5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbohydrazide | 903517-57-7

• 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-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbohydrazide
• 英文别名: 5-(4-Chlorophenyl)-1-phenyl-1h-pyrazole-3-carbohydrazide；5-(4-chlorophenyl)-1-phenylpyrazole-3-carbohydrazide
• CAS: 903517-57-7
• 化学式: C₁₆H₁₃ClN₄O
• 分子量: 312.758
• InChiKey: SNUIZJUIIYFGJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbohydrazide 在 2-substituted 3-methoxyprop-2-enenitrile 作用下， 以 乙醇 为溶剂， 以58%的产率得到5-(4-chlorophenyl)-N'-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbonyl)-1-phenyl-1H-pyrazole-3-carbohydrazide
  参考文献：
  名称：

  新型对称的N，N'-二酰基肼和2-（1,2,3-三唑-4-基）-1,3,4-恶二唑的合成

  摘要：

  背景：当前研究的目的是通过使用2-氰基-3-甲氧基丙烯酸乙酯或2-（甲氧基亚甲基）丙二腈作为有机催化剂氧化酸性碳酰肼来合成新型对称的N，N'-二酰基肼。另外，在沸腾的磷酰氯中，由酸性碳酰肼与各种羧酸反应，合成了新型的2-（1,2,3-三唑-4-基）-1,3,4-恶二唑。 方法：采用简便的合成方法，使用市售化学品合成目标化合物。同样，通过使用分析和光谱数据以及单一的X射线晶体结构来阐明获得的产物的结构。 结果：方便地合成了一系列新颖的对称N，N'-二酰基肼，2-（1,2,3-三唑-4-基）-1,3,4-恶二唑和醛N-酰基hydr。和简单的程序。 结论：引入了新的一步合成方法，可生产多种对称的N，N'-二酰基肼和2-（1,2,3-三唑-4-基）-1,3,4-恶二唑，得自相应的酰肼。

  DOI：

  10.2174/1570178614666170524130223
• 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 6.0h， 生成 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbohydrazide
  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 and Antimicrobial Activity of Some Novel Substituted 3-(Thiophen-2-yl)pyrazole-based Heterocycles
  作者：Bakr F. Abdel-Wahab、Abdelbasset A. Farahat、Ghada E. A. Awad、Gamal A. El-Hiti

  DOI：10.2174/1570180814666170327162447

  日期：2017.10.3

  Background: A series of novel substituted 3-(thiophen-2-yl)pyrazoles was synthesized efficiently and in high yields using simple and convenient procedures starting from 1-phenyl-3- (thiophen-2-yl)-1H-pyrazole-4-carbaldehyde. Methods: The structures of the newly synthesized products were established and their antimicrobial activities were investigated against some bacteria and fungi. Results and Conclusion:

  背景：从1-苯基-3-（噻吩-2-基）-1H-吡唑-4开始，使用简单便捷的方法，高效，高收率地合成了一系列新型取代的3-（噻吩-2-基）吡唑。 -甲醛 方法：建立新合成产物的结构，并研究其对某些细菌和真菌的抗菌活性。 结果与结论：与标准的抗菌药物和抗真菌药物相比，该产品对被测微生物表现出优异的抗菌活性。
• 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.
• Synthesis of New Symmetrical <i>N, N</i>'-Diacylhydrazines and 2-(1,2,3- Triazol-4-yl)-1,3,4-oxadiazoles
  作者：Bakr F. Abdel-Wahab、Mohammad Hayal Alotaibi、Gamal A. El-Hiti

  DOI：10.2174/1570178614666170524130223

  日期：2017.8.22

  Background: The aim of the current research was to synthesize novel symmetrical N,N'- diacylhydrazines through oxidation of acid carbohydrazide using ethyl 2-cyano-3-methoxyacrylate or 2-(methoxymethylene)malononitrile as organo-catalyst. Also, novel 2-(1,2,3-triazol-4-yl)-1,3,4- oxadiazoles from the reaction of acid carbohydrazides with various carboxylic acids in boiling phosphoryl chloride were

  背景：当前研究的目的是通过使用2-氰基-3-甲氧基丙烯酸乙酯或2-（甲氧基亚甲基）丙二腈作为有机催化剂氧化酸性碳酰肼来合成新型对称的N，N'-二酰基肼。另外，在沸腾的磷酰氯中，由酸性碳酰肼与各种羧酸反应，合成了新型的2-（1,2,3-三唑-4-基）-1,3,4-恶二唑。 方法：采用简便的合成方法，使用市售化学品合成目标化合物。同样，通过使用分析和光谱数据以及单一的X射线晶体结构来阐明获得的产物的结构。 结果：方便地合成了一系列新颖的对称N，N'-二酰基肼，2-（1,2,3-三唑-4-基）-1,3,4-恶二唑和醛N-酰基hydr。和简单的程序。 结论：引入了新的一步合成方法，可生产多种对称的N，N'-二酰基肼和2-（1,2,3-三唑-4-基）-1,3,4-恶二唑，得自相应的酰肼。