trans-methyl-3β-<(6-deoxy-α-L-mannopyranosyl)oxy>14β,21-epoxychola-4,20(21),22-trienolide | 114829-74-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: trans-methyl-3β-<(6-deoxy-α-L-mannopyranosyl)oxy>14β,21-epoxychola-4,20(21),22-trienolide
• 英文别名: methyl 3β-<(6-deoxy-α-L-mannopyranosyl)oxy>-14β,21-epoxychola-4,20,22-trien-24-oate；methyl 14β,21-epoxychola-4,20,22-trienoate；methyl (E)-3-[(1S,2R,7S,10R,11S,14R,15R)-10,14-dimethyl-7-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-18-oxapentacyclo[13.3.2.01,14.02,11.05,10]icosa-5,16-dien-16-yl]prop-2-enoate
• CAS: 114829-74-2
• 化学式: C₃₁H₄₄O₈
• 分子量: 544.686
• InChiKey: KHGXSGGOJSAQTO-RECXVUGTSA-N

物化性质

• 沸点：
  683.8±55.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  trans-methyl-3β-<(6-deoxy-α-L-mannopyranosyl)oxy>14β,21-epoxychola-4,20(21),22-trienolide 在 盐酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以78%的产率得到trans-3β-<(6-deoxy-α-L-mannopyranosyl)oxy>-14β,21-epoxychola-4,20(21),22-trienoic acid
  参考文献：
  名称：

  Studies on cardiac ingredients of plants. V. Chemical transformation of proscillaridin and biological activities of derivatives.

  摘要：

  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。

  DOI：

  10.1248/cpb.36.48
• 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 trans-methyl-3β-<(6-deoxy-α-L-mannopyranosyl)oxy>14β,21-epoxychola-4,20(21),22-trienolide
  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

• Photochemical transformation of bufadienolide into 14β,21-epoxycholanes via photolytic methanolysis
  作者：Takahiro Tanase、Nobutoshi Murakami、Akito Nagatsu、Jinsaku Sakakibara

  DOI：10.1039/p19930002217

  日期：——

  A naturally occurring bufadienolide, proscillaridin 1a, and its aglycone, scillarenin 1b, were subjected to photolysis in MeOH with a high-pressure mercury are lamp to afford novel 14β, 21-epoxy-21-methoxycholadienes 2a–4a and 2b–4b and 14β,21-epoxy -22-methoxycholadienes 5a, 5b, 6a and 6b, along with 14β,21-epoxycholatrienes 7a and 7b. These structures were elucidated from spectroscopical evidence

  天然存在的bufadienolide，proscillaridin 1a及其糖苷配基，scillarenin 1b在MeOH和高压汞灯中进行光解，得到新颖的14β，21-环氧-21-甲氧基胆二烯2a-4a，2b-4b和14β ，21-环氧-22-甲氧基胆二烯5a，5b，6a和6b，以及14β，21-环氧胆甾烯7a和7b。从包括NOE实验在内的光谱证据阐明了这些结构。
• Studies on cardiac ingredients. Part VI: Photochemical transformation of bufadienolide.
  作者：Nobutoshi MURAKAMI、Takahiro TANASE、Shin-ichi NAGAI、Taisei UEDA、Jinsaku SAKAKIBARA

  DOI：10.1248/cpb.39.1330

  日期：——

  The photolysis of a bufadienolide glycoside, proscillaridin (1), in MeOH with a high-pressure mercury arc lamp afforded the three novel compounds (2-4) with a 14β, 21-epoxy-21-methoxychola-4, 20(22)-diene skeleton, and the known compound (5). The structures of 2, 3, and 4 were elucidated spectroscopically.

  使用高压汞弧灯在甲醇中光解蟾蜍二烯内酯糖苷 Proscillaridin (1)，得到三种具有 14β, 21-epoxy-21-methoxychola-4, 20(22) 的新型化合物 (2-4) -二烯骨架，以及已知的化合物(5)。通过光谱阐明了2、3和4的结构。
• 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。
• MORI, JUN;NAGAI, SHIN-ICHI SAKAKIBARA JINSAKU;TAKEYA, KAZUMI;HOTTA, YOSHI+, CHEM. AND PHARM. BULL., 36,(1988) N 1, 49-59
  作者：MORI, JUN、NAGAI, SHIN-ICHI SAKAKIBARA JINSAKU、TAKEYA, KAZUMI、HOTTA, YOSHI+

  DOI：——

  日期：——