Acetic acid (3S,8R,9S,10R,13S,14S,16S,17R)-17-hydroxy-10,13,16-trimethyl-17-(2-methyl-[1,3]dioxolan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester | 222056-04-4

• 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: Acetic acid (3S,8R,9S,10R,13S,14S,16S,17R)-17-hydroxy-10,13,16-trimethyl-17-(2-methyl-[1,3]dioxolan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
• CAS: 222056-04-4
• 化学式: C₂₆H₄₀O₅
• 分子量: 432.601
• InChiKey: XZOOTUFZADRWOP-DRCZJDEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3S,8R,9S,10R,13S,14S,16S,17R)-17-hydroxy-10,13,16-trimethyl-17-(2-methyl-[1,3]dioxolan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 在 对甲苯磺酸 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 17Α-羟基-16Β-甲基孕烯醇
  参考文献：
  名称：

  Androgenic and anti-androgenic effects of progesterone derivatives with different halogens as substituents at the C-6 position

  摘要：

  The pharmacological activities of four pregnane derivatives: 17 alpha-hydroxy-16 beta-methylpregna-4,6-diene-3,20-dione (7), 17 alpha-acetoxy-16 beta-methylpregna-4,6-diene-3,20-dione (8), 17 alpha-acetoxy-6-bromo-16 beta-methylpregna-4,6-diene-3,20-dione (10), and 17 alpha-acetoxy-6-chloro-16 beta-methylpregna-4,6-diene-3,20-dione (11), were determined. The derivatives were evaluated on gonadectomized male hamster flank organs and seminal vesicles. The results indicate that topical applications of testosterone (T) on the flank organs increased the diameter of the pigmented spot. Similarly, the same phenomenon occurred on the glands treated with compound 11, whereas compound 10 decreased the size of the spot significantly. In this study, we determined the effects of several new steroids on the conversion of T to DHT in flank organs and seminal vesicles. The results show that compound 10 inhibited T conversion to DHT, but compound 11, at a dose of 200 mu g, stimulated T conversion in both flank organs and seminal vesicles. However, when 2 mg of compound 11 was applied, it inhibited the conversion of T to DHT, suggesting that this compound also represses gonadotropin release. The difference between compounds 10 and II involves the electronegativity of the halogen at the C-6 position of the progesterone skeleton. These data clearly indicate that by decreasing the electronegativity of the halogen at C-6 (compound 10), 5 alpha-reductase is inhibited in both tissues and at different pHs. On the other hand, when the electronegativity of the halogen atom was increased (11), there was a much lower inhibitory effect on the conversion of T to DHT. (C) 1999 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00018-5
• 作为产物：
  描述：

  16-脱氢孕烯醇酮乙酸酯 在 吡啶 、 copper(l) iodide 、 hydroxide 、 双氧水 、 对甲苯磺酸 、 原甲酸三甲酯 作用下， 以 四氢呋喃 为溶剂， 反应 102.0h， 生成 Acetic acid (3S,8R,9S,10R,13S,14S,16S,17R)-17-hydroxy-10,13,16-trimethyl-17-(2-methyl-[1,3]dioxolan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Androgenic and anti-androgenic effects of progesterone derivatives with different halogens as substituents at the C-6 position

  摘要：

  The pharmacological activities of four pregnane derivatives: 17 alpha-hydroxy-16 beta-methylpregna-4,6-diene-3,20-dione (7), 17 alpha-acetoxy-16 beta-methylpregna-4,6-diene-3,20-dione (8), 17 alpha-acetoxy-6-bromo-16 beta-methylpregna-4,6-diene-3,20-dione (10), and 17 alpha-acetoxy-6-chloro-16 beta-methylpregna-4,6-diene-3,20-dione (11), were determined. The derivatives were evaluated on gonadectomized male hamster flank organs and seminal vesicles. The results indicate that topical applications of testosterone (T) on the flank organs increased the diameter of the pigmented spot. Similarly, the same phenomenon occurred on the glands treated with compound 11, whereas compound 10 decreased the size of the spot significantly. In this study, we determined the effects of several new steroids on the conversion of T to DHT in flank organs and seminal vesicles. The results show that compound 10 inhibited T conversion to DHT, but compound 11, at a dose of 200 mu g, stimulated T conversion in both flank organs and seminal vesicles. However, when 2 mg of compound 11 was applied, it inhibited the conversion of T to DHT, suggesting that this compound also represses gonadotropin release. The difference between compounds 10 and II involves the electronegativity of the halogen at the C-6 position of the progesterone skeleton. These data clearly indicate that by decreasing the electronegativity of the halogen at C-6 (compound 10), 5 alpha-reductase is inhibited in both tissues and at different pHs. On the other hand, when the electronegativity of the halogen atom was increased (11), there was a much lower inhibitory effect on the conversion of T to DHT. (C) 1999 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00018-5