Journal Description
Molbank
Molbank
is a peer-reviewed, open access journal comprised of a unique collection of one-compound-per-paper short notes on synthetic compounds and natural products. Molbank has been published online quarterly since 2009 (previously published irregularly).
- 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 13.1 days after submission; acceptance to publication is undertaken in 2.9 days (median values for papers published in this journal in the second half of 2022).
- 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.
Latest Articles
Synthesis and Characterization of New Potential Hypoxia-Sensitive Azo-thiacalix[4]arenes Derivatives
Molbank 2023, 2023(1), M1570; https://doi.org/10.3390/M1570 (registering DOI) - 31 Jan 2023
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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
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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 2a–b) 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.
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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
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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
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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.
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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
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
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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.
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(This article belongs to the Collection Heterocycle Reactions)
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2-Furyl-6-nitro-1,2,4-triazolo [1,5-a]pyrimidin-7-one
by
, , , , and
Molbank 2023, 2023(1), M1563; https://doi.org/10.3390/M1563 - 23 Jan 2023
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
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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.
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(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)
by
, , , , and
Molbank 2023, 2023(1), M1564; https://doi.org/10.3390/M1564 - 23 Jan 2023
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.
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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.
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(This article belongs to the Section Organic Synthesis)
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5-Vinyl-1H-tetrazole
by
, , , , , , , , , and
Molbank 2023, 2023(1), M1565; https://doi.org/10.3390/M1565 - 23 Jan 2023
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
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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.
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(This article belongs to the Section Organic Synthesis)
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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
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}
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(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.
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(This article belongs to the Section Organic Synthesis)
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Open AccessCommunication
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
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.
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(This article belongs to the Collection Heterocycle Reactions)
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Open AccessCommunication
Carboxybetaine and Carboxybetaine Ester Derivatives of Tetra(dodecyloxyphenyl)-calix[4]resorcinarene: Synthesis, Self-Assembly and In Vitro Toxicity
by
, , , , , , , and
Molbank 2023, 2023(1), M1562; https://doi.org/10.3390/M1562 - 22 Jan 2023
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
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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.
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(This article belongs to the Section Organic Synthesis)
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(R)-N-Benzyl-N-(1-phenylethyl)cyclohexanamine
by
, , , and
Molbank 2023, 2023(1), M1561; https://doi.org/10.3390/M1561 - 20 Jan 2023
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
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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.
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(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
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.
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(This article belongs to the Section Organic Synthesis)
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Open AccessCommunication
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
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
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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.
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(This article belongs to the Special Issue Molecules from Side Reactions II)
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Supplementary material:
Supplementary File 1 (ZIP, 664 KiB)
Supplementary File 2 (MOL, 1 KiB)
Supplementary File 3 (INCHI, 442 B)
Supplementary File 4 (MOL, 1 KiB)
Supplementary File 5 (MOL, 3 KiB)
Supplementary File 6 (INCHI, 888 B)
Supplementary File 7 (MOL, 3 KiB)
Supplementary File 8 (MOL, 1 KiB)
Supplementary File 9 (INCHI, 393 B)
Supplementary File 10 (MOL, 1 KiB)
Supplementary File 1 (ZIP, 664 KiB)
Supplementary File 2 (MOL, 1 KiB)
Supplementary File 3 (INCHI, 442 B)
Supplementary File 4 (MOL, 1 KiB)
Supplementary File 5 (MOL, 3 KiB)
Supplementary File 6 (INCHI, 888 B)
Supplementary File 7 (MOL, 3 KiB)
Supplementary File 8 (MOL, 1 KiB)
Supplementary File 9 (INCHI, 393 B)
Supplementary File 10 (MOL, 1 KiB)
Open AccessShort Note
3-(1-Ethylamino-ethylidene)-1-methyl-pyrrolidine-2,4-dione
Molbank 2023, 2023(1), M1556; https://doi.org/10.3390/M1556 - 17 Jan 2023
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.
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(This article belongs to the Section Organic Synthesis)
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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
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
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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.
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(This article belongs to the Section Natural Products)
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Supplementary material:
Supplementary File 1 (PDF, 608 KiB)
Supplementary File 2 (MOL, 2 KiB)
Supplementary File 4 (MOL, 2 KiB)
Supplementary File 1 (PDF, 608 KiB)
Supplementary File 2 (MOL, 2 KiB)
Supplementary File 4 (MOL, 2 KiB)
Open AccessCommunication
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
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.
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(This article belongs to the Section Organic Synthesis)
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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
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.
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(This article belongs to the Section Organic Synthesis)
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Open AccessEditorial
Acknowledgment to the Reviewers of Molbank in 2022
Molbank 2023, 2023(1), M1555; https://doi.org/10.3390/M1555 - 16 Jan 2023
Abstract
High-quality academic publishing is built on rigorous peer review [...]
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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
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.
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(This article belongs to the Section Organic Synthesis)
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Supplementary material:
Supplementary File 1 (PDF, 965 KiB)
Supplementary File 2 (MOL, 2 KiB)
Supplementary File 3 (INCHI, 554 B)
Supplementary File 4 (MOL, 2 KiB)
Supplementary File 5 (MOL, 2 KiB)
Supplementary File 7 (MOL, 2 KiB)
Supplementary File 8 (MOL, 2 KiB)
Supplementary File 10 (MOL, 2 KiB)
Supplementary File 11 (MOL, 2 KiB)
Supplementary File 13 (MOL, 2 KiB)
Supplementary File 1 (PDF, 965 KiB)
Supplementary File 2 (MOL, 2 KiB)
Supplementary File 3 (INCHI, 554 B)
Supplementary File 4 (MOL, 2 KiB)
Supplementary File 5 (MOL, 2 KiB)
Supplementary File 7 (MOL, 2 KiB)
Supplementary File 8 (MOL, 2 KiB)
Supplementary File 10 (MOL, 2 KiB)
Supplementary File 11 (MOL, 2 KiB)
Supplementary File 13 (MOL, 2 KiB)
Open AccessCommunication
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
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.
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(This article belongs to the Collection Heterocycle Reactions)
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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
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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.
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