3β-[(tri-O'-benzoyl-α-L-rhamnopyranosyl)oxy]-21-nitro-5β-pregnane-14β,20(R)-diol | 189102-09-8

• 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-[(tri-O'-benzoyl-α-L-rhamnopyranosyl)oxy]-21-nitro-5β-pregnane-14β,20(R)-diol
• CAS: 189102-09-8
• 化学式: C₄₈H₅₇NO₁₂
• 分子量: 839.98
• InChiKey: OYDHMCWVEFXOPU-FWZUQCSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  61.0
• 可旋转键数：
  11.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  180.96
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3β-[(tri-O'-benzoyl-α-L-rhamnopyranosyl)oxy]-21-nitro-5β-pregnane-14β,20(R)-diol 在 甲醇 、 4-二甲氨基吡啶 、 乙酸酐 作用下， 以 乙醚 为溶剂， 反应 17.45h， 生成 20(R)-methoxy-21-nitro-3β-(α-L-rhamnopyranosyloxy)-5β-pregnan-14β-ol
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 17β-Substituted 14β-Hydroxysteroid 3-(α-l-Rhamnopyranoside)s:  Steroids That Bind to the Digitalis Receptor

  摘要：

  The preparation of 17 beta-substituted 14 beta-hydroxysteroid C-3 alpha-L-rhamnopyranosides is described. These derivatives have a 14 beta,20-ether, 14 beta,20-lactone, or 17 beta-CH2CH2OH, -CH2CH2NH2, -CH=CHNO2(E), -CH=CHCOOH(E), -CH(OH)CH2NO2(R), -CH(OMe)CH2NO2(R), -CH2CH2COOH, or -CH(OH)CH2NH2(R) group. Derivatives were assayed in a radioligand binding assay for [H-3]ouabain in membranes from canine heart muscle. The digitalis ''receptor'' comprises isoenzymes of the ion-pumping enzyme, Na+,K+-ATPase. The 17 beta-CH=CHNO2(E), 17 beta-CH=CHCOOH(E), and 17 beta-CH(OMe)CH2NO2(R) derivatives were the most potent and equivalent to ouabain with low-nanomolar IC50 values. The very potent binding affinity of the disubstituted compound 17 beta-CH(OMe)CH2NO2(R) further demonstrates that 17 beta-unsaturated substitution is not required for potent binding affinity. This observation may be of value in the separation of cardiotonic and cardiotoxic effects. Tosylation of the 17 beta-CH2OH, prepared from the 17 beta-CHO by lithium aluminum hydride reduction, yielded the 14 beta,17 beta-ether. Synthesis of the 17 beta-CH2COOH gave the epimeric 14 alpha,17 alpha- and 14 beta, 17 beta-lactones. Structures have been established by NMR analysis.

  DOI：

  10.1021/jm960880l
• 作为产物：
  描述：

  硝基甲烷 、 14-hydroxy-3β-<(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy>-21-nor-5β,14β-pregnane-20-carboxaldehyde 在 potassium fluoride 作用下， 以 异丙醇 为溶剂， 反应 16.0h， 以38%的产率得到3β-[(tri-O'-benzoyl-α-L-rhamnopyranosyl)oxy]-21-nitro-5β-pregnane-14β,20(R)-diol
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 17β-Substituted 14β-Hydroxysteroid 3-(α-l-Rhamnopyranoside)s:  Steroids That Bind to the Digitalis Receptor

  摘要：

  The preparation of 17 beta-substituted 14 beta-hydroxysteroid C-3 alpha-L-rhamnopyranosides is described. These derivatives have a 14 beta,20-ether, 14 beta,20-lactone, or 17 beta-CH2CH2OH, -CH2CH2NH2, -CH=CHNO2(E), -CH=CHCOOH(E), -CH(OH)CH2NO2(R), -CH(OMe)CH2NO2(R), -CH2CH2COOH, or -CH(OH)CH2NH2(R) group. Derivatives were assayed in a radioligand binding assay for [H-3]ouabain in membranes from canine heart muscle. The digitalis ''receptor'' comprises isoenzymes of the ion-pumping enzyme, Na+,K+-ATPase. The 17 beta-CH=CHNO2(E), 17 beta-CH=CHCOOH(E), and 17 beta-CH(OMe)CH2NO2(R) derivatives were the most potent and equivalent to ouabain with low-nanomolar IC50 values. The very potent binding affinity of the disubstituted compound 17 beta-CH(OMe)CH2NO2(R) further demonstrates that 17 beta-unsaturated substitution is not required for potent binding affinity. This observation may be of value in the separation of cardiotonic and cardiotoxic effects. Tosylation of the 17 beta-CH2OH, prepared from the 17 beta-CHO by lithium aluminum hydride reduction, yielded the 14 beta,17 beta-ether. Synthesis of the 17 beta-CH2COOH gave the epimeric 14 alpha,17 alpha- and 14 beta, 17 beta-lactones. Structures have been established by NMR analysis.

  DOI：

  10.1021/jm960880l