6,7-Dibromo-4-methoxyisatin | 158920-10-6

• 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: 6,7-Dibromo-4-methoxyisatin
• 英文别名: 6,7-dibromo-4-methoxy-1H-indole-2,3-dione
• CAS: 158920-10-6
• 化学式: C₉H₅Br₂NO₃
• 分子量: 334.952
• InChiKey: KVXBEQUKQPQKEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-Dibromo-4-methoxyisatin 在 四丁基硫酸氢铵 ammonium hydroxide 、 sodium hydroxide 、 硼烷 、 双氧水 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 78.0h， 生成 6-(6-Bromoindol-3-yl)-3-<(6,7-dibromo-4-methoxy)indol-3-yl>-3-hydroxy-1-methyl-2,5-piperazinedione
  参考文献：
  名称：

  Total Synthesis of (.+-.)-Dragmacidin: A Cytotoxic Bis(indole)alkaloid of Marine Origin

  摘要：

  The total synthesis of the cytotoxic marine alkaloid, (+/-)-dragmacidin, trans-6,7-dibromo-3-[5-(6-bromo-1H-indol-3-yl)-4-methyl-2-piperazinyl]-1H-indol-4-ol, is described. The synthesis proceeds through the condensation of (6-bromoindol-3-yl)-alpha-(methylamino)acetonitrile with (6,7-dibromo-4-methoxyindol-3-yl)-alpha-oxoacetyl chloride. The product of this condensation was converted in two steps to an intermediate containing the central diketopiperazine ring which after reduction and deprotection gave the racemic natural product along with its cis isomer. An efficient preparation of 6,7-dibromo-4-methoxyindole is also presented.

  DOI：

  10.1021/jo00101a051
• 作为产物：
  描述：

  三氯乙醛 、 2,3-Dibromo-5-methoxyaniline 在 盐酸 、 甲烷磺酸 、 盐酸羟胺 、 sodium sulfate 作用下， 生成 6,7-Dibromo-4-methoxyisatin
  参考文献：
  名称：

  Total Synthesis of (.+-.)-Dragmacidin: A Cytotoxic Bis(indole)alkaloid of Marine Origin

  摘要：

  The total synthesis of the cytotoxic marine alkaloid, (+/-)-dragmacidin, trans-6,7-dibromo-3-[5-(6-bromo-1H-indol-3-yl)-4-methyl-2-piperazinyl]-1H-indol-4-ol, is described. The synthesis proceeds through the condensation of (6-bromoindol-3-yl)-alpha-(methylamino)acetonitrile with (6,7-dibromo-4-methoxyindol-3-yl)-alpha-oxoacetyl chloride. The product of this condensation was converted in two steps to an intermediate containing the central diketopiperazine ring which after reduction and deprotection gave the racemic natural product along with its cis isomer. An efficient preparation of 6,7-dibromo-4-methoxyindole is also presented.

  DOI：

  10.1021/jo00101a051

文献信息

• Imino-Indeno[1,2-c] quinoline derivatives, their preparation processes, and pharmaceutical compositions comprising the same
  申请人：Tzeng Cherng-Chyi

  公开号：US20090111987A1

  公开（公告）日：2009-04-30

  Disclosed herein are novel imino-indeno[1,2-c]quinoline derivatives of formula (I): or a pharmaceutically acceptable salt or solvate thereof, wherein each of the substituents is given the definition as set forth in the Specification and Claims. Also disclosed are the preparation processes of these derivatives, their synthetic precursors and their uses in the manufacture of pharmaceutical compositions for use in the treatment of cancers.

  本文披露了一种新型的imino-indeno[1,2-c]quinoline衍生物，其化学式为(I)：或其药用可接受的盐或溶剂，其中每个取代基的定义如规范和权利要求所述。还披露了这些衍生物的制备过程、它们的合成前体以及它们在制造用于治疗癌症的药物组合物中的用途。
• US7829567B2
  申请人：——

  公开号：US7829567B2

  公开（公告）日：2010-11-09
• Total Synthesis of (.+-.)-Dragmacidin: A Cytotoxic Bis(indole)alkaloid of Marine Origin
  作者：Biao Jiang、Joanne M. Smallheer、Carol Amaral-Ly、Mark A. Wuonola

  DOI：10.1021/jo00101a051

  日期：1994.11

  The total synthesis of the cytotoxic marine alkaloid, (+/-)-dragmacidin, trans-6,7-dibromo-3-[5-(6-bromo-1H-indol-3-yl)-4-methyl-2-piperazinyl]-1H-indol-4-ol, is described. The synthesis proceeds through the condensation of (6-bromoindol-3-yl)-alpha-(methylamino)acetonitrile with (6,7-dibromo-4-methoxyindol-3-yl)-alpha-oxoacetyl chloride. The product of this condensation was converted in two steps to an intermediate containing the central diketopiperazine ring which after reduction and deprotection gave the racemic natural product along with its cis isomer. An efficient preparation of 6,7-dibromo-4-methoxyindole is also presented.