N-(4-溴-2-硝基-5-三氟甲基苯基)乙酰胺 | 157554-76-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-溴-2-硝基-5-三氟甲基苯基)乙酰胺
• 英文名称: N-[4-bromo-2-nitro-5-(trifluoromethyl)phenyl]acetamide
• CAS: 157554-76-2
• 化学式: C₉H₆BrF₃N₂O₃
• 分子量: 327.057
• InChiKey: RWLYLAWSMVHCEI-UHFFFAOYSA-N

物化性质

• 沸点：
  400.9±45.0 °C(Predicted)
• 密度：
  1.776±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(4-溴-2-硝基-5-三氟甲基苯基)乙酰胺 在 sodium hydroxide 、 tin(ll) chloride 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 4-溴-5-氟-1,2-苯二胺
  参考文献：
  名称：

  Design of Potent, Orally Available Antagonists of the Transient Receptor Potential Vanilloid 1. Structure−Activity Relationships of 2-Piperazin-1-yl-1H-benzimidazoles

  摘要：

  The vanilloid receptor-1 ( VR1 or TRPV1) is a membrane-bound, nonselective cation channel that is predominantly expressed by peripheral neurons sensing painful stimuli. TRPV1 antagonists produce antihyperalgesic effects in animal models of inflammatory and neuropathic pain. Herein, we describe the synthesis and the structure-activity relationships of a series of 2-(4-pyridin-2-ylpiperazin-1-yl)-1H-benzo-[ d] imidazoles as novel TRPV1 antagonists. Compound 46ad was among the most potent analogues in this series. This compound was orally bioavailable in rats and was efficacious in blocking capsaicin-induced flinch in rats in a dose-dependent manner. Compound 46ad also reversed thermal hyperalgesia in a model of inflammatory pain, which was induced by complete Freund's adjuvant ( CFA).

  DOI：

  10.1021/jm060065y
• 作为产物：
  描述：

  5-乙酰胺基-2-溴三氟甲苯 在 硫酸 、 硝酸 作用下， 反应 3.0h， 生成 N-(4-溴-2-硝基-5-三氟甲基苯基)乙酰胺
  参考文献：
  名称：

  [EN] BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS VANILLOID RECEPTOR LIGANDS
  [FR] DERIVES DE BENZIMIDAZOLES ET UTILISATION DE CEUX-CI EN TANT QUE LIGANDS DU RECEPTEUR VANILLOIDE

  摘要：

  式（I）的化合物在治疗辣椒素受体介导的疾病方面很有用，如炎症性或神经病痛以及涉及感觉神经功能的疾病，如哮喘、类风湿性关节炎、骨关节炎、炎症性肠道疾病、尿失禁、偏头痛和牛皮癣。

  公开号：

  WO2004035549A1

文献信息

• [EN] BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS VANILLOID RECEPTOR LIGANDS<br/>[FR] DERIVES DE BENZIMIDAZOLES ET UTILISATION DE CEUX-CI EN TANT QUE LIGANDS DU RECEPTEUR VANILLOIDE
  申请人：AMGEN INC

  公开号：WO2004035549A1

  公开（公告）日：2004-04-29

  Compounds of formula (I) are useful in the treatment of vanilloid-receptor-meditated diseases, such as inflammatory or neuropathic pain and diseases involving sensory nerve function such as asthma, rheumatoid arthritis, osteoarthritis, inflammatory bowel disorders, urinary incontinence, migraine and psoriasis.

  式（I）的化合物在治疗辣椒素受体介导的疾病方面很有用，如炎症性或神经病痛以及涉及感觉神经功能的疾病，如哮喘、类风湿性关节炎、骨关节炎、炎症性肠道疾病、尿失禁、偏头痛和牛皮癣。
• Vanilloid receptor ligands and their use in treatments
  申请人：Amgen Inc.

  公开号：US20040152690A1

  公开（公告）日：2004-08-05

  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, bums, 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.

  治疗苯并咪唑和含有苯并咪唑的组合物，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症、紧张性头痛、一般炎症、关节炎、风湿病、骨关节炎、炎症性肠病、炎症性眼疾、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、慢性炎症病状、炎症性疼痛及相关的高敏感性和痛觉过敏、神经痛及相关的高敏感性和痛觉过敏、糖尿病神经病疼痛、烧伤后疼痛、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、胃肠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、头发生长、血管运动或过敏性鼻炎、支气管疾病或膀胱疾病。
• HETEROCYCLYC SULFONAMIDES HAVING EDG-1 ANTAGONISTIC ACTIVITY
  申请人：Grewal Gurmit

  公开号：US20100029643A1

  公开（公告）日：2010-02-04

  The invention relates to chemical compounds of formula (I), (Ia) and (Ib) or pharmaceutically acceptable salts thereof, which possess Edg-1 antagonistic activity and are accordingly useful for their anti-cancer activity and thus in methods of treatment of the human or animal body. The invention also relates to processes for the manufacture of said chemical compounds, to pharmaceutical compositions containing them and to their use in the manufacture of medicaments for use in the production of an anti-cancer effect in a warm-blooded animal, such as man.

  该发明涉及化学式（I），（Ia）和（Ib）或其药学上可接受的盐的化合物，其具有Edg-1拮抗活性，因此在抗癌活性和人或动物体的治疗方法中有用。该发明还涉及制造上述化学化合物的过程，含有它们的制药组合物以及在制造用于在温血动物（如人）中产生抗癌效果的药物的制造中使用它们。
• VANILLOID RECEPTOR LIGANDS AND THEIR USE IN TREATMENTS
  申请人：Balan Chenera

  公开号：US20090143575A1

  公开（公告）日：2009-06-04

  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 necrotizing agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.

  治疗苯并咪唑及其含量物，用于急性、炎症性和神经痛、牙痛、一般头痛、偏头痛、集群性头痛、混合血管和非血管综合症、紧张型头痛、一般炎症、关节炎、风湿性疾病、骨关节炎、炎症性肠病、炎症性眼病、炎症性或不稳定的膀胱疾病、牛皮癣、有炎症成分的皮肤病、慢性炎症状况、炎症性疼痛和相关的高敏感性和触痛、神经痛和相关的高敏感性和触痛、糖尿病神经病疼痛、烧伤后疼痛、交感神经维持的疼痛、去感觉综合症、哮喘、上皮组织损伤或功能障碍、单纯疱疹、呼吸、泌尿、胃肠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、一般胃肠疾病、胃溃疡、十二指肠溃疡、腹泻、坏死性剂引起的胃损伤、头发生长、血管运动或过敏性鼻炎、支气管疾病或膀胱疾病。
• BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS VANILLOID RECEPTOR LIGANDS
  申请人：Amgen Inc.

  公开号：EP1551811A1

  公开（公告）日：2005-07-13