2-Phenylamino-propionic acid (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-3-vinyl-dodecahydro-benzo[f]chromen-6-yl ester | 115076-92-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-Phenylamino-propionic acid (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-3-vinyl-dodecahydro-benzo[f]chromen-6-yl ester
• 英文别名: [(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-3-ethenyl-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-5,6,6a,8,9,10-hexahydro-2H-benzo[f]chromen-6-yl] 2-anilinopropanoate
• CAS: 115076-92-1
• 化学式: C₂₉H₄₁NO₇
• 分子量: 515.647
• InChiKey: UZVJPABWPYEKCK-RVSCTZCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-Phenylamino-propionic acid (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-3-vinyl-dodecahydro-benzo[f]chromen-5-yl ester 在 sodium methylate 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-Phenylamino-propionic acid (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-3-vinyl-dodecahydro-benzo[f]chromen-6-yl ester
  参考文献：
  名称：

  Cardiovascular effects of new water-soluble derivatives of forskolin

  摘要：

  A series of 6- and 7-aminoacyl derivatives of 7-deacetylforskolin was prepared to provide water-soluble derivatives of the potent cardioactive diterpenoid forskolin. The compounds were evaluated for positive inotropic and blood pressure lowering properties in pharmacological models. Several derivatives displayed potent positive inotropic activity in guinea pig atria (EC50 = 0.16-3.0 micrograms/mL). In the most active compounds, the amino moiety of the aminoacyl chain corresponded to a cyclic amine, and the acyl moiety to a C2-C4 alkanoyl group. In vivo biological evaluation led to the selection of 6-(piperidinoacetyl)-7-deacetylforskolin hydrochloride (49) as a candidate for clinical development.

  DOI：

  10.1021/jm00118a002

文献信息

• Neue polyoxygenierte Labdan-Derivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Medikamente
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0217372A2

  公开（公告）日：1987-04-08

  Die vorliegende Erfindung betrifft polyoxygenierte Labdan-Derivate. die als Substituenten eine oder mehrere Aminoacyigruppen tragen, sowie ein Verfahren zu ihrer Herstellung. Die pharmakologischen Eigenschaften der erfindungsgemäßen Verbindungen machen sie für die Verwendung bei der Behandlung von Herz- und Kreisiauferkrankungen, Hypertonie. Glaukom, Aliergien, Bronchokonstriktion und als immunomodulatoren geeignet.

  本发明涉及以一个或多个氨基酰基为取代基的聚氧拉布烷衍生物及其制备方法。 本发明化合物的药理特性使其适用于治疗心脏和循环系统疾病、高血压、青光眼、过敏、支气管收缩和心血管疾病。本发明的化合物还可用于治疗高血压、青光眼、过敏、支气管收缩和免疫调节剂。
• KHANDELWAL, Y.;RAJESHWARI, K.;RAJAGOPALAN, R.;SWAMY, LAKSHMI;DOHADWALLA, +, J. MED. CHEM., 31,(1988) N 10, C. 1872-1879
  作者：KHANDELWAL, Y.、RAJESHWARI, K.、RAJAGOPALAN, R.、SWAMY, LAKSHMI、DOHADWALLA, +

  DOI：——

  日期：——
• Cardiovascular effects of new water-soluble derivatives of forskolin
  作者：Y. Khandelwal、K. Rajeshwari、R. Rajagopalan、Lakshmi Swamy、A. N. Dohadwalla、N. J. De Souza、R. H. Rupp

  DOI：10.1021/jm00118a002

  日期：1988.10

  A series of 6- and 7-aminoacyl derivatives of 7-deacetylforskolin was prepared to provide water-soluble derivatives of the potent cardioactive diterpenoid forskolin. The compounds were evaluated for positive inotropic and blood pressure lowering properties in pharmacological models. Several derivatives displayed potent positive inotropic activity in guinea pig atria (EC50 = 0.16-3.0 micrograms/mL). In the most active compounds, the amino moiety of the aminoacyl chain corresponded to a cyclic amine, and the acyl moiety to a C2-C4 alkanoyl group. In vivo biological evaluation led to the selection of 6-(piperidinoacetyl)-7-deacetylforskolin hydrochloride (49) as a candidate for clinical development.