Anti Human Immunodeficiency Virus Type 1 (HIV-1) Agents 4. Discovery of 5,5′-(p-Phenylenebisazo)-8-hydroxyquinoline Sulfonates as New HIV-1 Inhibitors in Vitro

• Published in: Chemical & Pharmaceutical Bulletin Vol. 58; no. 7; pp. 976 - 979
• Main Authors: Zeng, Xi-Wen, Huang, Ning, Xu, Hui, Yang, Wen-Bin, Yang, Liu-Meng, Qu, Huan, Zheng, Yong-Tang
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.07.2010; Pharmaceutical Society of Japan; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: 8-hydroxyquinoline; acquired immune-deficiency syndrome; Anti-HIV Agents - chemical synthesis; Anti-HIV Agents - chemistry; Anti-HIV Agents - toxicity; Antiviral activity; Cell Line, Tumor; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Drug Discovery; HIV-1 - drug effects; Human immunodeficiency virus 1; Humans; Hydroxyquinolines - chemical synthesis; Hydroxyquinolines - chemistry; Hydroxyquinolines - toxicity; inhibitor; Life Sciences & Biomedicine; Pharmacology & Pharmacy; Physical Sciences; Science & Technology; Structure-Activity Relationship; sulfonate; human immunodeficiency virus-1; sulfonate; acquired immune-deficiency syndrome; 8-hydroxyquinoline; inhibitor
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.58.976

To search for compounds with superior anti-human immunodeficiency virus type 1 (HIV-1) activity, ten 5,5′-(p-phenylenebisazo)-8-hydroxyquinoline sulfonates (4a—j) were synthesized and preliminarily evaluated as HIV-1 inhibitors in vitro for the first time. Some compounds demonstrated anti-HIV-1 activity, especially 5,5′-(p-phenylenebisazo)-8-hydroxyquinoline p-ethylbenzenesulfonate (4g) and 5,5′-(p-phenylenebisazo)-8-hydroxyquinoline p-chlorobenzenesulfonate (4i) showed the more potent anti-HIV-1 activity with 50% effective concentration (EC50) values of 2.59 and 4.01 μg/ml, and therapeutic index (TI) values of 31.77 and 24.51, respectively.