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Synthesis of (1′ S *,2 R *,3 R *)‐ and (1′ S *,2 R *,3 S *)‐ N ‐arylsulfonyl‐2‐(1′‐halogenethyl)‐3‐methylindolines and their selective toxicity against SH‐SY5Y cell line
Author(s) -
Gataullin Rail R.,
Zileeva Zulfia R.,
Maksimova Marina A.,
Zainullina Liana F.,
Vakhitova Yuliya V.
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3861
Subject(s) - chemistry , sulfonamide , tosyl , dichloromethane , aniline , jurkat cells , stereochemistry , ether , acetonitrile , iodine , diethyl ether , medicinal chemistry , halogen , solvent , organic chemistry , t cell , immune system , immunology , biology , alkyl
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 (2 R *,3 R *)‐ and (2 R *,3 S *)‐ N ‐arylsulfonyl‐2‐(1‐halogenoethyl)‐3‐methylindoline derivatives showed cytotoxic activity against HEK293 cells, SH‐SY5Y, Jurkat, and HepG2 cell lines. The compounds (2 R *,3 S *)‐ N ‐arylsulfonyl‐7‐bromo‐2‐(1‐halogenoethyl)‐3‐methylindoline cis‐ 4a , stereoisomeric (2 R *,3 R *)‐ trans‐ 4h and (2 R *,3 S *)‐ N ‐tosyl‐7‐chloro‐2‐(1‐halogenoethyl)‐3‐methylindoline cis‐ 4h demonstrated selective toxicity against SH‐SY5Y cell line (IC 50 ≈ 3 ÷ 5 μM), and did not affect HEK293, Jurkat, and HepG2 cells.