3-(4-chlorobenzylidene)-5-(4-chlorophenyl)-2(3H)-furanone | 32544-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-chlorobenzylidene)-5-(4-chlorophenyl)-2(3H)-furanone
• 英文别名: 5-(4-chlorophenyl)-3-[(4-chlorophenyl)methylidene]furan-2-one
• CAS: 32544-93-7
• 化学式: C₁₇H₁₀Cl₂O₂
• 分子量: 317.171
• InChiKey: FVKNBYKHNNEYAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(4-chlorobenzylidene)-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58%的产率得到5-(4-chlorobenzyl)-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-chlorobenzylidene)-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。
• Novel Butenolide Derivatives as Dual-Chitinase Inhibitors to Arrest the Growth and Development of the Asian Corn Borer
  作者：Renxuan Zou、Xiang Li、Xi Jiang、Dongmei Shi、Qing Han、Hongxia Duan、Qing Yang

  DOI：10.1021/acs.jafc.3c06714

  日期：2024.3.6

  OfChtI and OfChi-h are considered potential targets for the control of Asian corn borer (Ostrinia furnacalis). In this work, the previously reported OfChtI inhibitor 5f was found to show certain inhibitory activity against OfChi-h (Ki = 5.81 μM). Two series of novel butenolide derivatives based on lead compound 5f were designed with the conjugate skeleton, contributing to the π-binding interaction

  Of ChtI 和Of Chi-h 被认为是控制亚洲玉米螟 ( Ostriniafurnacalis ) 的潜在目标。在这项工作中，发现先前报道的Of ChtI抑制剂5f对Of Chi-h表现出一定的抑制活性（ K i = 5.81 μM）。基于先导化合物5f ，设计并合成了两个系列的新型丁烯酸内酯衍生物，其具有共轭骨架，有助于与几丁质酶的π结合相互作用。浓度为 10 μM 的化合物4a-l和7a-p分别对Of ChtI 和Of Chi-h 表现出优异的抑制活性。化合物4h被发现是一种良好的双几丁质酶抑制剂，对Of ChtI和Of Chi-h的K i值分别为1.82和2.00 μM。通过分子对接进行的抑制机制研究表明，π-π堆积相互作用对于新型丁烯酸内酯衍生物对两种不同几丁质酶的抑制活性至关重要。初步生物测定表明4h对亚洲玉米螟有一定的生长抑制作用。丁烯酸内酯样类似物应作为有前景的新型双几
• 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.
• 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.