1,3-bis(5-bromo-1-methyl-1H-indole-3-yl)propane-1,3-dione | 959682-87-2

• 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: 1,3-bis(5-bromo-1-methyl-1H-indole-3-yl)propane-1,3-dione
• CAS: 959682-87-2
• 化学式: C₂₁H₁₆Br₂N₂O₂
• 分子量: 488.178
• InChiKey: FMEXBSKIWODPHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,3-bis(5-bromo-1-methyl-1H-indole-3-yl)propane-1,3-dione 在 一水合肼 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 5-bromo-3-[3-(5-bromo-1-methylindol-3-yl)-1H-pyrazol-5-yl]-1-methylindole
  参考文献：
  名称：

  3,5-Bis(3′-indolyl)pyrazoles, analogues of marine alkaloid nortopsentin: Synthesis and antitumor properties

  摘要：

  series of 10 bis-indolylpyrazoles of type 9, 10 were obtained by cyclization of diketones 8 using hydrazine monohydrate or methylhydrazine in refluxing acetic acid/THF. Derivatives 9a,c,d were selected, by the National Cancer Institute (NCI, Bethesda, USA), to be evaluated against the full panel of about 60 human tumor cell lines derived from nine human cancer cell types and showed antiproliferative activity in the micromolar range. In particular, 9d, the most active compound was effective against all the tested cell lines with a GI(50) mean value of 3.23 mu M; TGI and LC50 values were 14.5 and 58.9 mu M having positive response on 91% and 41% of the tested cell lines, respectively. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.042
• 作为产物：
  描述：

  5-溴-1-甲基吲哚 、 丙二酰氯 以 二氯甲烷 为溶剂， 反应 2.0h， 以48%的产率得到1,3-bis(5-bromo-1-methyl-1H-indole-3-yl)propane-1,3-dione
  参考文献：
  名称：

  A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin

  摘要：

  通过 β-二羰基化合物 12a-e 和 1,2-二氮杂-1,3-二烯 (DD) 13 的一锅反应，制备了一系列取代的 1-[(叔丁氧羰基)氨基]-2-甲基-5-(1-甲基-1H-吲哚-3-基)-4-[(1-甲基-1H-吲哚-3-基)羰基]-1H-吡咯-3-羧酸乙酯，收率极高（82-98%）。衍生物 10a、c-e 是双吲哚生物碱托普生丁的脱氮类似物，经美国国家癌症研究所（Bethesda, MD, USA）在体外一剂一级抗癌试验中对约 60 种人类肿瘤细胞系进行筛选，结果显示，除化合物 9e 对非小细胞肺癌亚组的 HOP-92 细胞系和中枢神经系统亚组的 SNB-75 细胞系有中等活性外，其余化合物均无明显活性。

  DOI：

  10.3390/molecules18032518

文献信息

• Synthesis and antitumor activity of 2,5-bis(3′-indolyl)-furans and 3,5-bis(3′-indolyl)-isoxazoles, nortopsentin analogues
  作者：Patrizia Diana、Anna Carbone、Paola Barraja、Gerhard Kelter、Heinz-Herbert Fiebig、Girolamo Cirrincione

  DOI：10.1016/j.bmc.2010.04.061

  日期：2010.6.15

  A series of novel 2,5-bis(3'-indolyl)furans and 3,5-bis(3'-indolyl) isoxazoles were synthesized as antitumor agents. The antiproliferative activity was evaluated in vitro toward diverse human tumor cell lines. Initially 5 isoxazoles and 3 furan derivatives were tested against a panel of 10 human tumor cell lines and the most active derivatives 3c and 4a were selected to be evaluated in an extended panel of 29 cell lines. By exhibiting mean IC(50) values of 17.4 mu g/mL (3a) and 20.5 mu g/mL (4c), in particular 4c showed a high level of tumor selectivity toward the 29 cell lines. (C) 2010 Elsevier Ltd. All rights reserved.