methyl (14E)-14-ethylidene-6-methoxy-2-methyl-19-[(propanoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1^{9,15}.0^{1,9}.0^{3,8}.0^{12,17}]nonadeca-3(8),4,6-triene-19-carboxylate | 1225197-04-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 柯楠因类生物碱
• 英文名称: methyl (14E)-14-ethylidene-6-methoxy-2-methyl-19-[(propanoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1^{9,15}.0^{1,9}.0^{3,8}.0^{12,17}]nonadeca-3(8),4,6-triene-19-carboxylate
• 英文别名: methyl (1R,9S,11S,14E,15S,17S,19R)-14-ethylidene-6-methoxy-2-methyl-19-(propanoyloxymethyl)-18-oxa-2,12-diazahexacyclo[9.6.1.19,15.01,9.03,8.012,17]nonadeca-3(8),4,6-triene-19-carboxylate
• CAS: 1225197-04-5
• 化学式: C₂₆H₃₂N₂O₆
• 分子量: 468.55
• InChiKey: QFMJKUUFXXEIGZ-ANTLQJRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  alstiphyllanine G 、 丙酸酐 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到methyl (14E)-14-ethylidene-6-methoxy-2-methyl-19-[(propanoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1^{9,15}.0^{1,9}.0^{3,8}.0^{12,17}]nonadeca-3(8),4,6-triene-19-carboxylate
  参考文献：
  名称：

  Alstiphyllanines E–H, picraline and ajmaline-type alkaloids from Alstonia macrophylla inhibiting sodium glucose cotransporter

  摘要：

  Three new picraline-type alkaloids, alstiphyllanines E-G (1-3) and a new ajmaline-type alkaloid, alstiphyllanine H (4) were isolated from the leaves of Alstonia macrophylla together with 16 related alkaloids (5-20). Structures and stereochemistry of 1-4 were fully elucidated and characterized by 2D NMR analysis. Alstiphyllanines E and F (1 and 2) showed moderate Na+-glucose cotransporter (SGLT1 and SGLT2) inhibitory activity. A series of a hydroxy substituted derivatives 21-28 at C-17 of the picraline-type alkaloids have been derived as having potent SGLT inhibitory activity. 10-Methoxy-N(1)-methylburnamine-17-O-veratrate (6) exhibited potent inhibitory activity, suggesting that the presence of an ester side chain at C-17 may be important to show SGLT inhibitory activity. Structure activity relationship of alstiphyllanines on inhibitory activity of SGLT was discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.077

文献信息

• Alstiphyllanines E–H, picraline and ajmaline-type alkaloids from Alstonia macrophylla inhibiting sodium glucose cotransporter
  作者：Hiroko Arai、Yusuke Hirasawa、Abdul Rahman、Idha Kusumawati、Noor Cholies Zaini、Seizo Sato、Chihiro Aoyama、Jiro Takeo、Hiroshi Morita

  DOI：10.1016/j.bmc.2010.01.077

  日期：2010.3

  Three new picraline-type alkaloids, alstiphyllanines E-G (1-3) and a new ajmaline-type alkaloid, alstiphyllanine H (4) were isolated from the leaves of Alstonia macrophylla together with 16 related alkaloids (5-20). Structures and stereochemistry of 1-4 were fully elucidated and characterized by 2D NMR analysis. Alstiphyllanines E and F (1 and 2) showed moderate Na+-glucose cotransporter (SGLT1 and SGLT2) inhibitory activity. A series of a hydroxy substituted derivatives 21-28 at C-17 of the picraline-type alkaloids have been derived as having potent SGLT inhibitory activity. 10-Methoxy-N(1)-methylburnamine-17-O-veratrate (6) exhibited potent inhibitory activity, suggesting that the presence of an ester side chain at C-17 may be important to show SGLT inhibitory activity. Structure activity relationship of alstiphyllanines on inhibitory activity of SGLT was discussed. (C) 2010 Elsevier Ltd. All rights reserved.