Synthesis, Structural Investigation, Hirshfeld Surface Analysis, and Biological Evaluation of N‐(3-Cyanothiophen-2-yl)-2-(thiophen-2-yl)acetamide

Çakmak, Şükriye, Kansız, Sevgi, Azam, Mohammad , Ersanlı, Cem Cüneyt, Iḋil, Önder, Veyisoğlu, Aysel, Yakan, Hasan, Kütük, Halil and Chutia, Arunabhiram (2022) Synthesis, Structural Investigation, Hirshfeld Surface Analysis, and Biological Evaluation of N‐(3-Cyanothiophen-2-yl)-2-(thiophen-2-yl)acetamide. ACS Omega, 7 (13). ISSN 2470-1343

Full content URL: https://doi.org/10.1021/acsomega.2c00318

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Synthesis, Structural Investigation, Hirshfeld Surface Analysis, and Biological Evaluation of N‐(3-Cyanothiophen-2-yl)-2-(thiophen-2-yl)acetamide
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Abstract

ABSTRACT: In this study, a novel heterocyclic amide derivative, N-(3-cyanothiophen-2-yl)-2-(thiophen-2-yl)acetamide (I), was obtained by reacting 2-aminothiophene-3-carbonitrile with activated 2-(thiophen-2-yl)acetic acid in a N-acylation reaction and characterized by elemental analyses, FT-IR, 1H and 13C NMR spectroscopic studies, and single crystal X-ray crystallography. The crystal packing of I is stabilized by C−H···N and N−H···N hydrogen bonds. In addition, I was investigated computationally using the density functional theory (DFT) method with the B3LYP exchange and correlation functions in conjunction with the 16 6311++G(d,p) basis set in the gas phase. Fukui function (FF) analysis was also carried out. Electrophilicity-based charge transfer (ECT) method and charge transfer (ΔN) were computed to examine the interactions between I and DNA bases (such as guanine, thymine, adenine, and cytosine). The most important contributions to the Hirshfeld surface are H···H (21%), C···H (20%), S···H (19%), N···H (14%), and O···H (12%). An ABTS antioxidant assay was used to evaluate the in vitro antioxidant activity of I. The compound exhibited moderate antioxidant activity. The antimicrobial activity of the title molecule was investigated under aseptic conditions, using the microdilution method, against Gram-positive and Gram-negative bacterial strains, and it also demonstrated significant activity against yeasts (Candida glabrata ATCC 90030, Candida krusei ATCC 34135). The findings revealed that the molecule possesses significant antioxidant and antimicrobial properties.

Keywords:heterocyclic amide derivative, density functional theory, Fukui function, Electrophilicity-based charge transfer
Subjects:F Physical Sciences > F100 Chemistry
Divisions:College of Science > School of Chemistry
ID Code:48605
Deposited On:07 Apr 2022 10:52

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