Design and synthesis of selenazole-substituted ritonavir analogs. Issue 14 (1st August 2018)

• Record Type: Journal Article
• Authors: Qiao, Junfei; Zhao, Chuanfang; Liu, Jun; Du, Yuguo
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 28:Issue 14(2018)
• Page Start: 2379
• Page End: 2381
• Publication Date: 2018-08-01
• Subjects: Selenazole -- Ritonavir -- Antiviral -- Protease inhibitor -- One-pot reaction; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2018.06.027
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Two new ritonavir analogs were designed and synthesized taking advantages of one-pot cascade condensation of β-azido diselenide and alkyl acids. The prepared compounds exhibited good anti-HIV-1 activities as well as the positive SI values. Highlights: New method to make selenazole from β-azido diselenide and alkyl acids in one-pot. Two new selenazole-containing ritonavir analogs were designed and synthesized. The designed compounds exhibited promising anti-HIV-1 activities and SI values. Abstract: With the help of Surflex-Dock calculation, two ritonavir analogs in which one thioazole unit was replaced by selenazole have been designed and synthesized. The key selenazole structure was constructed from β-azido diselenide through a cascade diselenide cleavage/selenocarbonylation/Staudinger reduction/aza-Wittig reaction and a following MnO2 oxidation. The accordingly prepared compounds exhibited good anti-HIV-1 (IIIB) activities comparable to that of the original ritonavir, as well as the positive SI values.