3-[(4-Methoxyphenyl)methylidene]-5-(4-methylphenyl)furan-2-one | 101537-01-3

• 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-Methoxyphenyl)methylidene]-5-(4-methylphenyl)furan-2-one
• CAS: 101537-01-3
• 化学式: C₁₉H₁₆O₃
• mdl: MFCD00502248
• 分子量: 292.334
• InChiKey: JGOTVAXIWAWIIS-UHFFFAOYSA-N

物化性质

• 沸点：
  525.9±50.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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-Methoxyphenyl)methylidene]-5-(4-methylphenyl)furan-2-one 在 一水合肼 作用下， 以 丙醇 为溶剂， 反应 3.0h， 以43%的产率得到5-(4-methoxybenzyl)-3-(4-methylphenyl)-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：

  甲苯 在 aluminum (III) chloride 、 乙酸酐 、 三乙胺 作用下， 生成 3-[(4-Methoxyphenyl)methylidene]-5-(4-methylphenyl)furan-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of some new pyridazinone derivatives

  摘要：

  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.

  DOI：

  10.3109/14756366.2010.548810

文献信息

• Synthesis of Substituted Pyridazin-3-ones, 1,2-Oxazin-3-ones, and Furopyrimidines from (Arylmethylidene)furan-2(3H)-ones
  作者：T. V. Anis’kova、A. Yu. Egorova

  DOI：10.1134/s1070428018090208

  日期：2018.9

  Reactions of 5-substituted 3-(arylmethylidene)furan-2(3H)-ones with hydrazine hydrate, hydroxylamine, and guanidine involved opening of the furanone ring. Their hydrazinolysis under mild conditions afforded acyclic 4-oxoalkanoic acid hydrazides which underwent heterocyclization to substituted pyridazinones in boiling ethanol. The presence of an alkyl substituent in the 5-position of the initial furanone

  5-取代的3-（芳基亚甲基）呋喃-2（3 H）-酮与水合肼，羟胺和胍的反应涉及呋喃酮环的打开。它们在温和条件下的肼分解作用提供了无环的4-氧代链烷酸酰肼，它们在沸腾的乙醇中杂环化成取代的哒嗪酮。在初始呋喃酮的5-位上烷基取代基的存在有利于杂环化并形成吡唑烷酮衍生物。3-（芳基亚甲基）呋喃-2（3 H）-one与羟胺和胍的反应也产生了新的六元杂环，2 H -1,2-恶嗪-3（4 H）-one和4,6-双取代的3,4-二氢呋喃[2,3- d ]嘧啶-2-胺。
• 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.