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Design and synthesis of benzothiazole/thiophene-4H-chromene hybrids.

ABSTRACT: A library of 4H-chromene derivatives with heterocyclic substituent's at the 3 and 4-positions was synthesized in a convenient DBU catalysed three component synthesis between salicylaldehyde, acetonitrile derivatives and thiazolidinedione to afford 2-amino-3-benzothiazole-4-heterocycle-4H-chromenes and 2-amino-3-thiophenoyl-4-heterocycle-4H-chromenes derivatives in ethanol and a mixture of ethanol and water (1 : 1) at room temperature. The significance of this protocol is the feasibility of incorporating substituents simultaneously at the 3 and 4 positions of 4H-chromenes in an efficient three component reaction.

SUBMITTER: Pazhanivel L

PROVIDER: S-EPMC9091940 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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Design and synthesis of benzothiazole/thiophene-4H-chromene hybrids.

Pazhanivel Lakshmanan L Gnanasambandam Vasuki V

RSC advances 20181213 73

A library of 4H-chromene derivatives with heterocyclic substituent's at the 3 and 4-positions was synthesized in a convenient DBU catalysed three component synthesis between salicylaldehyde, acetonitrile derivatives and thiazolidinedione to afford 2-amino-3-benzothiazole-4-heterocycle-4H-chromenes and 2-amino-3-thiophenoyl-4-heterocycle-4H-chromenes derivatives in ethanol and a mixture of ethanol and water (1 : 1) at room temperature. The significance of this protocol is the ...[more]

PMID: 35558789

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Project description:BackgroundIn the era of resistance, the design and search for new "small" molecules with a narrow spectrum of activity that target a protein or enzyme specific to a certain bacterium with high selectivity and minimal side effects remains an urgent problem of medicinal chemistry. In this regard, we developed and successfully implemented a strategy for the search for new hybrid molecules, namely, the not broadly known [2-(3-R-1H-[1,2,4]-triazol-5-yl)phenyl]amines. They can act as "building blocks" and allow for the introduction of certain structural motifs into the desired final products in order to enhance the antistaphylococcal effect.MethodsThe "one-pot" synthesis of the latter is based on the conversion of substituted 4-hydrazinoquinazolines or substituted 2-aminobenzonitriles and carboxylic acid derivatives to the target products. The possible molecular mechanism of the synthesized compounds (DNA gyrase inhibitors) was investigated and discussed using molecular docking, and their further study for antistaphylococcal activity was substantiated.ResultsA significant part of the obtained compounds showed high antibacterial activity against Staphylococcus aureus (MIC: 10.1-62.4 µM) and 5-bromo-2-(3-(furan-3-yl)-1H-1,2,4-triazol-5-yl)aniline and 5-fluoro-2-(3-(thiophen-3-yl)-1H-1,2,4-triazol-5-yl)aniline, with MICs of 5.2 and 6.1 µM, respectively, approaching the strength of the effect of the reference drug, "Ciprofloxacin" (MIC: 4.7 µM). The conducted SAR and ADME analyses confirm the prospects of the further structural modification of these compounds. The obtained [2-(3-R-1H-[1,2,4]-triazol-5-yl)phenyl]amines reveal significant antimicrobial activity and deserve further structural modification and detailed study as effective antistaphylococcal agents. The SAR analysis revealed that the presence of a cycloalkyl or electron-rich heterocyclic fragment in the third position of the triazole ring was essential for the antibacterial activity of the obtained compounds. At the same time, the introduction of a methyl group into the aniline moiety led to an enhancement of activity. The introduction of halogen into the aniline fragment has an ambiguous effect on the level of antistaphylococcal activity and depends on the nature of the substituent in the third position.ConclusionsObtained [2-(3-R-1H-[1,2,4]-triazol-5-yl)phenyl]amines reveal significant antistaphylococcal activity and deserve for further detailed study as effective antibacterial agents.

Dataset Information

Design and synthesis of benzothiazole/thiophene-4H-chromene hybrids.

Publications

Design and synthesis of benzothiazole/thiophene-4<i>H</i>-chromene hybrids.

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