3-(4-methoxybenzylidene)-5-(4-chlorophenyl)-2(3H)-furanone | 134529-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-methoxybenzylidene)-5-(4-chlorophenyl)-2(3H)-furanone
• 英文别名: 5-(4-chloro-phenyl)-3-(4-methoxy-benzylidene)-3H-furan-2-one；5-(4-Chlorophenyl)-3-[(4-methoxyphenyl)methylidene]furan-2-one
• CAS: 134529-29-6；6781-84-6
• 化学式: C₁₈H₁₃ClO₃
• 分子量: 312.752
• InChiKey: JQKUSMYLIRFCPC-UHFFFAOYSA-N

物化性质

• 熔点：
  214 °C(Solv: methanol (67-56-1); chloroform (67-66-3))
• 沸点：
  537.1±50.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-methoxybenzylidene)-5-(4-chlorophenyl)-2(3H)-furanone 在 一水合肼 作用下， 以 丙醇 为溶剂， 反应 3.0h， 以61%的产率得到5-(4-methoxybenzyl)-3-(4-chlorophenyl)-1,6-dihydro-6-pyridazinone
  参考文献：
  名称：

  SYNTHESIS AND ANTITUBERCULAR ACTIVITY OF PYRIDAZINONE DERIVATIVES

  摘要：

  Two series of pyridazinone derivatives (19-34) were synthesized and evaluated for antitubercular activities against Mycobacterium tuberculosis H(37)Rv strain. The results illustrated that among the synthesized compounds, compound 25, 5-(4-hydroxy-3-methoxybenzyl)-3-(4-chloro-phenyl)-1,6-dihydro-6-pyridazinone emerged as a lead compound with good antitubercular activity. Four more compounds, (21, 22, 29 & 33) were significant in their antitubercular action.

  DOI：

  10.4067/s0717-97072011000300013
• 作为产物：
  描述：

  氯苯 生成 3-(4-methoxybenzylidene)-5-(4-chlorophenyl)-2(3H)-furanone
  参考文献：
  名称：

  SYNTHESIS AND ANTITUBERCULAR ACTIVITY OF PYRIDAZINONE DERIVATIVES

  摘要：

  Two series of pyridazinone derivatives (19-34) were synthesized and evaluated for antitubercular activities against Mycobacterium tuberculosis H(37)Rv strain. The results illustrated that among the synthesized compounds, compound 25, 5-(4-hydroxy-3-methoxybenzyl)-3-(4-chloro-phenyl)-1,6-dihydro-6-pyridazinone emerged as a lead compound with good antitubercular activity. Four more compounds, (21, 22, 29 & 33) were significant in their antitubercular action.

  DOI：

  10.4067/s0717-97072011000300013

文献信息

• Synthesis and pharmacological evaluation of 2(3H)-furanones and 2(3H)-pyrrolones, combining analgesic and anti-inflammatory properties with reduced gastrointestinal toxicity and lipid peroxidation
  作者：M.M. Alam、Asif Husain、S.M. Hasan、Suruchi、T. Anwer

  DOI：10.1016/j.ejmech.2008.10.030

  日期：2009.6

  ulcerogenic and lipid peroxidation actions. Some of the newly synthesized compounds showed good anti-inflammatory and analgesic activities with low GI toxicity and reduced lipid peroxidation. The biological activity was found to improve upon replacement of oxygen of furanone ring with benzylamine moiety i.e. 1-benzylpyrrolones. Similarly, compounds containing halogen group(s), compounds 15 and 17, showed

  一系列3-亚芳基-5-（4-氯-苯基）-2-（3 ħ） -呋喃酮（2 - 13）和它们的氮类似物1- benzylpyrrolones（14 - 18）的合成。对化合物的抗炎，镇痛，促溃疡和脂质过氧化作用进行了评估。一些新合成的化合物显示出良好的抗炎和镇痛活性，胃肠道毒性低，脂质过氧化作用降低。发现通过用苄胺部分即1-苄基吡咯烷酮代替呋喃酮环的氧可以提高生物学活性。同样，含卤素基团的化合物，化合物15和17，具有较高程度的抗炎活性，其活性与标准品相当。这些化合物在乙酸诱导的扭体试验（外围作用）和热板试验（中枢作用）中显示出有趣的镇痛活性。还测试了这些化合物的致溃疡和脂质过氧化作用，与标准品相比，显示出优异的胃肠道安全性以及脂质过氧化作用的降低。
• Synthesis and biological evaluation of some new pyridazinone derivatives
  作者：Asif Husain、Sushma Drabu、Nitin Kumar、M. Mumtaz Alam、Aftab Ahmad

  DOI：10.3109/14756366.2010.548810

  日期：2011.10.1

  A series of pyridazinone derivatives (19-34) were synthesized with an aim to synthesize safer anti-inflammatory agents. The compounds were evaluated for their anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation (LPO) actions. The percentage inhibition in edema at different time intervals indicated that compounds 20, 26, 28 and 34 exhibited good anti-inflammatory potential, comparable with that of ibuprofen (85.77%) within a range of 67.48-77.23%. The results illustrate that 5-(4-fluoro-benzyl)-3-(4-chloro-phenyl)-1,6-dihydro-6-pyridazinone (26) and 5-(4-chloro-benzyl)-3-(4-chloro-phenyl)-1,6-dihydro-6-pyridazinone (20) showed best anti-inflammatory activity. Furthermore, activity is more in case of chloro substitution as compared with methyl-substitution. The compounds synthesized were also evaluated for their ulcerogenic and LPO action and showed superior gastrointestinal safety profile along with reduction in LPO as compared with that of the ibuprofen.
• Hashem, A. I.; El-Kousy, S. M.; El-Torgoman, A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 875 - 876
  作者：Hashem, A. I.、El-Kousy, S. M.、El-Torgoman, A.、Salama, G. M.

  DOI：——

  日期：——
• SYNTHESIS AND ANTITUBERCULAR ACTIVITY OF PYRIDAZINONE DERIVATIVES
  作者：ASIF HUSAIN、AFTAB AHMAD、ANIL BHANDARI、VEERMA RAM

  DOI：10.4067/s0717-97072011000300013

  日期：——

  Two series of pyridazinone derivatives (19-34) were synthesized and evaluated for antitubercular activities against Mycobacterium tuberculosis H(37)Rv strain. The results illustrated that among the synthesized compounds, compound 25, 5-(4-hydroxy-3-methoxybenzyl)-3-(4-chloro-phenyl)-1,6-dihydro-6-pyridazinone emerged as a lead compound with good antitubercular activity. Four more compounds, (21, 22, 29 & 33) were significant in their antitubercular action.