(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic acid 4-(3H-1,2-dithiole-3-thione-5-yl)phenyl ester | 1088434-86-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic acid 4-(3H-1,2-dithiole-3-thione-5-yl)phenyl ester
• 英文别名: 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl ester 5Z-heptenoic acid；ACS 67；ACS67；(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic acid 4-(3H-1,2-dithiole-3-thione-5-yl)-phenyl ester；5-Heptenoic acid, 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-, 4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl ester, (5Z)-；[4-(5-sulfanylidenedithiol-3-yl)phenyl] (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
• CAS: 1088434-86-9
• 化学式: C₃₂H₃₈O₅S₃
• 分子量: 598.849
• InChiKey: JEEWZRQQYWVJCX-WEWVERJPSA-N

物化性质

• 溶解度：
  乙醇中≤2mg/ml；DMSO 中≤20mg/ml；二甲基甲酰胺中≤30mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  8

制备方法与用途

ACS67是一种F系列前列腺素(PG)类似物，用于治疗青光眼。研究显示，ACS67能够降低眼内压(IOP)，增加葡萄膜炎性兔眼中房液中还原型谷胱甘肽和cGMP的水平，并具有神经保护作用，能刺激谷胱甘肽(GSH)水平。

反应信息

• 作为产物：
  描述：

  胆维他 在 4-二甲氨基吡啶 吡啶盐酸盐 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 15.42h， 生成 (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic acid 4-(3H-1,2-dithiole-3-thione-5-yl)phenyl ester
  参考文献：
  名称：

  WO2008/146105

  摘要：

  公开号：

文献信息

• PROSTAGLANDIN PHARMACEUTICAL COMPOSITIONS
  申请人：Del Soldato Piero

  公开号：US20100168216A1

  公开（公告）日：2010-07-01

  The present invention relates to new prostaglandin derivatives having improved pharmacological activity and enhanced tolerability. They can be employed for the treatment of glaucoma and ocular hypertension.

  本发明涉及新的前列腺素衍生物，具有改善的药理活性和增强的耐受性。它们可用于治疗青光眼和眼压增高。
• New prostaglandin derivative for glaucoma treatment
  作者：Elena Perrino、Caterina Uliva、Cecilia Lanzi、Piero Del Soldato、Emanuela Masini、Anna Sparatore

  DOI：10.1016/j.bmcl.2009.02.007

  日期：2009.3

  A hydrogen sulphide-releasing derivative of latanoprost acid (ACS 67) was synthesized and tested in vivo to evaluate its activity on reduction of intraocular pressure and tolerability. Glutathione (GSH) and cGMP content were also measured in the aqueous humour. The increased reduction of intraocular pressure, with a marked increase of GSH and cGMP and the related potential neuroprotective properties, make this compound interesting for the treatment of glaucoma. This is the first time that an application of a hydrogen sulphide-releasing molecule is reported for the treatment of ocular diseases. (C) 2009 Elsevier Ltd. All rights reserved.
• WO2008/146105
  申请人：——

  公开号：——

  公开（公告）日：——