methyl 1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylate | 884850-97-9

• 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 1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylate
• 英文别名: Methyl 1-(4-methoxyphenyl)pyrazole-4-carboxylate
• CAS: 884850-97-9
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: FBTSXRYMIDTPCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylate 在 盐酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 N-(benzylideneamino)-1-(4-methoxyphenyl)pyrazole-4-carboxamide
  参考文献：
  名称：

  Synthesis and leishmanicidal activities of 1-(4-X-phenyl)-N′-[(4-Y-phenyl)methylene]-1H-pyrazole-4-carbohydrazides

  摘要：

  1H-pyrazole-4-carbohydrazides were synthesized and their leishmanicidal in vitro activities and cytotoxic effects were investigated. The drugs prototypes of these new compounds (ketoconazole, benznidazole, allopurinol and pentamidine) were also tested. It was found that among all the 1H-pyrazole-4-carbohydrazides derivatives examined, the most active compounds were those with X = Br, Y = NO2 (27) and X = NO2, Y = Cl (15) derivatives which showed to be most effective on promastigotes forms of L. amazonensis than on L. chagasi and L. braziliensis species. When tested against murine peritoneal macrophages as mammalian host cell controls of toxicity, 1-(4-Br-phenyl)-N'-[(4-NO2-phenyl)methylene]-1H-pyrazole-4-carbohydrazides (27) (EC50 = 50 mu M 1(-1)) and 1-(4-NO2-phenyl)-N'-[(4-Cl-phenyl)methylene]-1H-pyrazole-4-carbohydrazides (15) EC50 = 80 mu M 1(-1))] was reasonably toxic. However, both compounds were less toxic than pentamidine and ketoconazole. These results provide new perspectives on the development of drugs with activities against Leishmania parasite. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.007
• 作为产物：
  描述：

  1-(4-methoxyphenyl)pyrazole-4-carbonyl chloride 、 甲醇 反应 2.0h， 以86%的产率得到methyl 1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  Synthesis and leishmanicidal activities of 1-(4-X-phenyl)-N′-[(4-Y-phenyl)methylene]-1H-pyrazole-4-carbohydrazides

  摘要：

  1H-pyrazole-4-carbohydrazides were synthesized and their leishmanicidal in vitro activities and cytotoxic effects were investigated. The drugs prototypes of these new compounds (ketoconazole, benznidazole, allopurinol and pentamidine) were also tested. It was found that among all the 1H-pyrazole-4-carbohydrazides derivatives examined, the most active compounds were those with X = Br, Y = NO2 (27) and X = NO2, Y = Cl (15) derivatives which showed to be most effective on promastigotes forms of L. amazonensis than on L. chagasi and L. braziliensis species. When tested against murine peritoneal macrophages as mammalian host cell controls of toxicity, 1-(4-Br-phenyl)-N'-[(4-NO2-phenyl)methylene]-1H-pyrazole-4-carbohydrazides (27) (EC50 = 50 mu M 1(-1)) and 1-(4-NO2-phenyl)-N'-[(4-Cl-phenyl)methylene]-1H-pyrazole-4-carbohydrazides (15) EC50 = 80 mu M 1(-1))] was reasonably toxic. However, both compounds were less toxic than pentamidine and ketoconazole. These results provide new perspectives on the development of drugs with activities against Leishmania parasite. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.007

文献信息

• Organic photoredox-catalyzed oxidative azolation of unactivated fluoroarenes
  作者：Guodong Ju、Yalong Li、Yingsheng Zhao

  DOI：10.1039/d3ob01041d

  日期：——

  6-triphenylpyrrolium tetrafluoroborate (TPT) is used as an organic photocatalyst for the nucleophilic aromatic substitution of unactivated fluoroarenes with pyrazole derivatives (SNAr) to form azole arenes. The use of organic photoredox catalysis enables the easy operation of this method under mild conditions. Various fluorinated aromatic compounds are suitable electrophiles for this transformation.

  廉价且市售的 2,4,6-三苯基吡咯四氟硼酸盐 (TPT) 被用作有机光催化剂，用于用吡唑衍生物 (SN Ar) 亲核芳香取代未活化的氟芳烃以形成唑芳烃。有机光氧化还原催化的使用使得该方法在温和条件下易于操作。各种氟化芳香族化合物是适合该转化的亲电子试剂。
• ^<i>n</i>Bu₃P-Catalyzed Desulfonylative [3 + 2] Cycloadditions of Allylic Carbonates with Arylazosulfones to Pyrazole Derivatives
  作者：Qi Zhang、Ling-Guo Meng、Kuai Wang、Lei Wang

  DOI：10.1021/ol503735c

  日期：2015.2.20

  Highly efficient (Bu3P)-Bu-n-catalyzed desulfonylative [3 + 2] cycloadditions of allylic carbonates with arylazosulfones were developed for the synthesis of pyrazole derivatives. The reactions proceed smoothly under mild conditions to generate corresponding annulation products in good to excellent yields.
• Synthesis and leishmanicidal activities of 1-(4-X-phenyl)-N′-[(4-Y-phenyl)methylene]-1H-pyrazole-4-carbohydrazides
  作者：A BERNARDINO、A GOMES、K CHARRET、A FREITAS、G MACHADO、M CANTOCAVALHEIRO、L LEON、V AMARAL

  DOI：10.1016/j.ejmech.2005.10.007

  日期：2006.1

  1H-pyrazole-4-carbohydrazides were synthesized and their leishmanicidal in vitro activities and cytotoxic effects were investigated. The drugs prototypes of these new compounds (ketoconazole, benznidazole, allopurinol and pentamidine) were also tested. It was found that among all the 1H-pyrazole-4-carbohydrazides derivatives examined, the most active compounds were those with X = Br, Y = NO2 (27) and X = NO2, Y = Cl (15) derivatives which showed to be most effective on promastigotes forms of L. amazonensis than on L. chagasi and L. braziliensis species. When tested against murine peritoneal macrophages as mammalian host cell controls of toxicity, 1-(4-Br-phenyl)-N'-[(4-NO2-phenyl)methylene]-1H-pyrazole-4-carbohydrazides (27) (EC50 = 50 mu M 1(-1)) and 1-(4-NO2-phenyl)-N'-[(4-Cl-phenyl)methylene]-1H-pyrazole-4-carbohydrazides (15) EC50 = 80 mu M 1(-1))] was reasonably toxic. However, both compounds were less toxic than pentamidine and ketoconazole. These results provide new perspectives on the development of drugs with activities against Leishmania parasite. (c) 2005 Elsevier SAS. All rights reserved.