methyl 5‐chlorosulfonyl‐2‐phenyl‐1,3‐oxazole‐4‐carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 5‐chlorosulfonyl‐2‐phenyl‐1,3‐oxazole‐4‐carboxylate
• 英文别名: Methyl 5-(chlorosulfonyl)-2-phenyl-1,3-oxazole-4-carboxylate；methyl 5-chlorosulfonyl-2-phenyl-1,3-oxazole-4-carboxylate
• 化学式: C₁₁H₈ClNO₅S
• 分子量: 301.707
• InChiKey: MOZDCIVMRJGFTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  94.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5‐chlorosulfonyl‐2‐phenyl‐1,3‐oxazole‐4‐carboxylate 、 4-氟苄脒盐酸盐 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 以58%的产率得到
  参考文献：
  名称：

  Synthesis of methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates and their reactions with amines and amidines

  摘要：

  Previously unknown methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates have been synthesized. Their reactions with amines and amidines have yielded the corresponding sulfonamides and 6H, 7H-[1,3]oxazolo[5,4-d] pyrimidin-7-ones.

  DOI：

  10.1134/s1070363214080210
• 作为产物：
  描述：

  methyl ester of 3,3-dichloro-2-benzoylaminoacrylic acid 在 sodium hydrogen sulfide 、 氯 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 36.5h， 生成 methyl 5‐chlorosulfonyl‐2‐phenyl‐1,3‐oxazole‐4‐carboxylate
  参考文献：
  名称：

  Synthesis of methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates and their reactions with amines and amidines

  摘要：

  Previously unknown methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates have been synthesized. Their reactions with amines and amidines have yielded the corresponding sulfonamides and 6H, 7H-[1,3]oxazolo[5,4-d] pyrimidin-7-ones.

  DOI：

  10.1134/s1070363214080210

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。
• 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.