(3R,3aR,5aS,5bR,8S,10aS,10bS)-3-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-8-hydroxy-3a,5b-dimethyl-1,2,3,4,5,5a,6,7,8,9,10a,10b-dodecahydrocyclopenta[a]fluorene-10-carbaldehyde | 1088422-47-2

• 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: (3R,3aR,5aS,5bR,8S,10aS,10bS)-3-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-8-hydroxy-3a,5b-dimethyl-1,2,3,4,5,5a,6,7,8,9,10a,10b-dodecahydrocyclopenta[a]fluorene-10-carbaldehyde
• CAS: 1088422-47-2
• 化学式: C₂₉H₄₈O₂
• 分子量: 428.699
• InChiKey: DAZOMMYHPADYCA-BSPNSOLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  穿贝海绵甾醇22,23-二氢多孔甾醇24-γ-乙基胆固醇 在 臭氧 、 二甲基硫 、 lithium hydroxide 作用下， 以 乙醚 、 甲醇 为溶剂， 反应 24.08h， 生成 (3R,3aR,5aS,5bR,8S,10aS,10bS)-3-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-8-hydroxy-3a,5b-dimethyl-1,2,3,4,5,5a,6,7,8,9,10a,10b-dodecahydrocyclopenta[a]fluorene-10-carbaldehyde
  参考文献：
  名称：

  Synthesis and in vitro biological evaluation of ring B abeo-sterols as novel inhibitors of Mycobacterium tuberculosis

  摘要：

  A series of 3b-hydroxy steroid analogues possessing a contracted cyclopentane B-ring were prepared based on the initial activity screening of a recently reported naturally occurring marine 5(6-->7) abeo-sterol against Mycobacterium tuberculosis. All of the novel ring B abeo-sterols synthesized showed good inhibitory activity, whereas none of the starting steroids based on the common 3 beta-hydroxy-Delta(5)-cholestane nucleus, proved to be active. Therefore, the 5(6-->7) abeo-sterol nucleus present in compounds 3, 5, 7, 9, and 11 represents a novel scaffold for the development of new antitubercular agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.029

文献信息

• Synthesis and in vitro biological evaluation of ring B abeo-sterols as novel inhibitors of Mycobacterium tuberculosis
  作者：Xiaomei Wei、Abimael D. Rodríguez、Yuehong Wang、Scott G. Franzblau

  DOI：10.1016/j.bmcl.2008.09.029

  日期：2008.10

  A series of 3b-hydroxy steroid analogues possessing a contracted cyclopentane B-ring were prepared based on the initial activity screening of a recently reported naturally occurring marine 5(6-->7) abeo-sterol against Mycobacterium tuberculosis. All of the novel ring B abeo-sterols synthesized showed good inhibitory activity, whereas none of the starting steroids based on the common 3 beta-hydroxy-Delta(5)-cholestane nucleus, proved to be active. Therefore, the 5(6-->7) abeo-sterol nucleus present in compounds 3, 5, 7, 9, and 11 represents a novel scaffold for the development of new antitubercular agents. (C) 2008 Elsevier Ltd. All rights reserved.