4-[1-oxo-3-(4-nitrophenyl)-2-propenyl]-3-(3-chloro-4-fluorophenyl)sydnone | 1366133-65-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-[1-oxo-3-(4-nitrophenyl)-2-propenyl]-3-(3-chloro-4-fluorophenyl)sydnone
• 英文别名: 1-[3-(3-chloro-4-fluorophenyl)-5-oxooxadiazol-3-ium-4-ylidene]-3-(4-nitrophenyl)prop-2-en-1-olate
• CAS: 1366133-65-4
• 化学式: C₁₇H₉ClFN₃O₅
• 分子量: 389.727
• InChiKey: QHRDAXFMSURUGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113.18
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  3-(3-chloro-4-fluorophenyl)sydnone 在 四磷十氧化物 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 4-[1-oxo-3-(4-nitrophenyl)-2-propenyl]-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

文献信息

• Ultrasound Assisted One Pot Synthesis, Spectral, Antimicrobial and Antioxidant Studies of Novel 4-[1-Oxo-3-(substituted phenyl)-2-propenyl]-3-substituted Phenyl Sydnones
  作者：Sachin K. Bhosale、Shreenivas R. Deshpande、Rajendra D. Wagh

  DOI：10.14233/ajchem.2015.18864

  日期：——

  4-[1-Oxo-3-(substituted aryl)-2-propenyl]-3-substituted phenyl sydnones (2a-i, 3a-i, 4a-i) are synthesized by ultrasonication method. The synthesis was carried out by reaction of 4-acetyl-3- (substituted phenyl)sydnones (1a-i) with various substituted aryl aldehydes (Ar-CHO). The structures of compounds were established by using NMR, IR, MS and elemental analysis. Compounds were evaluated for antibacterial, antifungal and antioxidant activity. Some of the synthesized compounds have shown good to moderate activity against gram negative bacteria whereas compounds 3c, 4c and 4f have shown marked activity against fungal strains. The compounds 2c, 3c, 4f have shown potent antioxidant activity as compared to reference standards. The compound 4f (IC50 = 3.17 μM) is the most potent with methyl group as substituent showing good antioxidant activity even at very low concentrations. The ultrasonic method of synthesis was found to be simple, reduces reaction time and gives good yield when compared with traditional methods of synthesis.

  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。