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Synthesis and Anti‐ HIV Activity of 4‐(Naphthalen‐1‐yl)‐1,2,5‐thiadiazol‐3‐hydroxyl Derivatives
Author(s) -
Rai Diwakar,
Chen Wenmin,
Zhan Peng,
Liu Hong,
Tian Ye,
Liang Xin,
De Clercq Erik,
Pannecouque Christophe,
Balzarini Jan,
Liu Xinyong
Publication year - 2014
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.12328
Subject(s) - chemistry , reverse transcriptase , stereochemistry , human immunodeficiency virus (hiv) , docking (animal) , nucleoside , combinatorial chemistry , biochemistry , virology , rna , biology , medicine , nursing , gene
A series of 4‐(naphthalen‐1‐yl)‐1,2,5‐thiadiazol‐3‐hydroxyl derivatives ( Ia – Im and II a – II e ) designed as novel HIV ‐1 non‐nucleoside reverse transcriptase inhibitors ( NNRTI s) was synthesized via an expeditious route and evaluated for their anti‐ HIV activities in MT ‐4 cell cultures. All the synthesized compounds were structurally confirmed by spectral analyses. Biological results showed that three analogues displayed moderate inhibitory activity against wild‐type (wt) HIV ‐1 replication with EC 50 values ranging from 16 to 22 μ m . Molecular docking of compound Ih with wt HIV ‐1 RT was performed to understand the binding mode between these inhibitors and the wt HIV ‐1 RT and to rationalize some SAR s.