3β-[(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy]-17β-methylene-5β-androstane 14β,20-epoxide | 188976-61-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 3β-[(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy]-17β-methylene-5β-androstane 14β,20-epoxide
• 英文别名: [(2S,3S,4R,5R,6R)-4,5-dibenzoyloxy-6-[[(1S,2R,5R,7S,10S,11S,14R,15S)-10,14-dimethyl-17-oxapentacyclo[13.2.2.01,14.02,11.05,10]nonadecan-7-yl]oxy]-2-methyloxan-3-yl] benzoate
• CAS: 188976-61-6
• 化学式: C₄₇H₅₄O₉
• 分子量: 762.94
• InChiKey: XRVGLUGQKSXDIZ-XYMWFOEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  56
• 可旋转键数：
  11
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3β-[(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy]-17β-methylene-5β-androstane 14β,20-epoxide 在 氨 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以85%的产率得到3β-(α-L-rhamnopyranosyloxy)-17β-methylene-5β-androstane 14β,20-epoxide
  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：

  14-hydroxy-3β-<(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy>-21-nor-5β,14β-pregnane-20-carboxaldehyde 在 吡啶 、 lithium tri(t-butoxy)aluminum hydride 、 对甲苯磺酰氯 作用下， 以 乙醚 为溶剂， 反应 16.0h， 生成 3β-[(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy]-17β-methylene-5β-androstane 14β,20-epoxide
  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

文献信息

• Synthesis and Structure−Activity Relationships of 17β-Substituted 14β-Hydroxysteroid 3-(α-<scp>l</scp>-Rhamnopyranoside)s:  Steroids That Bind to the Digitalis Receptor
  作者：John F. Templeton、Yangzhi Ling、Kirk Marat、Frank S. LaBella

  DOI：10.1021/jm960880l

  日期：1997.5.1

  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.