4-acetyl-3-(3-chloro-4-fluorophenyl)sydnone | 1366133-70-1

• 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: 4-acetyl-3-(3-chloro-4-fluorophenyl)sydnone
• CAS: 1366133-70-1
• 化学式: C₁₀H₆ClFN₂O₃
• 分子量: 256.621
• InChiKey: OWQJPPNQUJCBEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  70.04
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-acetyl-3-(3-chloro-4-fluorophenyl)sydnone 、 4-氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 以93%的产率得到4-[1-oxo-3-(4-chlorophenyl)-2-propenyl]-3-(3-chloro-4-fluorophenyl)sydnone
  参考文献：
  名称：

  Ultrasound Assisted One Pot Synthesis, Spectral, Antimicrobial and Antioxidant Studies of Novel 4-[1-Oxo-3-(substituted phenyl)-2-propenyl]-3-substituted Phenyl Sydnones

  摘要：

  采用超声法合成了 4-[1-氧代-3-（取代的芳基）-2-丙烯基]-3-取代苯基茚酮 (2a-i、3a-i、4a-i)。合成是通过 4-乙酰基-3-（取代苯基）茚酮（1a-i）与各种取代芳基醛（Ar-CHO）反应进行的。化合物的结构是通过核磁共振、红外光谱、质谱和元素分析确定的。评估了化合物的抗菌、抗真菌和抗氧化活性。一些合成化合物对革兰氏阴性菌具有良好至中等程度的活性，而化合物 3c、4c 和 4f 则对真菌菌株具有明显的活性。与参考标准相比，化合物 2c、3c 和 4f 具有很强的抗氧化活性。以甲基为取代基的化合物 4f（IC50 = 3.17 μM）的抗氧化活性最强，即使在很低的浓度下也能显示出良好的抗氧化活性。与传统的合成方法相比，超声波合成法简单、反应时间短、产量高。

  DOI：

  10.14233/ajchem.2015.18864
• 作为产物：
  描述：

  3-(3-chloro-4-fluorophenyl)sydnone 、 溶剂黄146 在 四磷十氧化物 作用下， 生成 4-acetyl-3-(3-chloro-4-fluorophenyl)sydnone
  参考文献：
  名称：

  Fluorine bearing sydnones with styryl ketone group: synthesis and their possible analgesic and anti-inflammatory activities

  摘要：

  In continuation of structure activity relationship studies, a panel of fluorine containing sydnones with styryl ketone group 4-[1-oxo-3-(substituted aryl)-2-propenyl]-3-(3-chloro-4-fluorophenyl) sydnones 2a-i, was synthesized as better analgesic and anti-inflammatory agents. The title compounds were formed by condensing 4-acetyl-3-(3-chloro-4-fluorophenyl) sydnone with various substituted aryl aldehydes, characterized by spectral studies and evaluated at 100 mg\kg b.w., p.o. for analgesic, anti-inflammatory and ulcerogenic activities. Compounds 2c and 2e showed good analgesic effect in acetic acid-induced writhing while none showed significant activity in hot plate assay in mice. In carrageenan-induced rat paw oedema test, compound 2c and 2f exhibited good anti-inflammatory effect at 3rd h, whereas compounds 2c, 2e, 2d, 2g and 2h showed activity in croton oil induced ear oedema assay in mice. Compounds 2c and 2e were less ulcerogenic than ibuprofen in rats, when tested by ulcer index method. Compounds with electron attracting substituents such as 2c and 2e were found to be promising in terms of the ratio of efficacy and adverse effect. These compounds generally exhibited better activity than those of earlier series signifying fluorine substitution.

  DOI：

  10.3109/14756366.2011.586345