前列腺素F1β | 10164-73-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 前列腺素F1β
• 英文名称: prostaglandin F1β
• 英文别名: Prostaglandin F1beta；7-[(1R,2R,3R,5R)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]heptanoic acid
• CAS: 10164-73-5
• 化学式: C₂₀H₃₆O₅
• 分子量: 356.503
• InChiKey: DZUXGQBLFALXCR-JQXWHSLNSA-N

物化性质

• 沸点：
  526.5±50.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：>50mg/mL； DMSO：>50mg/mL；乙醇：>75mg/mL； PBS pH 7.2：>2 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  、 前列腺素Bx 、 前列腺素 D2 、 前列腺素F1Alpha 、 地诺前列素 、 15-酮前列腺素 F2Alpha 、 6-酮前列腺素 、 拉坦前列素 、 (9alpha,11alpha)-9,11-二羟基-6,15-二氧代-原甾-1-酸 、 前列腺素F1β 、 (5Z,8beta,9beta,11alpha,13E,15S)-9,11,15-三羟基前列腺-5,13-二烯-1-酸 、 11beta-前列腺素 and in f2alpha 、 前列腺素 J2 生成 前列腺素 A1
  参考文献：
  名称：

  Enhancement of skin pigmentation by prostaglandins

  摘要：

  本发明涉及一种组合物，包括一种载体和一种前列腺素，其在人体黑色素细胞中促进黑色素合成，从而增强人体皮肤的色素，并且还可以包括溶酶体靶向药物、磷酸二酯酶抑制剂和/或甲基黄嘌呤，并提供了使用该组合物的方法。使用该组合物可以促进人体皮肤晒黑，并增加对紫外线辐射的光保护。

  公开号：

  US05905091A1
• 作为产物：
  描述：

  前列地尔 、 硼氢化钠 生成 前列腺素F1β
  参考文献：
  名称：

  SHEVCHENKO, V. P.;LAZURKINA, T. YU.;MYASOEDOV, N. F., BIOORGAN. XIMIYA, 14,(1988) N 4, 536-540

  摘要：

  DOI：

文献信息

• AMINO ACID SALTS OF PROSTAGLANDINS
  申请人：DeLong Mitchell A.

  公开号：US20100105775A1

  公开（公告）日：2010-04-29

  The present invention is directed to novel amino acid prostaglandin salts and methods of making and using them.

  本发明涉及新型氨基酸前列腺素盐及其制备和使用方法。
• Depentyl analogues of 11-deoxy-prostaglandin E.sub.1
  申请人：Miles Laboratories, Inc.

  公开号：US04065493A1

  公开（公告）日：1977-12-27

  Depentyl analogues of prostaglandins A, E, and F having no C-16 to C-20 carbon atoms. The analogues correspond to the formula ##STR1## wherein: L is methylene, ethylene, or trimethylene; K is ethylene or cis-vinylene; M is carbonyl, .alpha.-hydroxymethylene, or .beta.-hydroxymethylene; N is methylene or methine, provided that N is methine only if P is methine and M is carbonyl; P is methylene, ethylene, .alpha.-hydroxymethylene or methine, provided that P is methine only if N is methine; and, R is carboxyl; hydroxymethylene, alkoxycarbonyl, the alkyl portion of said alkoxycarbonyl being a lower alkyl, or a pharmacologically acceptable non-toxic carboxy salt. The analogues are prepared by first converting a trans-1-iodo-3-alkoxy-1-propene to the corresponding lithio compound. This lithio compound then combines with the hexamethylphosphorous triamide complex of copper (I) pentyne to give an alkenylcopper species. Reacting this alkenylcopper compound with the appropriate 2-substituted-cyclopent-2-enone or 2-substituted-cyclohex-2-enone gives the desired depentyl prostaglandins.

  Depentyl类前列腺素A、E和F的类似物没有C-16到C-20碳原子。该类类似物对应于以下式子：##STR1## 其中：L为亚甲基、乙烯或三亚甲基；K为乙烯或顺式乙烯基；M为羰基、α-羟甲基或β-羟甲基；N为亚甲基或亚胺基，但仅当P为亚胺基且M为羰基时，N为亚胺基；P为亚甲基、乙烯、α-羟甲基或亚胺基，但仅当N为亚胺基时，P为亚胺基；R为羧基、羟甲基、烷氧羰基，所述烷氧羰基的烷基部分为低级烷基，或药理学上可接受的无毒羧酸盐。该类类似物的制备方法是首先将反式-1-碘-3-烷氧基-1-丙烯转化为相应的锂化合物。然后，该锂化合物与铜（I）戊炔的六甲基膦三胺络合物结合，形成烯丙基铜物种。将该烯丙基铜化合物与适当的2-取代环戊-2-酮或2-取代环己-2-酮反应，即可得到所需的Depentyl前列腺素。
• Depentyl analogues of PGF.sub.1
  申请人：Miles Laboratories, Inc.

  公开号：US04099017A1

  公开（公告）日：1978-07-04

  Depentyl analogues of prostaglandins A, E, and F having no C-16 to C-20 carbon atoms. The analogues correspond to the formula ##STR1## wherein: L is methylene, ethylene, or trimethylene; K is ethylene or cis-vinylene; M is carbonyl, .alpha.-hydroxymethylene, or .beta.-hydroxymethylene; N is methylene or methine, provided that N is methine only if P is methine and M is carbonyl; P is methylene, ethylene, .alpha.-hydroxymethylene or methine, provided that P is methine only if N is methine; and, R is carboxyl; hydroxymethylene, alkoxycarbonyl, the alkyl portion of said alkoxycarbonyl being a lower alkyl, or a pharmacologically acceptable non-toxic carboxy salt. The analogues are prepared by first converting a trans-1-iodo-3-alkoxy-1-propene to the corresponding lithio compound. This lithio compound then combines with the hexamethylphosphorous triamide complex of copper (I) pentyne to give an alkenylcopper species. Reacting this alkenylcopper compound with the appropriate 2-substituted-cyclopent-2-enone or 2-substituted-cyclohex-2-enone gives the desired depentyl prostaglandins.

  具有没有C-16到C-20碳原子的前列腺素A，E和F的Depentyl类似物。这些类似物对应于以下公式## STR1 ##其中：L是亚甲基，乙烯或三亚甲基；K是乙烯或顺式乙烯基；M是羰基，α-羟甲基或β-羟甲基；N是亚甲基或亚甲基，只有当P是亚甲基且M是羰基时，N才是亚甲基；P是亚甲基，乙烯，α-羟甲基或亚甲基，只有当P是亚甲基时，N才是亚甲基；和R是羧基；羟甲基，烷氧羰基，其烷基部分为低烷基，或药理学上可接受的无毒羧酸盐。这些类似物首先通过将反式-1-碘-3-烷氧基-1-丙烯转化为相应的锂化合物来制备。然后，这种锂化合物与铜(I)戊炔的六甲基膦三胺配合物结合，形成烯基铜物种。将这种烯基铜化合物与适当的2-取代环戊-2-酮或2-取代环己-2-酮反应，即可得到所需的Depentyl前列腺素。
• Depentyl analogues of PGE.sub.2
  申请人：Miles Laboratories, Inc.

  公开号：US04099016A1

  公开（公告）日：1978-07-04

  Depentyl analogues of prostaglandins A, E, and F having no C-16 to C-20 carbon atoms. The analogues correspond to the formula ##STR1## wherein: L is methylene, ethylene, or trimethylene; K is ethylene or cis-vinylene; M is carbonyl, .alpha.-hydroxymethylene, or .beta.-hydroxymethylene; N is methylene or methine, provided that N is methine only if P is methine and M is carbonyl; P is methylene, ethylene, .alpha.-hydroxymethylene or methine, provided that P is methine only if N is methin; and, R is carboxyl; hydroxymethylene, alkoxycarbonyl, the alkyl portion of said alkoxycarbonyl being a lower alkyl, or a pharmacologically acceptable non-toxic carboxy salt. The analogues are prepared by first converting a trans-1-iodo-3-alkoxy-1-propene to the corresponding lithio compound. This lithio compound then combines with the hexamethylphosphorous triamide complex of copper(I) pentyne to give an alkenylcopper species. Reacting this alkenylcopper compound with the appropriate 2-substituted-cyclopent-2-enone or 2-substituted-cyclohex-2-enone gives the desired depentyl prostaglandins.

  Depentyl类前列腺素A，E和F的类似物，没有C-16到C-20碳原子。这些类似物对应于公式##STR1##其中：L为亚甲基，乙烯或三亚甲基；K为乙烯或顺式乙烯基；M为羰基，α-羟甲基或β-羟甲基；N为亚甲基或甲烷基，但仅当P为甲烷基且M为羰基时，N才为甲烷基；P为亚甲基，乙烯，α-羟甲基或甲烷基，但仅当N为甲烷基时，P才为甲烷基；R为羧基；羟甲基，烷氧羰基，其烷基部分为低烷基，或药理学上可接受的无毒羧酸盐。这些类似物首先通过将反-1-碘-3-烷氧基-1-丙烯转化为相应的锂化合物来制备。然后，该锂化合物与铜(I)戊炔六甲基膦酰胺复合物结合，形成烯丙基铜物种。将此烯丙基铜化合物与适当的2-取代环戊-2-酮或2-取代环己-2-酮反应，即可得到所需的依赖酯基前列腺素。
• Depentyl analogues of PGE.sub.1
  申请人：Miles Laboratories, Inc.

  公开号：US04100356A1

  公开（公告）日：1978-07-11

  Depentyl analogues of prostaglandins A, E, and F having no C-16 to C-20 carbon atoms. The analogues correspond to the formula ##STR1## wherein: L is methylene, ethylene or trimethylene; K is ethylene or cis-vinylene; M is carbonyl, .alpha.-hydroxymethylene, or .beta.-hydroxymethylene; N is methylene or methine, provided that N is methine only if P is methine and M is carbonyl; P is methylene, ethylene, .alpha.-hydroxymethylene or methine, provided that P is methine only if N is methine; and, R is carboxyl; hydroxymethylene, alkoxycarbonyl, the alkyl portion of said alkoxycarbonyl being a lower alkyl, or a pharmacologically acceptable non-toxic carboxy salt. The analogues are prepared by first converting a trans-1-iodo-3-alkoxy-1-propene to the corresponding lithio compound. This lithio compound then combines with the hexamethylphosphorous triamide complex of copper(I) pentyne to give an alkenylcopper species. Reacting this alkenylcopper compound with the appropriate 2-substituted-cyclopent-2-enone or 2-substituted-cyclohex-2-enone gives the desired depentyl prostaglandins.

  Depentyl类前列腺素A、E和F的类似物，其C-16到C-20碳原子不存在。该类似物对应于以下式子：##STR1##其中：L为亚甲基、乙烯或三亚甲基；K为乙烯或顺式-乙烯基；M为羰基、α-羟甲亚基或β-羟甲亚基；N为亚甲基或亚甲基，但仅当P为亚甲基且M为羰基时，N才为亚甲基；P为亚甲基、乙烯、α-羟甲亚基或亚甲基，但仅当N为亚甲基时，P才为亚甲基；R为羧基；羟甲亚基、烷氧羰基，其烷基部分为较低的烷基，或药理学上可接受的无毒羧酸盐。该类似物首先通过将反-1-碘-3-烷氧基-1-丙烯转化为相应的锂化合物来制备。然后，该锂化合物与铜(I)戊炔的六甲基膦酰胺配合物结合，形成烯基铜物种。将该烯基铜化合物与适当的2-取代环戊-2-酮或2-取代环己-2-酮反应，即可得到所需的Depentyl前列腺素。