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

IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI:10.1134/S1070428024090240
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,&nbsp;F. Çelik,&nbsp;H. İ. Güler,&nbsp;Ş. Direkel,&nbsp;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,&nbsp;F. Çelik,&nbsp;H. İ. Güler,&nbsp;Ş. Direkel,&nbsp;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}
引用次数: 0

摘要

以 3-甲基噻吩-2-甲醛和 3,4,5-三甲氧基苯胺为原料合成了 1-(3-甲基噻吩-2-基)-N-(3,4,5-三甲氧基苯基)甲亚胺(1,MTM),并通过傅立叶变换红外光谱、1H 和 13C NMR 光谱对其进行了表征。对标题化合物的几何结构进行了优化,并通过量子化学方法计算了其电子(FMO、NLO、MEP、NBO)、光谱(NMR、IR、UV)和热力学性质。计算得出的几何参数与实验得出的几何参数进行了比较。采用肉汤微稀释法测试了化合物 1 对婴儿利什曼原虫的杀利什曼活性,发现在所研究的浓度范围内,该化合物对婴儿利什曼原虫具有高效的杀利什曼活性。通过与锥硫蛋白还原酶(TRe)的分子对接分析,确定了导致抗利什曼病活性的可能相互作用。对接结果表明标题化合物具有很高的抑制常数,支持其抗利什曼病活性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

摘要图片

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
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.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
CiteScore
1.40
自引率
25.00%
发文量
139
审稿时长
3-6 weeks
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.
期刊最新文献
Synthesis, Biological Evaluation, and Computational Study of Novel 1,2,3‐Triazole‐Tethered Chalcone Derivatives Iodination of Phenylacetylene and Some Transformations of the Resulting Iodo Derivatives Novel Thiazolinone Derivatives: Synthesis, Biological Evaluation, and In Silico Studies Efficient Route to N-Substituted β-Amido Ketone Scaffold Using Bismuth Nitrate-Catalyzed One-Pot MCR Protocol Efficient Synthesis of 8-Fluoro-10-methyl-3,4-dihydrobenzo[b][1,6]naphthyridine-2(1H)-carboxamides and Their Cytotoxic Activity
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1