4-[(17-oxo-5-androsten-3β-yl)oxy]-4-oxobutanoic acid | 61082-99-3

• 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: 4-[(17-oxo-5-androsten-3β-yl)oxy]-4-oxobutanoic acid
• CAS: 61082-99-3
• 化学式: C₂₃H₃₂O₅
• 分子量: 388.504
• InChiKey: ZRXKPMPYFANAFF-MPQCOTKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  80.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[(17-oxo-5-androsten-3β-yl)oxy]-4-oxobutanoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 生成
  参考文献：
  名称：

  Design of potent inhibitors for Schistosoma japonica glutathione S-transferase

  摘要：

  We implemented both structure-based drug design and the concept of polyvalency to discover a series of potent and unsymmetrical Schistosoma japonicum glutathione S-transferase (SjGST) inhibitors 10-12. This strategy achieved not only an excellent enhancement (10- to 490-fold) in the inhibitory potency, compared to the monofunctional analogues 1-5, but was also an effective modification by selecting a hydrophobic moiety with a flexible linker. The designed compounds with a low micromolar hit demonstrate special values in refining the new generation of SjGST inhibitors. The stoichiometry of the binding is one inhibitor molecule per SjGST monomer via isothermal titration calorimetric measurement. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.077
• 作为产物：
  描述：

  Acetic acid (3S,8R,9S,10R,13S,14S)-17-cyano-3-hydroxy-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 在 吡啶 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 生成 4-[(17-oxo-5-androsten-3β-yl)oxy]-4-oxobutanoic acid
  参考文献：
  名称：

  A new class of long-acting hormonal steroid preparation: synthesis of dimeric androgens coupled at C3-C3 and C-17-C3 and of an androgen-progestogen combination

  摘要：

  3beta-Hydroxy-4-androsten-17-one was prepared from 4-androsten-3,17-dione according to the method of Klimstra and Colton (1) and dimerized by means of esterification with succinic acid. The reduction with lithium-tri-t-butoxyaluminium hydride gave a testosterone derivative coupled between C3-C3 which showed after a single injection of 10 mg a protracted but relatively weak androgenic effect in castrated male rats. The direct esterification of testosterone hemisuccinate with 4-androsten-3beta, 17beta-diol gave the testosterone derivative coupled between C17-C3 which showed a more even and more protracted time response curve than testosterone enanthate. The testosterone-ethynodiol succinate also coupled between C17-C3, showed an androgenic depot-effect similar to that of the dimeric C17-C3 testosterone derivative.

  DOI：

  10.1016/0039-128x(76)90128-8