Synthesis of novel Schiff base benzamides via ring opening of thienylidene azlactones for potential antimicrobial activities

Karanth, Subbulakshmi N.; Narayana, B.; Kunhanna, Sarojini Balladka; Shashidhara, K. S.; Yegneswaran, Prakash Peralam

doi:10.1007/s11164-018-3362-8

Cited by 2 publications

(1 citation statement)

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“…It is also an important functional group and essential component of many pharmaceuticals, natural products, agrochemicals, and polymers. , Recently, the chemistry of amide compounds has recently been a fascinating field of research. Some of these compounds have been shown to have significant antifungal, antibacterial, , antioxidant, − insecticide, anticonvulsant, analgesic, antitumor, anti-inflammatory, and anti-HSV activity. − Additionally, amides also have a broad range of different applications in polymers, dyes, and liquid crystals. ,, …”

Section: Introductionmentioning

confidence: 99%

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

et al. 2022

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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, 1 H and 13 C 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 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 (Δ N ) 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.

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