methyl 1-(4-bromophenyl)-1H-pyrazole-4-carboxylate | 884850-98-0

• 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-bromophenyl)-1H-pyrazole-4-carboxylate
• 英文别名: methyl 1-(4-bromophenyl)pyrazole-4-carboxylate
• CAS: 884850-98-0
• 化学式: C₁₁H₉BrN₂O₂
• 分子量: 281.109
• InChiKey: HARJKSBCLBBPAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-(4-bromophenyl)-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 1-(4-bromophenyl)-N-[(4-ethoxyphenyl)methylideneamino]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-溴苯基)吡唑-4-甲醛 在 chromium(VI) oxide 、 氯化亚砜 、 硫酸 作用下， 反应 3.0h， 生成 methyl 1-(4-bromophenyl)-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

• Solvent-free and montmorillonite K10-catalyzed domino reactions for the synthesis of pyrazoles with alkynylester as a dual synthon
  作者：Sesuraj Babiola Annes、Rajendhiran Saritha、Saravanan Subramanian、Bhaskaran Shankar、Subburethinam Ramesh

  DOI：10.1039/d0gc00162g

  日期：——

  4-trisubstituted and 1,4-disubstituted pyrazole derivatives. The reaction proceeded via nucleophilic attack of enamine from an intermediate on the β-carbon of an amino acrylate. Experimental outcomes clearly revealed that organic solvents had an adverse effect upon pyrazole formation, and that an oxidative condition in the presence of the reusable clay favored formation of the 1,3,4-trisubstituted pyrazole. The clay

  具有高度区域选择性，无溶剂和蒙脱土K10粘土催化的多米诺骨牌工艺与空前的闭环C-C键形成反应被描述用于合成新的1,3,4-三取代和1,4-类二取代吡唑衍生物。该反应通过烯胺的中间体的亲核攻击从氨基丙烯酸酯的β-碳上进行。实验结果清楚地表明，有机溶剂对吡唑的形成有不利影响，并且在可重复使用的粘土存在下的氧化条件有利于1,3,4-三取代的吡唑的形成。在N-溴琥珀酰亚胺催化剂存在下，粘土在高温下热解后得到1，4-二取代的吡唑。
• 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.