N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)furan-2-carboxamide | 301354-56-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)furan-2-carboxamide
• 英文别名: N-(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)furan-2-carboxamide
• CAS: 301354-56-3
• 化学式: C₁₆H₁₅N₃O₃
• 分子量: 297.313
• InChiKey: IAHMZITZHFBRBT-UHFFFAOYSA-N

物化性质

• 溶解度：
  26.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  糠酸（呋喃甲酸） 在 吡啶 、 氯化亚砜 作用下， 反应 2.0h， 生成 N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)furan-2-carboxamide
  参考文献：
  名称：

  Detailed investigation of anticancer activity of sulfamoyl benz(sulfon)amides and 1H–pyrazol–4–yl benzamides: An experimental and computational study

  摘要：

  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.

  DOI：

  10.1016/j.ejphar.2018.05.011

文献信息

• 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。
• De novo design and synthesis of HIV-1 integrase inhibitors
  作者：Mahindra T Makhija、Rajesh T Kasliwal、Vithal M Kulkarni、Nouri Neamati

  DOI：10.1016/j.bmc.2004.02.005

  日期：2004.5

  Existing AIDS therapies are out of reach for most HIV-infected people in developing countries and, where available, they are limited by their toxicity and their cost. New anti-HIV agents are needed urgently to combat emerging viral resistance and reduce the side effects associated with currently available drugs. Toward this end, LeapFrog, a de novo drug design program was used to design novel, potent, and selective inhibitors of HIV-1 integrase. The designed compounds were synthesized and tested for in vitro inhibition of HIV-1 integrase. Out of the 25 compounds that were designed, and synthesized, four molecules (compounds 23, 26, 43, and 59) showed moderate to low inhibition of HIV-1 integrase for 3'-processing and 3'-strand transfer activities. Nonetheless, these compounds possess structural features not seen in known HIV-1 integrase inhibitors and thus can serve as excellent leads for further optimization of anti-HIV-1 integrase activity. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.