5-[2-(Benzo[b]thien-2-yl)ethenyl]-2,2-dimethyl-3(2H)-furanone | 138958-45-9

• 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: 5-[2-(Benzo[b]thien-2-yl)ethenyl]-2,2-dimethyl-3(2H)-furanone
• 英文别名: 5-[(E)-2-(1-benzothiophen-2-yl)ethenyl]-2,2-dimethylfuran-3-one
• CAS: 138958-45-9
• 化学式: C₁₆H₁₄O₂S
• 分子量: 270.352
• InChiKey: NMBFCOJIAVTPOR-BQYQJAHWSA-N

物化性质

• 沸点：
  436.3±44.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-3-丁炔-2-醇 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 三乙胺 、 三氯氧磷 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 18.0h， 生成 5-[2-(Benzo[b]thien-2-yl)ethenyl]-2,2-dimethyl-3(2H)-furanone
  参考文献：
  名称：

  Synthesis and antiulcer activity of novel 5-(2-ethenyl substituted)-3(2H)-furanones

  摘要：

  In order to investigate new antiulcer agents, spizofurone 1 (AG-629) was fragmented and reassembled to generate 5-phenyl-2,2-dimethyl-3(2H)-furanone (bullatenone, 2). Because of the antiulcer activity of 2,5-phenyl-substituted 2,2-dimethyl-3(2H)-furanones (3-6) were made and shown to have poor activity. Insertion of an ethenyl link between the furanone and phenyl rings gave 5-(2-phenylethenyl)-2,2-dimethyl-3(2H)-furanone (7). This compound had better activity than 2. Compounds 8-41 were synthesized to evaluate the SAR in 5-(2-ethenyl substituted)-3(2H)-furanones. Electron-withdrawing substituents on the aromatic ring (8, 10, 19, and 20) gave 2-3-fold higher activity. Further increases in the activity were found when the phenyl ring was replaced by heterocyclic nuclei. Compounds that contained a thiophene (29), pyridine (24-26), or quinoline ring (32) had the best activity. Replacement of the methyl group on the furanone ring with a phenyl (34) or p-fluorophenyl (40) substituent in the 2-pyridine series gave compounds with activity that ranked with the best obtained in this study. The best compounds from the above SAR studies were evaluated in the ethanol-necrosis model for duration of cytoprotection action. Compounds 19, 24, and 29, which had the best duration of action, were tested with AG-629 in the acidified aspirin and indomethacin-induced lesion models. Only compound 24 had equivalent activity with AG-629 in both models.

  DOI：

  10.1021/jm00085a003

文献信息

• US4966905A
  申请人：——

  公开号：US4966905A

  公开（公告）日：1990-10-30
• US5001126A
  申请人：——

  公开号：US5001126A

  公开（公告）日：1991-03-19
• US5010102A
  申请人：——

  公开号：US5010102A

  公开（公告）日：1991-04-23
• US5017601A
  申请人：——

  公开号：US5017601A

  公开（公告）日：1991-05-21