(2R,3R,17R)-2,3-dihydro-2,17-cyclo-aureanindol-15-ene-21-yl acetate | 1202026-06-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (2R,3R,17R)-2,3-dihydro-2,17-cyclo-aureanindol-15-ene-21-yl acetate
• 英文别名: [(1R,2R,10R,12S,13R,17S)-12,13,17-trimethyl-3-azapentacyclo[10.7.1.02,10.04,9.016,20]icosa-4,6,8,16(20)-tetraen-17-yl]methyl acetate
• CAS: 1202026-06-9
• 化学式: C₂₅H₃₃NO₂
• 分子量: 379.543
• InChiKey: PSCMEKJMTKPDGD-CYMUHRKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R,17R)-2,3-dihydro-2,17-cyclo-aureanindol-15-ene-21-yl acetate 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 以27%的产率得到17R-2,17-cyclo-aureanindol-15-ene-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：

  aureanindol-16-ene-21-ol 在 吡啶 、 氢碘酸 作用下， 以 苯 为溶剂， 反应 2.5h， 生成 (2R,3R,17R)-2,3-dihydro-2,17-cyclo-aureanindol-15-ene-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

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。