3-hydroxy-N-methyl-N-(2,2-diphenyl)ethenyl-5-trifluoromethylbenzo[b]thiophene-2-carboxamide | 102565-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-hydroxy-N-methyl-N-(2,2-diphenyl)ethenyl-5-trifluoromethylbenzo[b]thiophene-2-carboxamide
• 英文别名: N-(2,2-diphenylethenyl)-3-hydroxy-N-methyl-5-(trifluoromethyl)-1-benzothiophene-2-carboxamide
• CAS: 102565-32-2
• 化学式: C₂₅H₁₈F₃NO₂S
• 分子量: 453.485
• InChiKey: KBCXBIXJINQCPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  68.8
• 氢给体数：
  1
• 氢受体数：
  6

文献信息

• Benzothiophenes, their production and use, and compositions containing them
  申请人：Merck & Co., Inc.

  公开号：EP0160408A1

  公开（公告）日：1985-11-06

  N-Alkenyl-3-hydroxybenzo [b] thiophene-2-carboxamide derivatives of formula) and their pharmaceutically acceptable salts, are novel. In the formula, each of R, R1, R2, R3 and R4 is selected from various hydrocarbons (including heteroaryl), acyl, and acyl- substituted hydrocarbon groups and their ring-substituted derivatives; or R1, R2 and R3 can be halo, or R' and R2 joined to form certain tricyclic bivalent residues, or R4 is -CR1=CR2R3, and n is 0, 1, or 2. These compounds are prepared by (1) treating a substituted 2-halobenzoate with thioacetamide followed by N-alkenylation with appropriate agents, such as aldehydes, ketones, enol ethers, epoxides, acetals or ketals; (2) treating a substituted thiosalicylate with an appropriately substituted halocetamide, followed by dehydration; and (3) further synthetic modification of compounds prepared above. These compounds have been found to be effective inhibitors of both cyclooxygenase and lipoxygenase and thereby useful in the treatment of pain, fever, inflammation, arthritic conditions, asthma, allergic disorders, skin diseases, cardiovascular disorders, psoriasis, inflammatory bowel disease, glaucoma or other prostaglandins and/or leukotriene mediated diseases. Furthermore, these compounds have been found to exhibit cytoprotective activity which does not involve the inhibition of gastric acid secretion but can be used as relatively low dosages for increasing the resistance of gastro-intestinal mucosa to strong irritants. They are included in pharmaceutical compositions.

  式）的 N-烯基-3-羟基苯并[b]噻吩-2-甲酰胺衍生物及其药学上可接受的盐是新颖的。 及其药学上可接受的盐类是新型的。式中，R、R1、R2、R3 和 R4 各选自各种烃（包括杂芳基）、酰基和酰基取代的烃基及其环取代衍生物；或者 R1、R2 和 R3 可以是卤代物，或者 R' 和 R2 连接形成某些三环二价残基，或者 R4 是-CR1＝CR2R3，n 是 0、1 或 2。这些化合物的制备方法是：(1) 用硫代乙酰胺处理取代的 2-卤代苯甲酸酯，然后用适当的制剂（如醛、酮、烯醇醚、环氧化物、乙醛或酮）进行 N-烯化；(2) 用适当取代的卤代乙酰胺处理取代的硫代水杨酸酯，然后脱水；(3) 对上述制备的化合物进行进一步合成修饰。 已发现这些化合物是环氧化酶和脂氧合酶的有效抑制剂，因此可用于治疗疼痛、发热、炎症、关节炎、哮喘、过敏性疾病、皮肤病、心血管疾病、牛皮癣、炎症性肠病、青光眼或其他前列腺素和/或白三烯介导的疾病。此外，这些化合物 还具有细胞保护活性，这种活性不涉及抑制胃酸分泌，但剂量相对较低，可用于增强胃肠道粘膜对强刺激物的抵抗力。它们已被纳入药物组合物中。
• US4760086A
  申请人：——

  公开号：US4760086A

  公开（公告）日：1988-07-26
• US5068248A
  申请人：——

  公开号：US5068248A

  公开（公告）日：1991-11-26