2-(1-trityl-1H-imidazol-4-yl)benzonitrile | 450415-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-(1-trityl-1H-imidazol-4-yl)benzonitrile
• 英文别名: 2-(1-Trityl-1H-imidazol-4-yl)-benzonitrile；2-(1-tritylimidazol-4-yl)benzonitrile
• CAS: 450415-80-2
• 化学式: C₂₉H₂₁N₃
• 分子量: 411.506
• InChiKey: SMLKYPJICULARP-UHFFFAOYSA-N

物化性质

• 沸点：
  610.4±43.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-trityl-1H-imidazol-4-yl)benzonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 2-(1-trityl-1H-imidazol-4-yl)benzylamine
  参考文献：
  名称：

  Discovery and Evaluation of Potent P₁ Aryl Heterocycle-Based Thrombin Inhibitors

  摘要：

  In an effort to discover potent, clinically useful thrombin inhibitors, a rapid analogue synthetic approach was used to explore the P-1 region. Various benzylamines were coupled to a pyridine/pyrazinone P-2-P-3 template. One compound with an o-thiadiazole benzylic substitution was found to have a thrombin K-i of 0.84 nM. A study of ortho-substituted five-membered-ring heterocycles was undertaken and subsequently demonstrated that the o-triazole and tetrazole rings were optimal. Combination of these potent P-1 aryl heterocycles with a variety of P-2-P-3 groups produced a compound with an extraordinary thrombin inhibitory activity of 1.4 pM. It is hoped that this potency enhancement in P-1 will allow for more diversification in the P-2-P-3 region to ultimately address additional pharmacological concerns.

  DOI：

  10.1021/jm030303e
• 作为产物：
  描述：

  4-(2-溴苯)-1H-咪唑 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 2-(1-trityl-1H-imidazol-4-yl)benzonitrile
  参考文献：
  名称：

  Discovery and Evaluation of Potent P₁ Aryl Heterocycle-Based Thrombin Inhibitors

  摘要：

  In an effort to discover potent, clinically useful thrombin inhibitors, a rapid analogue synthetic approach was used to explore the P-1 region. Various benzylamines were coupled to a pyridine/pyrazinone P-2-P-3 template. One compound with an o-thiadiazole benzylic substitution was found to have a thrombin K-i of 0.84 nM. A study of ortho-substituted five-membered-ring heterocycles was undertaken and subsequently demonstrated that the o-triazole and tetrazole rings were optimal. Combination of these potent P-1 aryl heterocycles with a variety of P-2-P-3 groups produced a compound with an extraordinary thrombin inhibitory activity of 1.4 pM. It is hoped that this potency enhancement in P-1 will allow for more diversification in the P-2-P-3 region to ultimately address additional pharmacological concerns.

  DOI：

  10.1021/jm030303e

文献信息

• [EN] THROMBIN INHIBITORS<br/>[FR] INHIBITEURS DE LA THROMBINE
  申请人：MERCK & CO INC

  公开号：WO2002064140A1

  公开（公告）日：2002-08-22

  Compounds of the invention are useful in inhibiting thrombin and associated thrombotic occlusions having the following structure: or a pharmaceutically acceptable salt thereof, wherein R2 is R3 is selected from the group consisting of 1) hydrogen, 2) halogen, 3) C 1-4 alkyl, 4) C 3-7 cycloalkyl, 5) CF3, 6) OCF3, 7) C 1-4 alkoxy, and 8) cyano; and R12 is a 5-membered heteroaryl ring having 2, 3, or 4 heteroatoms, provided that at least 1 heteroatom is N, and at most 1 of the heteroatoms is S, said ring being unsubstituted or substituted, at any one ring atom, with CH3.

  本发明的化合物在抑制凝血酶和相关的血栓闭塞方面有用，其结构如下：或其药学上可接受的盐，其中R2和R3选自以下组：1）氢，2）卤素，3）C 1-4 烷基，4）C 3-7 环烷基，5）CF3，6）O ，7）C 1-4 醇基，8）氰基；R12是一个具有2、3或4个杂原子的5元杂环芳基环，其中至少1个杂原子是N，至多1个杂原子是S，所述环未取代或在任何一个环原子上用CH3取代。
• Thrombin inhibitors
  申请人：——

  公开号：US20040097730A1

  公开（公告）日：2004-05-20

  Compounds of the invention are useful in inhibiting thrombin and associated thrombotic occlusions having the following structure: or a pharmaceutically acceptable salt thereof, wherein R2 is R3 is selected from the group consisting of 1) hydrogen, 2) halogen, 3) C 1-4 alkyl, 4) C 3-7 cycloalkyl, 5) CF3, 6) OCF3, 7) C 1-4 alkoxy, and 8) cyano; and R12 is a 5-membered heteroaryl ring having 2, 3, or 4 heteroatoms, provided that at least 1 heteroatom is N, and at most 1 of the heteroatoms is S, said ring being unsubstituted or substituted, at any one ring atom, with CH3. 1

  本发明的化合物具有以下结构，或其药学上可接受的盐，在抑制凝血酶和相关血栓闭塞方面有用，其中R2和R3从以下组中选择：1）氢，2）卤素，3）C 1-4 烷基，4）C 3-7 环烷基，5）CF3，6）O ，7）C 1-4 烷氧基和8）氰基；而R12是一个5元杂环芳基环，其中含有2、3或4个杂原子，至少1个杂原子是N，且最多1个杂原子是S，所述环在任何一个环原子上未取代或被取代，该取代基为CH3.
• THROMBIN INHIBITORS
  申请人：Merck & Co., Inc.

  公开号：EP1359913A1

  公开（公告）日：2003-11-12
• US7026324B2
  申请人：——

  公开号：US7026324B2

  公开（公告）日：2006-04-11