2-[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbonyl]-N-phenylhydrazinecarbothioamide | 1257530-09-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbonyl]-N-phenylhydrazinecarbothioamide
• 英文别名: 1-[[5-(4-Chlorophenyl)-1-phenylpyrazole-3-carbonyl]amino]-3-phenylthiourea；1-[[5-(4-chlorophenyl)-1-phenylpyrazole-3-carbonyl]amino]-3-phenylthiourea
• CAS: 1257530-09-8
• 化学式: C₂₃H₁₈ClN₅OS
• 分子量: 447.948
• InChiKey: FZKZOAWVTUTTEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbonyl]-N-phenylhydrazinecarbothioamide 在 硫酸 作用下， 以45%的产率得到5-[5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]-N-phenyl-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Synthesis, anti-HSV-1, and cytotoxic activities of some new pyrazole- and isoxazole-based heterocycles

  摘要：

  Ethyl 2,4-dioxo-4-(p-chloro)phenylbutyrate 2 obtained by condensation of 4-chloroacetophenone with diethyl oxalate was converted to 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbohydrazide 5 and 5-(4-chlorophenyl)isoxazole-3-carbohydrazide 6 in good yields. Treatment of 5 or 6 with phenylisothiocyanate and reaction of the resulting thiosemicarbazide 7 or 8 with chloroacetic acid and 4-fluorobenzaldehyde, phenacyl bromides gave the corresponding 4-thiazolidinone 9 or 10 or 1,3-thiazoles 11 or 12, respectively. While the intramolecular cyclization of 7 or 8 in concentrated sulfuric acid afforded 1,3,4-thiadiazoles 13 or 14. The reactivity of hydrazide 5 or 6 towards fluorinated aldehyde, hydrazonoyl chloride, and beta-ketoester was studied to give fluorinated hydrazones, bis-hydrazones, and pyrazoles 15-23. The newly synthesized compounds were screened for their antiviral activity, and compound 19 reduced the number of viral plaques of Herpes simplex type-1 (HSV-1) by 69%. The detailed synthesis and spectroscopic and biological data are reported.

  DOI：

  10.1007/s00044-010-9420-4
• 作为产物：
  描述：

  4-(4-氯苯基)-2,4-二氧代丁酸乙酯 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 2-[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbonyl]-N-phenylhydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis, anti-HSV-1, and cytotoxic activities of some new pyrazole- and isoxazole-based heterocycles

  摘要：

  Ethyl 2,4-dioxo-4-(p-chloro)phenylbutyrate 2 obtained by condensation of 4-chloroacetophenone with diethyl oxalate was converted to 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbohydrazide 5 and 5-(4-chlorophenyl)isoxazole-3-carbohydrazide 6 in good yields. Treatment of 5 or 6 with phenylisothiocyanate and reaction of the resulting thiosemicarbazide 7 or 8 with chloroacetic acid and 4-fluorobenzaldehyde, phenacyl bromides gave the corresponding 4-thiazolidinone 9 or 10 or 1,3-thiazoles 11 or 12, respectively. While the intramolecular cyclization of 7 or 8 in concentrated sulfuric acid afforded 1,3,4-thiadiazoles 13 or 14. The reactivity of hydrazide 5 or 6 towards fluorinated aldehyde, hydrazonoyl chloride, and beta-ketoester was studied to give fluorinated hydrazones, bis-hydrazones, and pyrazoles 15-23. The newly synthesized compounds were screened for their antiviral activity, and compound 19 reduced the number of viral plaques of Herpes simplex type-1 (HSV-1) by 69%. The detailed synthesis and spectroscopic and biological data are reported.

  DOI：

  10.1007/s00044-010-9420-4

文献信息

• Synthesis, anti-HSV-1, and cytotoxic activities of some new pyrazole- and isoxazole-based heterocycles
  作者：Kamal M. Dawood、Hassan Abdel-Gawad、Hanan A. Mohamed、Farid A. Badria

  DOI：10.1007/s00044-010-9420-4

  日期：2011.9

  Ethyl 2,4-dioxo-4-(p-chloro)phenylbutyrate 2 obtained by condensation of 4-chloroacetophenone with diethyl oxalate was converted to 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbohydrazide 5 and 5-(4-chlorophenyl)isoxazole-3-carbohydrazide 6 in good yields. Treatment of 5 or 6 with phenylisothiocyanate and reaction of the resulting thiosemicarbazide 7 or 8 with chloroacetic acid and 4-fluorobenzaldehyde, phenacyl bromides gave the corresponding 4-thiazolidinone 9 or 10 or 1,3-thiazoles 11 or 12, respectively. While the intramolecular cyclization of 7 or 8 in concentrated sulfuric acid afforded 1,3,4-thiadiazoles 13 or 14. The reactivity of hydrazide 5 or 6 towards fluorinated aldehyde, hydrazonoyl chloride, and beta-ketoester was studied to give fluorinated hydrazones, bis-hydrazones, and pyrazoles 15-23. The newly synthesized compounds were screened for their antiviral activity, and compound 19 reduced the number of viral plaques of Herpes simplex type-1 (HSV-1) by 69%. The detailed synthesis and spectroscopic and biological data are reported.