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比马前列素

比马前列素

CAS号:155206-00-1
英文名:bimatoprost
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化合物简介
Bimatoprost (marketed in the US, Canada and Europe by Allergan, under the trade name Lumigan) is a prostaglandin analog used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. It reduces intraocular pressure (IOP) by increasing the outflow of aqueous fluid from the eyes. In December 2008, the indication to lengthen eyelashes was approved by the U.S. Food and Drug Administration (FDA); the cosmetic formulation of bimatoprost is sold as Latisse .
基本信息
编号系统
物化性质
安全信息
生产方法及用途
生产方法
以(3aR,4R,5R,6as)-六氢-4-(3-氧-5-苯基-1E-戊烯基)-5-(p-苯基丁酰氧基)-2H-环戊并[b]呋喃-2-酮为原料。 经还原反应,然后将呋喃环上的羰基还原为羟基,水解后再和戊酸的三苯基膦缩合,得到7-(1R,2R,3R,5S)-3,5-二羟基-2-[(3S)-5-苯基-3-[(四氢-2-H-吡喃-2-基)氧]-1E-戊烯基]环戊基]-5Z-庚烯酸。 水解脱去戊烯基侧链的羟基上的保护基。再和碘甲烷溶于二甲基甲酰胺,Cs2CO3作用下得到甲酯,最后和乙胺水溶液反应,得到产物。
用途
比马前列腺素(Bimatoprost)是由美国Allergan公司研制和开发的一类高效能的降眼压药物,它在药理学上很独特,是一种合成的前列腺素酰胺类,具有很强的降眼压作用。比马前列腺素可能是通过水解为游离酸后作用于FP类前列腺素受体,从而治疗青光眼比马前列腺素常用浓度为0.03%。
上游原料
(R)-2-allyl-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone (Z)-7-[(1r,2r,3r,5s)-3,5-二羟基-2-((e)-(s)-3-羟基-5-苯基-1-戊烯)-环戊基]-5-庚烯酸甲酯 5-溴戊酸 乙胺 (3aR,4R,5R,6aS)-4-((S,E)-3-((2-methoxyethoxy)methoxy)-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol sodium 5-(triphenyl-l<sup>5</sup>-phosphanylidene)pentanoate 5-bromo-N-ethylpentanamide 7-[3,5-dihydroxy-2-(3-hydroxy-5-phenylpent-1-enyl)-cyclopentyl]-5-heptenoic acid (2,5-dioxopyrrolidin-1-yl) ester 正丙胺 (S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane (3aR,4R,5R,6aS)-4-[3S-(p-nitrobenzoyloxy)-5-phenyl-1E-pentenyl]-5-(benzoyloxy)-hexahydro-2H-cyclopenta[b]furan-2-one 比马前列素异丙酯 (Z)-methyl 7-((1R,2R,3R,5S)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpent-1-en-1-yl)-5-hydroxycyclopentyl)hept-5-enoate (5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-enyl)-5-hydroxycyclopentyl)-N-ethylhept-5-enamide 4-羧丁基三苯基溴化膦 (3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-ol 拉坦前列素中间体 (Z)-7-((1R,2R,3R,5S)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpent-1-en-1-yl)-5-hydroxycyclopentyl)hept-5-enoic acid (3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((E)-3-hydroxy-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one (3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one PPB-lactoltriol 5-{[二甲基(2-甲基-2-丙基)硅烷基]氧基}-2-氧代六氢-2H-环戊二烯并[b]呋喃-4-甲醛 (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S,E)-3-((2-methoxyethoxy)methoxy)-5-phenylpent-1-enyl)cyclopentyl)-N-ethylhept-5-enamide tert-butyl((S,1E)-1-((3aR,4R,6aS)-2-methoxy-5-((trimethylsilyloxy)methylene)hexahydro-2H-cyclopenta[b]furan-4-yl)-5-phenylpent-1-en-3-yloxy)dimethylsilane bimataprost L-arginine salt 5-溴戊酰氯 (Z)-7-[(1R,2R,3S,5S)-3,5-二羟基-2-[(E)-3-羟基-5-苯基戊-1-烯基]环戊基]庚-5-烯酸 (3aR,4R,5R,6aS)-5-hydroxy-4-((S,E)-3-((2-methoxyethoxy)methoxy)-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one (3aR,4R,5R,6aS)-六氢-4-[(1E,3S)-3-羟基-5-苯基-1-戊烯-1-基]-2-氧代-2H-环戊[b]呋喃-5-基酯[1,1'-联苯]-4-羧酸 (9S,11R,15S)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinor-5Z,13E-prostadienoate 2-氧代-4-苯丁基磷酸二甲酯