Design, synthesis, antitubercular and antiviral properties of new spirocyclic indole derivatives.

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Monatshefte Fur Chemie Pub Date : 2019-01-01 Epub Date: 2019-07-17 DOI:10.1007/s00706-019-02457-9

Gökçe Cihan-Üstündağ, Lieve Naesens, Dilek Şatana, Gonca Erköse-Genç, Emel Mataracı-Kara, Gültaze Çapan

{"title":"Design, synthesis, antitubercular and antiviral properties of new spirocyclic indole derivatives.","authors":"Gökçe Cihan-Üstündağ, Lieve Naesens, Dilek Şatana, Gonca Erköse-Genç, Emel Mataracı-Kara, Gültaze Çapan","doi":"10.1007/s00706-019-02457-9","DOIUrl":null,"url":null,"abstract":"Abstract: A series of indole-based spirothiazolidinones have been designed, synthesized and evaluated, in vitro, for their antitubercular, antiviral, antibacterial, and antifungal activities. The structures of the new compounds were established by IR, 1H NMR, 13C NMR (proton decoupled, APT, and DEPT), electrospray ionization mass spectrometry, and microanalysis. Compounds bearing a phenyl substituent at position 8 of the spiro ring, exhibited significant antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 at concentrations of 3.9 and 7.8 µM. Still, some of the tested compounds displayed activity on mycobacteria with MIC values of 16 and 31 µM. Four of the indole-spirothiazolidinone derivatives were found to be moderately active against Punta Toro virus, yellow fever virus or Sindbis virus in Vero cells. The antiviral EC50 values were in the range of 1.9-12 µM and the selectivity index (ratio of cytotoxic to antivirally effective concentration) was above 10 in some cases. The most potent effect was seen with the compound that is methylated at positions 2 and 8 of the spirothiazolidinone system.Graphic abstract: ","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"150 8","pages":"1533-1544"},"PeriodicalIF":1.7000,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00706-019-02457-9","citationCount":"17","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Monatshefte Fur Chemie","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1007/s00706-019-02457-9","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2019/7/17 0:00:00","PubModel":"Epub","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 17

Abstract

Abstract: A series of indole-based spirothiazolidinones have been designed, synthesized and evaluated, in vitro, for their antitubercular, antiviral, antibacterial, and antifungal activities. The structures of the new compounds were established by IR, ¹H NMR, ¹³C NMR (proton decoupled, APT, and DEPT), electrospray ionization mass spectrometry, and microanalysis. Compounds bearing a phenyl substituent at position 8 of the spiro ring, exhibited significant antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 at concentrations of 3.9 and 7.8 µM. Still, some of the tested compounds displayed activity on mycobacteria with MIC values of 16 and 31 µM. Four of the indole-spirothiazolidinone derivatives were found to be moderately active against Punta Toro virus, yellow fever virus or Sindbis virus in Vero cells. The antiviral EC₅₀ values were in the range of 1.9-12 µM and the selectivity index (ratio of cytotoxic to antivirally effective concentration) was above 10 in some cases. The most potent effect was seen with the compound that is methylated at positions 2 and 8 of the spirothiazolidinone system.

Graphic abstract:

Abstract Image

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

新型螺环吲哚衍生物的设计、合成、抗结核和抗病毒性能。

摘要:设计、合成了一系列吲哚基螺噻唑烷酮类化合物，并对其抗结核、抗病毒、抗菌和抗真菌活性进行了体外评价。通过IR、1H NMR、13C NMR(质子解耦、APT和DEPT)、电喷雾质谱和微量分析等手段确定了新化合物的结构。在螺旋环8位含有苯基取代基的化合物在3.9和7.8µM浓度下对结核分枝杆菌H37Rv ATCC 27294表现出显著的抗结核活性。尽管如此，一些被测化合物对分枝杆菌的MIC值为16和31µM时显示出活性。在Vero细胞中发现四种吲哚-螺噻唑烷酮衍生物对蓬塔托罗病毒、黄热病病毒或辛德比斯病毒具有中等活性。抗病毒EC50值在1.9 ~ 12µM范围内，部分病例的选择性指数(细胞毒性与抗病毒有效浓度之比)在10以上。最有效的效果是在螺噻唑烷酮系统的2和8位甲基化的化合物。图形抽象:

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文去求助

来源期刊

Monatshefte Fur Chemie 化学-化学综合

CiteScore

3.70

自引率

5.60%

发文量

116

审稿时长

3.3 months

期刊介绍： "Monatshefte für Chemie/Chemical Monthly" was originally conceived as an Austrian journal of chemistry. It has evolved into an international journal covering all branches of chemistry. Featuring the most recent advances in research in analytical chemistry, biochemistry, inorganic, medicinal, organic, physical, structural, and theoretical chemistry, Chemical Monthly publishes refereed original papers and a section entitled "Short Communications". Reviews, symposia in print, and issues devoted to special fields will also be considered.