2-(2,6-Dihalo-phenyl)-3-heteroaryl-2-ylmethyl-1, 3-thiazolidin-4-ones: Anti-HIV agents

• Published in: Chemical biology & drug design Vol. 72; no. 2; pp. 147 - 154
• Main Authors: Rawal, Ravindra K, Tripathi, Rajkamal, Kulkarni, Smitha, Paranjape, R, Katti, S.B, Pannecouque, Christophe, De Clercq, Erik
• Format: Journal Article
• Language: English
• Published: Oxford, UK Oxford, UK : Blackwell Publishing Ltd 01-08-2008; Blackwell Publishing Ltd
• Subjects: 4-thiazolidinones; anti-HIV activity; Anti-HIV Agents - chemical synthesis; Anti-HIV Agents - chemistry; Anti-HIV Agents - pharmacology; Cell Line; HIV-1 - drug effects; HIV-1RT; Human immunodeficiency virus; Human immunodeficiency virus 1; Humans; Molecular Structure; NNRTIs; Structure-Activity Relationship; Thiazolidines - chemistry; Thiazolidines - pharmacology
• ISSN: 1747-0277; 1747-0285
• DOI: 10.1111/j.1747-0285.2008.00683.x

A diversity of novel 2-aryl-3-heteroaryl-2-ylmethyl-1,3-thiazolidin-4-ones were designed and synthesized by reacting heteroaryl-2-ylmethyl amine with various 2,6-dihalosubstituted benzaldehydes and mercaptoacetic acid. The title compounds were evaluated for human immunodeficiency virus type-1 (HIV-1) reverse transcriptase (RT) inhibitory activity. The results of in vitro assays showed that some of the compounds were effective inhibitors of HIV-1 reverse transcriptase enzyme at micromolar concentrations with less cytotoxicity in both MT-4 cells as well as acutely infected human T-lymphoid CEM cells. Compounds 4h and 4k emerged as moderately more potent with EC₅₀ are at 0.20 and 0.21 μ m as compared to reference parent compound thiazolobenzimidazoles EC₅₀ 0.35 μ m in MT-4 cells.