3β-acetoxy-5-pregnen-21-oic acid | 23330-16-7

• 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: 3β-acetoxy-5-pregnen-21-oic acid
• 英文别名: 3β-acetoxypregn-5-en-21-oic acid；3β-Acetoxy-Δ⁵-pregnen-21-saeure；3β-acetoxy-pregnen-(5)-oic acid-(21)；3β-Acetoxy-pregnen-(5)-saeure-(21)；3beta-Acetoxypregn-5-en-21-oic acid；2-[(3S,8S,9S,10R,13R,14S,17R)-3-acetyloxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]acetic acid
• CAS: 23330-16-7
• 化学式: C₂₃H₃₄O₄
• 分子量: 374.521
• InChiKey: VYJMTDQISHITBT-VWIVDJIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-5-pregnen-21-oic acid 在 palladium on activated charcoal 氢气 作用下， 生成 3β-Acetoxy-5α-pregnan-21-saeure
  参考文献：
  名称：

  Steroids and related natural products. LIV. Bufadienolides. 7. Synthesis of 3.beta.-acetoxy-5.alpha.-l4.alpha.-bufa-20,22-dienolide

  摘要：

  DOI：

  10.1021/jo00830a031
• 作为产物：
  描述：

  3β-acetoxyetienic acid 在 草酰氯 、 silver(I) acetate 作用下， 以 1,4-二氧六环 、 乙醚 、 水 、 甲苯 为溶剂， 反应 4.17h， 生成 3β-acetoxy-5-pregnen-21-oic acid
  参考文献：
  名称：

  New steroidal oxazolines, benzoxazoles and benzimidazoles related to abiraterone and galeterone

  摘要：

  Seven new oxazoline, benzoxazole and benzimidazole derivatives were synthesized from 3 beta-acetoxyandrosta-5,16-dien-17-carboxylic, 3 beta-acetoxyandrost-5-en-17 beta-carboxylic and 3 beta-acetoxypregn-5-en-21-oic acids. Docking to active site of human 17 alpha-hydroxylase/17,20-lyase revealed that all oxazolines, as well as benzoxazoles and benzimidazoles comprising Delta(16) could form stable complexes with enzyme, in which steroid moiety is positioned similarly to that of abiraterone and galeterone, and nitrogen atom coordinates heme iron, while 16,17-saturated benzoxazoles and benzimidazoles could only bind in a position where heterocycle is located nearly parallel to heme plane. Modeling of the interaction of new benzoxazole and benzimidazole derivatives with androgen receptor revealed the destabilization of helix 12, constituting activation function 2 (AF2) site, by mentioned compounds, similar to one induced by known antagonist galeterone. The synthesized compounds inhibited growth of prostate carcinoma LNCaP and PC-3 cells at 96 h incubation; the potency of 2'-(3-hydroxyandrosta-5,16-dien-17-yl)-4',5'-dihydro-1',3'-oxazole and 2'-(3 beta-hydroxyandrosta-5,16-dien-17-yl)-benzimidazole was superior and could inspire further investigations of these compounds as potential anti-cancer agents.

  DOI：

  10.1016/j.steroids.2019.108534

文献信息

• Über Steroide und Sexualhormone. (109. Mitteilung). Über zwei weitere Homologe der digitaloiden Aglucone
  作者：Pl. A. Plattner、E. Hardegger、H. Bucher

  DOI：10.1002/hlca.660280117

  日期：——
• Drasar, Pavel; Pouzar, Vladimir; Cerny, Ivan, Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 4, p. 1224 - 1232
  作者：Drasar, Pavel、Pouzar, Vladimir、Cerny, Ivan、Havel, Miroslav

  DOI：——

  日期：——
• Schreck,W., Diss. <E.T.H. Zuerick 1941> S. 53
  作者：Schreck,W.

  DOI：——

  日期：——