methyl aureanindol-16-ene-21-oate | 1202026-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl aureanindol-16-ene-21-oate
• 英文别名: methyl (1S,5S,6R,8aS)-5-(1H-indol-3-ylmethyl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylate
• CAS: 1202026-03-6
• 化学式: C₂₄H₃₁NO₂
• 分子量: 365.516
• InChiKey: NNODWARDQFGXKL-GEPCJHAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl aureanindol-16-ene-21-oate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.25h， 生成 aureanindol-16-en-21-yl acetate
  参考文献：
  名称：

  Synthesis and biological activity of polyalthenol and pentacyclindole analogues

  摘要：

  A series of indole sesquiterpenes analogues of polyalthenol and pentacyclindole have been synthesized starting from ent-halimic acid in order to test their biological activity. These analogues include diverse oxidation levels at the sesquiterpenyl moiety and different functionalization on the indole ring. All synthetic derivatives were tested against a representative panel of Gram positive and Gram negative bacterial strains, and the human solid tumour cell lines A549 (non-small cell lung), HBL-100 (breast), HeLa (cervix), SW1573 (non-small cell lung), T-47D (breast) and WiDr (colon). Overall, the compounds presented activity against the cancer cell lines. The resulting lead, displaying a polyalthenol scaffold, showed GI50 values in the range 1.2-5.7 1.1M against all cell lines tested. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.012
• 作为产物：
  描述：

  methyl (1S,5S,6R,8aS)-1,5,6-trimethyl-5-(3-oxopropyl)-1,2,3,5,6,7,8,8a-octahydronaphthalene-1-carboxylate 、 苯肼 在 溶剂黄146 作用下， 反应 4.0h， 以95%的产率得到methyl aureanindol-16-ene-21-oate
  参考文献：
  名称：

  通过3-（丁-3-烯基）吲哚衍生物的环化反应合成六氢咔唑

  摘要：

  描述了产生具有六氢咔唑结构的多环化合物的3-（丁-3-烯基）吲哚衍生物的新环化。在这一反应中，一步就生成了三个立体异构中心，该过程可以被认为是氨基胺和微管蛋白A之间生物遗传关系的证据。

  DOI：

  10.1016/j.tet.2009.09.090

文献信息

• Synthesis of hexahydrocarbazoles by cyclisation of 3-(but-3-enyl) indole derivatives
  作者：Isidro S. Marcos、Rosalina F. Moro、Isabel Costales、Miguel A. Escola、Pilar Basabe、David Díez、Julio G. Urones

  DOI：10.1016/j.tet.2009.09.090

  日期：2009.12

  A new cyclisation of 3-(but-3-enyl) indole derivatives that produces policyclic compounds with a hexahydrocarbazole structure is described. In this reaction three stereogenic centres are generated in one step, and this process can be considered as evidence of the biogenetic relationship between anominine and tubingensin A.

  描述了产生具有六氢咔唑结构的多环化合物的3-（丁-3-烯基）吲哚衍生物的新环化。在这一反应中，一步就生成了三个立体异构中心，该过程可以被认为是氨基胺和微管蛋白A之间生物遗传关系的证据。
• Synthesis and biological activity of polyalthenol and pentacyclindole analogues
  作者：Isidro S. Marcos、Rosalina F. Moro、Isabel Costales、Pilar Basabe、David Díez、Ana Gil、Faustino Mollinedo、Fátima Pérez-de la Rosa、Eduardo Pérez-Roth、José M. Padrón

  DOI：10.1016/j.ejmech.2013.12.012

  日期：2014.2

  A series of indole sesquiterpenes analogues of polyalthenol and pentacyclindole have been synthesized starting from ent-halimic acid in order to test their biological activity. These analogues include diverse oxidation levels at the sesquiterpenyl moiety and different functionalization on the indole ring. All synthetic derivatives were tested against a representative panel of Gram positive and Gram negative bacterial strains, and the human solid tumour cell lines A549 (non-small cell lung), HBL-100 (breast), HeLa (cervix), SW1573 (non-small cell lung), T-47D (breast) and WiDr (colon). Overall, the compounds presented activity against the cancer cell lines. The resulting lead, displaying a polyalthenol scaffold, showed GI50 values in the range 1.2-5.7 1.1M against all cell lines tested. (C) 2013 Elsevier Masson SAS. All rights reserved.