N-(5-(2-oxo-2H-chromen-3-yl)-1,3,4-oxadiazol-2-yl)benzamide | 1350468-46-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-(5-(2-oxo-2H-chromen-3-yl)-1,3,4-oxadiazol-2-yl)benzamide
• 英文别名: N-[5-(2-oxochromen-3-yl)-1,3,4-oxadiazol-2-yl]benzamide
• CAS: 1350468-46-0
• 化学式: C₁₈H₁₁N₃O₄
• 分子量: 333.303
• InChiKey: MBOCPETVVYJFOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(5-(cyanomethyl)-1,3,4-oxadiazol-2-yl)benzamide 、 水杨醛 在 哌啶 、 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以72%的产率得到N-(5-(2-oxo-2H-chromen-3-yl)-1,3,4-oxadiazol-2-yl)benzamide
  参考文献：
  名称：

  Synthesis and antitumor evaluation of some new 1,3,4-oxadiazole-based heterocycles

  摘要：

  The synthetic strategies and characterization of some novel 1,3,4-oxadiazole derivatives carrying different pharmacophores and heterocyclic rings that are relevant to potential antitumor and cytotoxic activities are described. The antitumor activities of the newly synthesized compounds were evaluated according to the protocol of the National Cancer Institute (NCI) in-vitro disease-oriented human cells screening panel assay. The results revealed that five compounds, namely 2, 7a, ha, 12b, and 17; displayed promising in-vitro antitumor activity in the 4-cell lines assay. Incorporating a thiazole ring to 1,3,4-oxadiazole skeleton resulted in better antitumor activities than those displayed by the pyrazole and thiophene ring systems. Transformation of 1,3,4-oxadiazole 2 to N-(6-amino-7H-pyrazolo[5,1-c][1,2,4] triazol-3-yl)benzamide (15) diminished the antitumor activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.12.013

文献信息

• Synthesis and biological evaluation of 2,5-disubstituted 1,3,4-oxadiazole derivatives with both COX and LOX inhibitory activity
  作者：Mymoona Akhter、Nayeema Akhter、M. M. Alam、M. S. Zaman、Rikta Saha、A. Kumar

  DOI：10.3109/14756366.2010.550890

  日期：2011.12.1

  Dual cyclooxygenase/lipoxygenase (COX/LOX) inhibitors constitute a valuable alternative to classical nonsteroidal anti-inflammatory drugs (NSAIDs) and selective COX-2 inhibitors for the treatment of inflammatory diseases. A series of 3-(5-phenyl/phenylamino-[1,3,4]oxadiazol-2-yl)-chromen-2-one and N-[5-(2-oxo-2H-chromen-3-yl)-[1,3,4] oxadiazol-2-yl]-benzamide derivatives were synthesized and screened for anti-inflammatory, analgesic activity. All the derivatives prepared are active in inhibiting oedema induced by carrageenan. Compound 4e was found more potent with 89% of inhibition followed by compound 4b (86%). Compounds with >70% of anti-inflammatory activity were tested for analgesic, ulcerogenic, and lipid peroxidation profile. Selected compounds were also evaluated for inhibition of COXs (COX-1 and COX-2) and LOXs (LOX-5, LOX-12, and LOX-15). Compound 4e was comparatively selective for COX-2, LOX-5, and LOX-15. Study revealed that these derivatives were more effective than ibuprofen with reduced side effects. It can be suggested that these derivatives could be used to develop more potent and safer NSAIDs.
• Synthesis and antitumor evaluation of some new 1,3,4-oxadiazole-based heterocycles
  作者：Samir Bondock、Shymaa Adel、Hassan A. Etman、Farid A. Badria

  DOI：10.1016/j.ejmech.2011.12.013

  日期：2012.2

  The synthetic strategies and characterization of some novel 1,3,4-oxadiazole derivatives carrying different pharmacophores and heterocyclic rings that are relevant to potential antitumor and cytotoxic activities are described. The antitumor activities of the newly synthesized compounds were evaluated according to the protocol of the National Cancer Institute (NCI) in-vitro disease-oriented human cells screening panel assay. The results revealed that five compounds, namely 2, 7a, ha, 12b, and 17; displayed promising in-vitro antitumor activity in the 4-cell lines assay. Incorporating a thiazole ring to 1,3,4-oxadiazole skeleton resulted in better antitumor activities than those displayed by the pyrazole and thiophene ring systems. Transformation of 1,3,4-oxadiazole 2 to N-(6-amino-7H-pyrazolo[5,1-c][1,2,4] triazol-3-yl)benzamide (15) diminished the antitumor activity. (C) 2011 Elsevier Masson SAS. All rights reserved.