1-{4-[N-(pyridin-3-ylmethoxycarbonyl)-aminomethyl]benzoyl}imidazole | 255894-58-7

• 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: 1-{4-[N-(pyridin-3-ylmethoxycarbonyl)-aminomethyl]benzoyl}imidazole
• 英文别名: 1-{4-[N-(pyridin-3-ylmethoxycarbonyl)aminomethyl]benzoyl}imidazole；pyridin-3-ylmethyl N-[[4-(imidazole-1-carbonyl)phenyl]methyl]carbamate
• CAS: 255894-58-7
• 化学式: C₁₈H₁₆N₄O₃
• 分子量: 336.35
• InChiKey: LPTGYIYCAKDUAV-UHFFFAOYSA-N

物化性质

• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  86.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  邻苯二胺 、 1-{4-[N-(pyridin-3-ylmethoxycarbonyl)-aminomethyl]benzoyl}imidazole 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 恩替诺特
  参考文献：
  名称：

  Synthesis and Histone Deacetylase Inhibitory Activity of New Benzamide Derivatives

  摘要：

  Newly synthesized benzamide derivatives were evaluated for their inhibitory activity against histone deacetylase. The structure of these derivatives was unrelated to the known inhibitors, and IC50 values of the active compounds were in the range of 2-50 mu M. Structure-activity relationship on the benzanilide moiety showed that the 2'-substituent, an amino or hydroxy group, was indispensable for inhibitory activity. Although the electronic influence of the substituent in the anilide moiety showed only a small effect on inhibitory activity, the steric factor in the anilide moiety, especially at positions 3'and 4', played an important role in interaction with the enzyme. Among these benzamide derivatives, MS-275 (1), which showed significant antitumor activity in vivo, has been selected for further investigation.

  DOI：

  10.1021/jm980565u
• 作为产物：
  描述：

  3-吡啶甲醇 在 草酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 11.0h， 生成 1-{4-[N-(pyridin-3-ylmethoxycarbonyl)-aminomethyl]benzoyl}imidazole
  参考文献：
  名称：

  Synthesis and Histone Deacetylase Inhibitory Activity of New Benzamide Derivatives

  摘要：

  Newly synthesized benzamide derivatives were evaluated for their inhibitory activity against histone deacetylase. The structure of these derivatives was unrelated to the known inhibitors, and IC50 values of the active compounds were in the range of 2-50 mu M. Structure-activity relationship on the benzanilide moiety showed that the 2'-substituent, an amino or hydroxy group, was indispensable for inhibitory activity. Although the electronic influence of the substituent in the anilide moiety showed only a small effect on inhibitory activity, the steric factor in the anilide moiety, especially at positions 3'and 4', played an important role in interaction with the enzyme. Among these benzamide derivatives, MS-275 (1), which showed significant antitumor activity in vivo, has been selected for further investigation.

  DOI：

  10.1021/jm980565u

文献信息

• Method of producing benzamide derivatives
  申请人：Mitsui Chemicals, Inc.

  公开号：US06320078B1

  公开（公告）日：2001-11-20

  In the case that a selectively monoacylated phenylenediamine derivative which is useful as any of medicines, agricultural chemicals, animal drugs and the intermediates of chemicals is prepared by reacting a benzoic acid derivative with a phenylenediamine derivative, the benzoic acid derivative is converted into a benzoyl imidazole derivative and this benzoyl imidazole derivative is then reaction with the phenylenediamine derivative, whereby the improvement of a preparation efficiency and the high selectivity of the monoacylation can be achieved, the steps of protection and deprotection being omitted.

  在一个选择性地单酰化的苯二胺衍生物的情况下，该衍生物作为药物、农药、兽药和化学品的中间体是有用的，通过将苯甲酸衍生物与苯二胺衍生物反应来制备，所述苯甲酸衍生物被转化为苯甲酰亚胺衍生物，然后这个苯甲酰亚胺衍生物再与苯二胺衍生物反应，通过这种方式可以实现在不进行保护和脱保护步骤的情况下提高制备效率和单酰化的高度选择性。
• US6320078B1
  申请人：——

  公开号：US6320078B1

  公开（公告）日：2001-11-20