Discovery of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti-HIV-1 agents

• Published in: Bioorganic & medicinal chemistry letters Vol. 11; no. 13; pp. 1793 - 1796
• Main Authors: Barreca, Maria Letizia, Chimirri, Alba, De Luca, Laura, Monforte, Anna-Maria, Monforte, Pietro, Rao, Angela, Zappalà, Maria, Balzarini, Jan, De Clercq, Erik, Pannecouque, Christophe, Witvrouw, Myriam
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 09.07.2001; Elsevier
• Subjects: Anti-HIV Agents - chemistry; Anti-HIV Agents - pharmacology; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antiviral agents; Biological and medical sciences; HIV-1 - drug effects; HIV-1 - physiology; Medical sciences; Pharmacology. Drug treatments; Reverse Transcriptase Inhibitors - chemistry; Reverse Transcriptase Inhibitors - pharmacology; Structure-Activity Relationship; Thiazoles - chemistry; Thiazoles - pharmacology; Virus Replication - drug effects; Five membered ring; RNA-directed DNA polymerase; HIV-1 virus; Nitrogen heterocycle; Non nucleoside compound; Lactam; Pyridine derivatives; Structure activity relation; Chlorine Organic compounds; Antiviral; Inhibition; Chemical synthesis; Sulfur nitrogen heterocycle; Enzyme; Transferases; Benzene derivatives; Retroviridae; Enzyme inhibitor; Virus replication cycle; Lentivirus; In vitro; Virus; Nucleotidyltransferases; Fluorine Organic compounds; Human immunodeficiency virus
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(01)00304-3

Design, synthesis and anti-HIV activity of a series of 2,3-diaryl-1,3-thiazolidin-4-ones are reported. Some derivatives proved to be highly effective in inhibiting HIV-1 replication at nanomolar concentrations thereby acting as non-nucleoside HIV-1 RT inhibitors (NNRTIs). SAR studies evidenced that the nature of the substituents at the 2 and 3 positions of the thiazolidinone nucleus largely influenced the in vitro anti-HIV activity of this new class of potent antiviral agents. Design, synthesis and anti-HIV activity of a series of 2,3-diaryl-1,3-thiazolidin-4-ones are reported.