3-(4-chloro-phenyl)-4-formyl-sydnone | 86870-34-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(4-chloro-phenyl)-4-formyl-sydnone
• 英文别名: 3-(4-Chlorophenyl)-4-formyloxadiazol-3-ium-5-olate；3-(4-chlorophenyl)-4-formyloxadiazol-3-ium-5-olate
• CAS: 86870-34-0
• 化学式: C₉H₅ClN₂O₃
• 分子量: 224.603
• InChiKey: IBHLWLBOSRLOPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.49
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3-(4-chloro-phenyl)-4-formyl-sydnone 在 iron(III) chloride 、 sodium citrate 、 柠檬酸 作用下， 以 乙醇 、 水 为溶剂， 反应 12.17h， 生成 3-(p-chlorophenyl)-4-[6'-(6''-chlorocoumarin-3''-yl)-imidazo[2,1-b][1,3,4]thiadiazol-2'-yl]-sydnone
  参考文献：
  名称：

  Synthesis of novel imidazo[2,1-b][1,3,4]thiadiazoles appended to sydnone as anticancer agents

  摘要：

  A novel series of 3-aryl-4{6'-(6''-substituted-coumarin-3''-yl) imidazo[2,1-b][1,3,4]thiadiazol-2'-yl}-sydnones 5h-5s were synthesized and screened for their anticancer and DNA cleavage activities and analyzed for pharmacological parameters such as toxicity, drug-likeliness, and drug score for oral bioavailability. In vitro toxicity assay was carried out by assessing the survival E. coli AB1157 (wild type) cultures. Some of the compounds have shown significant anticancer activities also.

  DOI：

  10.1007/s00044-012-0441-z
• 作为产物：
  描述：

  3-(4-氯苯基)-1,2,3-氧杂二氮唑-3-鎓-5-酸内盐 、 N-甲基甲酰苯胺 在 三氯氧磷 作用下， 生成 3-(4-chloro-phenyl)-4-formyl-sydnone
  参考文献：
  名称：

  设计，对接研究和分子碘催化的透明质酸酶抑制剂苯并[a]黄嘌呤酮一衍生物的合成

  摘要：

  设计了一系列新颖的苯并[ a ]黄体酮11（12 H）-一衍生物4a - m并进行了对接研究。由3-芳基-4-甲酰基sydnones 1a – m，β-萘酚和二甲酮在分子碘作为催化剂的条件下合成标题化合物，并对其在体外对透明质酸酶的抑制作用进行了评估。

  DOI：

  10.1007/s00044-016-1655-2

文献信息

• Synthesis of novel 2-(3′-aryl-sydnon-4′-ylidene)-5′-substituted-[1,3,4]-thiadiazolylamines and [1,3,4]-thiadiazol-2′-yl-3-oxo-[1,2,4]-triazoles as antimicrobial agents
  作者：Soujanya Bansode、Ravindra Kamble

  DOI：10.1007/s00044-011-9596-2

  日期：2012.6

  The title compounds (3g-n) and (6g-n) were synthesized using 3-arylsydnones as synthons, and the structures were confirmed by IR, H-1 NMR, FAB mass and CHN analysis. These compounds were evaluated for their antibacterial and the antifungal activities in terms of minimum inhibitory concentrations (MICs) against the bacterial strains E. coli, B. cereus, and the fungal strains A. niger, C. albicans. Some of the compounds have shown significant activities.
• Dallacker,F.; Kern,J., Chemische Berichte, 1966, vol. 99, p. 3830 - 3835
  作者：Dallacker,F.、Kern,J.

  DOI：——

  日期：——
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  作者：Hung, Wei-Jing、Tien, Hsien-Ju、Chou, Tzoo-Ming、Tien, Ling-Ling、Wu, Cheng-Kwei

  DOI：——

  日期：——
• Hung, Wei-Jing; Tien, Hsien-Ju; Yu, Hsien-Cheng, Journal of the Chinese Chemical Society, 1994, vol. 41, # 1, p. 39 - 45
  作者：Hung, Wei-Jing、Tien, Hsien-Ju、Yu, Hsien-Cheng

  DOI：——

  日期：——
• Synthesis of novel imidazo[2,1-b][1,3,4]thiadiazoles appended to sydnone as anticancer agents
  作者：Gireesh Tegginamath、Ravindra R. Kamble、Tasneem Taj、Pramod P. Kattimani、Gangadhar Y. Meti

  DOI：10.1007/s00044-012-0441-z

  日期：2013.9

  A novel series of 3-aryl-46'-(6''-substituted-coumarin-3''-yl) imidazo[2,1-b][1,3,4]thiadiazol-2'-yl}-sydnones 5h-5s were synthesized and screened for their anticancer and DNA cleavage activities and analyzed for pharmacological parameters such as toxicity, drug-likeliness, and drug score for oral bioavailability. In vitro toxicity assay was carried out by assessing the survival E. coli AB1157 (wild type) cultures. Some of the compounds have shown significant anticancer activities also.