3β-acetoxy-5β-pregn-14-en-20-one | 18221-13-1

• 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: 3β-acetoxy-5β-pregn-14-en-20-one
• 英文别名: 3beta-Acetoxy-5beta-pregn-14-en-20-one；[(3S,5R,8R,9S,10S,13R,17S)-17-acetyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 18221-13-1
• 化学式: C₂₃H₃₄O₃
• 分子量: 358.521
• InChiKey: JUAATDNYHZEPLN-FCFLTHKLSA-N

物化性质

• 沸点：
  452.9±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-5β-pregn-14-en-20-one 在 sodium cyanoborohydride 、 溶剂黄146 、 对甲苯磺酰肼 、 zinc(II) iodide 作用下， 生成 3β-acetoxy-5β-pregn-14-ene
  参考文献：
  名称：

  A New Approach to the Design of Novel Inhibitors of Na⁺,K⁺-ATPase:  17α-Substituted Seco-D 5β-Androstane as Cassaine Analogues

  摘要：

  A new three-dimensional model for the relative binding mode of cassaine 1 and digitoxigenin 2 at the digitalis receptor site is proposed on the basis of the structural and conformational similarities among 1, 2 and its 14,15-seco analogues 3 and 4. Accordingly, the speculation that also 17 alpha-substituted derivatives of the digitalis 5 beta,14 beta-androstane skeleton could efficiently bind to the Na+,K+-ATPase receptor is put forward and verified through the synthesis of some related compounds. The binding affinity shown by 2-(N,N-dimethylamino)ethyl 3 beta,14-dihydroxy-5 beta,14 beta-androstane-17 alpha-acrylate 6 (IC50 = 5.89 mu M) and, much more significantly, by the corresponding 14,15-seco-14-oxo derivative 9 (IC50 = 0.12 mu M) substantiates the new hypothesis and opens new prospects to the design of novel inhibitors of Na+,K+-ATPase as potential positive inotropic compounds.

  DOI：

  10.1021/jm980108d
• 作为产物：
  描述：

  Sioraside 在 吡啶 、 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 9.0h， 生成 3β-acetoxy-5β-pregn-14-en-20-one
  参考文献：
  名称：

  A pregnane glycoside from Streblus asper

  摘要：

  DOI：

  10.1016/0031-9422(92)80075-p

文献信息

• Studies on the synthesis of cardiotonic steroids. I. Efficient synthesis of cardenolides.
  作者：EIICHI YOSHII、TORU KOIZUMI、HIROKAZU IKESHIMA、KYUICHI OZAKI、ICHIHIRO HAYASHI

  DOI：10.1248/cpb.23.2496

  日期：——

  Practical synthetic methods of natural cardenolides are illustrated in the syntheses of xysmalogenin and digitoxigenin. The new routes employ pregn-14-en-20-one as key intermediate which was prepared by partial reduction of 14, 16-dien-20-one with triphenylstannane or triethylsilane. A general and efficient method was devised for obtaining cardenolides consisting of (1) 21-methylsulfenylation of pregnen-20-one, (2) the reaction of the resulting 21-methylthio derivative with bromoacetate and zinc, (3) alumina chromatography of epoxy ester obtained from the S-methylated Reformatsky product.

  天然卡登诺酮的实用合成方法在xysmalogenin和digitoxigenin的合成中得到了展示。这些新路线使用孕苯-14-烯-20-酮作为关键中间体，该中间体通过用三苯基锡或三乙基硅烷对14, 16-二烯-20-酮进行部分还原制备。设计了一种通用且高效的方法来获得卡登诺酮，包括：（1）孕烯-20-酮的21-甲基亚硫酰化；（2）将得到的21-甲基硫衍生物与溴乙酸酯和锌反应；（3）对从S-甲基化Reformatsky产物中获得的环氧酯进行铝土矿柱层析。
• Seco-d steroids active on the cardiovascular system, processes for their
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：US05955632A1

  公开（公告）日：1999-09-21

  New seco-D steroid derivatives, processes for their preparation and pharmaceutical compositions are provided, which are active on the cardiovascular system. The seco-D steroid derivatives have the following general formula (I): ##STR1##

  本发明提供了新的seco-D类类固醇衍生物、其制备方法和药物组合物，其对心血管系统具有活性。这些seco-D类类固醇衍生物具有以下通式(I)：##STR1##
• Theil, Fritz; Lindig, Claus; Repke, Kurt, Zeitschrift fur Chemie, 1980, vol. 20, # 10, p. 372 - 373
  作者：Theil, Fritz、Lindig, Claus、Repke, Kurt

  DOI：——

  日期：——
• New seco-D steroids active on the cardiovascular system, processes for their preparation and pharmaceutical compositions containing them
  申请人：SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0825177B1

  公开（公告）日：2000-04-05
• US5955632A
  申请人：——

  公开号：US5955632A

  公开（公告）日：1999-09-21