1-((8S,9S,13S,14S)-3-Methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)-ethanone | 273208-40-5

• 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: 1-((8S,9S,13S,14S)-3-Methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)-ethanone
• 英文别名: 1-[(8S,9S,13S,14S)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 273208-40-5
• 化学式: C₂₁H₂₈O₂
• 分子量: 312.452
• InChiKey: ILVARFYPEVEZSJ-MEYGQTPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-((8S,9S,13S,14S)-3-Methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)-ethanone 在 盐酸 、 高氯酸 、 potassium tert-butylate 、 水 作用下， 以 四氢呋喃 、 甲醇 、 水 、 叔丁醇 为溶剂， 反应 144.0h， 生成 (2R,3R)-2-((8S,9S,13S,14S)-3-Methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)-6-methyl-hept-4-yne-2,3,6-triol
  参考文献：
  名称：

  A stereoselective synthesis of 1,2-diols from α-hydroxyaldehydes

  摘要：

  DOI：

  10.1016/s0040-4039(00)98430-2
• 作为产物：
  描述：

  3-甲氧基雌酮 在 sodium t-butanolate 作用下， 以 乙二醇二甲醚 、 乙醚 、 乙醇 为溶剂， 反应 0.5h， 生成 1-((8S,9S,13S,14S)-3-Methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)-ethanone
  参考文献：
  名称：

  A novel cross-species inhibitor to study the function of CatSper Ca²⁺ channels in sperm

  摘要：

  Background and PurposeSperm from many species share the sperm‐specific Ca2+ channel CatSper that controls the intracellular Ca2+ concentration and, thereby, the swimming behaviour. A growing body of evidence suggests that the mechanisms controlling the activity of CatSper and its role during fertilization differ among species. A lack of suitable pharmacological tools has hampered the elucidation of the function of CatSper. Known inhibitors of CatSper exhibit considerable side effects and also inhibit Slo3, the principal K+ channel of mammalian sperm. The compound RU1968 was reported to suppress Ca2+ signaling in human sperm by an unknown mechanism. Here, we examined the action of RU1968 on CatSper in sperm from humans, mice, and sea urchins.Experimental ApproachWe resynthesized RU1968 and studied its action on sperm from humans, mice, and the sea urchin Arbacia punctulata by Ca2+ fluorimetry, single‐cell Ca2+ imaging, electrophysiology, opto‐chemistry, and motility analysis.Key ResultsRU1968 inhibited CatSper in sperm from invertebrates and mammals. The compound lacked toxic side effects in human sperm, did not affect mouse Slo3, and inhibited human Slo3 with about 15‐fold lower potency than CatSper. Moreover, in human sperm, RU1968 mimicked CatSper dysfunction and suppressed motility responses evoked by progesterone, an oviductal steroid known to activate CatSper. Finally, RU1968 abolished CatSper‐mediated chemotactic navigation in sea urchin sperm.Conclusion and ImplicationsWe propose RU1968 as a novel tool to elucidate the function of CatSper channels in sperm across species.

  DOI：

  10.1111/bph.14355