M. Evecen, F. Çelik, H. İ. Güler, Ş. Direkel, Y. Ünver
{"title":"1-(3-甲基噻吩-2-基)-N-(3,4,5-三甲氧基苯基)甲亚胺:合成、光谱特性、抗利什曼病活性以及 DFT 和 In Silico 研究","authors":"M. Evecen, F. Çelik, H. İ. Güler, Ş. Direkel, Y. Ünver","doi":"10.1134/S1070428024090240","DOIUrl":null,"url":null,"abstract":"<p>1-(3-Methylthiophen-2-yl)-<i>N</i>-(3,4,5-trimethoxyphenyl)methanimine (<b>1</b>, MTM) was synthesized from 3-methylthiophene-2-carbaldehyde and 3,4,5-trimethoxyaniline and characterized by FTIR and <sup>1</sup>H and <sup>13</sup>C NMR spectra. The geometric structure of the title compound was optimized, and its electronic (FMO, NLO, MEP, NBO), spectroscopic (NMR, IR, UV), and thermodynamic properties were calculated by quantum chemicial methods. The calculated and experimental geometric parameters were compared with each other. Compound <b>1</b> was tested for leishmanicidal activity against <i>Leishmania infantum</i> by the broth microdilution method and was found to be efficient against <i>Leishmania infantum</i> promastigotes in the concentration range studied. Possible interactions responsible for the antileishmanial activity were determined by molecular docking analysis against trypanothione reductase (TRe). The docking results demonstrated high inhibition constant of the title compound and supported its antileishmanial activity.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8000,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"1-(3-Methylthiophene-2-yl)-N-(3,4,5-trimethoxyphenyl)methanimine: Synthesis, Spectroscopic Characterization, Antileishmanial Activity, and DFT and In Silico Studies\",\"authors\":\"M. Evecen, F. Çelik, H. İ. Güler, Ş. Direkel, Y. Ünver\",\"doi\":\"10.1134/S1070428024090240\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>1-(3-Methylthiophen-2-yl)-<i>N</i>-(3,4,5-trimethoxyphenyl)methanimine (<b>1</b>, MTM) was synthesized from 3-methylthiophene-2-carbaldehyde and 3,4,5-trimethoxyaniline and characterized by FTIR and <sup>1</sup>H and <sup>13</sup>C NMR spectra. The geometric structure of the title compound was optimized, and its electronic (FMO, NLO, MEP, NBO), spectroscopic (NMR, IR, UV), and thermodynamic properties were calculated by quantum chemicial methods. The calculated and experimental geometric parameters were compared with each other. Compound <b>1</b> was tested for leishmanicidal activity against <i>Leishmania infantum</i> by the broth microdilution method and was found to be efficient against <i>Leishmania infantum</i> promastigotes in the concentration range studied. Possible interactions responsible for the antileishmanial activity were determined by molecular docking analysis against trypanothione reductase (TRe). The docking results demonstrated high inhibition constant of the title compound and supported its antileishmanial activity.</p>\",\"PeriodicalId\":766,\"journal\":{\"name\":\"Russian Journal of Organic Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.8000,\"publicationDate\":\"2024-11-07\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Russian Journal of Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1134/S1070428024090240\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1134/S1070428024090240","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
1-(3-Methylthiophene-2-yl)-N-(3,4,5-trimethoxyphenyl)methanimine: Synthesis, Spectroscopic Characterization, Antileishmanial Activity, and DFT and In Silico Studies
1-(3-Methylthiophen-2-yl)-N-(3,4,5-trimethoxyphenyl)methanimine (1, MTM) was synthesized from 3-methylthiophene-2-carbaldehyde and 3,4,5-trimethoxyaniline and characterized by FTIR and 1H and 13C NMR spectra. The geometric structure of the title compound was optimized, and its electronic (FMO, NLO, MEP, NBO), spectroscopic (NMR, IR, UV), and thermodynamic properties were calculated by quantum chemicial methods. The calculated and experimental geometric parameters were compared with each other. Compound 1 was tested for leishmanicidal activity against Leishmania infantum by the broth microdilution method and was found to be efficient against Leishmania infantum promastigotes in the concentration range studied. Possible interactions responsible for the antileishmanial activity were determined by molecular docking analysis against trypanothione reductase (TRe). The docking results demonstrated high inhibition constant of the title compound and supported its antileishmanial activity.
期刊介绍:
Russian Journal of Organic Chemistry is an international peer reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis.