2-(2,6-Dichloro-benzyl)-1H-imidazole-4-carboxylic acid | 748769-95-1

• 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: 2-(2,6-Dichloro-benzyl)-1H-imidazole-4-carboxylic acid
• 英文别名: 2-[(2,6-dichlorophenyl)methyl]-1H-imidazole-5-carboxylic acid
• CAS: 748769-95-1
• 化学式: C₁₁H₈Cl₂N₂O₂
• 分子量: 271.103
• InChiKey: KEHDEJGDBCJRTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2,6-Dichloro-benzyl)-1H-imidazole-4-carboxylic acid 在 potassium carbonate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(2,6-Dichloro-benzyl)-1-methyl-1H-imidazole-4-carboxylic acid (4-trifluoromethyl-phenyl)-amide
  参考文献：
  名称：

  Synthesis and evaluation of thiazole carboxamides as vanilloid receptor 1 (TRPV1) antagonists

  摘要：

  A thiazole derivative, 2-(2,6-dichlorobenzyl)-N-(4-isopropylphenyl) thiazole-4-carboxamide (1), was identified as a TRPV1 antagonist. We synthesized various thiazole analogs and evaluated them for their ability to block capsaicin- or acid-induced calcium influx in TRPV1-expressing CHO cells. The IC50 values of the most potent antagonists were ca. 0.050 mu M in these assays. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.100
• 作为产物：
  描述：

  2-(2,6-Dichloro-benzyl)-1H-imidazole-4-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 2-(2,6-Dichloro-benzyl)-1H-imidazole-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and evaluation of thiazole carboxamides as vanilloid receptor 1 (TRPV1) antagonists

  摘要：

  A thiazole derivative, 2-(2,6-dichlorobenzyl)-N-(4-isopropylphenyl) thiazole-4-carboxamide (1), was identified as a TRPV1 antagonist. We synthesized various thiazole analogs and evaluated them for their ability to block capsaicin- or acid-induced calcium influx in TRPV1-expressing CHO cells. The IC50 values of the most potent antagonists were ca. 0.050 mu M in these assays. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.100

文献信息

• Vanilloid receptor ligands and their use in treatments
  申请人：Amgen Inc.

  公开号：EP1818333A1

  公开（公告）日：2007-08-15

  Compounds having the general structure and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritus, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.

  具有以下一般结构的化合物 以及含有这些化合物的组合物，用于治疗急性、炎症性和神经性疼痛、牙 痛、一般头痛、偏头痛、丛集性头痛、混合血管性和非血管性综合征、紧张 性头痛、一般炎症、关节炎、风湿性疾病、骨关节炎、炎症性肠道疾病、炎症性眼部疾病、炎症性或不稳定型膀胱疾病、牛皮癣、伴有炎症成分的皮肤不适、慢性炎症、炎症性疼痛及相关的痛觉减退和痛觉过敏、神经性疼痛及相关的痛觉减退和痛觉过敏、糖尿病神经病变性疼痛、因痛症、交感神经维持性疼痛、去感觉综合征、哮喘、上皮组织损伤或功能障碍、单纯疱疹、呼吸道、泌尿生殖道、胃肠道或血管部位的内脏运动障碍、伤口、烧伤、皮肤过敏反应、瘙痒症、白癜风、一般胃肠道疾病、胃溃疡、十二指肠溃疡、腹泻、坏死剂引起的胃部病变、毛发生长、血管运动性或过敏性鼻炎、支气管疾病或膀胱疾病。
• US7265138B2
  申请人：——

  公开号：US7265138B2

  公开（公告）日：2007-09-04
• Synthesis and evaluation of thiazole carboxamides as vanilloid receptor 1 (TRPV1) antagonists
  作者：Ning Xi、Yunxin Bo、Elizabeth M. Doherty、Christopher Fotsch、Narender R. Gavva、Nianhe Han、Randall W. Hungate、Lana Klionsky、Qingyian Liu、Rami Tamir、Shimin Xu、James J.S. Treanor、Mark H. Norman

  DOI：10.1016/j.bmcl.2005.08.100

  日期：2005.12

  A thiazole derivative, 2-(2,6-dichlorobenzyl)-N-(4-isopropylphenyl) thiazole-4-carboxamide (1), was identified as a TRPV1 antagonist. We synthesized various thiazole analogs and evaluated them for their ability to block capsaicin- or acid-induced calcium influx in TRPV1-expressing CHO cells. The IC50 values of the most potent antagonists were ca. 0.050 mu M in these assays. (c) 2005 Elsevier Ltd. All rights reserved.