1-p-nitropenylpyrazole-4-carboxylic acid | 68287-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-p-nitropenylpyrazole-4-carboxylic acid
• 英文别名: 1-(4-nitrophenyl)-1H-pyrazole-4-carboxylic acid；1-(4-Nitro-phenyl)-1H-pyrazol-4-carbonsaeure；1-(4-nitrophenyl)pyrazole-4-carboxylic acid
• CAS: 68287-79-6
• 化学式: C₁₀H₇N₃O₄
• mdl: MFCD08696936
• 分子量: 233.183
• InChiKey: FHLYLGPMPNMDKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 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：
  101
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  1-p-nitropenylpyrazole-4-carboxylic acid 在 盐酸 、 氯化亚砜 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.5h， 生成 N-[(4-ethoxyphenyl)methylideneamino]-1-(4-nitrophenyl)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：

  4-硝基苯肼盐酸盐 在 盐酸 、 potassium permanganate 、 三氟乙酸 作用下， 以 乙醇 、 水 为溶剂， 反应 14.0h， 生成 1-p-nitropenylpyrazole-4-carboxylic acid
  参考文献：
  名称：

  由塞来昔布和扑热息痛通过分子杂交设计的新化合物的分子对接和药理/毒理学评估。

  摘要：

  非甾体类抗炎药在世界范围内普遍使用。然而，它们具有若干不利影响，表明需要开发新的，更有效和安全的抗炎和止痛药。这项研究旨在设计，合成和进行LQFM-102的药理/毒理学研究，该研究是由塞来昔布和扑热息痛通过分子杂交设计的。为了评估该化合物的镇痛作用，我们进行了福尔马林引起的疼痛，热板和甩尾试验。在角叉菜胶诱发的爪水肿和胸膜炎试验中评估了LQFM-102的抗炎作用。还分析了指示毒性的生化标志物AST，ALT，GSH，尿素和肌酐，以及长期服用LQFM-102后的胃病变指数。此外，通过分子对接评价了LQFM-102与COX酶的相互作用。在所有实验方案中，以与LQFM-102等摩尔的剂量将塞来昔布或扑热息痛用作阳性对照。LQFM-102在测试的两个阶段均减轻了福尔马林引起的疼痛。但是，该化合物在热板和甩尾试验中并未增加对热刺激的潜伏期，表明该效应涉及外周机制。此外，LQFM-102减少爪水肿，多形

  DOI：

  10.1007/s10787-018-0516-7

文献信息

• Takamizawa; Hayashi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 339,343
  作者：Takamizawa、Hayashi

  DOI：——

  日期：——
• Khan, Misbahul Ain; Ribeiro, Jorge, Polish Journal of Chemistry, 1987, vol. 61, # 4-6, p. 569 - 572
  作者：Khan, Misbahul Ain、Ribeiro, Jorge

  DOI：——

  日期：——
• GHOSH C. K.; MUKHOPADHYAY K. K., J. INDIAN CHEM. SOC., 1978, 55, NO 3 268-271
  作者：GHOSH C. K.、 MUKHOPADHYAY K. K.

  DOI：——

  日期：——
• 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.
• Molecular docking and pharmacological/toxicological assessment of a new compound designed from celecoxib and paracetamol by molecular hybridization
  作者：Daiany P. B. da Silva、Iziara F. Florentino、Dayane M. da Silva、Roberta C. Lino、Carina S. Cardoso、Lorrane K. S. Moreira、Géssica A. Vasconcelos、Daniela C. Vinhal、Anna C. D. Cardoso、Bianca Villavicencio、Hugo Verli、Boniek G. Vaz、Luciano M. Lião、Luiz C. da Cunha、Ricardo Menegatti、Elson A. Costa

  DOI：10.1007/s10787-018-0516-7

  日期：2018.10

  effective and safe anti-inflammatory and analgesic drugs. This research aimed to design, synthesize and carry out a pharmacological/toxicological investigation of LQFM-102, which was designed from celecoxib and paracetamol by molecular hybridization. To evaluate the analgesic effect of this compound, we performed formalin-induced pain, hot plate and tail flick tests. The anti-inflammatory effect of LQFM-102

  非甾体类抗炎药在世界范围内普遍使用。然而，它们具有若干不利影响，表明需要开发新的，更有效和安全的抗炎和止痛药。这项研究旨在设计，合成和进行LQFM-102的药理/毒理学研究，该研究是由塞来昔布和扑热息痛通过分子杂交设计的。为了评估该化合物的镇痛作用，我们进行了福尔马林引起的疼痛，热板和甩尾试验。在角叉菜胶诱发的爪水肿和胸膜炎试验中评估了LQFM-102的抗炎作用。还分析了指示毒性的生化标志物AST，ALT，GSH，尿素和肌酐，以及长期服用LQFM-102后的胃病变指数。此外，通过分子对接评价了LQFM-102与COX酶的相互作用。在所有实验方案中，以与LQFM-102等摩尔的剂量将塞来昔布或扑热息痛用作阳性对照。LQFM-102在测试的两个阶段均减轻了福尔马林引起的疼痛。但是，该化合物在热板和甩尾试验中并未增加对热刺激的潜伏期，表明该效应涉及外周机制。此外，LQFM-102减少爪水肿，多形