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

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dc.authoridAzam, Mohammad/0000-0002-4274-2796
dc.authoridChutia, Arunabhiram/0000-0002-5897-1729
dc.authoridCAKMAK, Sukriye/0000-0002-2221-0098
dc.authoridVeyisoglu, Aysel/0000-0002-1406-5513
dc.authoridYAKAN, HASAN/0000-0002-4428-4696
dc.contributor.authorCakmak, Sukriye
dc.contributor.authorKansiz, Sevgi
dc.contributor.authorAzam, Mohammad
dc.contributor.authorErsanli, Cem Cuneyt
dc.contributor.authorIdil, Onder
dc.contributor.authorVeyisoglu, Aysel
dc.contributor.authorYakan, Hasan
dc.date.accessioned2025-03-23T19:35:50Z
dc.date.available2025-03-23T19:35:50Z
dc.date.issued2022
dc.departmentSinop Üniversitesi
dc.description.abstractIn 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, H-1 and C-13 NMR spectroscopic studies, and single crystal X-ray crystallography. The crystal packing of I is stabilized by C-H center dot center dot center dot N and N-H center dot center dot center dot 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 (Delta 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 center dot center dot center dot H (21%), C center dot center dot center dot H (20%), S center dot center dot center dot H (19%), N center dot center dot center dot H (14%), and O center dot center dot center dot 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.
dc.description.sponsorshipKing Saud University, Riyadh, Saudi Arabia [RSP-2021/147]; Sinop University [SHMYO-1901-17-25]
dc.description.sponsorshipThe authors acknowledge the financial support through Researchers Supporting Project Number (RSP-2021/147), King Saud University, Riyadh, Saudi Arabia. This study was supported by Sinop University as a Scientific Research Project (Project No.: SHMYO-1901-17-25). The authors acknowledge the Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer.
dc.identifier.doi10.1021/acsomega.2c00318
dc.identifier.endpage11329
dc.identifier.issn2470-1343
dc.identifier.issue13
dc.identifier.pmid35415358
dc.identifier.scopus2-s2.0-85127867857
dc.identifier.scopusqualityQ1
dc.identifier.startpage11320
dc.identifier.urihttps://doi.org/10.1021/acsomega.2c00318
dc.identifier.urihttps://hdl.handle.net/11486/5947
dc.identifier.volume7
dc.identifier.wosWOS:000783991200045
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherAmer Chemical Soc
dc.relation.ispartofAcs Omega
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WOS_20250323
dc.subjectCrystal-Structure
dc.subjectAmino-Acids
dc.subjectEfficient
dc.subjectPeptides
dc.subjectAmides
dc.titleSynthesis, Structural Investigation, Hirshfeld Surface Analysis, and Biological Evaluation of N-(3-Cyanothiophen-2-yl)-2-(thiophen-2yl)acetamide
dc.typeArticle

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