2-(1H-imidazol-1-yl)-3-methyl-1H-indole | 90833-98-0

• 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-1-yl)-3-methyl-1H-indole
• 英文别名: 2-imidazol-1-yl-3-methyl-1H-indole；2-(1-imidazolyl)-3-methyl-indole；2-(1-Imidazolyl)-3-methylindole
• CAS: 90833-98-0
• 化学式: C₁₂H₁₁N₃
• 分子量: 197.239
• InChiKey: LLDXJQVVAXBXHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1H-imidazol-1-yl)-3-methyl-1H-indole 生成 1-(p-carboxybenzyl)-2-(1-imidazolyl)-3-methylindole
  参考文献：
  名称：

  RENFROE, H. B.

  摘要：

  DOI：
• 作为产物：
  描述：

  咪唑 、 3-甲基吲哚 在 sodium hydroxide 、 溴 作用下， 以 1,4-二氧六环 、 盐酸 为溶剂， 生成 2-(1H-imidazol-1-yl)-3-methyl-1H-indole
  参考文献：
  名称：

  N-Substituted-2-(1-imidazolyl)indoles

  摘要：

  各种1-羧基酸取代的2-(1-咪唑基)吲哚及其功能衍生物是高度特异的血栓素合酶抑制剂。包括它们的合成、药物组合物、利用这些化合物进行治疗的方法以及用于它们合成的中间体。

  公开号：

  US04539410A1

文献信息

• Thromboxane synthetase inhibitory N-substituted-2-(1-imidazolyl)indoles
  申请人：Ciba-Geigy Corporation

  公开号：US04436746A1

  公开（公告）日：1984-03-13

  Various 1-carboxylic acid substituted-2-(1-imidazolyl)indoles and functional derivatives thereof are highly specific thromboxane synthetase inhibitors. Synthesis of, pharmaceutical compositions thereof, and methods of treatment utilizing such compounds are included.

  各种1-羧基取代的2-(1-咪唑基)吲哚及其功能衍生物是高度特异的血栓素合成酶抑制剂。包括这些化合物的合成、药物组合物以及利用这些化合物进行治疗的方法。
• Imidazole derivatives and salts thereof, their synthesis, and pharmaceutical formulations
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0003560A2

  公开（公告）日：1979-08-22

  Pharmaceutical formulations comprising an imidazole (or pharmaceutically acceptable salt thereof) of formula: wherein (i) A is an aliphatic hydrocarbon residue of from 1 to 4 carbon atoms and R is a naphthyl, tetrahydronaphthyl, heterocyclyl, arylthio, arylalkylthio, aryloxy, arylalkyloxy, arylhydroxymethylene, arylcarbonyl, arylalkylcarbonyl, alkyloxy, alkylthio or a substituted cycloalkyl or cycloalkenyl group or (ii) A is a -S02- group and R is aryl or heterocyclyl or (iii) A is a chemical bond and R is a heterocyclyl or substituted phenyl group, or (iv) A is an aliphatic hydrocarbon residue of from 1 to 3 carbon atoms and R is a halophenyl group. Some of these imidazoles and salts are novel. Methods of preparing the imidazoles are disclosed. The imidazoles and their salts are useful in the treatment or prophylaxis of thrombo-embolic conditions.

  药物制剂，包含式中的咪唑（或其药学上可接受的盐）： 其中 (i) A 是 1 至 4 个碳原子的脂族烃残基，R 是萘基、四氢萘基、杂环基、芳硫基、芳烷硫基、芳氧基、芳烷氧基、芳羟甲基、芳羰基、芳烷基羰基、烷氧基、烷硫基或取代的环烷基或环烯基，或 (ii) A 是-S02-基团，R 是芳基或杂环基，或 (iii) A 是化学键，R 是杂环基或取代苯基，或 (iv) A 是 1 至 3 个碳原子的脂肪烃残基，R 是卤代苯基。 其中一些咪唑和盐是新型的。 这些咪唑的制备方法已经公开。咪唑及其盐类可用于治疗或预防血栓栓塞。
• N-substituted-2-(1-imidazolyl)-indoles
  申请人：CIBA-GEIGY AG

  公开号：EP0107618A1

  公开（公告）日：1984-05-02

  The invention concerns compounds with thromboxane synthetase inhibitor properties of the formula I wherein Ri represents hydrogen or lower alkyl; lm represents 1-imidazolyl unsubstituted or substituted by lower alkyl, carboxy, lower alkoxycarbonyl or carbamoyl; R2 and R3 independently represent hydrogen, lower alkyl, halogen, trifluoromethyl, hydroxy, lower alkoxy, lower alkyl-(thio, sulfinyl or sulfonyl), or R2 and R3 together when attached to adjacent carbons represent lower alkylenedroxy; A represents alkylene of 1 to 12 carbon atoms, alkenylene of 2 to 12 carbon atoms, alkynylene of 2 to 12 carbon atoms, lower alkylenephenylene-lower al- kylene, lower alkylenephenylene, phenylene-lower alkylene, phenylene, a direct bond, lower alkylene-(thio or oxy)-lower alkylene, (thio- or oxy)-phenylene, lower alkylene-(thio- or oxy)-p) enylene, Phenylene-(thio or oxy)-lower alkylene or phenyl one lower alkenylene: B represents carboxy. lower alkoxycarbonyl, carbamoyl, mono- or di-lower alkylcarbamoyl, cyano, hydroxymethyl, hydroxycarbamoyl, 5-tetrazolyl or formyl; the N-oxides thereof; and salts thereof. They are prepared, for example, by condensing a compound corresponding to the formula I, in which the nitrogen atom carries only a hydrogen atom, with a reactive functional derivative of a compound of the formula HOCH2-A-B.

  本发明涉及具有血栓素合成酶抑制剂特性的式 I 化合物 其中Ri代表氢或低级烷基；lm代表未取代的或被低级烷基、羧基、低级烷氧基羰基或氨基甲酰基取代的1-咪唑基；R2和R3独立地代表氢、低级烷基、卤素、三氟甲基、羟基、低级烷氧基、低级烷基-（硫基、亚磺酰基或磺酰基），或R2和R3一起连接到相邻碳时代表低级烷基二氧基；A 代表 1 至 12 个碳原子的亚烷基、2 至 12 个碳原子的亚烯基、2 至 12 个碳原子 的亚炔基、低级亚烷基亚苯基、低级亚烷基亚苯基、亚苯基-低级亚烷基、苯基、直接键、低亚烷基-(硫代或氧基)-低亚烷基、(硫代或氧基)-亚苯基、低亚烷基-(硫代或氧基)-亚 苯基、苯基-(硫代或氧基)-低亚烷基或苯基一低烯基：B 代表羧基。它们包括：低级烷氧基羰基、氨基甲酰基、单或双低级烷基氨基甲酰基、氰基、羟甲基、羟基氨基甲酰基、5-四唑基或甲酰基；它们的 N-氧化物；以及它们的盐。 例如，通过将氮原子只带一个氢原子的式 I 所对应的化合物与式 HOCH2-A-B 所对应的化合物的活性官能团衍生物缩合，就可以制备这些化合物。
• Iodine-Catalyzed Oxidative Cross-Coupling of Indoles and Azoles: Regioselective Synthesis of <i>N</i>-Linked 2-(Azol-1-yl)indole Derivatives
  作者：Danupat Beukeaw、Kwanchanok Udomsasporn、Sirilata Yotphan

  DOI：10.1021/jo502933e

  日期：2015.4.3

  A highly efficient iodine-catalyzed regioselective oxidative cross-coupling of an indole C-H bond and azole N-H bond is described. This metal-free reaction can be easily carried out at room temperature under mild and environmentally friendly conditions and provides a series of N-linked 2-(azol-1-yl)indole derivatives in moderate to excellence yields.
• Metal-Free Coupling of Azoles with 2- and 3-Haloindoles Providing Access to Novel 2- or 3-(Azol-1-yl)indole Derivatives
  作者：Martin Poirier、Sébastien Goudreau、Jason Poulin、Jolaine Savoie、Pierre L. Beaulieu

  DOI：10.1021/ol100685p

  日期：2010.5.21

  Thermal or microwave-mediated heating of 2- or 3-haloindoles with azoles (pK(a) < 8) provides a straightforward, metal-free, and environmentally friendly access to novel 2-(azol-1-yl)indoles. Furthermore, previously unknown 2,3-bis(azolyl-1-yl)indoles can be prepared from 2,3-dihaloindoles by sequential reaction with two distinct azoles. This operationally simple acid-catalyzed process delivers novel indole derivatives in fair to excellent yields and expands the chemical diversity of substitutions that can be introduced on this medicinally important scaffold.