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Molbank, Volume 2023, Issue 1 (March 2023) – 47 articles

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Communication
Heteronuclear Bimetallic Complexes with 3d and 4f Elements
Molbank 2023, 2023(1), M1577; https://doi.org/10.3390/M1577 (registering DOI) - 03 Feb 2023
Abstract
Three heteronuclear bimetallic complexes [Cu(MeOH)(L)Ln(NO3)3] (1-Ce; Ln = Ce, 1-Pr; Ln = Pr, and 1-Nd; Ln = Nd) were prepared using H2L (1,3-bis[(3-methoxysalicylidene)amino]-2,2-dimethylpropane) in methanol, affording the complexes as green crystalline materials. These [...] Read more.
Three heteronuclear bimetallic complexes [Cu(MeOH)(L)Ln(NO3)3] (1-Ce; Ln = Ce, 1-Pr; Ln = Pr, and 1-Nd; Ln = Nd) were prepared using H2L (1,3-bis[(3-methoxysalicylidene)amino]-2,2-dimethylpropane) in methanol, affording the complexes as green crystalline materials. These can be prepared in a one-pot synthesis from 2,2-dimethylpropan-1,3-diamine, o-vanillin, copper(II) nitrate, and Ln(III) nitrate (Ln = Ce, Pr, Nd). X-ray crystallography, high-resolution mass spectrometry, and UV-vis spectroscopy were used to characterize the bimetallic complexes. All three complexes showed the copper center adopting a five-coordinate square pyramidal geometry and the lanthanoid cation adopting a ten-coordinate geometry. Full article
(This article belongs to the Section Structure Determination)
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(Z)-3-(Dicyanomethylene)-4-((5-fluoro-3,3-dimethyl-1-(3-phenylpropyl)-3H-indol-1-ium-2-yl) methylene)-2-(((E)-5-fluoro-3,3-dimethyl-1-(3-phenylpropyl)indolin-2-ylidene)methyl) cyclobut-1-en-1-olate
Molbank 2023, 2023(1), M1576; https://doi.org/10.3390/M1576 (registering DOI) - 03 Feb 2023
Abstract
Recent literature on this topic highlights the significance of adding malononitrile moiety and halogen substituents to the squaraine scaffold to create redshifted fluorophores into the near-infrared optical region. Herein, a redshifted hydrophobic squaraine dye is synthesized via a three-step pathway. The reported dye [...] Read more.
Recent literature on this topic highlights the significance of adding malononitrile moiety and halogen substituents to the squaraine scaffold to create redshifted fluorophores into the near-infrared optical region. Herein, a redshifted hydrophobic squaraine dye is synthesized via a three-step pathway. The reported dye is characterized by spectroscopic techniques, such as 1H NMR, 19F NMR, 13C NMR, and high-resolution mass spectroscopy. Optical properties are also reported using absorbance and fluorescence studies. The hydrophobicity of the dye was studied with absorbance and fluorescence spectroscopy in water–methanol mixtures and showed J-aggregates as the water concentration increased. Density functional theory calculations were conducted to assess its electron delocalization as well as observe the three-dimensional geometry of the dye as a result of the dicyanomethylene modification and the two bulky phenyl groups. Full article
(This article belongs to the Collection Heterocycle Reactions)
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tert-Butyl 2-Amino-3-cyano-5-oxo-4-phenyl-5,7-dihydropyrano[2,3-c]pyrrole-6(4H)-carboxylate
Molbank 2023, 2023(1), M1575; https://doi.org/10.3390/M1575 - 03 Feb 2023
Abstract
Organocatalyzed synthesis of tert-butyl 2-amino-3-cyano-5-oxo-4-phenyl-5,7-dihydropyrano[2,3-c]pyrrole-6(4H)-carboxylate, prepared from Boc-tetramic acid and benzylidenemalononitrile, is disclosed. Two bifunctional noncovalent organocatalysts were employed, yielding the product as a racemic mixture in both cases. The structure of the new synthesized compound was confirmed [...] Read more.
Organocatalyzed synthesis of tert-butyl 2-amino-3-cyano-5-oxo-4-phenyl-5,7-dihydropyrano[2,3-c]pyrrole-6(4H)-carboxylate, prepared from Boc-tetramic acid and benzylidenemalononitrile, is disclosed. Two bifunctional noncovalent organocatalysts were employed, yielding the product as a racemic mixture in both cases. The structure of the new synthesized compound was confirmed by high resolution mass-spectrometry, 1H- and 13C-NMR, HSQC, and IR spectroscopy. Full article
(This article belongs to the Section Organic Synthesis)
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Correction
Correction: Rajakulendran et al. Fosbergenone: 3-[2-(1,2,5,5-Tetramethyl-7-oxo-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-yl)ethyl]-2,5-dihydrofuran-2-one. Molbank 2022, 2022, M1391
Molbank 2023, 2023(1), M1574; https://doi.org/10.3390/M1574 - 02 Feb 2023
Viewed by 39
Abstract
In the original publication [...] Full article
(This article belongs to the Section Natural Products)
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6-Chloro-3-nitro-2-[(phenylsulfonyl)methyl]imidazo[1,2-b]pyridazine
Molbank 2023, 2023(1), M1573; https://doi.org/10.3390/M1573 - 01 Feb 2023
Viewed by 140
Abstract
As part of our ongoing scaffold-hopping work on an antikinetoplastid 3-nitroimidazo[1,2-a]pyridine scaffold, we explored 3-nitroimidazo[1,2-b]pyridazine as a potential new antikinetoplastid series. Using conditions previously described by our lab, we obtained 6-chloro-3-nitro-2-[(phenylsulfonyl)methyl]imidazo[1,2-b]pyridazine with 54% yield. In vitro activity [...] Read more.
As part of our ongoing scaffold-hopping work on an antikinetoplastid 3-nitroimidazo[1,2-a]pyridine scaffold, we explored 3-nitroimidazo[1,2-b]pyridazine as a potential new antikinetoplastid series. Using conditions previously described by our lab, we obtained 6-chloro-3-nitro-2-[(phenylsulfonyl)methyl]imidazo[1,2-b]pyridazine with 54% yield. In vitro activity of this compound was evaluated against both the promastigote form of Leishmania donovani, the axenic amastigote form of Leishmania infantum and the trypomastigote blood stream form of Trypanosomabrucei brucei, and its influence on cell viability was assessed on the HepG2 cell line. However, despite good activity against the trypomastigote blood stream form of T. b. brucei (EC50 = 0.38 µM), it showed poor solubility in both HepG2 (CC50 > 7.8 µM) and L. infantum axenic amastigotes (EC50 > 1.6 µM) culture media, associated with a loss of activity against the promastigote form of L. infantum (EC50 > 15.6 µM). Full article
(This article belongs to the Collection Heterocycle Reactions)
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Communication
(3-(1H-Indol-3-yl)-2-(7,8,12,13-tetraoxa-10-azaspiro[5.7]tridecan-10-yl)propanoic acid) with Cytotoxic Activity
Molbank 2023, 2023(1), M1572; https://doi.org/10.3390/M1572 - 01 Feb 2023
Viewed by 159
Abstract
An efficient method for the synthesis of 3-(1H-indol-3-yl)-2-(7,8,12,13-tetraoxa-10-azaspiro[5.7]tridecan-10-yl)propanoic acid) via condensation of 7,8,10,12,13-pentaoxaspiro[5.7]tridecane with tryptophan under the action of a catalyst based on Sm(NO3)3·6H2O has been developed. A high cytotoxic activity of eight-membered azadiperoxide against [...] Read more.
An efficient method for the synthesis of 3-(1H-indol-3-yl)-2-(7,8,12,13-tetraoxa-10-azaspiro[5.7]tridecan-10-yl)propanoic acid) via condensation of 7,8,10,12,13-pentaoxaspiro[5.7]tridecane with tryptophan under the action of a catalyst based on Sm(NO3)3·6H2O has been developed. A high cytotoxic activity of eight-membered azadiperoxide against tumor cells Jurkat, K562, U937, and HL60 was established. Additionally, this compound is an inducer of apoptosis and affects the cell cycle. Full article
(This article belongs to the Collection Heterocycle Reactions)
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Communication
Crystal Structure of 2-[(1E)-2-(4-Fluorophenyl)diazenyl]-1H-imidazole
Molbank 2023, 2023(1), M1571; https://doi.org/10.3390/M1571 - 01 Feb 2023
Viewed by 115
Abstract
The molecule of the title compound adopts a twisted geometry with a rotation of approximately 30° between the mean planes of the imidazole and phenyl rings. The crystal structure displays hydrogen bonded chains as a result of N–H···N interactions between the imidazole rings [...] Read more.
The molecule of the title compound adopts a twisted geometry with a rotation of approximately 30° between the mean planes of the imidazole and phenyl rings. The crystal structure displays hydrogen bonded chains as a result of N–H···N interactions between the imidazole rings of neighboring molecules. These H-bonded chains are assembled into flat molecular layers parallel to the (121) plane. Two intermolecular interactions, involving inversion-related molecules belonging to adjacent molecular layers, contribute significantly to the stabilization of the crystal. Full article
(This article belongs to the Topic Heterocyclic Carbene Catalysis)
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Communication
Synthesis and Characterization of New Potential Hypoxia-Sensitive Azo-thiacalix[4]arenes Derivatives
Molbank 2023, 2023(1), M1570; https://doi.org/10.3390/M1570 - 31 Jan 2023
Viewed by 94
Abstract
The subject of this article is new potential hypoxia-sensitive azo-thiacalix[4]arenes derivatives in the 1,3-alternate configuration. Previously, it was shown that azo derivatives of calix[4]arene in the cone conformation form complexes with rhodamine dyes. The present work is devoted to the synthesis of new [...] Read more.
The subject of this article is new potential hypoxia-sensitive azo-thiacalix[4]arenes derivatives in the 1,3-alternate configuration. Previously, it was shown that azo derivatives of calix[4]arene in the cone conformation form complexes with rhodamine dyes. The present work is devoted to the synthesis of new azo derivatives using the thiacalix[4]arene platform. A new highly productive method for the synthesis of thiacalixarene with four anionic sulfonate azo fragments on the lower rim (compounds 2ab) for further complexation with the most common cationic dyes is reported. The chemical structures of the products obtained were established based on 1H and 13C NMR, IR spectroscopy, MALDI TOF mass spectrometry, and elemental analysis. Full article
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2-{9-(10-Bromoanthracenyl)}-1,3-dihydro-1H-[d]-1,3,2-benzodiazaborole
Molbank 2023, 2023(1), M1569; https://doi.org/10.3390/M1569 - 27 Jan 2023
Viewed by 279
Abstract
In this paper, a synthesis and characterization of a novel three coordinate 2-{9-(10-Bromoanthracenyl)}-1,3-dihydro-1H-[d]-1,3,2-benzodiazaborole from a cyclo-condensation reaction of o-phenylenediamine and 10-bromoanthracene-9-boronic acid is described. The desired product was obtained in 0.343 g (92% yields) with its structure characterized [...] Read more.
In this paper, a synthesis and characterization of a novel three coordinate 2-{9-(10-Bromoanthracenyl)}-1,3-dihydro-1H-[d]-1,3,2-benzodiazaborole from a cyclo-condensation reaction of o-phenylenediamine and 10-bromoanthracene-9-boronic acid is described. The desired product was obtained in 0.343 g (92% yields) with its structure characterized by 1H, 11B, 13C NMR, HRMS and FT-IR. Full article
(This article belongs to the Collection Heterocycle Reactions)
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N-isobutyl-1,8-bis(isobutylamino)-naphthalimide
Molbank 2023, 2023(1), M1568; https://doi.org/10.3390/M1568 - 27 Jan 2023
Viewed by 271
Abstract
Naphthalimides make up a class of organic molecules characterised by excellent spectroscopic properties due to their extended conjugate system. Furthermore, various asymmetric or symmetric compounds can be obtained from naphthalimides by the different functionalization that can be performed on the nitrogen and/or on [...] Read more.
Naphthalimides make up a class of organic molecules characterised by excellent spectroscopic properties due to their extended conjugate system. Furthermore, various asymmetric or symmetric compounds can be obtained from naphthalimides by the different functionalization that can be performed on the nitrogen and/or on the aromatic rings. The introduction of a wide range of substituents in different positions allows chemical and spectroscopic properties to be regulated. In this contribution, we report the synthesis and characterization of a new 4,5-amino-1,8-naphthalimide bearing three isobutyl substituents. Full article
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Communication
Synthesis of Pentacycloundecane (PCUD) Based Spiro-Pyrano-Cage Framework via Ring-Closing Metathesis
Molbank 2023, 2023(1), M1567; https://doi.org/10.3390/M1567 - 23 Jan 2023
Viewed by 362
Abstract
Here, we demonstrate a short synthetic route to pyrano cage systems containing pentacycloundecane units by employing ring-closing metathesis (RCM) as a key step. These cage systems were constructed starting with readily available starting materials by adopting atomic economic processes such as cycloadditions (Diels-Alder [...] Read more.
Here, we demonstrate a short synthetic route to pyrano cage systems containing pentacycloundecane units by employing ring-closing metathesis (RCM) as a key step. These cage systems were constructed starting with readily available starting materials by adopting atomic economic processes such as cycloadditions (Diels-Alder reaction and [2+2] cycloaddition), Grignard addition, and olefin metathesis. The key building block, such as hexacyclic cage dione, was prepared from 1,4-naphthoquinone derivative and freshly cracked 1,3-cyclopentadiene. Some of these heterocyclic motifs are useful in biological chemistry and valuable as key synthons for high-energy-density materials. Full article
(This article belongs to the Collection Heterocycle Reactions)
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(4-(Adamantan-1-yl)-1-(isopropyl)-1H-imidazol-2-yl)methanol
Molbank 2023, 2023(1), M1566; https://doi.org/10.3390/M1566 - 23 Jan 2023
Viewed by 303
Abstract
(4-(Adamantan-1-yl)-1-(isopropyl)-1H-imidazol-2-yl)methanol was prepared through a five-step process starting from commercially available 1-acetyladamantane. Each step proceeded in moderate-to-excellent yields and the overall yield across five steps was 28%. The compound was identified and characterized by 1H and 13C{1H} [...] Read more.
(4-(Adamantan-1-yl)-1-(isopropyl)-1H-imidazol-2-yl)methanol was prepared through a five-step process starting from commercially available 1-acetyladamantane. Each step proceeded in moderate-to-excellent yields and the overall yield across five steps was 28%. The compound was identified and characterized by 1H and 13C{1H} NMR, high-resolution mass spectroscopy, and elemental analysis. This compound and its derivatives have the potential to be used as precursors to the synthesis of biomimetic chelating ligands. Full article
(This article belongs to the Section Organic Synthesis)
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5-Vinyl-1H-tetrazole
Molbank 2023, 2023(1), M1565; https://doi.org/10.3390/M1565 - 23 Jan 2023
Viewed by 347
Abstract
Highly purified 5-vinyl-1H-tetrazole was synthesized, which is in great demand in modern medicine and industry as a monomer for obtaining nitrogen-rich macromolecular compounds and a reagent for the complete synthesis of biological compounds. The molecular structure was studied experimentally with sequential [...] Read more.
Highly purified 5-vinyl-1H-tetrazole was synthesized, which is in great demand in modern medicine and industry as a monomer for obtaining nitrogen-rich macromolecular compounds and a reagent for the complete synthesis of biological compounds. The molecular structure was studied experimentally with sequential X-ray diffraction analysis and theoretically with ab initio quantum chemical calculations. The data from differential scanning calorimetry, nuclear magnetic resonance (1H, 13C, 1H-15N, HMBC), high-resolution mass spectrometry and vibrational spectroscopy were analyzed. The results are useful for evaluating the possibility of extending the polymerization of 5-vinyl-1H-tetrazole to synthesize polymers with predictable molecular weight and thermodynamic parameters. Full article
(This article belongs to the Section Organic Synthesis)
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Cis-(3-benzyloxy-1,1-cyclobutanedicarboxylato κ2O,O′)bis(1-methyl-1H-pyrazole)platinum(II)
Molbank 2023, 2023(1), M1564; https://doi.org/10.3390/M1564 - 23 Jan 2023
Viewed by 276
Abstract
A huge variety of types of cancer makes it necessary to search for new effective drugs with a defined molecular target. Modification of substituents in ligands based on 3-hydroxy-1,1-cyclobutanedicarboxylic acid are one of the effective directions to design a better version of carboplatin. [...] Read more.
A huge variety of types of cancer makes it necessary to search for new effective drugs with a defined molecular target. Modification of substituents in ligands based on 3-hydroxy-1,1-cyclobutanedicarboxylic acid are one of the effective directions to design a better version of carboplatin. In the present study, we combined in one molecule a derivative of 3-hydroxycyclobutane-1,1-dicarboxylic acid and N-methylpyrazole as a carrier ligand. The antiproliferative of the novel complex Pt(II) was established for cell lines HCT116, MCF7, A549, and WI38 by means of a standard MTT colorimetric assay. Full article
(This article belongs to the Section Organic Synthesis)
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2-Furyl-6-nitro-1,2,4-triazolo [1,5-a]pyrimidin-7-one
Molbank 2023, 2023(1), M1563; https://doi.org/10.3390/M1563 - 23 Jan 2023
Viewed by 356
Abstract
A sodium salt of 2-(fur-2-yl)-6-nitro-1,2,4-triazolo[1,5-a]pyrimidin-7-one as a close structural analogue of ZM-241385 was obtained. This heterocycle can serve as an effector for A2a adenosine receptors and possesses antiseptic activity. The structures of compounds were confirmed based on the data of [...] Read more.
A sodium salt of 2-(fur-2-yl)-6-nitro-1,2,4-triazolo[1,5-a]pyrimidin-7-one as a close structural analogue of ZM-241385 was obtained. This heterocycle can serve as an effector for A2a adenosine receptors and possesses antiseptic activity. The structures of compounds were confirmed based on the data of 1H, 13C NMR spectroscopy, IR spectroscopy, and an elemental analysis. The structure of sodium salt 2-furyl-6-nitro-1,2,4-triazolo[1,5-a]pyrimidin-7-one was confirmed by an X-ray diffraction analysis. Full article
(This article belongs to the Section Organic Synthesis)
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Communication
Carboxybetaine and Carboxybetaine Ester Derivatives of Tetra(dodecyloxyphenyl)-calix[4]resorcinarene: Synthesis, Self-Assembly and In Vitro Toxicity
Molbank 2023, 2023(1), M1562; https://doi.org/10.3390/M1562 - 22 Jan 2023
Viewed by 325
Abstract
Amphiphilic calix[4]resorcinarenes are a class of macrocyclic compounds with broad potential utility including nanomedicine. Here the synthesis of new carboxybetaine and carboxybetaine ester calix[4]resorcinarene bearing 4-(dodecyloxy)phenyl groups on the lower rim is presented. The compounds were characterized by 1H-NMR, 13C-NMR, 2D [...] Read more.
Amphiphilic calix[4]resorcinarenes are a class of macrocyclic compounds with broad potential utility including nanomedicine. Here the synthesis of new carboxybetaine and carboxybetaine ester calix[4]resorcinarene bearing 4-(dodecyloxy)phenyl groups on the lower rim is presented. The compounds were characterized by 1H-NMR, 13C-NMR, 2D NMR, IR, ESI and elemental analysis. The critical association concentration values are 1.00 × 10−5 and 1.18 × 10−5 mol·L−1 for carboxybetain and ester, respectively. The hemolytic activity of the macrocycles and their cytotoxicity against normal (WI-38, Chang liver) and tumor cells (M-HeLa) are also estimated. Full article
(This article belongs to the Section Organic Synthesis)
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(R)-N-Benzyl-N-(1-phenylethyl)cyclohexanamine
Molbank 2023, 2023(1), M1561; https://doi.org/10.3390/M1561 - 20 Jan 2023
Viewed by 253
Abstract
The preparation and characterization of a new chiral tertiary dibenzylamine are described. These molecules are well known in the literature for their high neuropharmacological potential. The general synthetic pathway is based on asymmetric Aza–Michael addition of chiral (R)-N-benzyl-N [...] Read more.
The preparation and characterization of a new chiral tertiary dibenzylamine are described. These molecules are well known in the literature for their high neuropharmacological potential. The general synthetic pathway is based on asymmetric Aza–Michael addition of chiral (R)-N-benzyl-N-(α-methylbenzyl)amide to methyl cyclohex-1-en-carboxilate obtaining the β-amino ester, followed by carboxylic acid hydrolysis and subsequent Barton descarboxylation. Interestingly, it is a general synthetic procedure of a wide range of chiral amines by careful choice of insaturated esters and alkylation of the chiral enolate in the initial reaction. The new tertiary dibenzylamine molecule is fully characterized by NMR Spectroscopy (1H and 13C), as well by High-Resolution Mass Spectrometry and Infrared Spectroscopy. Full article
(This article belongs to the Section Organic Synthesis)
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Methyl 3-Bromo-5-carbamoylisothiazole-4-carboxylate
Molbank 2023, 2023(1), M1560; https://doi.org/10.3390/M1560 - 19 Jan 2023
Viewed by 178
Abstract
Reaction of methyl 3-bromo-5-cyanoisothiazole-4-carboxylate with conc. H2SO4 gave methyl 3-bromo-5-carbamoylisothiazole-4-carboxylate in 93% yield. The compound was fully characterized. Full article
(This article belongs to the Section Organic Synthesis)
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Communication
Obtainment of Threo and Erythro Isomers of the 6-Fluoro-3-(2,3,6,7,8,9-hexahydronaphtho[2,3-b][1,4]dioxin-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxamide
Molbank 2023, 2023(1), M1559; https://doi.org/10.3390/M1559 - 18 Jan 2023
Viewed by 292
Abstract
2,6-difluorobenzamides have been deeply investigated as antibacterial drugs in the last few decades. Several 3-substituted-2,6-difluorobenzamides have proved their ability to interfere with the bacterial cell division cycle by inhibiting the protein FtsZ, the key player of the whole process. Recently, we developed a [...] Read more.
2,6-difluorobenzamides have been deeply investigated as antibacterial drugs in the last few decades. Several 3-substituted-2,6-difluorobenzamides have proved their ability to interfere with the bacterial cell division cycle by inhibiting the protein FtsZ, the key player of the whole process. Recently, we developed a novel family of 1,4-tetrahydronaphthodioxane benzamides, having an ethoxy linker, which reached sub-micromolar MICs towards Gram-positive Staphylococcus aureus and Bacillus subtilis. A further investigation of their mechanism of action should require the development of a fluorescent probe, and the consequent definition of a synthetic pathway for its obtainment. In the present work, we report the obtainment of an unexpected bicyclic side product, 6-fluoro-3-(2,3,6,7,8,9-hexahydronaphtho[2,3-b][1,4]dioxin-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxamide, coming from the substitution of one aromatic fluorine by the in situ formed alkoxy group, in the final opening of an epoxide intermediate. This side product was similarly achieved, in good yields, by opening the ring of both erythro and threo epoxides, and the two compounds were fully characterized using HRMS, 1H-NMR, 13C-NMR, HPLC and DSC. Full article
(This article belongs to the Special Issue Molecules from Side Reactions II)
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2,3-Bis((E)-4-hydroxybenzylidene)-N1,N4-bis(4-methylbenzyl)succinamide
Molbank 2023, 2023(1), M1558; https://doi.org/10.3390/M1558 - 17 Jan 2023
Viewed by 239
Abstract
Lignans and neolignans are dimeric natural products with an extraordinary variety of structures and biological properties. Diphenylbutadienes are a subclass of lignans rarely found in nature with cannabisin G being the most representative example. This lignan, found in Cannabis sativa seed, has shown [...] Read more.
Lignans and neolignans are dimeric natural products with an extraordinary variety of structures and biological properties. Diphenylbutadienes are a subclass of lignans rarely found in nature with cannabisin G being the most representative example. This lignan, found in Cannabis sativa seed, has shown anti-inflammatory and antioxidant activity among other biological properties. Different methodologies have been reported for the synthesis of cannabis G to be employed in new biological studies. We report herein a green and concise procedure based on the use of Trametes versicolor laccase for the synthesis of a new diphenylbutadiene. The developed procedure may be employed for the synthesis of cannabisin G and other analogues. Full article
(This article belongs to the Section Natural Products)
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Communication
Synthesis of 3-Bromo-4-phenylisothiazole-5-carboxylic Acid and 3-Bromoisothiazole-5-carboxylic Acid
Molbank 2023, 2023(1), M1557; https://doi.org/10.3390/M1557 - 17 Jan 2023
Viewed by 408
Abstract
Reactions of 3-bromo-4-phenylisothiazole-5-carboxamide and 3-bromoisothiazole-5-carboxamide with NaNO2 (4 equiv.), in TFA, at ca. 0 °C gave the carboxylic acid products in 99% and 95% yields, respectively. The two compounds were fully characterized. Full article
(This article belongs to the Section Organic Synthesis)
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3-(1-Ethylamino-ethylidene)-1-methyl-pyrrolidine-2,4-dione
Molbank 2023, 2023(1), M1556; https://doi.org/10.3390/M1556 - 17 Jan 2023
Viewed by 298
Abstract
3-(1-Ethylamino-ethylidene)-1-methyl-pyrrolidine-2,4-dione was obtained as an unexpected product in a three-step synthesis starting with o-nitrobenzoyl sarcosine, acetoacetanilide and ethylamine. The compound showed moderate antibacterial activity against S. aureus and E. coli. Full article
(This article belongs to the Section Organic Synthesis)
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Editorial
Acknowledgment to the Reviewers of Molbank in 2022
Molbank 2023, 2023(1), M1555; https://doi.org/10.3390/M1555 - 16 Jan 2023
Viewed by 210
Abstract
High-quality academic publishing is built on rigorous peer review [...] Full article
Short Note
5,5,7,7-Tetrametyl-6,7-dihydro-5H-dibenzo[c,e]azepine
Molbank 2023, 2023(1), M1554; https://doi.org/10.3390/M1554 - 16 Jan 2023
Viewed by 276
Abstract
5,5,7,7-Tetrametyl-6,7-dihydro-5H-dibenzo[c,e]azepine has been synthesized as a possible pro-chiral (or tropos) unit for the construction of a chiral catalyst and as a molecular chirality sensor for the absolute configuration assignment by chiroptical spectroscopy. A straightforward synthetic strategy [...] Read more.
5,5,7,7-Tetrametyl-6,7-dihydro-5H-dibenzo[c,e]azepine has been synthesized as a possible pro-chiral (or tropos) unit for the construction of a chiral catalyst and as a molecular chirality sensor for the absolute configuration assignment by chiroptical spectroscopy. A straightforward synthetic strategy for the preparation of the title compound in high overall yield through sequential addition of the four methyl groups on benzylic positions has been described. A VT-NMR study was used to determine the rotational barrier of the aryl–aryl bond in this biphenylazepine, revealing its torsional flexibility at room temperature, which makes the biphenylazepine suitable as both a chirality probe and a tropos moiety in chiral ligands. Full article
(This article belongs to the Section Organic Synthesis)
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3-Chloro-4-(p-tolyl)isothiazole-5-carbonitrile
Molbank 2023, 2023(1), M1553; https://doi.org/10.3390/M1553 - 13 Jan 2023
Viewed by 281
Abstract
A reaction of 3-chloroisothiazole-5-carbonitrile with 1-iodo-4-methylbenzene (2 equiv.) produced 3-chloro-4-(p-tolyl)isothiazole-5-carbonitrile in a 60% yield. The compound was fully characterized. Full article
(This article belongs to the Section Organic Synthesis)
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3-(3,4-Dichlorophenyl)-5-(1H-indol-5-yl)-1,2,4-oxadiazole
Molbank 2023, 2023(1), M1552; https://doi.org/10.3390/M1552 - 13 Jan 2023
Viewed by 253
Abstract
3-(3,4-Dichlorophenyl)-5-(1H-indol-5-yl)-1,2,4-oxadiazole was synthesized via the condensation of 3,4-dichlorobenzamidoxime and methyl 1H-indole-5-carboxylate using a superbasic medium (NaOH/DMSO). The compound was tested as a potential inhibitor of human monoamine oxidase (MAO) A and B. It demonstrated a notable inhibition with an [...] Read more.
3-(3,4-Dichlorophenyl)-5-(1H-indol-5-yl)-1,2,4-oxadiazole was synthesized via the condensation of 3,4-dichlorobenzamidoxime and methyl 1H-indole-5-carboxylate using a superbasic medium (NaOH/DMSO). The compound was tested as a potential inhibitor of human monoamine oxidase (MAO) A and B. It demonstrated a notable inhibition with an IC50 value of 0.036 μM for the MAO-B and isoform specificity. The product was characterized by 1H-NMR, 13C-NMR, and HRMS. In conclusion, the new active MAO-B inhibitor may serve as a candidate for the future discovery of therapeutic agents for neurodegenerative disorders such as Parkinson’s disease. Full article
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Communication
Synthesis of Bis(1,2,3-triazolyl)alkanes in Superbasic and Solvent-Free Conditions
Molbank 2023, 2023(1), M1551; https://doi.org/10.3390/M1551 - 13 Jan 2023
Viewed by 467
Abstract
Nucleophilic substitution reactions between 1,2,3-triazole and dibromomethane or 1,2-dirbomoethane in a superbasic medium potassium hydroxide–dimethyl sulfoxide gave mixtures of the isomeric bis(1,2,3-triazolyl)alkanes, in which (1,2,3-triazol-1-yl)(1,2,3-triazol-2-yl)alkanes and bis(1,2,3-triazol-2-yl)alkanes were the dominating products, while bis(triazol-1-yl)alkanes were detected only in trace amounts. The same products could [...] Read more.
Nucleophilic substitution reactions between 1,2,3-triazole and dibromomethane or 1,2-dirbomoethane in a superbasic medium potassium hydroxide–dimethyl sulfoxide gave mixtures of the isomeric bis(1,2,3-triazolyl)alkanes, in which (1,2,3-triazol-1-yl)(1,2,3-triazol-2-yl)alkanes and bis(1,2,3-triazol-2-yl)alkanes were the dominating products, while bis(triazol-1-yl)alkanes were detected only in trace amounts. The same products could also be obtained under solvent-free conditions in a neat reaction mixture. The proposed methods are economically feasible, do not require using toxic solvents or catalysts, and make the (1,2,3-triazol-2-yl)-derivatives, inaccessible by alkyne-azide cycloaddition (click) reactions, readily available. Full article
(This article belongs to the Collection Heterocycle Reactions)
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Short Note
4-[Bis(thiazol-2-ylamino)methyl]phenol
Molbank 2023, 2023(1), M1550; https://doi.org/10.3390/M1550 - 12 Jan 2023
Viewed by 261
Abstract
We have designed and synthesized novel bis-thiazole derivative. A 4-[bis(thiazol-2-ylamino)methyl]phenol was efficiently prepared in 71% yield by the reaction of 2-aminothiazole with 4-hydroxybenzaldehyde in ethanol for 24 h. The structure of newly obtained compound was characterized by 1H, 13C NMR and [...] Read more.
We have designed and synthesized novel bis-thiazole derivative. A 4-[bis(thiazol-2-ylamino)methyl]phenol was efficiently prepared in 71% yield by the reaction of 2-aminothiazole with 4-hydroxybenzaldehyde in ethanol for 24 h. The structure of newly obtained compound was characterized by 1H, 13C NMR and mass spectrometry. Bis-thiazole derivative exhibits high tyrosinase inhibitory activity with an IC50 value of 29.71 μM. This inhibitory activity is 2.4 times higher than that of activity of kojic acid (IC50 72.27 µM) and almost 13 times higher than that of ascorbic acid (IC50 385.6 µM). Obtained data suggest that the presented compound may be a leading candidate for a tyrosinase inhibitor. Full article
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Short Note
Methyl 5′-Chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro-[chromene-2,2′-indoline]-6-carboxylate
Molbank 2023, 2023(1), M1549; https://doi.org/10.3390/M1549 - 12 Jan 2023
Viewed by 312
Abstract
Spiropyrans modified with reactive polyfunctional substituents are of great interest as building blocks for the creation of various smart systems with controllable properties for materials science and biomedicine. In this study, a new highly modified spiropyran of the indoline series, methyl 5′-chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro[chromene-2,2′-indoline]-6-carboxylate, was [...] Read more.
Spiropyrans modified with reactive polyfunctional substituents are of great interest as building blocks for the creation of various smart systems with controllable properties for materials science and biomedicine. In this study, a new highly modified spiropyran of the indoline series, methyl 5′-chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro[chromene-2,2′-indoline]-6-carboxylate, was obtained via the cyclocondensation reaction from 5-chloro-1,2,3,3-tetramethyl-3H-indolium perchlorate and methyl 3,5-diformyl-2,4-dihydroxy-benzoate. The molecular structure of the target compound was confirmed by 1H, 13C NMR, and IR spectroscopy, as well as LC/MS and elemental analysis. Photochemical studies revealed photochromic activity for the obtained spiropyran at room temperature. The photoinduced merocyanine form demonstrated an enhanced lifetime and fluorescent properties in the red region of the spectrum. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
2-{[4-(4-Bromophenyl)piperazin-1-yl)]methyl}-4-(3-chlorophenyl)-5-(4-methoxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
Molbank 2023, 2023(1), M1548; https://doi.org/10.3390/M1548 - 12 Jan 2023
Viewed by 274
Abstract
The novel compound 2-{[4-(4-bromophenyl)piperazin-1-yl)]methyl}-4-(3-chlorophenyl-5-(4-methoxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione is obtained in good yield via a three-step protocol. The product’s structure is assigned by HRMS, IR, 1H and 13C NMR experiments. Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1

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