1,3-bis(1-methyl-1H-indole-3-yl)propane-1,3-dione | 959682-83-8

• 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(1-methyl-1H-indole-3-yl)propane-1,3-dione
• CAS: 959682-83-8
• 化学式: C₂₁H₁₈N₂O₂
• 分子量: 330.386
• InChiKey: OTTPJVRMMMEPPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  25.0
• 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(1-methyl-1H-indole-3-yl)propane-1,3-dione 在 盐酸羟胺 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以42%的产率得到3,3'-isoxazole-3,5-diylbis(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：

  吲哚 在 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1,3-bis(1-methyl-1H-indole-3-yl)propane-1,3-dione
  参考文献：
  名称：

  二氟硼二吲哚酮酸盐的合成、表征、荧光性质和 DFT 建模

  摘要：

  我们报告了一种简单而有效的策略，通过二氟硼化（BF2bdks 复合物）增强可见光谱中生物相容性双吲哚二酮（bdks）的荧光。发射光谱证明荧光量子产率从百分之几增加到>0.7。这种巨大的增量基本上与吲哚（-H、-Cl 和 -OCH3）的取代无关，并且对应于非辐射衰变机制方面激发态的显着稳定：非辐射衰变率降低了在二氟硼化时，从 109 s−1 到 108 s−1 高达一个数量级。激发态的稳定性足以实现大规模的 1O2 光敏化生产。评估了不同的时间相关 (TD) 密度泛函理论 (DFT) 方法模拟化合物电子特性的能力，其中 TD-B3LYP-D3 提供了最准确的激发能。计算将 bdks 和 BF2bdks 电子光谱中的第一个活性光学跃迁与 S0 → S1 跃迁相关联，分别对应于电子密度从吲哚到氧或 O-BF2-O 单元的转变。

  DOI：

  10.3390/molecules28124688

文献信息

• A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin
  作者：Anna Carbone、Virginia Spanò、Barbara Parrino、Cristina Ciancimino、Orazio Attanasi、Gianfranco Favi

  DOI：10.3390/molecules18032518

  日期：——

  A series of substituted ethyl 1-[(tert-butoxycarbonyl)amino]-2-methyl-5- (1-methyl-1H-indol-3-yl)-4-[(1-methyl-1H-indol-3-yl)carbonyl]-1H-pyrrole-3-carboxylates were prepared in excellent yields (82-98%) by one-pot reactions between β-dicarbonyl compounds 12a–e and 1,2-diaza-1,3-diene (DD) 13. Derivatives 10a,c–e, deazaanalogues of the bis-indole alkaloid topsentin, screened by the National Cancer Institute (Bethesda, MD, USA) in the in vitro one dose primary anticancer assay against a panel of about 60 human tumor cell lines, showed no significant activity, with the exception of compound 9e, which showed moderate activity against the HOP-92 cell line of the non small cell lung cancer sub-panel and the SNB-75 cell line of the CNS sub-panel.

  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。
• 3,5-Bis(3′-indolyl)pyrazoles, analogues of marine alkaloid nortopsentin: Synthesis and antitumor properties
  作者：Patrizia Diana、Anna Carbone、Paola Barraja、Annamaria Martorana、Ornella Gia、Lisa DallaVia、Girolamo Cirrincione

  DOI：10.1016/j.bmcl.2007.09.042

  日期：2007.11

  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.