4-[(3S,8R,9S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-1-N,2-N-bis(2-methylpropyl)benzene-1,2-dicarboxamide | 141351-96-4

• 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-[(3S,8R,9S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-1-N,2-N-bis(2-methylpropyl)benzene-1,2-dicarboxamide
• CAS: 141351-96-4
• 化学式: C₄₁H₆₂N₂O₈
• 分子量: 710.952
• InChiKey: SQKVLMSQNRGPAN-SRNUHKLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  51
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  异丁胺 、 dimethyl 4-<3β-<(6-deoxy-α-L-mannopyranosyl)oxy>-14β-hydroxyandrost-4-en-17β-yl>phthalate 以 甲醇 为溶剂， 反应 72.0h， 以40%的产率得到4-[(3S,8R,9S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-1-N,2-N-bis(2-methylpropyl)benzene-1,2-dicarboxamide
  参考文献：
  名称：

  Studies on Cardiac Ingredients of Plants. IX. Chemical Transformation of Proscillaridin by Utilizing Its 1,4-Cycloadducts as Key Compounds and Biological Activities of Their Derivatives.

  摘要：

  通过强心苷 proscillaridin（1）与乙酰二羧酸二甲酯和丙炔酸甲酯的 Diels-Alder 反应制备了三种具有碳甲氧基或二甲氧基邻苯二甲酰基的芳香族化合物（2-4），并将其转化为醇、羧酸和酰胺。利用来自狗肾脏和离体豚鼠乳头肌的 Na+、K+-腺苷三磷酸酶（Na+、K+-ATP 酶），对所得衍生物的生物活性进行了评估。虽然所得衍生物的生物活性不如 1，但对位取代的苄醇类（5）、甲基苄酰胺类（9a 和 10a）和乙基苄酰胺类（9b 和 10b）对 Na+、K+-ATPase 活性的抑制作用几乎与天然存在的强心甙类（如地高辛和地高辛）相同。

  DOI：

  10.1248/cpb.40.327

文献信息

• Studies on Cardiac Ingredients of Plants. IX. Chemical Transformation of Proscillaridin by Utilizing Its 1,4-Cycloadducts as Key Compounds and Biological Activities of Their Derivatives.
  作者：Takahiro TANASE、Nobutoshi MURAKAMI、Shin-ichi NAGAI、Taisei UEDA、Jinsaku SAKAKIBARA、Hiroaki ANDO、Yoshihiro HOTTA、Kazumi TAKEYA

  DOI：10.1248/cpb.40.327

  日期：——

  Three aromatic compounds (2-4) possessing a carbomethoxyl group or a dimethoxyphthaloyl group, prepared by the Diels-Alder reaction of the cardiac glycoside, proscillaridin (1), with dimethyl acetylenedicarboxylate and methyl propiolate, were transformed into alcohols, carboxylic acids and amides. The biological activities of hte resulting derivatives were evaluated by the use of Na+, K+-adenosine triphosphatase (Na+, K+-ATPase) from dog kidney and isolated guinea-pig papillary muscle. Although the biological activities of the resulting derivatives were less potent than that of 1, a para-substituted benzylalcohol (5), methylbenzamides (9a and 10a), and ethylbenzamides (9b and 10b) inhibited the activity of Na+, K+-ATPase almost as potently as naturally occurring cardiac glycosides such as digoxin and digitoxin.

  通过强心苷 proscillaridin（1）与乙酰二羧酸二甲酯和丙炔酸甲酯的 Diels-Alder 反应制备了三种具有碳甲氧基或二甲氧基邻苯二甲酰基的芳香族化合物（2-4），并将其转化为醇、羧酸和酰胺。利用来自狗肾脏和离体豚鼠乳头肌的 Na+、K+-腺苷三磷酸酶（Na+、K+-ATP 酶），对所得衍生物的生物活性进行了评估。虽然所得衍生物的生物活性不如 1，但对位取代的苄醇类（5）、甲基苄酰胺类（9a 和 10a）和乙基苄酰胺类（9b 和 10b）对 Na+、K+-ATPase 活性的抑制作用几乎与天然存在的强心甙类（如地高辛和地高辛）相同。