5,6,11,12,17,18,23,24-octahydrocyclododeca[1,2-b:4,5-b': 7,8-b":10,11-b'"]tetraindole

• 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: 5,6,11,12,17,18,23,24-octahydrocyclododeca[1,2-b:4,5-b': 7,8-b":10,11-b'"]tetraindole
• 英文别名: 5,6,11,12,17,18,23,24-octahydrocyclododeca[1,2-b:4,5-b':7,8-b'':10,11-b''']tetraindole；10,20,30,40-tetrazanonacyclo[31.7.0.03,11.04,9.013,21.014,19.023,31.024,29.034,39]tetraconta-1(33),3(11),4,6,8,13(21),14,16,18,23(31),24,26,28,34,36,38-hexadecaene
• 化学式: C₃₆H₂₈N₄
• 分子量: 516.645
• InChiKey: GFMFKAGRKAFRON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  40
• 可旋转键数：
  0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.2
• 氢给体数：
  4
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  芦竹碱 在 sodium 、 硫酸二甲酯 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以75%的产率得到5,6,11,12,17,18-hexahydrocyclononane[1,2-b:4,5-b':7,8-b'']triindole
  参考文献：
  名称：

  Convenient Synthesis of 5,6,11,12,17,18- Hexahydrocyclononal[1,2-b:4,5-b‘:7,8-b‘ ‘]triindole, a Novel Phytoestrogen

  摘要：

  An efficient one-pot synthesis is described of 5,6,11,12,17,18-hexahydrocyclononal[1,2-b:4,5-b':7,8-b"]triindole (CTr), a potent estrogen agonist from food plants. For the procedure, gramine is treated with dimethyl sulfate and sodium in ethanol at room temperature. Quenching of the reaction with water and workup of the product provides CTr in approximately 75% yield.

  DOI：

  10.1021/jo020415y

文献信息

• Synthesis and Biological Evaluation of a γ-Cyclodextrin-based Formulation of the Anticancer Agent 5,6,11,12,17,18,23,24- Octahydrocyclododeca[1,2-b:4,5-b’:7,8-b’’:10,11-b’’’]tetraindole (CTet)
  作者：Simone Lucarini、Mauro De Santi、Francesca Antonietti、Giorgio Brandi、Giuseppe Diamantini、Alessandra Fraternale、Maria Filomena Paoletti、Andrea Tontini、Mauro Magnani、Andrea Duranti

  DOI：10.3390/molecules15064085

  日期：——

  5,6,11,12,17,18,23,24-octahydrocyclododeca[1,2-b:4,5-b’:7,8-b’’:10,11- b’’’]tetrai ndole (CTet), an indole-3-carbinol (I3C) metabolite endowed with anticancer properties, is poorly soluble in the solvents most frequently used in biological tests. This study indicates that the use of γ-cyclodextrin (γ-CD) avoids this problem. Formulated with γ-CD CTet is a potent inhibitor of DNA synthesis in both estrogen receptor positive (MCF-7) and estrogen receptor negative (MDA-MB-231) human breast cell lines (IC50 = 1.20 ± 0.04 μM and 1.0 ± 0.1 μM, respectively).

  5,6,11,12,17,18,23,24-八氢环十二烷[1,2-b:4,5-b':7,8-b'':10,11-b''']四吲哚（CTet）是一种具有抗癌特性的吲哚-3-甲醇（I3C）代谢物，在生物测试中最常用的溶剂中溶解度很低。本研究表明，使用γ-环糊精（γ-CD）可避免这一问题。用 γ-CD 配制的 CTet 是雌激素受体阳性（MCF-7）和雌激素受体阴性（MDA-MB-231）人类乳腺细胞系 DNA 合成的强效抑制剂（IC50 分别为 1.20 ± 0.04 μM 和 1.0 ± 0.1 μM）。
• A practical and expeditious method for the preparation of the potential anticancer agent 5,6,11,12,17,18,23,24-octahydrocyclododeca[1,2-b:4,5-b′:7,8-b″:10,11-b‴]tetraindole (CTet)
  作者：Simone Lucarini、Francesca Antonietti、Andrea Tontini、Paola Mestichelli、Mauro Magnani、Andrea Duranti

  DOI：10.1016/j.tetlet.2011.03.117

  日期：2011.6

  A new synthetic method to obtain the potential anticancer agent 5,6,11,12,17,18,23,24-octahydrocyclododeca[1,2-6:4,5-b':7,8-b '':10,11-b''']tetraindole ((let), starting from 1H-indole-3-carboxaldehyde and sulfamide, is described. Although a mixture of CTet and cyclic indole trimer (CTr) is formed, higher CTet/CTr ratio (4:6) and Cret yield (15%) make our protocol more favorable than those reported in the literature. A discussion on the possible reaction mechanism is reported. (C) 2011 Elsevier Ltd. All rights reserved,
• Tetramerous derivative of indole-3-carbinol with anti-carcinogenic activity and method of synthesis of said derivative
  申请人：Universita' Degli Studi Di Urbino

  公开号：EP1395595B1

  公开（公告）日：2012-02-15
• US7645788B2
  申请人：——

  公开号：US7645788B2

  公开（公告）日：2010-01-12
• Convenient Synthesis of 5,6,11,12,17,18- Hexahydrocyclononal[1,2-<i>b</i>:4,5-<i>b</i>‘:7,8-<i>b</i>‘ ‘]triindole, a Novel Phytoestrogen
  作者：Richard E. Staub、Leonard F. Bjeldanes

  DOI：10.1021/jo020415y

  日期：2003.1.1

  An efficient one-pot synthesis is described of 5,6,11,12,17,18-hexahydrocyclononal[1,2-b:4,5-b':7,8-b"]triindole (CTr), a potent estrogen agonist from food plants. For the procedure, gramine is treated with dimethyl sulfate and sodium in ethanol at room temperature. Quenching of the reaction with water and workup of the product provides CTr in approximately 75% yield.