2,2-dimethyl-5-[2-(4-pyridinyl)ethenyl]-3(2H)-furanone | 138958-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,2-dimethyl-5-[2-(4-pyridinyl)ethenyl]-3(2H)-furanone
• 英文别名: 2,2-dimethyl-5-[(E)-2-pyridin-4-ylethenyl]furan-3-one
• CAS: 138958-38-0
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: SMWMSECMTNHLLV-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(3-甲基-5-异恶唑基)-2-丙醇 在 palladium on activated charcoal 盐酸 、 六甲基磷酰三胺 、 氢气 、 三氟乙酸酐 、 lithium diisopropyl amide 作用下， 反应 3.0h， 生成 2,2-dimethyl-5-[2-(4-pyridinyl)ethenyl]-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

• Anti-ulcer 5-(2-substituted ethenyl)-3-(2H)-furanones
  申请人：American Home Products Corporation

  公开号：US04966905A1

  公开（公告）日：1990-10-30

  A compound of the formula: ##STR1## in which R is alkyl, phenyl or halophenyl; R.sup.2 is substituted phenyl having from 1 to 3 substituents selected from halo, alkyl, alkylthio, alkylsulfonyl, cyano, trifluoromethyl, or R.sup.2 is pyridinyl, pyrazinyl, quinolinyl, N-alkylpyrrolyl, thienyl, benzothienyl, or furyl; and n is 1 or 2, are cytoprotective anti-ulcer agents.

  该化合物的化学式为：##STR1## 在其中R为烷基、苯基或卤代苯基；R.sup.2为取代苯基，其中取代基从卤素、烷基、烷基硫、烷基磺酰基、氰基、三氟甲基中选择1至3个取代基，或者R.sup.2为吡啶基、吡啉基、喹啉基、N-烷基吡咯基、噻吩基、苯并噻吩基或呋喃基；n为1或2，是细胞保护抗溃疡剂。
• 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