2,2-dimethyl-5-[(E)-2-(2-naphthyl)ethenyl]-3(2H)-furanone | 138958-34-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2-dimethyl-5-[(E)-2-(2-naphthyl)ethenyl]-3(2H)-furanone
• 英文别名: 2,2-dimethyl-5-[(E)-2-naphthalen-2-ylethenyl]furan-3-one
• CAS: 138958-34-6
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: AAMKSVHOWMBWTM-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

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 sodium hydroxide 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 13.0h， 生成 2,2-dimethyl-5-[(E)-2-(2-naphthyl)ethenyl]-3(2H)-furanone
  参考文献：
  名称：

  New 5-(2-ethenylsubstituted)-3(2H)-furanones with in vitro antiproliferative activity

  摘要：

  A convenient route to new 3(2H)-furanones is described through hydrogenolysis and subsequent acidic hydrolysis of isoxazoles. The antiproliferative activity of title compounds were evaluated against leukemia-, carcinoma-, neuroblastoma-, and sarcoma-derived human cell lines in comparison to the natural compound geiparvarin. The structure activity relationship indicated that the maximum in vitro antiproliferative activity correlates with the presence of a heterocyclic ring on the ethenyl moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00776-2

文献信息

• Synthesis and antiulcer activity of novel 5-(2-ethenyl substituted)-3(2H)-furanones
  作者：Steven W. Felman、Ivo Jirkovsky、Kevin A. Memoli、Luis Borella、Cheryl Wells、Jim Russell、Jim Ward

  DOI：10.1021/jm00085a003

  日期：1992.4

  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.
• New 5-(2-ethenylsubstituted)-3(2H)-furanones with in vitro antiproliferative activity
  作者：Stefano Chimichi、Marco Boccalini、Barbara Cosimelli、Francesco Dall'Acqua、Giampietro Viola

  DOI：10.1016/s0040-4020(03)00776-2

  日期：2003.7

  A convenient route to new 3(2H)-furanones is described through hydrogenolysis and subsequent acidic hydrolysis of isoxazoles. The antiproliferative activity of title compounds were evaluated against leukemia-, carcinoma-, neuroblastoma-, and sarcoma-derived human cell lines in comparison to the natural compound geiparvarin. The structure activity relationship indicated that the maximum in vitro antiproliferative activity correlates with the presence of a heterocyclic ring on the ethenyl moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.