5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-hydroxypropyl)hydantoin | 78420-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-hydroxypropyl)hydantoin
• 英文别名: (R-(R*,R*))-3-(3-Cyclohexyl-3-hydroxypropyl)-2,5-dioxo-imidazolidine-4-heptanoic acid；7-[(4R)-3-[(3R)-3-cyclohexyl-3-hydroxypropyl]-2,5-dioxoimidazolidin-4-yl]heptanoic acid
• CAS: 78420-15-2
• 化学式: C₁₉H₃₂N₂O₅
• 分子量: 368.473
• InChiKey: ZIDQIOZJEJFMOH-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  BW245C 在 sodium hydroxide 作用下， 反应 22.0h， 以0.159 g的产率得到5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-hydroxypropyl)hydantoin
  参考文献：
  名称：

  杂环前列腺素类似物。第3部分。一些乙内酰脲前列腺素类似物的构型与生物活性的关系

  摘要：

  合成了5-（6-羧基己基）-1-（3-环己基-3-羟丙基）乙内酰脲的两种非对映异构体的对映体。该系列中对血小板凝集的有效抑制与相应于天然抑制剂（例如前列腺素E 1和D 2）的构型有关。

  DOI：

  10.1039/p19810000706

文献信息

• Optically active hydantoin derivatives, their synthesis, pharmaceutical formulations containing them, and intermediates
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0019223A1

  公开（公告）日：1980-11-26

  Compounds of formula (I) having only two optically active centres, may exist as four isomers, each of which may be prepared by resolving a racemic amino-diester intermediate in the preparation thereof. The racemic amino-diester is selectively hydrolysed to the corresponding mono-ester which is acylated and subsequently selectively deacylated to produce the resolved mono-ester. Isomers of compounds of formula (I) having a particular configuration are biologically more active than the corresponding isomers having other configurations and are useful in medicine, either as the raw compound or in a pharmaceutical formulation, for example in inhibiting platelet aggregation.

  式 (I) 化合物 只有两个光学活性中心，可以存在四种异构体，每种异构体都可以通过分解制备过程中的外消旋氨基二酯中间体来制备。外消旋氨基二酯被选择性水解为相应的单酯，单酯被酰化，随后选择性脱酰化，生成已解析的单酯。 具有特定构型的式 (I) 化合物异构体比具有其他构型的相应异构体具有更高的生物活性，可作为原料化合物或药物制剂用于医药领域，例如抑制血小板聚集。
• TOPICAL APPLICATION OF TRAVOPROST FOR COMBATING HAIR LOSS
  申请人：Rethore Sandrine

  公开号：US20100190853A1

  公开（公告）日：2010-07-29

  Travoprost medicament compositions for non-daily topical application are useful for simulating or inducing the growth and/or decreasing the loss and/or increasing the density and/or reducing the heterogeneity in the diameter of human hair shafts/follicles, e.g., for the treatment of androgenic alopecia, such medicament compositions being at least twice applied over a time interval of greater than 24 hours.
• US8227514B2
  申请人：——

  公开号：US8227514B2

  公开（公告）日：2012-07-24
• US8980948B2
  申请人：——

  公开号：US8980948B2

  公开（公告）日：2015-03-17
• Heterocyclic prostaglandin analogues. Part 3. The relationship of configuration to biological activity for some hydantoin prostaglandin analogues
  作者：Michael A. Brockwell、A. Gordon Caldwell、Norman Whittaker、Michael J. Begley

  DOI：10.1039/p19810000706

  日期：——

  The enantiomers of the two diastereoisomers of 5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-hydroxypropyl)hydantoin have been synthesised. Potent inhibition of platelet aggregation in this series is associated with the configuration corresponding to that in the natural inhibitors, such as prostaglandins E1 and D2.

  合成了5-（6-羧基己基）-1-（3-环己基-3-羟丙基）乙内酰脲的两种非对映异构体的对映体。该系列中对血小板凝集的有效抑制与相应于天然抑制剂（例如前列腺素E 1和D 2）的构型有关。