5-(4-Chloro-phenylsulfanyl)-2-p-tolyl-oxazole-4-carbonitrile | 537709-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-Chloro-phenylsulfanyl)-2-p-tolyl-oxazole-4-carbonitrile
• 英文别名: 5-[(4-Chlorophenyl)sulfanyl]-2-(4-methylphenyl)-1,3-oxazole-4-carbonitrile；5-(4-chlorophenyl)sulfanyl-2-(4-methylphenyl)-1,3-oxazole-4-carbonitrile
• CAS: 537709-72-1
• 化学式: C₁₇H₁₁ClN₂OS
• 分子量: 326.806
• InChiKey: UOCIDIQCXHCTFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  75.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-Chloro-phenylsulfanyl)-2-p-tolyl-oxazole-4-carbonitrile 在 双氧水 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 生成 2-(4-Methylphenyl)-5-[(4-methylphenyl)sulfonyl]-1,3-oxazole-4-carbonitrile
  参考文献：
  名称：

  摘要：

  Enamides of the general formula Cl2C=C(X)NHCOR1, where X = CN, COOAlk, CONH2, P(O)(OEt)(2), P(O)Ph-2, PPh3 Cl-, were treated in succession with alkane- or arenethiols and silver carbonate to obtain 5-alkyl(aryl)thio-2-R-1-4-X-1,3-oxazoles with high selectivity. The latter were converted into the corresponding sulfonyl derivatives. Unlike 2-acylamino-3,3-dichloroacrylonitriles which react with sodium hydrogen sulfide in a nonselective fashion, reactions of derivatives like Cl(ArS)C=C(CN)NHCOR1 with NaHS lead to hitherto unknown 5-arylthio-4-thiocarbamoyl-2-R-1-1,3-oxazoles whose structure was confirmed both by spectral methods and by cyclocondensation with bromoacetophenone according to Hantzsch. Heating of some 2-aryl-5-mercapto-4-X-1,3-oxazoles with benzenethiols results in recyclization into the corresponding 2,4-disubstituted 5-arylthio-1,3-thiazoles, presumably due to prototropic tautomerism in the 5-mercapto-oxazole fragment.

  DOI：

  10.1023/a:1023333011230
• 作为产物：
  描述：

  N-(2,2-二氯-1-氰基乙烯基)-4-甲基苯甲酰胺 在 三乙胺 、 silver carbonate 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 5-(4-Chloro-phenylsulfanyl)-2-p-tolyl-oxazole-4-carbonitrile
  参考文献：
  名称：

  摘要：

  Enamides of the general formula Cl2C=C(X)NHCOR1, where X = CN, COOAlk, CONH2, P(O)(OEt)(2), P(O)Ph-2, PPh3 Cl-, were treated in succession with alkane- or arenethiols and silver carbonate to obtain 5-alkyl(aryl)thio-2-R-1-4-X-1,3-oxazoles with high selectivity. The latter were converted into the corresponding sulfonyl derivatives. Unlike 2-acylamino-3,3-dichloroacrylonitriles which react with sodium hydrogen sulfide in a nonselective fashion, reactions of derivatives like Cl(ArS)C=C(CN)NHCOR1 with NaHS lead to hitherto unknown 5-arylthio-4-thiocarbamoyl-2-R-1-1,3-oxazoles whose structure was confirmed both by spectral methods and by cyclocondensation with bromoacetophenone according to Hantzsch. Heating of some 2-aryl-5-mercapto-4-X-1,3-oxazoles with benzenethiols results in recyclization into the corresponding 2,4-disubstituted 5-arylthio-1,3-thiazoles, presumably due to prototropic tautomerism in the 5-mercapto-oxazole fragment.

  DOI：

  10.1023/a:1023333011230

文献信息

• Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues
  作者：Maryna V. Kachaeva、Diana M. Hodyna、Nataliya V. Obernikhina、Stepan G. Pilyo、Yulia S. Kovalenko、Volodymyr M. Prokopenko、Oleksiy D. Kachkovsky、Volodymyr S. Brovarets

  DOI：10.1002/jhet.3711

  日期：2019.11

  the relative position of the boundary levels (HOMO end LUMO). The quantum‐chemical modeling was performed; the special parameter φ0 for 1,3‐oxazole derivatives correlates with the experimental results. Quantum‐chemical calculations of the special parameter φ0 allow modeling the pharmacological activity of 1,3‐oxazole derivatives by introducing donor or acceptor substituents at position 2 or 5. This work

  合成了一系列新的1,3-恶唑衍生物，它们在第5位含有供体和受体取代基。这些物质被认为是人类肿瘤细胞系中潜在活性的抗癌药效团，其衍生自九种癌症类型，包括肺癌，结肠癌，黑色素瘤，肾癌，卵巢癌，脑癌，白血病，乳腺癌和前列腺癌。初步的体外单剂量抗癌筛选显示，第5位具有受体取代基的化合物（例如–C（O）OMe，–CN）会抑制大多数细胞系的生长，而具有供体取代基的化合物（例如–NHR位置5的-SR）实际上不抑制癌细胞系的生长。可以假定1,3-恶唑衍生物的药理活性取决于5位取代基的供体/受体性质。0，其中考虑了边界水平的相对位置（HOMO结束LUMO）。进行了量子化学建模；特殊参数φ 0为与实验结果-1,3-唑衍生物相关因素。特殊参数的量子化学计算φ 0允许通过在2位或5引入供体或受体取代基建模1,3-恶唑衍生物的药理活性这项工作可能是有益的化学家开发的潜在的生物活性的靶合成化合物。