank 2022, 2022(1), M1329; https://doi.org/10.3390/M1329 - 30 Jan 2022
Cited by 6 | Viewed by 3181
Abstract
New quercetin-based derivatives are synthesized in an easily accessible one-pot manner. The method is based on the reaction of quercetin with in situ formed electrophilic N-alkoxycarbonylazolium ions. The position of the newly formed C-C bond and structure were spectrally characterized by 1D, [...] Read more.
New quercetin-based derivatives are synthesized in an easily accessible one-pot manner. The method is based on the reaction of quercetin with in situ formed electrophilic N-alkoxycarbonylazolium ions. The position of the newly formed C-C bond and structure were spectrally characterized by 1D, 2D 1H, 13C-NMR, IR, and MS analysis. Thus, in all cases, good regioselectivity in the C-8 position for the obtained products was demonstrated. The obtained compounds were evaluated for their DPPH and ABTS free radical scavenging activity and compared to natural compounds—quercetin and rutin. Full article
(This article belongs to the Section Organic Synthesis)
Show Figures

Graphical abstract

7 pages, 632 KiB  
Short Note
2,2-Dichloro-N-[5-[2-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydro-2H-pyrazol-2-yl]-2-oxoethyl]sulfanyl-1,3,4-thiadiazol-2-yl]acetamide
by Ihor Yushyn, Serhii Holota and Roman Lesyk
Molbank 2022, 2022(1), M1328; https://doi.org/10.3390/M1328 - 28 Jan 2022
Cited by 3 | Viewed by 2434
Abstract
The pharmacophore hybridization approach is widely used for the design of drug-like small molecules with anticancer properties. In the present work, a “cost-effective” approach to the synthesis of the novel non-condensed pyrazoline-bearing hybrid molecule with 1,3,4-thiadiazole and dichloroacetic acid moieties is proposed. The [...] Read more.
The pharmacophore hybridization approach is widely used for the design of drug-like small molecules with anticancer properties. In the present work, a “cost-effective” approach to the synthesis of the novel non-condensed pyrazoline-bearing hybrid molecule with 1,3,4-thiadiazole and dichloroacetic acid moieties is proposed. The 5-amino-1,3,4-thiadiazole-2-thiol was used as a starting reagent, and the synthetic strategy includes stepwise alkylation of the sulfur atom and acylation of the nitrogen atom to obtain the target title compound. The structure of the synthesized 2,2-dichloro-N-[5-[2-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydro-2H-pyrazol-2-yl]-2-oxoethyl]sulfanyl-1,3,4-thiadiazol-2-yl]acetamide (yield 90%) was confirmed by 1H, 13C, 2D NMR and LC-MS spectra. Anticancer activity in “60 lines screening” (NCI DTP protocol) was studied in vitro for the title compound. Full article
Show Figures

Graphical abstract

10 pages, 1640 KiB  
Communication
N,N′-Diarylformamidine Dithiocarbamate Ag(I) Cluster and Coordination Polymer
by Segun D. Oladipo and Bernard Omondi
Molbank 2022, 2022(1), M1327; https://doi.org/10.3390/M1327 - 28 Jan 2022
Cited by 7 | Viewed by 2526
Abstract
An Ag(I)formamidine cluster Ag6L16 (1) and an Ag(I)formamidine coordination polymer Ag7(L2)2 2 (L1 = N,N′-bis(2,6-disopropylphenyl) formamidine dithiocarbamate and L2 = N,N′-mesityl formamidine dithiocarbamate) have been synthesized [...] Read more.
An Ag(I)formamidine cluster Ag6L16 (1) and an Ag(I)formamidine coordination polymer Ag7(L2)2 2 (L1 = N,N′-bis(2,6-disopropylphenyl) formamidine dithiocarbamate and L2 = N,N′-mesityl formamidine dithiocarbamate) have been synthesized from the reactions of L1 and L2 with AgNO3 respectively. The complexes were characterized using spectroscopic and analytical methods, including single-crystal X-ray diffraction. In the structure of 1, a six vertex distorted square bi-pyramidal octahedron is formed from an Ag6 core. The N,N′-bis(2,6-disopropylphenyl) formamidine dithiocarbamate ligands stabilize this core through two main –CS2 bridging modes giving a propeller like structure. In the structure of 2, each of the two Ag(I) centers are bridged by two N,N′-mesityl formamidine dithiocarbamate ligands forming 8-member Ag2(CS2)2 metallacycles with an inversion center in the middle of the Ag—Ag argentophilic bond. The metallacycles are connected through Ag—S bonds forming ribbons in the crystallographic a-axis. The Ag(I) centers are coordinated to two N,N′-mesitylformamidine dithiocarbamates through the dithiocarbamate S atoms. The thermal decomposition of complexes 1 and 2 had similar thermograms with one major weight loss activity and the formation of elemental silver particles thereafter. Full article
(This article belongs to the Section Structure Determination)
Show Figures

Figure 1

6 pages, 1280 KiB  
Short Note
2-Nitro-1-vinyl-1H-imidazole
by Afonso Santine M. M. Velez, Gabriela Alves de Souza, Paulo Pitasse-Santos, Douglas Chaves de Alcântara Pinto, Debora Decote-Ricardo and Marco Edilson Freire de Lima
Molbank 2022, 2022(1), M1326; https://doi.org/10.3390/M1326 - 27 Jan 2022
Viewed by 2983
Abstract
Nitroimidazoles are pharmacophoric groups responsible for important antiparasitic activity against several infectious diseases. 2-Nitroimidazoles are found in some antiparasitic drugs and are one of the main moieties responsible for the biological activities exhibited. As an example, we can mention the drug benznidazole, the [...] Read more.
Nitroimidazoles are pharmacophoric groups responsible for important antiparasitic activity against several infectious diseases. 2-Nitroimidazoles are found in some antiparasitic drugs and are one of the main moieties responsible for the biological activities exhibited. As an example, we can mention the drug benznidazole, the only drug available in Brazil for the treatment of Chagas disease. This work describes an efficient methodology for the synthesis of 2-nitro-1-vinyl-1H-imidazole through a simple and direct approach, as well as its full characterization and biological assessment. The antiparasitic evaluation of 2-nitro-1-vinyl-1H-imidazole against Trypanosoma cruzi (Tulahuen C2C4-LacZ strain) showed IC50 = 4.8 μM on amastigotes and low cytotoxicity against LLC-MK2 cells (IC50 > 500 μM), validating 2-nitro-1-vinyl-1H-imidazole as a biologically active structural subunit for anti-T. cruzi activity. The results presented herein demonstrate that 2-nitro-1-vinyl-1H-imidazole can be easily obtained, possessing great potential for use in the design of new antichagasic drugs through a molecular hybridization strategy using known coupling reactions. Full article
Show Figures

Graphical abstract

2 pages, 165 KiB  
Editorial
Acknowledgment to Reviewers of Molbank in 2021
by Molbank Editorial Office
Molbank 2022, 2022(1), M1325; https://doi.org/10.3390/M1325 - 27 Jan 2022
Viewed by 1515
Abstract
Rigorous peer-reviews are the basis of high-quality academic publishing [...] Full article
Previous Issue
Next Issue
Back to TopTop