1-(2-aminobenzyl)benzotriazole | 403599-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1-(2-aminobenzyl)benzotriazole
• 英文别名: 2-[(benzotriazol-1-yl)methyl]phenylamine；2-(1H-1,2,3-Benzotriazol-1-ylmethyl)aniline；2-(benzotriazol-1-ylmethyl)aniline
• CAS: 403599-76-8
• 化学式: C₁₃H₁₂N₄
• 分子量: 224.265
• InChiKey: SJDIUDDDNBDZBW-UHFFFAOYSA-N

物化性质

• 沸点：
  471.4±28.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-aminobenzyl)benzotriazole 在 硫酸 、 sodium nitrite 作用下， 以60%的产率得到2-(1H-Benzotriazol-1-ylmethyl)phenol
  参考文献：
  名称：

  New 5-substituted-1-(2-hydroxybenzoyl)-benzotriazoles, potassium channel activators. IV

  摘要：

  This paper reports the synthesis of a series of new 5-substituted-1-(2-hydroxybenzoyl)-benzotriazoles, which have been tested for their activity as possible activators of potassium channels. In rat aortic rings, the 'opened' derivatives 1a-f, intermediates of synthesis, showed vasorelaxing properties, with appreciable values of potency. However, the most remarkable effects were recorded for the 2-hydroxybenzoylbenzotriazoles 3a-f, which showed full vasorelaxing efficacy and high potency values. The introduction of a 2-hydroxybenzyl substituent in the 1 position of the benzotriazole ring (compound 7) strongly decreased the activity, showing the importance of the electron-acceptor carbonyl function. The best compound, 3b, was further investigated, in order to evaluate the possible mechanism of action involved in the vasodilator activity. In the vascular model, different potassium channel blockers inhibited the effects of the compound, and an increase of the levels of membrane depolarisation induced a significant reduction of the recorded responses. Compound 3b was also tested in a model of isolated rat heart, retroperfused through the aorta and submitted to a global ischemia/reperfusion cycle. In such an experimental condition, 3b showed an interesting cardioprotective activity. All the above observations are in agreement with the hypothesis of a mechanism linked to the activation of potassium channels. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01146-6
• 作为产物：
  描述：

  1-(2-nitrobenzyl)-1H-benzo[d][1,2,3]triazole 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以93%的产率得到1-(2-aminobenzyl)benzotriazole
  参考文献：
  名称：

  New 5-substituted-1-(2-hydroxybenzoyl)-benzotriazoles, potassium channel activators. IV

  摘要：

  This paper reports the synthesis of a series of new 5-substituted-1-(2-hydroxybenzoyl)-benzotriazoles, which have been tested for their activity as possible activators of potassium channels. In rat aortic rings, the 'opened' derivatives 1a-f, intermediates of synthesis, showed vasorelaxing properties, with appreciable values of potency. However, the most remarkable effects were recorded for the 2-hydroxybenzoylbenzotriazoles 3a-f, which showed full vasorelaxing efficacy and high potency values. The introduction of a 2-hydroxybenzyl substituent in the 1 position of the benzotriazole ring (compound 7) strongly decreased the activity, showing the importance of the electron-acceptor carbonyl function. The best compound, 3b, was further investigated, in order to evaluate the possible mechanism of action involved in the vasodilator activity. In the vascular model, different potassium channel blockers inhibited the effects of the compound, and an increase of the levels of membrane depolarisation induced a significant reduction of the recorded responses. Compound 3b was also tested in a model of isolated rat heart, retroperfused through the aorta and submitted to a global ischemia/reperfusion cycle. In such an experimental condition, 3b showed an interesting cardioprotective activity. All the above observations are in agreement with the hypothesis of a mechanism linked to the activation of potassium channels. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01146-6

文献信息

• Novel pyridine derivative and pyrimidine derivative
  申请人：Matsushima Tomohiro

  公开号：US20050277652A1

  公开（公告）日：2005-12-15

  A compound represented by the following formula, a salt thereof or a hydrate of the foregoing has an excellent hepatocyte growth factor receptor (HGFR) inhibitory activity, and exhibits anti-tumor activity, angiogenesis inhibitory activity and cancer metastasis inhibitory activity. [R 1 represents C 1-6 alkyl or the like; R 2 and R 3 represent hydrogen; R 4 , R 5 , R 6 , and R 7 may be the same or different and each represents hydrogen, halogen, C 1-6 alkyl or the like; R 8 represents hydrogen or the like; R 9 represents C 1-6 alkyl or the like; V 1 represents oxygen or the like; V 2 represents oxygen or sulfur; W represents —NH— or the like; X represents —CH═, nitrogen or the like; and Y represents oxygen or the like.]

  以下化合物的分子式，其盐或前述水合物具有出色的肝细胞生长因子受体（HGFR）抑制活性，并表现出抗肿瘤活性、抑制血管生成活性和抑制癌转移活性。 [R 1 代表C 1-6 烷基或类似物；R 2 和R 3 代表氢；R 4 ，R 5 ，R 6 和R 7 可以相同也可以不同，每个代表氢、卤素、C 1-6 烷基或类似物；R 8 代表氢或类似物；R 9 代表C 1-6 烷基或类似物；V 1 代表氧或类似物；V 2 代表氧或硫；W代表—NH—或类似物；X代表—CH═、氮或类似物；Y代表氧或类似物。]
• <i>n</i>-butyllithium-mediated reactions of 1-(2-azidoarylmethyl)- 1<i>H</i>-benzotriazoles with alkyl halides
  作者：Taehoon Kim、Kyongtae Kim

  DOI：10.1002/jhet.275

  日期：——

  n-BuLi (2.5 equiv.) in THF at −78°C, followed by an addition of alkyl halides such as allyl, benzyl, and ethyl bromides with stirring for 2 h at room temperature afforded 2-(dialkylamino)-3-(benzotriazol-1-yl)-2H-indazoles (), 3-(benzotriazol- 1-yl)-2H-indazoles (), 2-[(benzotriazol-1-yl)methyl]arylamine (), and 2-[(benzotriazol-1-yl)(alkyl) methyl]arylamine (). J. Heterocyclic Chem., 2010.

  1-（2-叠氮芳基甲基）-1 H-苯并三唑的处理（），在-78°C下于THF中加入正丁基锂（2.5当量），然后在室温下搅拌2小时后加入烷基卤，例如烯丙基，苄基和乙基溴，得到2-（二烷基氨基）-3 -（苯并三唑-1-基）-2 H-吲唑（），3-（苯并三唑-1-基）-2 H-吲唑类（），2-[（（苯并三唑-1-基）甲基]芳基胺（）和2-[（（苯并三唑-1-基）（烷基）甲基]芳基胺（）。J.杂环化​​学.2010。
• Novel pyridine derivatives and pyrimidine derivatives (3)
  申请人：Matsushima Tomohiro

  公开号：US20080319188A1

  公开（公告）日：2008-12-25

  A compound represented by the following formula, a salt thereof or a hydrate of the foregoing has an excellent hepatocyte growth factor receptor (HGFR) inhibitory activity, and exhibits anti-tumor activity, angiogenesis inhibitory activity and cancer metastasis inhibitory activity. [R 1 represents a 3- to 10-membered non-aromatic heterocyclic group or the like; R 2 and R 3 represent hydrogen; R 4 , R 5 , R 6 , and R 7 may be the same or different and each represents hydrogen, halogen, C 1-6 alkyl or the like; R 8 represents hydrogen or the like; R 9 represents a 3- to 10-membered non-aromatic heterocyclic group or the like; n represents an integer of 1 or 2; X represents —CH═, nitrogen or the like.]

  以下化合物，其盐或水合物，具有优异的肝细胞生长因子受体（HGFR）抑制活性，表现出抗肿瘤活性、抑制血管生成活性和癌症转移抑制活性。[其中，R1代表3-至10-成员的非芳香族杂环基团等；R2和R3代表氢；R4、R5、R6和R7可以相同或不同，每个代表氢、卤素、C1-6烷基或类似物；R8代表氢或类似物；R9代表3-至10-成员的非芳香族杂环基团等；n代表1或2的整数；X代表-CH═，氮或类似物。]
• Novel pyridine Derivative and Pyrimidine Derivative (1)
  申请人：Matsushima Tomohiro

  公开号：US20070270421A1

  公开（公告）日：2007-11-22

  A compound represented by the following formula, a salt thereof or a hydrate of the foregoing has an excellent hepatocyte growth factor receptor (HGFR) inhibitory activity, and exhibits anti-tumor activity, angiogenesis inhibitory activity and cancer metastasis inhibitory activity. [R 1 represents C 1-6 alkyl or the like; R 2 and R 3 represent hydrogen; R 4 , R 5 , R 6 , and R 7 may be the same or different and each represents hydrogen, halogen, C 1-6 alkyl or the like; R 8 represents hydrogen or the like; R 9 represents C 1-6 alkyl or the like; V 1 represents oxygen or the like; V 2 represents oxygen or sulfur; W represents —NH— or the like; X represents —CH═, nitrogen or the like; and Y represents oxygen or the like.]

  以下化合物的公式，其盐或水合物具有出色的肝细胞生长因子受体（HGFR）抑制活性，并表现出抗肿瘤活性，抑制血管生成活性和癌症转移抑制活性。 [其中，R1代表C1-6烷基或类似物; R2和R3代表氢; R4，R5，R6和R7可能相同或不同，每个代表氢，卤素，C1-6烷基或类似物; R8代表氢或类似物; R9代表C1-6烷基或类似物; V1代表氧或类似物; V2代表氧或硫; W代表—NH—或类似物; X代表—CH═、氮或类似物; Y代表氧或类似物。]
• NOVEL PYRIDINE DERIVATIVES AND PYRIMIDINE DERIVATIVES (3)
  申请人：MATSUSHIMA Tomohiro

  公开号：US20100075944A1

  公开（公告）日：2010-03-25

  A compound represented by the following formula, or a salt thereof or a hydrate of the foregoing, has excellent hepatocyte growth factor receptor (HGFR) inhibitory activity, and exhibits anti-tumor activity, angiogenesis inhibitory activity, and cancer metastasis inhibitory activity. R 1 represents a 3- to 10-membered non-aromatic heterocyclic group or the like; R 2 and R 3 represent hydrogen; R 4 , R 5 , R 6 , and R 7 may be the same or different and each represents hydrogen, halogen, C 1-6 alkyl or the like; R 8 represents hydrogen or the like; R 9 represents a 3- to 10-membered non-aromatic heterocyclic group or the like; n represents an integer of 1 or 2; X represents —CH═, nitrogen or the like.

  以下化合物的分子式，或其盐或水合物，具有出色的肝细胞生长因子受体（HGFR）抑制活性，并表现出抗肿瘤活性、抑制血管生成活性和癌症转移抑制活性。其中，R1代表3-10个成员的非芳香杂环基团等；R2和R3代表氢；R4、R5、R6和R7可以相同也可以不同，每个代表氢、卤素、C1-6烷基或类似物；R8代表氢或类似物；R9代表3-10个成员的非芳香杂环基团等；n代表1或2的整数；X代表-CH═、氮或类似物。