1-(3,5-difluorophenyl)-2-(4-(trifluoromethyl)phenyl)ethane-1,2-dione | 883876-62-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(3,5-difluorophenyl)-2-(4-(trifluoromethyl)phenyl)ethane-1,2-dione
• 英文别名: 1-(3,5-difluorophenyl)-2-[4-(trifluoromethyl)phenyl]ethane-1,2-dione
• CAS: 883876-62-8
• 化学式: C₁₅H₇F₅O₂
• 分子量: 314.211
• InChiKey: GVEQZQVQZQDJGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3,5-difluorophenyl)-2-(4-(trifluoromethyl)phenyl)ethane-1,2-dione 、 在 palladium on activated charcoal N,N-二异丙基乙胺 、 氢气 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以30%的产率得到1-(4-(3,5-difluorophenyl)-5-(4-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)-4-(3-(trifluoromethyl)-2-pyridinyl)piperazine
  参考文献：
  名称：

  Structure–activity relationship (SAR) investigations of substituted imidazole analogs as TRPV1 antagonists

  摘要：

  A novel series of 4,5-biarylimidazoles as TRPV1 antagonists were designed based on the previously reported 4,6-disubstituted benzimidazole series. The analogs were evaluated for their ability to block capsaicin- or acid-induced calcium influx in TRPV1-expressing CHO cells. These studies led to the identification of a highly potent and orally bioavailable TRPV1 antagonist, imidazole 33. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.08.044
• 作为产物：
  描述：

  2-(3,5-difluorophenyl)-1-(4-(trifluoromethyl)phenyl)ethanone 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 1-(3,5-difluorophenyl)-2-(4-(trifluoromethyl)phenyl)ethane-1,2-dione
  参考文献：
  名称：

  Structure–activity relationship (SAR) investigations of substituted imidazole analogs as TRPV1 antagonists

  摘要：

  A novel series of 4,5-biarylimidazoles as TRPV1 antagonists were designed based on the previously reported 4,6-disubstituted benzimidazole series. The analogs were evaluated for their ability to block capsaicin- or acid-induced calcium influx in TRPV1-expressing CHO cells. These studies led to the identification of a highly potent and orally bioavailable TRPV1 antagonist, imidazole 33. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.08.044

文献信息

• Vanilloid receptor ligands and their use in treatments
  申请人：Gore Keshav Vijay

  公开号：US20060084640A1

  公开（公告）日：2006-04-20

  Therapeutic benzimidazoles 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.

  治疗性苯并咪唑及含有它们的组合物，用于治疗急性、炎症性和神经痛、牙痛、普通头痛、偏头痛、集群头痛、混合血管和非血管综合征、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、炎症性或不稳定的膀胱疾病、牛皮癣、带有炎症成分的皮肤疾病、慢性炎症症状、炎症性疼痛及相关的过敏性疼痛和触痛、神经痛及相关的过敏性疼痛和触痛、糖尿病性神经病痛、烧灼性疼痛、交感神经维持性疼痛、去神经症候群、哮喘、上皮组织损伤或功能障碍、单纯疱疹、呼吸、泌尿、消化或血管区域内脏运动障碍、伤口、烧伤、过敏性皮肤反应、瘙痒、白癜风、一般胃肠道疾病、胃溃疡、十二指肠溃疡、腹泻、由坏死性剂引起的胃病变、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。
• IMIDAZOLE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
  申请人：Amgen, Inc

  公开号：EP1802605A1

  公开（公告）日：2007-07-04
• US7439360B2
  申请人：——

  公开号：US7439360B2

  公开（公告）日：2008-10-21
• [EN] IMIDAZOLE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS<br/>[FR] DERIVES D'IMIDAZOLE UTILISES EN TANT QUE LIGANDS DU RECEPTEUR DE LA VANILLOIDE
  申请人：AMGEN INC

  公开号：WO2006044527A1

  公开（公告）日：2006-04-27

  [EN] Therapeutic benzimidazoles 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.
  [FR] L'invention porte sur des benzimidazoles thérapeutiques et des compositions les contenant, pour le traitement de douleurs inflammatoires et neuropathiques aiguës, de douleurs dentaires, de maux de têtes, de migraines, d'algies vasculaires de la face, de syndromes vasculaires mixtes et de syndromes non vasculaires, de maux de tête aigus, d'inflammations générales, d'arthrite, de maladies rhumatismales, de l'arthrose, de troubles intestinaux inflammatoires, de maladies oculaires inflammatoires, de troubles de la vessie inflammatoires ou instables, du psoriasis, des troubles cutanés à tendance inflammatoire, de conditions inflammatoires chroniques, de douleurs inflammatoires et de l'hyperalgie et l'allodynie associées, de douleurs neuropathiques et de l'hyperalgie et l'allodynie associées, de douleurs neuropathiques diabétiques, de causalgie, de douleurs continues sympathiques, de syndromes de désafférentation, de l'asthme, de la dégradation ou du dysfonctionnement du tissu épithélial, de l'herpès, de perturbations de la mobilité viscérale dans des zones du système respiratoire, génito-urinaire, gastro-intestinal ou vasculaire, de blessures, de brûlures, de réactions cutanées allergiques, du prurit, du vitiligo, de troubles généraux du tube digestif, de l'ulcère gastrique, des ulcères duodénaux, de la diarrhée, des lésions gastriques induites par des agents nécrosants, de la croissance capillaire, de la rhinite vasomotrice ou allergique, de troubles bronchitiques ou de troubles de la vessie.