5-[(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-methoxypyridin-2-one | 114829-67-3

• 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: 5-[(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-methoxypyridin-2-one
• CAS: 114829-67-3
• 化学式: C₃₁H₄₅NO₈
• 分子量: 559.7
• InChiKey: RRCDTTPDEDADDN-IBGMNLGYSA-N

物化性质

• 沸点：
  697.7±65.0 °C(predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-[(3S,8R,9S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(3R,4S,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]pyran-2-one 生成 5-[(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-methoxypyridin-2-one
  参考文献：
  名称：

  MORI, JUN;NAGAI, SHIN-ICHI SAKAKIBARA JINSAKU;TAKEYA, KAZUMI;HOTTA, YOSHI+, CHEM. AND PHARM. BULL., 36,(1988) N 1, 49-59

  摘要：

  DOI：

文献信息

• Studies on cardiac ingredients of plants. V. Chemical transformation of proscillaridin and biological activities of derivatives.
  作者：JUN MORI、SHIN-ICHI NAGAI、JINSAKU SAKAKIBARA、KAZUMI TAKEYA、YOSHIHIRO HOTTA

  DOI：10.1248/cpb.36.48

  日期：——

  In order to investigate the relationship between the chemical structures and the biological activities of proscillaridin (1) and related compounds, transformations of the lactone (1) into the lactams (2a-i) with monoalkylamines, into 1, 4-cycloadducts (3, 5) with dimethyl acetylenedicarboxylate, and into epoxides (6-8) with tris(acetylacetonate)iron(III)-H2O2 have been under-taken. Further, alkoxyalkylation of the teriary C14β-hydroxy group was carried out with alkoxyalkyl halides. The biological activities of the resulting proscillaridin derivatives were studied by the use of isolated guinea-pig papillary muscle preparations and an Na+, K+-adenosine triphosphatase preparation from dog kidney.Although the activities of proscillaridin derivatives were less potent than that of 1, compounds 2a, 2g, 3 and 9 showed slightly expanded concentration ranges of positive inotropic effect development on guinea-pig papillary muscle preparations.A significant correlation was obtained between the van der Waals volumes (Vw) and pIC50 values of 1 and 2a-h (r=-0.09, p<0.01).

  为了研究前胡素（1）和相关化合物的化学结构与生物活性之间的关系，研究人员用单烷基胺将内酯（1）转化为内酰胺（2a-i），用乙炔二羧酸二甲酯将其转化为 1，4-氰基产物（3，5），用三（乙酰丙酮）铁（III）-H2O2 将其转化为环氧化物（6-8）。此外，还使用烷氧基烷基卤化物对三级 C14β- 羟基进行了烷氧基烷基化。通过使用分离的豚鼠乳头肌制备物和狗肾脏的 Na+、K+-腺苷三磷酸酶制备物，研究了所得到的前胡素衍生物的生物活性。虽然前胡素衍生物的活性不如前胡素1，但化合物2a、2g、3和9在豚鼠乳头肌制备物上显示出的正性肌力作用发展浓度范围略有扩大。