Journal Description
Molbank
Molbank
is an international, peer-reviewed, open access journal comprised of a unique collection of one-compound-per-paper short notes on synthetic compounds and natural products published quarterly online by MDPI.
- Open Access— free for readers, with article processing charges (APC) paid by authors or their institutions.
- High Visibility: indexed within Scopus, ESCI (Web of Science), Reaxys, CAPlus / SciFinder, and other databases.
- Rapid Publication: manuscripts are peer-reviewed and a first decision is provided to authors approximately 13.9 days after submission; acceptance to publication is undertaken in 3.8 days (median values for papers published in this journal in the first half of 2024).
- Recognition of Reviewers: reviewers who provide timely, thorough peer-review reports receive vouchers entitling them to a discount on the APC of their next publication in any MDPI journal, in appreciation of the work done.
Impact Factor:
0.6 (2023)
Latest Articles
Synthesis, Characterization, and Docking Study of a Novel Indole Derivative Containing a Tosyl Moiety as Anti-Oxidant Agent
Molbank 2024, 2024(3), M1857; https://doi.org/10.3390/M1857 - 26 Jul 2024
Abstract
Indole derivatives are key components of natural products and possess a wide range of biological and pharmaceutical applications. Here, we present the synthesis of a new indole derivative, namely 2-(1-ethyl-5-nitro-1H-indole-7-carbonyl)butyl 4-methylbenzenesulfonate. The structural elucidation of this compound was accomplished through comprehensive
[...] Read more.
Indole derivatives are key components of natural products and possess a wide range of biological and pharmaceutical applications. Here, we present the synthesis of a new indole derivative, namely 2-(1-ethyl-5-nitro-1H-indole-7-carbonyl)butyl 4-methylbenzenesulfonate. The structural elucidation of this compound was accomplished through comprehensive spectroscopic analysis, including Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS). Our molecular docking study revealed that this compound exhibits strong affinity towards tyrosinase, making it a promising candidate as an antioxidant agent.
Full article
(This article belongs to the Collection Heterocycle Reactions)
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Open AccessCommunication
Synthesis and Characterization of Novel Indazole–Sulfonamide Compounds with Potential MAPK1 Inhibitory Activity for Cancer Treatment
by
Nassima Saghdani, Abdelali Chihab, Nabil El Brahmi and Saïd El Kazzouli
Molbank 2024, 2024(3), M1858; https://doi.org/10.3390/M1858 - 26 Jul 2024
Abstract
Indazoles are a very important group of nitrogen-containing heterocycles with a wide range of biological and medicinal applications. These properties make them highly attractive for drug development, particularly when combined with sulfonamides to enhance their medicinal potential. In this work, we synthesized an
[...] Read more.
Indazoles are a very important group of nitrogen-containing heterocycles with a wide range of biological and medicinal applications. These properties make them highly attractive for drug development, particularly when combined with sulfonamides to enhance their medicinal potential. In this work, we synthesized an indazole-based sulfonamide, namely the 1-((2-chloro-5-methoxyphenyl)sulfonyl)-5-nitro-1H-indazole (3). The reduction of the nitro group of 5-nitroindazole (1) to its corresponding amine was also performed to yield compound (4). Both compounds’ structures were elucidated using various spectroscopic techniques such as 1H NMR, 13C NMR, infrared (IR), and high-resolution mass spectrometry (HRMS). Our molecular docking studies suggest that compounds (3) and (4) have a strong affinity for MAPK1, indicating their potential as cancer treatments.
Full article
(This article belongs to the Collection Heterocycle Reactions)
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Figure 1
Open AccessShort Note
N-(2-(Benzylamino)ethyl)-4-(naphthalene-1-sulfonamido)benzamide
by
Rosalba Leuci, Fulvio Loiodice and Luca Piemontese
Molbank 2024, 2024(3), M1856; https://doi.org/10.3390/M1856 - 25 Jul 2024
Abstract
In this study, we report the synthesis of N-(2-(benzylamino)ethyl)-4-(naphthalene-1-sulfonamido)benzamide, designed on the basis of the structures of the PPARγ partial agonist SR2067 and of the commercial acetylcholinesterase inhibitor drug donepezil, aiming for a multi-target approach for the therapy of elderly diseases, such as
[...] Read more.
In this study, we report the synthesis of N-(2-(benzylamino)ethyl)-4-(naphthalene-1-sulfonamido)benzamide, designed on the basis of the structures of the PPARγ partial agonist SR2067 and of the commercial acetylcholinesterase inhibitor drug donepezil, aiming for a multi-target approach for the therapy of elderly diseases, such as diabetes and Alzheimer’s disease. The compound was fully characterized by using 1H and 13C NMR, FT-IR and HRMS.
Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1
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Supplementary material:
Supplementary File 1 (PDF, 1169 KiB)
Supplementary File 2 (MOL, 5 KiB)
Supplementary File 3 (INCHI, 2 KiB)
Supplementary File 4 (MOL, 5 KiB)
Supplementary File 5 (MOL, 6 KiB)
Supplementary File 6 (INCHI, 2 KiB)
Supplementary File 7 (MOL, 6 KiB)
Supplementary File 8 (MOL, 4 KiB)
Supplementary File 9 (INCHI, 1 KiB)
Supplementary File 10 (MOL, 4 KiB)
Supplementary File 1 (PDF, 1169 KiB)
Supplementary File 2 (MOL, 5 KiB)
Supplementary File 3 (INCHI, 2 KiB)
Supplementary File 4 (MOL, 5 KiB)
Supplementary File 5 (MOL, 6 KiB)
Supplementary File 6 (INCHI, 2 KiB)
Supplementary File 7 (MOL, 6 KiB)
Supplementary File 8 (MOL, 4 KiB)
Supplementary File 9 (INCHI, 1 KiB)
Supplementary File 10 (MOL, 4 KiB)
Open AccessCommunication
Synthesis of Pyridinium Moiety Containing Triazolyl Purines
by
Aleksejs Burcevs, Māris Turks and Irina Novosjolova
Molbank 2024, 2024(3), M1855; https://doi.org/10.3390/M1855 - 24 Jul 2024
Abstract
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Pyridinium salts of 2-piperidinyl-6-triazolylpurine derivatives were obtained by the introduction of pyridinium moieties into the propane-1,3-diol fragment at the N(9) position of purine to enhance the solubility of 2-amino-6-triazolylpurine derivatives in water. Target structures were obtained using the tosylation of hydroxyl groups
[...] Read more.
Pyridinium salts of 2-piperidinyl-6-triazolylpurine derivatives were obtained by the introduction of pyridinium moieties into the propane-1,3-diol fragment at the N(9) position of purine to enhance the solubility of 2-amino-6-triazolylpurine derivatives in water. Target structures were obtained using the tosylation of hydroxyl groups of 2-(6-(4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)-2-(piperidin-1-yl)-9H-purin-9-yl)propane-1,3-diol, the subsequent introduction of pyridine, and ion exchange. The compounds were characterized using 1H- and 13C-NMR spectra, FTIR, UV–Vis, and HRMS data.
Full article
![](https://pub.mdpi-res.com/molbank/molbank-2024-M1855/article_deploy/html/images/molbank-2024-M1855-g001-550.jpg?1721835075)
Figure 1
Open AccessShort Note
N-(Benzothiazol-2-yl)-4-((5-chlorobenzoxazol-2-yl)amino)butanamide
by
Hugo Pilotzi-Xahuentitla, Gabriela del Carmen Canche-Naal, Rolffy Ruben Ortiz-Andrade, Gabriel Navarrete-Vázquez and Emanuel Hernández-Núñez
Molbank 2024, 2024(3), M1854; https://doi.org/10.3390/M1854 - 23 Jul 2024
Abstract
Benzazoles, such as benzoxazoles and benzothiazoles, are compounds with important biological and pharmacological activities and important intermediaries in synthesis. This report presents the synthesis of a butanamide derived from linking 5-chloro-2-aminobenzoxazole and 2-aminobenzothiazole via 4-chlorobutanoyl chloride. The corresponding compound N-(benzothiazol-2-yl)-4-((5-chlorobenzoxazol-2-yl)aminobutanamide was obtained
[...] Read more.
Benzazoles, such as benzoxazoles and benzothiazoles, are compounds with important biological and pharmacological activities and important intermediaries in synthesis. This report presents the synthesis of a butanamide derived from linking 5-chloro-2-aminobenzoxazole and 2-aminobenzothiazole via 4-chlorobutanoyl chloride. The corresponding compound N-(benzothiazol-2-yl)-4-((5-chlorobenzoxazol-2-yl)aminobutanamide was obtained at a 76% global yield using accessible starting materials and a methodology in two reaction steps. Furthermore, we conducted docking studies of this compound on 3-TOP protein to explore its potential as an antidiabetic agent.
Full article
(This article belongs to the Collection Molecules from Side Reactions)
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Figure 1
Open AccessCommunication
Synthesis of an Anion Receptor Using 3,6-Diaminophenanthrene as a Scaffold
by
Lau Halgreen and Hennie Valkenier
Molbank 2024, 2024(3), M1853; https://doi.org/10.3390/M1853 - 19 Jul 2024
Abstract
The synthesis of phosphate receptors represents an important avenue of research given the ubiquity of phosphate in biological and environmental systems. While many molecular scaffolds suitable for smaller anions are available either commercially or via reported synthetic routes, scaffolds suitable for larger anions
[...] Read more.
The synthesis of phosphate receptors represents an important avenue of research given the ubiquity of phosphate in biological and environmental systems. While many molecular scaffolds suitable for smaller anions are available either commercially or via reported synthetic routes, scaffolds suitable for larger anions such as phosphate are less common. In this work, we present a clear and straightforward synthesis of the basic molecular scaffold 3,6-diaminophenanthrene and of a novel 3,6-bisureidophenanthrene anion receptor prepared from this scaffold. Of the seven synthetic steps using readily available starting materials and reagents, only a single chromatographic purification step was required. The different interactions of the 3,6-bisureidophenanthrene-based anion receptor with phosphate and chloride are demonstrated. We expect that this convenient synthesis of the 3,6-diaminophenanthrene building block will pave the way for applications in many different fields of research, from materials science to supramolecular chemistry.
Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract
Open AccessShort Note
Diisoamyl (1R, 4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate
by
Brandon Quillian, Kennedy Musso, Elizabeth M. Vinson, Joseph G. Bazemore, Allison R. Marks and Clifford W. Padgett
Molbank 2024, 2024(3), M1852; https://doi.org/10.3390/M1852 - 18 Jul 2024
Abstract
Diisoamyl (1R,4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (2) was prepared by reacting exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (1) with isoamyl alcohol in the presence of a sulfuric acid catalyst under sonication conditions. Compound 2 was characterized by 1H, 13C NMR,
[...] Read more.
Diisoamyl (1R,4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (2) was prepared by reacting exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (1) with isoamyl alcohol in the presence of a sulfuric acid catalyst under sonication conditions. Compound 2 was characterized by 1H, 13C NMR, DEPT-135, infrared, and UV-vis spectroscopy. Gas chromatography–mass spectrometry, elemental analysis, and melting point determination were used to assess purity. The structure of compound 2 was also determined by single-crystal X-ray diffraction. It crystallizes in the monoclinic space group P21/c (14) with cell values of a = 15.5647(3) Å, b = 12.8969(2) Å, c = 9.0873(2) Å; β= 99.3920(10)°.
Full article
(This article belongs to the Section Organic Synthesis)
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Figure 1
Open AccessCommunication
Polymorphism of an Nα-Aroyl-N-Aryl-Phenylalanine Amide: An X-ray and Electron Diffraction Study
by
Markus Lang, Richard Goddard, Michael Patzer, Uday S. Ganapathy, Thomas Dick, Adrian Richter and Rüdiger W. Seidel
Molbank 2024, 2024(3), M1851; https://doi.org/10.3390/M1851 - 17 Jul 2024
Abstract
In view of the rise of drug-resistant tuberculosis and difficult-to-treat related diseases caused by non-tuberculous mycobacteria, there is an urgent need for antimycobacterial drug discovery. Nα-aroyl-N-aryl-phenylalanine amides (AAPs) have been identified as antimycobacterial agents and are subject to lead optimization.
[...] Read more.
In view of the rise of drug-resistant tuberculosis and difficult-to-treat related diseases caused by non-tuberculous mycobacteria, there is an urgent need for antimycobacterial drug discovery. Nα-aroyl-N-aryl-phenylalanine amides (AAPs) have been identified as antimycobacterial agents and are subject to lead optimization. The aim of the present study is to evaluate the impact of N-aryl ortho cyano substitution in a lead compound on the crystal and molecular structure and its in vitro activity against Mycobacterium abscessus. The title AAP can be conveniently synthesized from N-Boc-protected d-phenylalanine in two amide coupling steps using a previously established racemization-free method. Two polymorphic forms in the solid-state are described, as discovered by X-ray and electron diffraction. The introduction of a cyano group in the ortho position of the AAP N-aryl ring, however, leads to loss of in vitro activity against M. abscessus subsp. abscessus.
Full article
(This article belongs to the Section Structure Determination)
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Figure 1
Open AccessShort Note
Crystal Structure of Bis(1-butyl-1-methypyrrolidinium) Perthiodicarbonate Complex
by
Noël Pinaud, Yann Danten, Mathieu Marchivie, Marcel Besnard, Isabel Cabaço and Jean Guillon
Molbank 2024, 2024(3), M1849; https://doi.org/10.3390/M1849 - 15 Jul 2024
Abstract
Bis(1-butyl-1-methypyrrolidinium) perthiodicarbonate was obtained by the reaction of carbon disulfide with 1-butyl-1-methypyrrolidinium acetate ([BmPyrro][Ac]) in the liquid phase. Structural characterization of this original complex was achieved by single-crystal X-ray diffraction (SCXRD) analysis. The asymmetric unit of the title compound, C2S6
[...] Read more.
Bis(1-butyl-1-methypyrrolidinium) perthiodicarbonate was obtained by the reaction of carbon disulfide with 1-butyl-1-methypyrrolidinium acetate ([BmPyrro][Ac]) in the liquid phase. Structural characterization of this original complex was achieved by single-crystal X-ray diffraction (SCXRD) analysis. The asymmetric unit of the title compound, C2S6·2C9H20N, consisted of two crystallographically 1-methyl-1-butyl pyrrolidinium cations and one perthiodicarbonate anion. The complex C2S6·2C9H20N crystallized in the monoclinic space group, C 2/c, and possessed the following cell parameters: a = 16.0970(10) Å, b = 14.7140(9) Å, c = 12.3280(8) Å, α = 90°, β = 112.3730(12)°, γ = 90°, V = 2700.11 Å3, and Z = 8, Z’ = 0.5.
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(This article belongs to the Section Structure Determination)
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Graphical abstract
Open AccessShort Note
(1R,3R,5S,Z)-2-Ethylidene-6,6-dimethyl-3-vinylbicyclo[3.1.1]-heptane
by
Zhengjie He and William A. Donaldson
Molbank 2024, 2024(3), M1850; https://doi.org/10.3390/M1850 - 15 Jul 2024
Abstract
(1R,3R,5S,Z)-2-ethylidene-6,6-dimethyl-3-vinylbicyclo[3.1.1]heptane was prepared by hydrovinylation of nopadiene catalyzed by a cationic Ru complex. The structure was fully characterized by 1H- and 13C-NMR spectroscopy, including 2D-COSY and 2D-NOESY spectra, optical rotation, and combustion analysis.
[...] Read more.
(1R,3R,5S,Z)-2-ethylidene-6,6-dimethyl-3-vinylbicyclo[3.1.1]heptane was prepared by hydrovinylation of nopadiene catalyzed by a cationic Ru complex. The structure was fully characterized by 1H- and 13C-NMR spectroscopy, including 2D-COSY and 2D-NOESY spectra, optical rotation, and combustion analysis. In contrast to the previously reported 1,2-hydrovinylation of 1-vinylcycloalkenes by this catalyst, the reaction with nopadiene proceeds by 1,4-addition of ethylene.
Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1
Open AccessShort Note
(S,Z)-1,4-Bis(benzyloxy)hexa-3,5-dien-2-ol
by
Akihiro Iyoshi, Yo Miyazaki, Masakazu Tanaka and Atsushi Ueda
Molbank 2024, 2024(3), M1848; https://doi.org/10.3390/M1848 - 10 Jul 2024
Abstract
Naturally occurring carbohydrates serve as useful building blocks, and various derivatives have been employed in natural product syntheses. For instance, some aldoses can be converted to 1,3-dienes via the Wittig reaction at the anomeric carbon, accompanied by the E2 elimination of the C3-alkoxy
[...] Read more.
Naturally occurring carbohydrates serve as useful building blocks, and various derivatives have been employed in natural product syntheses. For instance, some aldoses can be converted to 1,3-dienes via the Wittig reaction at the anomeric carbon, accompanied by the E2 elimination of the C3-alkoxy group. However, there are few examples of terminal 1,3-diene synthesis. We report the synthesis of (S,Z)-1,4-bis(benzyloxy)hexa-3,5-dien-2-ol, featuring a terminal 1,3-diene and chiral secondary alcohol, derived from 2,3,5-tri-O-benzyl-d-arabinofuranose with methyltriphenylphosphonium bromide and potassium tert-butoxide in a single step. The synthesized terminal 1,3-diene demonstrated effective reactivity in a cross-metathesis reaction with cis-1,4-diacetoxy-2-butene.
Full article
(This article belongs to the Section Organic Synthesis)
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Figure 1
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Supplementary material:
Supplementary File 1 (PDF, 1404 KiB)
Supplementary File 2 (MOL, 4 KiB)
Supplementary File 3 (INCHI, 1 KiB)
Supplementary File 4 (MOL, 4 KiB)
Supplementary File 5 (MOL, 4 KiB)
Supplementary File 6 (INCHI, 1 KiB)
Supplementary File 7 (MOL, 4 KiB)
Supplementary File 8 (MOL, 5 KiB)
Supplementary File 9 (INCHI, 1 KiB)
Supplementary File 10 (MOL, 5 KiB)
Supplementary File 1 (PDF, 1404 KiB)
Supplementary File 2 (MOL, 4 KiB)
Supplementary File 3 (INCHI, 1 KiB)
Supplementary File 4 (MOL, 4 KiB)
Supplementary File 5 (MOL, 4 KiB)
Supplementary File 6 (INCHI, 1 KiB)
Supplementary File 7 (MOL, 4 KiB)
Supplementary File 8 (MOL, 5 KiB)
Supplementary File 9 (INCHI, 1 KiB)
Supplementary File 10 (MOL, 5 KiB)
Open AccessShort Note
Methyl and Benzyl (Ethyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-d-glucopyranosyl)uronate
by
Hannah S. Wootton and Gavin J. Miller
Molbank 2024, 2024(3), M1847; https://doi.org/10.3390/M1847 (registering DOI) - 9 Jul 2024
Abstract
Methyl and benzyl (ethyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-D-glucopyranosyl)uronate were synthesised from a protected thioglycoside in three steps. A regioselective ring opening of the benzylidene acetal with BH3.THF generated C6-OH material, which was subsequently oxidised using biphasic TEMPO/BAIB conditions. The
[...] Read more.
Methyl and benzyl (ethyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-D-glucopyranosyl)uronate were synthesised from a protected thioglycoside in three steps. A regioselective ring opening of the benzylidene acetal with BH3.THF generated C6-OH material, which was subsequently oxidised using biphasic TEMPO/BAIB conditions. The resultant uronic acid was esterified with either a methyl or benzyl moiety. The products were obtained on a multigram scale and fully characterised by 1H, 13C and 2D NMR, alongside MS and IR analysis.
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(This article belongs to the Section Organic Synthesis)
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Graphical abstract
Open AccessCommunication
A (2-(Pyrrolidin-1-yl)ethan-1-olate)(1-oxo-3-phenyl-1,4-dihydronaphthalen-2-olate) μ-Oxo-Bridged Dicopper(II) Dimeric Complex
by
Rylan Artis, Clifford W. Padgett, Kennedy Musso, Nathaniel Shank, Allison Marks and Brandon Quillian
Molbank 2024, 2024(3), M1846; https://doi.org/10.3390/M1846 (registering DOI) - 5 Jul 2024
Abstract
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The reaction of 2-(1H-pyrrol-1-yl)ethanol with 3-hydroxyflavone in the presence of copper(II) bromide yielded a dimeric copper(II) complex, [μ-O-(κ2-O,O-flav)(κ2-N,O-2PEO)Cu]2 (1) (flav = 3-hydroxyflavonolate; 2PEO = 2-(1H-pyrrol-1-yl)ethanolate) with both the
[...] Read more.
The reaction of 2-(1H-pyrrol-1-yl)ethanol with 3-hydroxyflavone in the presence of copper(II) bromide yielded a dimeric copper(II) complex, [μ-O-(κ2-O,O-flav)(κ2-N,O-2PEO)Cu]2 (1) (flav = 3-hydroxyflavonolate; 2PEO = 2-(1H-pyrrol-1-yl)ethanolate) with both the flav and 2PEO ligands bound to the copper(II) atom in a κ2-bonding mode. The dimer is held electrostatically by bridging oxygen atoms between two copper atoms. Complex 1 was characterized by single-crystal X-ray diffraction, infrared, and UV-Vis spectroscopy, elemental analysis, and melting point determination. The complex crystallizes in the monoclinic space group P21/n (14) with cell values of a = 11.85340(10) Å, b = 8.51480(10) Å, c = 23.8453(2) Å; β = 99.3920(10)°.
Full article
![](https://pub.mdpi-res.com/molbank/molbank-2024-M1846/article_deploy/html/images/molbank-2024-M1846-g001-550.jpg?1720178359)
Figure 1
Open AccessShort Note
trans-catena-Poly[[(bis-(µ-N,N′-bis[(pyridin-3-yl)methyl]ethanediamide))-diaqua-cadmium(II)] bis(nitrate) tetrahydrate)]
by
Anna Caria, Enrico Podda, M. Carla Aragoni, Riccardo Lai, Anna Pintus and Massimiliano Arca
Molbank 2024, 2024(3), M1845; https://doi.org/10.3390/M1845 - 3 Jul 2024
Abstract
The reaction between cadmium nitrate tetrahydrate and N,N′-bis(pyridin-3-ylmethyl)oxalamide (L) in a 1:3 molar ratio in a water/acetonitrile (1:6 v/v) mixture afforded single crystals of compound 1 suitable for X-ray diffraction analysis. Compound 1 consists of
[...] Read more.
The reaction between cadmium nitrate tetrahydrate and N,N′-bis(pyridin-3-ylmethyl)oxalamide (L) in a 1:3 molar ratio in a water/acetonitrile (1:6 v/v) mixture afforded single crystals of compound 1 suitable for X-ray diffraction analysis. Compound 1 consists of the coordination polymer (CP) [[Cd(L)2(OH2)2](NO3)2·4H2O]∞, in which CdII ions are bridged by neutral L antiperiplanar N-ligands in a wavy ribbon fashion developed along the c-axis. Two trans-disposed water molecules complete the pseudo-octahedral coordination geometry of the metal ion. The crystal packing of 1 revealed the interplay between π–π stacking interactions and an intricate hydrogen-bonded network involving oxalamides, nitrates, and water molecules. The donor properties of L and the intermolecular interactions in compound 1 are interpreted based on hybrid-DFT calculations.
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(This article belongs to the Section Structure Determination)
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Figure 1
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Supplementary material:
Supplementary File 1 (ZIP, 490 KiB)
Supplementary File 2 (MOL, 2 KiB)
Supplementary File 3 (INCHI, 590 B)
Supplementary File 4 (MOL, 2 KiB)
Supplementary File 5 (MOL, 2 KiB)
Supplementary File 6 (INCHI, 585 B)
Supplementary File 7 (MOL, 2 KiB)
Supplementary File 8 (MOL, 2 KiB)
Supplementary File 9 (INCHI, 589 B)
Supplementary File 10 (MOL, 2 KiB)
Supplementary File 11 (CIF, 158 KiB)
Supplementary File 1 (ZIP, 490 KiB)
Supplementary File 2 (MOL, 2 KiB)
Supplementary File 3 (INCHI, 590 B)
Supplementary File 4 (MOL, 2 KiB)
Supplementary File 5 (MOL, 2 KiB)
Supplementary File 6 (INCHI, 585 B)
Supplementary File 7 (MOL, 2 KiB)
Supplementary File 8 (MOL, 2 KiB)
Supplementary File 9 (INCHI, 589 B)
Supplementary File 10 (MOL, 2 KiB)
Supplementary File 11 (CIF, 158 KiB)
Open AccessShort Note
(Z)-N-Carbamoyl-4-hydroxy-4-(4-methoxyphenyl)-2-oxobut-3-enamide
by
Alexandra O. Derevnina, Anastasia A. Andreeva and Andrey N. Maslivets
Molbank 2024, 2024(3), M1844; https://doi.org/10.3390/M1844 - 29 Jun 2024
Abstract
The reaction of 5-(4-methoxyphenyl)furan-2,3-dione with urea in a 1:1 ratio when refluxed in a mixture of 1,2-dichloroethane-DMSO gives (Z)-N-carbamoyl-4-hydroxy-4-(4-methoxyphenyl)-2-oxobut-3-enamide in a good yield. This compound was fully characterized.
Full article
(This article belongs to the Collection Heterocycle Reactions)
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Figure 1
Open AccessShort Note
5(S)-((3aR,4R,6aR)-2,2-Dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-phenyl-4,5-dihydrooxazole
by
Liliana Boiaryna, Stéphane Guillarme and Christine Saluzzo
Molbank 2024, 2024(3), M1843; https://doi.org/10.3390/M1843 - 28 Jun 2024
Abstract
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5(S)-((3aR,4R,6aR)-2,2-Dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-phenyl-4,5-dihydrooxazole was synthesized from isosorbide in a three-step sequence, with an overall yield of 46%. The first reaction step involves a single regioselective ring-opening reaction of isosorbide with Me3SiI in the presence of
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5(S)-((3aR,4R,6aR)-2,2-Dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-phenyl-4,5-dihydrooxazole was synthesized from isosorbide in a three-step sequence, with an overall yield of 46%. The first reaction step involves a single regioselective ring-opening reaction of isosorbide with Me3SiI in the presence of acetone followed by an intramolecular nucleophilic substitution to transform the iodoalcohol into its corresponding epoxide. The last reaction allows the formation of the oxazoline ring directly from the epoxide with benzonitrile in the presence of BF3·Et2O.
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Scheme 1
Open AccessShort Note
Perfluoro-3-ethyl-1,2,3,10b-tetrahydrofluoranthene
by
Vladislav V. Komarov, Vyacheslav I. Krasnov, Victor M. Karpov, Dmitriy A. Parkhomenko and Tatyana V. Mezhenkova
Molbank 2024, 2024(3), M1842; https://doi.org/10.3390/M1842 - 25 Jun 2024
Abstract
The title compound was synthesized from perfluoro-1-ethyltetralin and 1,2,3,4-tetrafluorobenzene under the action of antimony pentafluoride as a mixture of cis- and trans-isomers in a 71% isolated yield. The structure and cis-/trans-configuration of the isomers were determined by NMR
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The title compound was synthesized from perfluoro-1-ethyltetralin and 1,2,3,4-tetrafluorobenzene under the action of antimony pentafluoride as a mixture of cis- and trans-isomers in a 71% isolated yield. The structure and cis-/trans-configuration of the isomers were determined by NMR (19F, 13C), 19F–19F COSY, and 19F–19F NOESY 2D NMR spectroscopy.
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(This article belongs to the Section Organic Synthesis)
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Figure 1
Open AccessCommunication
Ethyl 5-Hydroxy-2-methyl-1-(pyridin-2-ylmethyl)benzo[g]indole-3-carboxylate
by
Giuseppe Satta, Silvia Gaspa, Lidia De Luca, Luisa Pisano and Massimo Carraro
Molbank 2024, 2024(3), M1840; https://doi.org/10.3390/M1840 - 24 Jun 2024
Abstract
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Indole ring is widely represented in natural compounds, as well as in a great variety of drugs. In this paper, the synthesis of a 5-hydroxybenzoindole derivative carrying a pyridyl substituent on position 1 is reported. The method involved no chromatography for purification and
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Indole ring is widely represented in natural compounds, as well as in a great variety of drugs. In this paper, the synthesis of a 5-hydroxybenzoindole derivative carrying a pyridyl substituent on position 1 is reported. The method involved no chromatography for purification and used solvents and catalysts of very low toxicity.
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Figure 1
Open AccessCommunication
Structural Elucidation of a New Puzzling Compound Emerged from Doebner Quinoline Synthesis
by
Cristina Maria Al-Matarneh and Alina Nicolescu
Molbank 2024, 2024(3), M1841; https://doi.org/10.3390/M1841 - 24 Jun 2024
Abstract
The quinoline ring is found in many biologically active natural alkaloids and is still being highly exploited by researchers due to its numerous potential applications in fields ranging from pharmacology to material science. During our synthetic attempts for new quinoline-4-carboxylic acids, using an
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The quinoline ring is found in many biologically active natural alkaloids and is still being highly exploited by researchers due to its numerous potential applications in fields ranging from pharmacology to material science. During our synthetic attempts for new quinoline-4-carboxylic acids, using an extended version of the Doebner reaction, a new puzzling compound emerged when para-iodine aniline was reacted with salicylaldehyde and pyruvic acid in acetic acid as a reaction medium. The chemical structure of this new compound was established based on the information obtained from 1D and 2D NMR experiments (1H-, 13C-, and 15N-NMR), corroborated with MS spectrometry and IR spectroscopy. The photophysical properties (UV–vis and fluorescence) were also investigated. The proposed structure contains as the main elements a 1,4-dioxane-2,5-dione core symmetrically substituted with a propylidene chain that has attached to it a salicylaldehyde fragment and a pyrrole-2-one ring containing two 4-iodophenyl fragments. The isolation of this compound, reported here for the first time, is direct evidence that unexpected compounds can emerge from “classical” synthetic pathways when the right components are combined.
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(This article belongs to the Section Structure Determination)
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Graphical abstract
Open AccessCommunication
N-Methoxycarbonyl-9,12-Dimethoxy-Norchelerythrine: A Novel Antifungal Type-III Benzo[c]phenanthridine from Zanthoxylum simulans Hance Seedlings
by
Diego Cárdenas-Laverde, Diego Quiroga and Ericsson Coy-Barrera
Molbank 2024, 2024(2), M1839; https://doi.org/10.3390/M1839 - 21 Jun 2024
Abstract
Zanthoxylum simulans Hance, commonly known as Sichuan pepper, is a well-known medicinal plant recognized for its potential as a source of bioactive specialized metabolites. As part of our interest in natural antifungal compounds, the present study describes the discovery of an unreported N
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Zanthoxylum simulans Hance, commonly known as Sichuan pepper, is a well-known medicinal plant recognized for its potential as a source of bioactive specialized metabolites. As part of our interest in natural antifungal compounds, the present study describes the discovery of an unreported N-alcoxycarbonylbenzo[c]phenanthridinium salt, N-methoxycarbonyl-9,12-dimethoxy-norchelerythrine 1 (a type-III benzo[c]phenanthridine), isolated from Z. simulans seedlings, which were propagated under controlled greenhouse conditions. Six-month seedlings were harvested and subjected to cold acid–base extraction. Chromatographic techniques achieved the isolation of 1 from raw alkaloid extract. The structural elucidation of 1 was accomplished through comprehensive spectroscopic analysis, including nuclear magnetic resonance and high-resolution mass spectrometry. Fusarium oxysporum, a fungal pathogen responsible for substantial agricultural losses, was exposed to different concentrations of the novel compound, exhibiting potent antifungal efficacy (IC50 < 3 µM) and fungicide effects. These findings highlight the potential of benzophenanthridines as antifungal leads and underscore the importance of exploring natural products for agricultural applications.
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(This article belongs to the Section Natural Products)
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Figure 1
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