Synthesis of (1′S*,2R*,3R*)‐ and (1′S*,2R*,3S*)‐N‐arylsulfonyl‐2‐(1′‐halogenethyl)‐3‐methylindolines and their selective toxicity against SH‐SY5Y cell line,Journal of Heterocyclic Chemistry

当前位置： X-MOL 学术 › J. Heterocycl. Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Synthesis of (1′S*,2R*,3R*)‐ and (1′S*,2R*,3S*)‐N‐arylsulfonyl‐2‐(1′‐halogenethyl)‐3‐methylindolines and their selective toxicity against SH‐SY5Y cell line
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-01-08 , DOI: 10.1002/jhet.3861
Rail R. Gataullin ₁ , Zulfia R. Zileeva ₂ , Marina A. Maksimova ₂ , Liana F. Zainullina ₂ , Yuliya V. Vakhitova ₂

Affiliation

N‐tosyl‐2‐ and N‐tosyl‐4‐halogen‐substituted derivatives of 2‐(1‐methylbut‐2‐en‐1‐yl)aniline were synthesized and their molecular iodine‐mediated cyclization was investigated. The cyclization upon interaction of N‐tosyl‐6‐methyl‐2‐(1‐methylbut‐2‐en‐1‐yl)aniline with molecular iodine in methyl tert‐butyl ether or acetonitrile was studied, as well as the interaction of this sulfonamide with N‐bromosucinimide in dichloromethane. Synthesized (2R*,3R*)‐ and (2R*,3S*)‐N‐arylsulfonyl‐2‐(1‐halogenoethyl)‐3‐methylindoline derivatives showed cytotoxic activity against HEK293 cells, SH‐SY5Y, Jurkat, and HepG2 cell lines. The compounds (2R*,3S*)‐N‐arylsulfonyl‐7‐bromo‐2‐(1‐halogenoethyl)‐3‐methylindoline cis‐4a, stereoisomeric (2R*,3R*)‐trans‐4h and (2R*,3S*)‐N‐tosyl‐7‐chloro‐2‐(1‐halogenoethyl)‐3‐methylindoline cis‐4h demonstrated selective toxicity against SH‐SY5Y cell line (IC₅₀ ≈ 3 ÷ 5 μM), and did not affect HEK293, Jurkat, and HepG2 cells.

中文翻译：

（1'S *，2R *，3R *）-和（1'S *，2R *，3S *）-N-芳基磺酰基-2-（1'-卤代乙基）-3-甲基二氢吲哚的合成及其选择性毒性SH‐SY5Y细胞系

合成了2-（1-甲基丁-2-烯-1-基）苯胺的N-甲苯磺酰基-2-和N-甲苯磺酰基-4-卤素取代的衍生物，并研究了它们的分子碘介导的环化作用。研究了甲基叔丁基醚或乙腈中N-甲苯磺酰基-6-甲基-2-（1-甲基丁-2-烯-1-基）苯胺与分子碘相互作用时的环化反应磺酰胺与N-溴磺酰亚胺在二氯甲烷中。合成（2 R *，3 R *）‐和（2 R *，3 S *）‐ N-芳基磺酰基-2-（1-卤代乙基）-3-甲基吲哚啉衍生物对HEK293细胞，SH-SY5Y，Jurkat和HepG2细胞系具有细胞毒活性。化合物（2 R *，3 S *）- N-芳基磺酰基-7-溴-2-（1-卤代乙基）-3-甲基吲哚顺式4a，立体异构体（2 R *，3 R *）-反式4h和（2 - [R *，3小号*） - ñ甲苯磺酰基-7-氯-2-（1-卤代乙基）-3-甲基二氢吲哚顺式- 4H对SH-SY5Y细胞系表现出选择性毒性（IC ₅₀ ≈3÷5μM），并且不影响HEK293，Jurkat和HepG2细胞。

更新日期：2020-01-09

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11