4-cyano-2-(4-methylphenyl)-1,3-oxazole-5-sulfonyl chloride | 1416985-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-cyano-2-(4-methylphenyl)-1,3-oxazole-5-sulfonyl chloride
• 英文别名: 4-Cyano-2-(4-methylphenyl)-1,3-oxazole-5-sulfonyl chloride
• CAS: 1416985-32-4
• 化学式: C₁₁H₇ClN₂O₃S
• 分子量: 282.707
• InChiKey: GQCNSGLNCOBFRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-cyano-2-(4-methylphenyl)-1,3-oxazole-5-sulfonyl chloride 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 14.5h， 生成 C₁₅H₁₃N₅O
  参考文献：
  名称：

  2-Aryl-4-Cyano-1,3-Oxazole-5-磺酰氯与5-Amino-1 H -Pyrazoles和5-Amino-1 H -1,2,4-Triazole的反应

  摘要：

  2-芳基-4-氰基-1,3-恶唑-5-磺酰氯与5-氨基-3-R-1 H-吡唑和5-氨基-1 H -1,2,4-三唑的反应得到5-[（3-R-5-氨基-1 H-吡唑-1-基）磺酰基] -2-芳基-1,3-恶唑-4-碳腈和5-[（5-氨基-1 H -1,2,4-三唑-1-基磺酰基] -2-芳基-1,3-恶唑-4-腈。氢化钠对这些腈的作用导致消除二氧化硫和环缩合，生成新的杂环系统，即[1,3]恶唑并[5,4- d ]吡唑并[1,5- a ]-嘧啶和[ 1,3]恶唑[5,4- d ] [1,2,4]三唑[1,5- a ]嘧啶。

  DOI：

  10.1007/s10593-014-1450-2
• 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 sodium hydrogensulfide 、 氯 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 36.5h， 生成 4-cyano-2-(4-methylphenyl)-1,3-oxazole-5-sulfonyl chloride 、
  参考文献：
  名称：

  Synthesis of 2-aryl-4-cyano-1,3-oxazole-5-sulfonyl chlorides and N-substituted sulfonamides

  摘要：

  Oxidative chlorination of 2-aryl-5-benzylsulfanyl-1,3-oxazole-4-carbonitrile results in the previously unknown 4-cyano-1,3-oxazole-5-sulfonyl chlorides and N-substituted sulfonamides.

  DOI：

  10.1134/s1070363212110229

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。
• Interaction of 2-aryl-4-cyano-1,3-oxazole-5-sulfonyl chlorides with amidines
  作者：A. N. Kornienko、S. G. Pil’o、V. M. Prokopenko、E. B. Rusanov、V. S. Brovarets

  DOI：10.1134/s1070363213070165

  日期：2013.7

  Reaction of 4-cyano-1,3-oxazole-5-sulfonyl chlorides with amidines results in new 7-amino-1,3-oxazolo[5,4-d]pyrimidines. Their structure was confirmed by spectral methods and X-ray diffraction analysis.
• In vitro activity of novel derivatives of 1,3-oxazole-4-carboxylate and 1,3-oxazole-4-carbonitrile against human cytomegalovirus
  作者：Maryna V. Kachaeva、Stepan G. Pilyo、Caroll B. Hartline、Emma A. Harden、Mark N. Prichard、Victor V. Zhirnov、Volodymyr S. Brovarets

  DOI：10.1007/s00044-019-02365-x

  日期：2019.8

  Ten 5-functionalized derivatives of 1,3-oxazole-4-carboxylate and 1,3-oxazole-4-carbonitrile were synthesized and their antiviral activities against the human cytomegalovirus (HCMV) were evaluated in vitro. Bioassays showed that seven compounds exhibited considerably higher antiviral activity (EC50:<0.05M) against a normal laboratory HCMV strain (AD-169) in human foreskin fibroblast cells than Ganciclovir (EC50=0.32M), an anti-HCMV agent in clinical use. Additionally, the HCMV-resistant isolate (GDGr K-17) was tested for sensitivity to 1,3-oxazole derivatives with most antiviral potency against the strain AD169. A one of them (5-((2-hydroxyethyl)(methyl)amino)-2-(4-methylphenyl)-1,3-oxazole-4-carbonitrile) showed very high potency (EC50:<0.05; CC50: >150 mu M, and SI50=3125) towards the resistant isolate compared to standard drugs Cidofovir (EC50=0.10 mu M, CC50: >30 mu M and SI50: <4). But, in contrast to the primary assays, the antiviral activity of these compounds against both the normal strain and the resistant isolate of HCMV were considerably less than one of Cidofovir in secondary assay. These results provided evidence that derivatives of 1,3-oxazole could be useful for developing new anti-HCMV drugs.
• Synthesis of 2-aryl-4-cyano-1,3-oxazole-5-sulfonyl chlorides and N-substituted sulfonamides
  作者：A. N. Kornienko、S. G. Pil’o、V. M. Prokopenko、V. S. Brovarets

  DOI：10.1134/s1070363212110229

  日期：2012.11

  Oxidative chlorination of 2-aryl-5-benzylsulfanyl-1,3-oxazole-4-carbonitrile results in the previously unknown 4-cyano-1,3-oxazole-5-sulfonyl chlorides and N-substituted sulfonamides.
• Reaction of 2-Aryl-4-Cyano-1,3-Oxazole-5-Sulfonyl Chlorides With 5-Amino-1H-Pyrazoles and 5-Amino-1H-1,2,4-Triazole
  作者：A. N. Kornienko、S. G. Pil’o、A. P. Kozachenko、V. M. Prokopenko、E. B. Rusanov、V. S. Brovarets

  DOI：10.1007/s10593-014-1450-2

  日期：2014.4

  riles. The action of sodium hydride on these carbonitriles leads to the elimination of sulfur dioxide and cyclocondensation to give new heterocyclic systems, namely, [1,3]oxazolo[5,4-d]pyrazolo[1,5-a]-pyrimidine and [1,3]oxazolo[5,4-d][1,2,4]triazolo[1,5-a]pyrimidine.

  2-芳基-4-氰基-1,3-恶唑-5-磺酰氯与5-氨基-3-R-1 H-吡唑和5-氨基-1 H -1,2,4-三唑的反应得到5-[（3-R-5-氨基-1 H-吡唑-1-基）磺酰基] -2-芳基-1,3-恶唑-4-碳腈和5-[（5-氨基-1 H -1,2,4-三唑-1-基磺酰基] -2-芳基-1,3-恶唑-4-腈。氢化钠对这些腈的作用导致消除二氧化硫和环缩合，生成新的杂环系统，即[1,3]恶唑并[5,4- d ]吡唑并[1,5- a ]-嘧啶和[ 1,3]恶唑[5,4- d ] [1,2,4]三唑[1,5- a ]嘧啶。