title: Synthesis of piscidinol A derivatives and their ability to inhibit HIV-1 protease.
abstract: Four types of piscidinol A derivatives were synthesized and evaluated their ability to inhibit HIV-1 protease to understand their structure-activity relationships. Of these tirucallane-type triterpene derivatives, an A-seco derivative (1b) moderately inhibited human immunodeficiency virus (HIV) protease (IC50 38.2 μM). The 2,2-dimethyl succinic acid (DMS) acylated tirucallane derivatives (4b, 6a, and 7b, 50 < IC50 < 100 μM) were more inhibitory against HIV-1 PR than the others (PA, 2a, 4a, 4c-4d, 5a, 6b-6d, and 7a, IC50 > 100 μM). These findings indicated that the 2,3-seco-2,3-dioic acid (1b) and DMS-acylated tirucallane-type derivatives preferably inhibited HIV viral protease.
authors.affiliation: a Department of Pharmacy , Guiyang College of Traditional Chinese Medicine , Guiyang 550025 , China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Wei
authors.affiliation: b College of Life Sciences , Innermongolia University , Huhhot 01021 , China.
authors.forename: Chao-Mei
authors.initials: CM
authors.lastname: Ma
authors.affiliation: a Department of Pharmacy , Guiyang College of Traditional Chinese Medicine , Guiyang 550025 , China.
authors.forename: Tai-Bai
authors.initials: TB
authors.lastname: Jiang
authors.affiliation: a Department of Pharmacy , Guiyang College of Traditional Chinese Medicine , Guiyang 550025 , China.
authors.forename: Jiang
authors.initials: J
authors.lastname: Du
authors.affiliation: d Research Center for Quality Control of Natural Medicines , Guizhou Normal University , Guiyang 550002 , China.
authors.forename: Xing
authors.initials: X
authors.lastname: Zhou
authors.affiliation: a Department of Pharmacy , Guiyang College of Traditional Chinese Medicine , Guiyang 550025 , China.
authors.forename: Guo-Qing
authors.initials: GQ
authors.lastname: Liu
authors.affiliation: c Institute of Natural Medicine , University of Toyama , Toyama 930-0194 , Japan.
authors.forename: Masao
authors.initials: M
authors.lastname: Hattori
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016333:HIV Protease / Q000187:drug effects*; D015497:HIV-1 / Q000187:drug effects* / Q000201:enzymology; D006801:Humans; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D019380:Anti-HIV Agents; D014315:Triterpenes; C000605693:piscidinol A; C514393:tirucallane; D016333:HIV Protease; C514803:p16 protease, Human immunodeficiency virus 1
keywords: A-ring modified derivatives; HIV-1 protease; bi-acylated derivatives; mono-acylated derivatives; multi-acylated derivatives; piscidinol A