(2R,8'R,9'S,13'S,14'S)-13'-methylspiro[3H-furo[3,2-b]pyridine-2,17'-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene] | 1150106-19-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (2R,8'R,9'S,13'S,14'S)-13'-methylspiro[3H-furo[3,2-b]pyridine-2,17'-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene]
• CAS: 1150106-19-6
• 化学式: C₂₄H₂₇NO
• 分子量: 345.484
• InChiKey: VCRDCFBHNBPVIW-PJPYIVHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (8R,9S,13S,14S,17R)-17-[(3-bromopyridin-2-yl)methyl]-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol 在 palladium diacetate R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以79%的产率得到(2R,8'R,9'S,13'S,14'S)-13'-methylspiro[3H-furo[3,2-b]pyridine-2,17'-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene]
  参考文献：
  名称：

  [EN] STEROID-DERIVED CYCLOPAMINE ANALOGS AND METHODS FOR USING THE SAME IN THE PREVENTION OR TREATMENT OF CANCER
  [FR] ANALOGUES DE CYCLOPAMINE DÉRIVÉS DE STÉROÏDE ET PROCÉDÉS D'UTILISATION DE CES DERNIERS DANS LA PRÉVENTION OU LE TRAITEMENT DU CANCER

  摘要：

  本发明涉及类固醇衍生的环吡啶类似物，以及使用这些类似物来抑制声波刺猬信号传导并预防或治疗癌症的方法。还提供了一种从类固醇合成本发明的类似物的方法。

  公开号：

  WO2009058945A1

文献信息

• [EN] STEROID-DERIVED CYCLOPAMINE ANALOGS AND METHODS FOR USING THE SAME IN THE PREVENTION OR TREATMENT OF CANCER<br/>[FR] ANALOGUES DE CYCLOPAMINE DÉRIVÉS DE STÉROÏDE ET PROCÉDÉS D'UTILISATION DE CES DERNIERS DANS LA PRÉVENTION OU LE TRAITEMENT DU CANCER
  申请人：WISTAR INST

  公开号：WO2009058945A1

  公开（公告）日：2009-05-07

  The present invention relates to steroid-derived cyclopamine analogs and methods for using the same for inhibiting sonic hedgehog signaling and preventing or treating cancer. A method for synthesizing the analogs of the present invention from a steroid is also provided.

  本发明涉及类固醇衍生的环吡啶类似物，以及使用这些类似物来抑制声波刺猬信号传导并预防或治疗癌症的方法。还提供了一种从类固醇合成本发明的类似物的方法。
• Steroid-Derived Cyclopamine Analogs and Methods for Using the Same in the Prevention or Treatment of Cancer
  申请人：Dahmane Nadia

  公开号：US20100298281A1

  公开（公告）日：2010-11-25

  The present invention relates to steroid-derived cyclopamine analogs and methods for using the same for inhibiting sonic hedgehog signaling and preventing or treating cancer. A method for synthesizing the analogs of the present invention from a steroid is also provided.
• US8575141B2
  申请人：——

  公开号：US8575141B2

  公开（公告）日：2013-11-05
• US8669243B2
  申请人：——

  公开号：US8669243B2

  公开（公告）日：2014-03-11
• Studies Directed toward the Elucidation of the Pharmacophore of Steroid-Based Sonic Hedgehog Signaling Inhibitors
  作者：André K. Isaacs、Chaomei Xiang、Valérie Baubet、Nadia Dahmane、Jeffrey D. Winkler

  DOI：10.1021/ol202020c

  日期：2011.10.7

  Previous work from our laboratory has established that the readily available steroid-based analog 2 of cyclopamine 1 is, like 1, a highly potent inhibitor of Hedgehog signaling. The first structure-activity relationship studies on 2, i.e., the synthesis and biological evaluation of both the C-17 epi analog 4 and the C-3 deoxy analog 11, both of which are more potent than cyclopamine 1, are described. The implications of these results for the emerging pharmacophore of these Sonic Hedgehog signaling inhibitors are discussed.