2-(1H-imidazol-2-yl)-1H-indole | 1401958-81-3

• 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: 2-(1H-imidazol-2-yl)-1H-indole
• 英文别名: Indolylimidazole
• CAS: 1401958-81-3
• 化学式: C₁₁H₉N₃
• 分子量: 183.213
• InChiKey: LKXJUIISRKMRCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.5
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1H-imidazol-2-yl)-1H-indole 、 bis(3,4,5-trimethoxyphenyl)disulfide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 25.0~110.0 ℃ 、1.72 MPa 条件下， 反应 0.22h， 以22%的产率得到2-(1H-imidazol-2-yl)-3-(3,4,5-trimethoxyphenyl)sulfanyl-1H-indole
  参考文献：
  名称：

  Toward Highly Potent Cancer Agents by Modulating the C-2 Group of the Arylthioindole Class of Tubulin Polymerization Inhibitors

  摘要：

  New arylthioindole derivatives having different cyclic substituents at position 2 of the indole were synthesized as anticancer agents. Several compounds inhibited tubulin polymerization at submicromolar concentration and inhibited cell growth at low nanomolar concentrations. Compounds 18 and 57 were superior to the previously synthesized S. Compound 18 was exceptionally potent as an inhibitor of cell growth: it showed IC50 = 1.0 nM in MCF-7 cells, and it was uniformly active in the whole panel of cancer cells and superior to colchicine and combretastatin A-4. Compounds 18, 20, 55, and 57 were notably more potent than vinorelbine, vinblastine, and paclitaxel in the NCl/ADR-RES and Messa/Dx5 cell lines, which overexpress P-glycoprotein. Compounds 18 and 57 showed initial vascular disrupting effects in a tumor model of liver rhabdomyosarcomas at 15 mg/kg intravenous dosage. Derivative 18 showed water solubility and higher metabolic stability than 5 in human liver microsomes.

  DOI：

  10.1021/jm3013097
• 作为产物：
  描述：

  1H-吲哚-2-甲醛 在 碘苯二乙酸 、 potassium carbonate 作用下， 以 二甲基亚砜 、 叔丁醇 为溶剂， 反应 15.5h， 生成 2-(1H-imidazol-2-yl)-1H-indole
  参考文献：
  名称：

  Toward Highly Potent Cancer Agents by Modulating the C-2 Group of the Arylthioindole Class of Tubulin Polymerization Inhibitors

  摘要：

  New arylthioindole derivatives having different cyclic substituents at position 2 of the indole were synthesized as anticancer agents. Several compounds inhibited tubulin polymerization at submicromolar concentration and inhibited cell growth at low nanomolar concentrations. Compounds 18 and 57 were superior to the previously synthesized S. Compound 18 was exceptionally potent as an inhibitor of cell growth: it showed IC50 = 1.0 nM in MCF-7 cells, and it was uniformly active in the whole panel of cancer cells and superior to colchicine and combretastatin A-4. Compounds 18, 20, 55, and 57 were notably more potent than vinorelbine, vinblastine, and paclitaxel in the NCl/ADR-RES and Messa/Dx5 cell lines, which overexpress P-glycoprotein. Compounds 18 and 57 showed initial vascular disrupting effects in a tumor model of liver rhabdomyosarcomas at 15 mg/kg intravenous dosage. Derivative 18 showed water solubility and higher metabolic stability than 5 in human liver microsomes.

  DOI：

  10.1021/jm3013097

文献信息

• Non-Nucleoside Reverse Transcriptase Inhibitors
  申请人：Wolkenberg Scott E.

  公开号：US20100168097A1

  公开（公告）日：2010-07-01

  Compounds of Formula I: Formula (I); are HIV reverse transcriptase inhibitors, wherein R 1 , R 2 , R 3 , R 4 and R 5 are defined herein. The compounds of Formula (I) and their pharmaceutically acceptable salts are useful in the inhibition of HIV reverse transcriptase, the prophylaxis and treatment of infection by HIV and in the prophylaxis, delay in the onset, and treatment of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

  公式I的化合物：公式（I）的R1、R2、R3、R4和R5的定义如下，是HIV反转录酶抑制剂。公式（I）的化合物及其药学上可接受的盐在抑制HIV反转录酶、预防和治疗HIV感染以及预防、延缓发病和治疗艾滋病方面是有用的。这些化合物及其盐可以作为药物组成部分使用，可选地与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用。
• A method of reducing serum uric acid and/or increasing renal uric acid clearance with thromboxane synthetase inhibitor and/or thromboxane receptor antagonist
  申请人：CIBA-GEIGY AG

  公开号：EP0449764A2

  公开（公告）日：1991-10-02

  A method of reducing serum uric acid and/or increasing renal clearance of uric acid in a mammal in need thereof comprising administering to such mammal a uricosuric effective amount of a thromboxane synthetase inhibitor, a thromboxane receptor antagonist, or both in a combined uricosuric effective amount is disclosed. Compositions having one or more of the foregoing in combination with one or more uricosurics are also set forth and included within this invention.

  本发明公开了一种降低有需要的哺乳动物的血清尿酸和/或增加其肾脏对尿酸的清除率的方法，该方法包括向哺乳动物施用尿酸有效量的血栓素合成酶抑制剂、血栓素受体拮抗剂或两者的组合尿酸有效量。具有一种或多种上述物质与一种或多种尿素合剂的组合物也被提出并包括在本发明中。
• NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS
  申请人：Merck & Co., Inc.

  公开号：EP1898928A2

  公开（公告）日：2008-03-19
• MARKERS ASSOCIATED WITH SENSITIVITY TO INHIBITORS OF HUMAN DOUBLE MINUTE 2 (MDM2)
  申请人：Novartis AG

  公开号：EP2880447A2

  公开（公告）日：2015-06-10
• JPH02188579A
  申请人：——

  公开号：JPH02188579A

  公开（公告）日：1990-07-24