4-(2-Methyl-benzoimidazol-1-ylmethyl)-benzoic acid methyl ester | 170499-19-1

• 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: 4-(2-Methyl-benzoimidazol-1-ylmethyl)-benzoic acid methyl ester
• 英文别名: methyl 4-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)benzoate；methyl 4-(1H-2-methylbenzimidazol-1-ylmethyl)benzoate；methyl 4-(2-methylbenzimidazol-1-ylmethyl)benzoate；Methyl 4-[(2-methylbenzimidazol-1-yl)methyl]benzoate
• CAS: 170499-19-1
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: CLMFVZWFRYXBBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-Methyl-benzoimidazol-1-ylmethyl)-benzoic acid methyl ester 在 N-甲基吗啉 、 sodium hydride 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三氟乙酸 、 lithium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 N-methyl-4-[(2-methyl-1H-benzimidazol-1-yl)methyl]-N-[(3R)-pyrrolidin-3-yl]benzamide
  参考文献：
  名称：

  Pyrrolidin-3-yl-N-methylbenzamides as potent histamine 3 receptor antagonists

  摘要：

  On the basis of the previously reported benzimidazole 1,3'-bipyrrolidine benzamides (1), a series of related pyrrolidin-3-yl-N-methylbenzamides were synthesized and evaluated as H(3) receptor antagonists. In particular, compound 32 exhibits potent H(3) receptor binding affinity, improved pharmaceutical properties and a favorable in vivo profile. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.061
• 作为产物：
  描述：

  4-溴甲基苯甲酸甲酯 在 NaH 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 生成 4-(2-Methyl-benzoimidazol-1-ylmethyl)-benzoic acid methyl ester
  参考文献：
  名称：

  Platelet activating factor antagonists: imidazopyridine indoles

  摘要：

  本发明涉及具有公式##STR1##的化合物及其药用可接受的盐，这些化合物是PAF的强效拮抗剂，可用于治疗与PAF相关的疾病，包括哮喘、休克、呼吸窘迫综合征、急性炎症、移植器官排斥、胃肠道溃疡、过敏性皮肤病、迟发性细胞免疫、分娩、胎儿肺成熟和细胞分化。

  公开号：

  US05486525A1

文献信息

• Synthesis of N′-propylhydrazide analogs of hydroxamic inhibitors of histone deacetylases (HDACs) and evaluation of their impact on activities of HDACs and replication of hepatitis C virus (HCV)
  作者：Maxim V. Kozlov、Konstantin A. Konduktorov、Anastasia S. Shcherbakova、Sergey N. Kochetkov

  DOI：10.1016/j.bmcl.2019.06.006

  日期：2019.8

  N′-Propylhydrazide analogs of hydroxamic inhibitors of histone deacetylases (HDACs), including tubastatin A, vorinostat and belinostat, were synthesized. All prepared compounds inhibited HDAC1/2/3, but not HDAC6, except for one hydrazide analog of HDAC4/5/7 inhibitor that was completely inactive. A novel 4-substituted derivative of N′-propylbenzohydrazide with extremely high anti-HCV activity was discovered.

  合成了组蛋白脱乙酰基酶（HDACs）的异羟肟酸抑制剂的N'-丙酰肼类似物，包括tubastatin A，vorinostat和belinostat。除了一种完全无活性的HDAC4 / 5/7抑制剂的酰肼类似物外，所有制备的化合物均抑制HDAC1 / 2/3，但不抑制HDAC6。发现了具有极高抗HCV活性的N'-丙基苯甲酰肼的新型4-取代衍生物。
• AZACYCLYLBENZAMIDE DERIVATIVES AS HISTAMINE-3 ANTAGONISTS
  申请人：Zhou Dahui

  公开号：US20080293771A1

  公开（公告）日：2008-11-27

  The present invention provides a compound of formula I and the use thereof for the treatment of a central nervous system disorder related to or affected by the histamine-3 receptor

  本发明提供了一种I式化合物及其用于治疗与或受到组胺-3受体相关的中枢神经系统疾病的用途。
• Potent, exceptionally selective, orally bioavailable inhibitors of TNF-α Converting Enzyme (TACE): Novel 2-substituted-1H-benzo[d]imidazol-1-yl)methyl)benzamide P1′ substituents
  作者：Gregory R. Ott、Naoyuki Asakawa、Zhonghui Lu、Rajan Anand、Rui-Qin Liu、Maryanne B. Covington、Krishna Vaddi、Mingxin Qian、Robert C. Newton、David D. Christ、James M. Trzaskos、James J.-W. Duan

  DOI：10.1016/j.bmcl.2008.01.075

  日期：2008.3

  Novel ((2-substituted-1H-benzo[d]imidazol-1-yl)methyl)benzamides were found to be excellent P1' substituents in conjunction with unique constrained beta-amino hydroxamic acid scaffolds for the discovery of potent selective inhibitors of TNF-alpha Converting Enzyme (TACE). Optimized examples proved potent for TACE, exceptionally selective over a wide panel of MMP and ADAM proteases, potent in the suppression

  发现新型（（2-取代的-1H-苯并[d]咪唑-1-基）甲基）苯甲酰胺是出色的P1'取代基，结合独特的受约束的β-氨基异羟肟酸支架，可发现有效的TNF选择性抑制剂-alpha转换酶（TACE）。优化的实例证明了对TACE的有效作用，对多种MMP和ADAM蛋白酶具有极高的选择性，对抑制人全血中LPS诱导的TNF-α具有有效作用，并且具有口服生物利用度。
• HDAC INHIBITORS AND THERAPEUTIC METHODS USING THE SAME
  申请人：Kozikowski Alan

  公开号：US20140128408A1

  公开（公告）日：2014-05-08

  Histone deacetylases inhibitors (HDACIs) and compositions containing the same are disclosed. Methods of treating diseases and conditions wherein inhibition of HDAC provides a benefit, like a cancer, a neurodegenerative disorder, a peripheral neuropathy, a neurological disease, traumatic brain injury, stroke, hypertension, malaria, an autoimmune disease, autism, autism spectrum disorders, and inflammation, also are disclosed.

  本发明公开了组蛋白去乙酰化酶抑制剂（HDACIs）及其组成物。公开了治疗疾病和状况的方法，其中抑制HDAC提供了益处，如癌症、神经退行性疾病、周围神经病变、神经疾病、创伤性脑损伤、中风、高血压、疟疾、自身免疫疾病、自闭症、自闭症谱系障碍和炎症。
• Tricyclononene carboxamide derivatives as novel anti-HIV-1 agents
  作者：Ming-xin Dong、Jian Zhang、Xu-qing Peng、Hong Lu、Liu-hong Yun、Shibo Jiang、Qiu-yun Dai

  DOI：10.1016/j.ejmech.2010.05.070

  日期：2010.9

  By modifying the chemical structure of anti-orthopoxvirus compound ST-246, we designed and synthesized a series of tricyclononene carboxamide derivatives and tested their anti-HIV-1 activity and cytotoxicity. We found that benzoimidazol-containing compound 7g was highly effective in inhibiting HIV-1 R5 infection with an IC50 value of 0.41 mu M and a selectivity index of 292, but it exhibited no significant inhibitory activity on HIV-1 reverse transcriptase, integrase and protease. CoMFA was used to analyze structure-activity relationships with good predictive power (r(2) = 0.921; q(2) = 0.582). Moreover, the CoMFA model showed that the length of the molecule, the amide, and the amine moieties all played crucial roles in anti-HIV activity. These results suggest that 7g may serve as a lead for the development of novel anti-HIV-1 therapies. (C) 2010 Elsevier Masson SAS. All rights reserved.