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【结 构 式】 
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【药物名称】Bevirimat, Bevirimat Dimeglumine, PA-457, YK-FH312 【化学名称】[1S-(1alpha,3abeta,5aalpha,5bbeta,7aalpha,9beta,11abeta,11balpha,13abeta,13balpha)]-1-Isopropenyl-9-(3,3-dimethylsuccinyloxy)-5a,5b,8,8,11a-pentamethylperhydrocyclopenta[a]chrysene-3a-carboxylic acid 【CA登记号】174022-42-5 【 分 子 式 】C36H56O6 【 分 子 量 】584.84412 |
【开发单位】Biotech Research Laboratories (Originator), University of North Carolina (Originator), Panacos (Licensee), ViroLogic (Codevelopment) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY |
合成路线1
Betulinic acid (I) was extracted from the dried leaves of Syzygium claviforum. Acylation of (I) with 2,2-dimethylsuccinic anhydride (II) in the presence of DMAP in refluxing pyridine furnished the target 3’,3’-dimethylsuccinyl betulinic acid along with minor amounts of the undesired 2’,2’-dimethyl regioisomer (III), which were separated by means of preparative HPLC.
| 【3】 Kashiwada, Y.; Wang, H.K.; Nagao, T.; Kitanaka, S.; Yasuda, I.; Fujioka, T.; Yamagishi, T.; Cosentino, L.M.; Kozuka, M.; Okabe, H.; Ikeshiro, Y.; Hu, C.Q.; Yeh, E.; Lee, K.H.; Anti-AIDS agents.30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids. J Nat Prod 1998, 61, 9, 1090. |
| 【1】 Kashiwada, Y.; et al.; Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents. J Med Chem 1996, 39, 5, 1016. |
| 【2】 Hashimoto, F.; et al.; Anti-AIDS agents - XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives. Bioorg Med Chem 1997, 5, 12, 2133. |
| 【4】 Lee, K.-H.; Kashiwada, Y.; Hashimoto, F.; Cosentino, L.M.; Manak, M. (Biotech Research Laboratories; University of North Carolina); Betulinic acid derivs. and uses thereof. US 5679828; WO 9639033 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 51630 | (1R,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid | C30H48O3 | 详情 | 详情 | |
| (II) | 29295 | 3,3-dimethyldihydro-2,5-furandione | 17347-61-4 | C6H8O3 | 详情 | 详情 |
| (III) | 51631 | (1R,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[(3-carboxy-2,2-dimethylpropanoyl)oxy]-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid | C36H56O6 | 详情 | 详情 |