1-(4-溴苯基)-1H-吡唑-4-羧酸 | 138907-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(4-溴苯基)-1H-吡唑-4-羧酸
• 英文名称: 1-(4-bromophenyl)-1H-pyrazole-4-carboxylic acid
• 英文别名: 1-(4-bromophenyl)pyrazole-4-carboxylic acid
• CAS: 138907-85-4
• 化学式: C₁₀H₇BrN₂O₂
• mdl: MFCD09941736
• 分子量: 267.082
• InChiKey: GOJGAUFDFLULIK-UHFFFAOYSA-N

物化性质

• 熔点：
  202-203 °C
• 沸点：
  419.6±25.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-溴苯基)-1H-吡唑-4-羧酸 在 氯化亚砜 作用下， 反应 2.5h， 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
• 作为产物：
  描述：

  1-(4-溴苯基)-1H-吡唑-4-羧酸乙酯 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 17.0h， 以17%的产率得到1-(4-溴苯基)-1H-吡唑-4-羧酸
  参考文献：
  名称：

  Synthesis of Pyrazole-Carboxamides and Pyrazole-Carboxylic Acids Derivatives: Simple Methods to Access Powerful Building Blocks

  摘要：

  摘要：含有吡唑基团的混合系统展示了广泛的生物活性。为了获得含有吡唑环的新型混合物，本研究合成了二十种吡唑羧酸和二十种吡唑羧酰胺，采用简单的合成方法，作为开发新结构的基础。

  DOI：

  10.2174/1570178617999200728215322

文献信息

• Synthesis of Pyrazole-Carboxamides and Pyrazole-Carboxylic Acids Derivatives: Simple Methods to Access Powerful Building Blocks
  作者：Byanca Silva Ferreira、Rafaela Corrêa Silva、Bernardo Araújo Souto、Maurício Silva dos Santos

  DOI：10.2174/1570178617999200728215322

  日期：2021.5

  Hybrid systems containing pyrazole moiety show a wide spectrum of biological activities. To access novel hybrids with pyrazole ring, in this work we synthesized twenty pyrazole-carboxylic acids and twenty pyrazole-carboxamides, using simple synthetic methods, to be used as building blocks in the development of new structures.

  摘要：含有吡唑基团的混合系统展示了广泛的生物活性。为了获得含有吡唑环的新型混合物，本研究合成了二十种吡唑羧酸和二十种吡唑羧酰胺，采用简单的合成方法，作为开发新结构的基础。
• Synthesis and oxidation of all isomeric 2-(pyrazolyl)ethanols
  作者：Sergey P. Ivonin、Eduard B. Rusanov、Dmitriy M. Volochnyuk

  DOI：10.1007/s10593-020-02662-z

  日期：2020.3

  on recyclization reaction of 3-(dimethoxymethyl)-2-methoxytetrahydrofuran with hydrazines is described. Oxidation by KMnO4 led to 2-(pyrazol-4-yl)-2-oxoacetic acids. In contrast, 2-(pyrazol-5-yl)ethanol under similar conditions gave only pyrazole-5-carboxylic acid, which formed as a result of oxidation followed by decarbonylation. 2-(Pyrazol-3-yl)ethanol in this oxidation reaction gave a mixture of

  描述了一种基于3-（二甲氧基甲基）-2-甲氧基四氢呋喃与肼的再循环反应制备N-取代的2-（吡唑-4-基）乙醇的有效方法。用KMnO 4氧化产生2-（吡唑-4-基）-2-氧乙酸。相反，在类似条件下的2-（吡唑-5-基）乙醇仅产生吡唑-5-羧酸，其是通过氧化然后脱羰而形成的。在该氧化反应中的2-（吡唑-3-基）乙醇得到2-氧代-2-（吡唑-3-基）乙酸和吡唑-3-羧酸的混合物。
• Pyrazole-amides and -sulfonamides
  申请人：Atkinson N. Robert

  公开号：US20050049237A1

  公开（公告）日：2005-03-03

  Compounds, compositions and methods are provided which are useful in the treatment of diseases through the inhibition of sodium ion flux through voltage-dependent sodium channels. More particularly, the invention provides pyrazole-amides and -sulfonamides, compositions and methods that are useful in the treatment of central or peripheral nervous system disorders, particularly pain and chronic pain by blocking sodium channels associated with the onset or recurrance of the indicated conditions. The compounds, compositions and methods of the present invention are of particular use for treating neuropathic or inflammatory pain by the inhibition of ion flux through a channel that includes a PN3 subunit.

  本发明提供了一种通过抑制电压依赖性钠通道中的钠离子流来治疗疾病的化合物、组合物和方法。更具体地，本发明提供了吡唑酰胺和磺酰胺，以及其组合物和方法，这些化合物、组合物和方法对于治疗中枢或外周神经系统疾病特别是疼痛和慢性疼痛非常有用，通过阻止与所述疾病的发作或复发有关的钠通道。本发明的化合物、组合物和方法特别适用于通过抑制包括PN3亚基的通道中的离子流来治疗神经病理性或炎性疼痛。
• PYRAZOLE-AMIDES AND -SULFONAMIDES
  申请人：Atkinson N. Robert

  公开号：US20080064690A1

  公开（公告）日：2008-03-13

  Compounds, compositions and methods are provided which are useful in the treatment of diseases through the inhibition of sodium ion flux through voltage-dependent sodium channels. More particularly, the invention provides pyrazole-amides and -sulfonamides, compositions and methods that are useful in the treatment of central or peripheral nervous system disorders, particularly pain and chronic pain by blocking sodium channels associated with the onset or recurrance of the indicated conditions. The compounds, compositions and methods of the present invention are of particular use for treating neuropathic or inflammatory pain by the inhibition of ion flux through a channel that includes a PN3 subunit.

  本发明提供了一种通过抑制电压依赖性钠通道中的钠离子通量来治疗疾病的化合物、组合物和方法。更具体地，本发明提供了嘧唑酰胺和磺酰胺、组合物和方法，用于治疗中枢或外周神经系统障碍，特别是疼痛和慢性疼痛，通过阻断与指示条件的发生或复发有关的钠通道。本发明的化合物、组合物和方法特别适用于通过抑制包括PN3亚单位的通道中的离子通量来治疗神经病理性或炎症性疼痛。
• PYRAZOLE-AMIDES FOR USE IN THE TREATMENT OF PAIN
  申请人：Icagen, Inc.

  公开号：EP1451160B1

  公开（公告）日：2010-01-13