(E)-1-(3,4-dimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-(3,4-dimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
• 英文别名: (2E)-1-(3,4-Dimethoxyphenyl)-3-(1H-indol-3-YL)prop-2-EN-1-one
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: WHQKFHYEADSDIL-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  piperidine-1-carboxamidine hydrochloride 、 (E)-1-(3,4-dimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one 在 盐酸 、 sodium isopropylate 作用下， 以 异丙醇 为溶剂， 反应 8.0h， 生成 3-[6-(3,4-dimethoxyphenyl)-2-piperidin-1-ylpyrimidin-4-yl]-1H-indole
  参考文献：
  名称：

  Synthesis of substituted indole derivatives as a new class of antimalarial agents

  摘要：

  A series of substituted indole derivatives were synthesized and evaluated for their in vitro antimalarial activity against P. falciparum. Out of the 24 compounds synthesized six compounds have shown MIC of 1 mu g/mL. These compounds are in vitro several folds more active than pyrimethamine. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.011
• 作为产物：
  描述：

  3-吲哚甲醛 、 3,4-二甲氧基苯乙酮 在 哌啶 作用下， 以 乙醇 为溶剂， 以92%的产率得到(E)-1-(3,4-dimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one
  参考文献：
  名称：

  吲哚查耳酮：针对结核分枝杆菌的设计，合成，体外和计算机评估。

  摘要：

  设计并合成了吲哚查耳酮作为一组有希望的抗结核分枝杆菌H37Rv菌株的化合物。在此化合物库中，（E）-1-（呋喃-3-基）-3-（1H-吲哚-3-基）丙-2-烯-1-一（18），（E）-3- （1H-吲哚-3-基）-1-（噻吩-2-基）丙-2-烯-1-一（20）和（E）-2-（（1H-吲哚-2-基）亚甲基）环戊烷-1-酮（24）在50μg/ ml时显示出高抗结核活性，MIC值分别为210、197和236μM。电脑模拟研究表明，化合物18的结合模式类似于针对KasA蛋白的FAS-II抑制剂（如INH或硫霉素）。细胞毒性测定结果表明，化合物18、20和24对人巨核细胞和鼠B细胞无细胞毒性。

  DOI：

  10.1016/j.ejmech.2020.112358

文献信息

• Anti-inflammatory, analgesic and antipyretic 4,6-disubstituted 3-cyano-2-aminopyridines
  作者：Fedele Manna、Franco Chimenti、Adriana Bolasco、Bruna Bizzarri、Walter Filippelli、Amelia Filippelli、Luigi Gagliardi

  DOI：10.1016/s0223-5234(99)80057-9

  日期：1999.3

  4,6-diaryl and 4,6-aryl-indolyl substituted 3-cyano-2-aminopyridines were synthesized and submitted to evaluation for their anti-inflammatory, analgesic and antipyretic activity. The electronegativity of the substituents and their displacement on the 4- or 6-aryl ring of the 4,6-diaryl-3-cyano-2-aminopyridine nucleus (3a-q) influenced the anti-inflammatory activity which was higher in the presence of electron-realising groups. The introduction of the indol-3-yl substituent in the 4-position of the 3-cyano-2-aminopyridine nucleus (6a-x) increased the anti-inflammatory and analgesic power, but there was no evidence of the relationship among the electronic characteristic of the substituents, their displacement on the 6-phenyl ring and the activity. Conversely, the displacement of the 2-hydroxyphenyl group in the 4-position (4a-e) and of the indol-3-yl group in the 6-position (8h-w) decreased the anti-inflammatory activity. All derivatives did not show any significative antipyretic activity. (C) Elsevier, Paris.
• Synthesis of substituted indole derivatives as a new class of antimalarial agents
  作者：Anu Agarwal、Kumkum Srivastava、S.K. Puri、Prem M.S. Chauhan

  DOI：10.1016/j.bmcl.2005.04.011

  日期：2005.6

  A series of substituted indole derivatives were synthesized and evaluated for their in vitro antimalarial activity against P. falciparum. Out of the 24 compounds synthesized six compounds have shown MIC of 1 mu g/mL. These compounds are in vitro several folds more active than pyrimethamine. (c) 2005 Elsevier Ltd. All rights reserved.
• Indole chalcones: Design, synthesis, in vitro and in silico evaluation against Mycobacterium tuberculosis
  作者：Deepthi Ramesh、Annu Joji、Balaji Gowrivel Vijayakumar、Aiswarya Sethumadhavan、Maheswaran Mani、Tharanikkarasu Kannan

  DOI：10.1016/j.ejmech.2020.112358

  日期：2020.7

  compounds against H37Rv strain of Mycobacterium tuberculosis. Within this library of compounds, (E)-1-(furan-3-yl)-3-(1H-indol-3-yl)prop-2-en-1-one (18), (E)-3-(1H-indol-3-yl)-1-(thiophen-2-yl)prop-2-en-1-one (20) and (E)-2-((1H-indol-2-yl)methylene)cyclopentan-1-one (24) displayed high anti-tubercular activity at 50 μg/ml with MIC values of 210, 197 and 236 μM respectively. The in-silico studies revealed

  设计并合成了吲哚查耳酮作为一组有希望的抗结核分枝杆菌H37Rv菌株的化合物。在此化合物库中，（E）-1-（呋喃-3-基）-3-（1H-吲哚-3-基）丙-2-烯-1-一（18），（E）-3- （1H-吲哚-3-基）-1-（噻吩-2-基）丙-2-烯-1-一（20）和（E）-2-（（1H-吲哚-2-基）亚甲基）环戊烷-1-酮（24）在50μg/ ml时显示出高抗结核活性，MIC值分别为210、197和236μM。电脑模拟研究表明，化合物18的结合模式类似于针对KasA蛋白的FAS-II抑制剂（如INH或硫霉素）。细胞毒性测定结果表明，化合物18、20和24对人巨核细胞和鼠B细胞无细胞毒性。