1,4-bis(5-methoxy-1-methyl-1H-indole-3-yl)butane-1,4-dione | 937803-75-3

• 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: 1,4-bis(5-methoxy-1-methyl-1H-indole-3-yl)butane-1,4-dione
• CAS: 937803-75-3
• 化学式: C₂₄H₂₄N₂O₄
• 分子量: 404.466
• InChiKey: VVVIIRFSXXPHSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.46
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,4-bis(5-methoxy-1-methyl-1H-indole-3-yl)butane-1,4-dione 在 polyphosphoric acid 作用下， 反应 5.0h， 以55%的产率得到3,3'-furan-2,5-diylbis(5-methoxy-1-methyl-1H-indole)
  参考文献：
  名称：

  Synthesis and antitumor activity of 2,5-bis(3′-indolyl)-furans and 3,5-bis(3′-indolyl)-isoxazoles, nortopsentin analogues

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.04.061
• 作为产物：
  描述：

  5-甲氧基吲哚 在 TDA-1 potassium tert-butylate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 1,4-bis(5-methoxy-1-methyl-1H-indole-3-yl)butane-1,4-dione
  参考文献：
  名称：

  Synthesis and antitumor properties of 2,5-bis(3′-indolyl)thiophenes: Analogues of marine alkaloid nortopsentin

  摘要：

  A series of 11 bis-indolylthiophenes of type 8-10 were obtained by cyclization of diketones 4 and 7 using Lawesson's reagent. Derivatives 8c, 9c, 9d, and 10c were selected to be evaluated in the full panel of about 60 human tumor cell lines derived from nine human cancer cell types and showed antiproliferative activity generally in the micromolar range. The most sensitive cell lines were: CCRF-CEM, MOLT-4, HL60 (TB), and RPMI-8226 of the leukemia subpanel, HT29 and HCC-2998 cell lines of the colon sub-panel, NCI-H522 of the non-small cell lung cancer sub-panel, LOX IMVI of the melanoma sub-panel, and UO-31 of the renal cancer sub-panel. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.065

文献信息

• Synthesis and anti-tumor activity of marine alkaloids
  作者：Shiyang Zhou、Gangliang Huang、Guangying Chen

  DOI：10.1016/j.bmcl.2021.128009

  日期：2021.6

  Marine alkaloids were divided into five categories from the perspective of anti-tumor activity. The optimization process, chemical synthesis, anti-tumor activity evaluation and structure–activity relationship of various compounds were discussed.

  海洋生物碱从抗肿瘤活性的角度分为五类。讨论了各种化合物的优化过程、化学合成、抗肿瘤活性评价和构效关系。
• Synthesis and Antiproliferative Activity of 2,5-bis(3′-Indolyl)pyrroles, Analogues of the Marine Alkaloid Nortopsentin
  作者：Anna Carbone、Barbara Parrino、Paola Barraja、Virginia Spanò、Girolamo Cirrincione、Patrizia Diana、Armin Maier、Gerhard Kelter、Heinz-Herbert Fiebig

  DOI：10.3390/md11030643

  日期：——

  2,5-bis(3'-Indolyl)pyrroles, analogues of the marine alkaloid nortopsentin, were conveniently prepared through a three step procedure in good overall yields. Derivatives 1a and 1b exhibited concentration-dependent antitumor activity towards a panel of 42 human tumor cell lines with mean IC50 values of 1.54 μM and 0.67 μM, respectively. Investigating human tumor xenografts in an ex-vivo clonogenic assay

  2,5-双(3'-吲哚基)吡咯，海洋生物碱nortopsentin的类似物，通过三步程序以良好的总产率方便地制备。衍生物 1a 和 1b 对一组 42 种人类肿瘤细胞系表现出浓度依赖性抗肿瘤活性，平均 IC50 值分别为 1.54 μM 和 0.67 μM。在体外克隆形成试验中研究人类肿瘤异种移植物揭示了选择性抗肿瘤活性，而敏感的肿瘤模型分散在各种肿瘤组织类型中。