N-(1,5-二甲基-3-氧代-2-苯基吡唑-4-基)苯甲酰胺 | 5702-68-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: N-(1,5-二甲基-3-氧代-2-苯基吡唑-4-基)苯甲酰胺
• 英文名称: N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pryazol-4-yl)benzamide
• 英文别名: 4-{(N-benzoyl)amino}antipyrine；benzalaminophenazone；4-benzoylamino-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one；N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-benzamide；N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-benzamid；4-Benzamino-2,3-dimethyl-1-phenyl-pyrazolon-(5)；1-Phenyl-2,3-dimethyl-4-benzoylamino-5-pyrazolone；N-(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)benzamide
• CAS: 5702-68-1
• 化学式: C₁₈H₁₇N₃O₂
• 分子量: 307.352
• InChiKey: TWAXSNQMTXARTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  183 °C
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  N-(1,5-二甲基-3-氧代-2-苯基吡唑-4-基)苯甲酰胺 在 盐酸 作用下， 反应 6.0h， 生成 4-氨基安替比林
  参考文献：
  名称：

  Soliman, Pharmazie, 1981, vol. 36, # 2, p. 91 - 93

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酸 在 吡啶 、 氯化亚砜 作用下， 反应 5.0h， 生成 N-(1,5-二甲基-3-氧代-2-苯基吡唑-4-基)苯甲酰胺
  参考文献：
  名称：

  Synthesis, characterization and biological evaluation of N-(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)benzamides

  摘要：

  将模型化的h-GCAP的活性位点残基与模板h-PLAP进行比较。

  DOI：

  10.1039/c5ra17568b

文献信息

• Two Efficient <i>N</i>-Acylation Methods Mediated by Solid-Supported Reagents for Weakly Nucleophilic Heterocyclic Amines
  作者：Kyungjin Kim、Kang Le

  DOI：10.1055/s-1999-2987

  日期：1999.12

  Two efficient acylation methods utilizing solid-supported reagents have been developed for weakly nucleophilic heterocyclic amines. The novel approaches by chemoselective purification and polymeric-supported reagents facilitate library synthesis of diverse heterocyclic amides that are found in several pharmacophores.

  针对弱亲核性杂环胺，我们开发了两种利用固体支撑试剂的高效酰化方法。通过化学选择性纯化和聚合物支撑试剂的新方法促进了多种杂环胺的库合成，这些杂环胺可在多种药剂中找到。
• Detailed investigation of anticancer activity of sulfamoyl benz(sulfon)amides and 1H–pyrazol–4–yl benzamides: An experimental and computational study
  作者：Jamshed Iqbal、Syeda Abida Ejaz、Aamer Saeed、Mariya al-Rashida

  DOI：10.1016/j.ejphar.2018.05.011

  日期：2018.8

  Cancer is the second leading cause of mortality worldwide. Therapeutic approach to cancer is a multi-faceted one, whereby many cellular/enzymatic pathways have been discovered as important drug targets for the treatment of cancer. A major disadvantage of most of the currently available anticancer drugs is their non-selective cytotoxicity towards cancerous as well as healthy cells. Another major hurdle in cancer therapy is the development of resistance to anticancer drugs. This necessitates the discovery of new molecules with potent and selective cytotoxic activity towards only cancerous cells, with minimum or no damage to the normal/healthy cells. Herein we report detailed investigation into the anticancer activity of sulfamoyl benz(sulfon)amides (1a-1g, 2a-2k) and 1H-pyrazol-4-yl benzamides (3a-3j) against three cancer cell lines, breast cancer cells (MCF-7), bone-marrow cancer cells (K-562) and cervical cancer cells (HeLa). For comparison, screening against healthy baby hamster kidney cells (BHK-21) was carried out. All compounds exhibited selective cytotoxicity towards cancerous cells. Cell cycle analysis was carried out using flow cytometry, followed by fluorescence microscopic analysis. DNA interaction and docking studies were also carried out.
• Zorn; Schmidt, Pharmazie, 1957, vol. 12, p. 396,399
  作者：Zorn、Schmidt

  DOI：——

  日期：——
• Agarwal, R. K.; Rawat, H. K.; Srivastava, A. K., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1988, vol. 27, # 12, p. 1105 - 1108
  作者：Agarwal, R. K.、Rawat, H. K.、Srivastava, A. K.

  DOI：——

  日期：——
• Synthesis, characterization and biological evaluation of N-(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)benzamides
  作者：Aamer Saeed、Syeda Abida Ejaz、Asma Khurshid、Sidra Hassan、Mariya al-Rashida、Muhammad Latif、Joanna Lecka、Jean Sévigny、Jamshed Iqbal

  DOI：10.1039/c5ra17568b

  日期：——

  Comparison of active site residues of modelled h-GCAP with template h-PLAP.

  将模型化的h-GCAP的活性位点残基与模板h-PLAP进行比较。