(3S,5S,10S,13R,14R,17R)-17-((R)-1,5-Dimethyl-hexyl)-3-hydroxy-10,13,14-trimethyl-1,2,3,4,5,6,7,10,11,12,13,14,16,17-tetradecahydro-cyclopenta[a]phenanthren-15-one oxime | 123290-55-1

• 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: (3S,5S,10S,13R,14R,17R)-17-((R)-1,5-Dimethyl-hexyl)-3-hydroxy-10,13,14-trimethyl-1,2,3,4,5,6,7,10,11,12,13,14,16,17-tetradecahydro-cyclopenta[a]phenanthren-15-one oxime
• 英文别名: (3S,5S,10S,13R,14R,15E,17R)-15-hydroxyimino-10,13,14-trimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,11,12,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 123290-55-1
• 化学式: C₂₈H₄₇NO₂
• 分子量: 429.687
• InChiKey: IXCHTEVWRLWAJD-PIPCARKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,5S,10S,13R,14R,17R)-17-((R)-1,5-Dimethyl-hexyl)-3-hydroxy-10,13,14-trimethyl-1,2,3,4,5,6,7,10,11,12,13,14,16,17-tetradecahydro-cyclopenta[a]phenanthren-15-one oxime 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.25h， 生成 (1R,4aR,6aS,8S,10aS,12aR)-1-((R)-1,5-Dimethyl-hexyl)-4a,10a,12a-trimethyl-1,2,3,4,4a,5,6,6a,7,8,9,10,10a,11,12,12a-hexadecahydro-naphtho[1,2-h]quinolin-8-ol
  参考文献：
  名称：

  Design and synthesis of 14.alpha.-methyl-15-aza-D-homosterols as novel antimycotics

  摘要：

  A novel series of 14 alpha-methyl-15-aza-D-homosterols 3-7 has been synthesized. These compounds display significant antimycotic activity in vitro (MIC = 0.8-3.1 micrograms/mL) that compares quite favorably to the activity observed for fluconazole (MIC = 0.8 micrograms/mL). Azasterols 3 and 4 were active in vivo as reflected in the increased survival time of Candida albicans infected mice. The antimycotic activity of 3-7 is hypothesized to be a consequence of the inhibition of fungal 14,15-sterol reductase.

  DOI：

  10.1021/jm00164a065
• 作为产物：
  描述：

  Benzoic acid (3S,5S,10S,13R,14R,17R)-17-((R)-1,5-dimethyl-hexyl)-15-[(E)-hydroxyimino]-10,13,14-trimethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 在 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 12.0h， 生成 (3S,5S,10S,13R,14R,17R)-17-((R)-1,5-Dimethyl-hexyl)-3-hydroxy-10,13,14-trimethyl-1,2,3,4,5,6,7,10,11,12,13,14,16,17-tetradecahydro-cyclopenta[a]phenanthren-15-one oxime
  参考文献：
  名称：

  Design and synthesis of 14.alpha.-methyl-15-aza-D-homosterols as novel antimycotics

  摘要：

  A novel series of 14 alpha-methyl-15-aza-D-homosterols 3-7 has been synthesized. These compounds display significant antimycotic activity in vitro (MIC = 0.8-3.1 micrograms/mL) that compares quite favorably to the activity observed for fluconazole (MIC = 0.8 micrograms/mL). Azasterols 3 and 4 were active in vivo as reflected in the increased survival time of Candida albicans infected mice. The antimycotic activity of 3-7 is hypothesized to be a consequence of the inhibition of fungal 14,15-sterol reductase.

  DOI：

  10.1021/jm00164a065

文献信息

• US5034548A
  申请人：——

  公开号：US5034548A

  公开（公告）日：1991-07-23
• US5041432A
  申请人：——

  公开号：US5041432A

  公开（公告）日：1991-08-20