2-丙炔-1-基1H-吡咯-2-羧酸酯 | 685563-24-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-丙炔-1-基1H-吡咯-2-羧酸酯
• 英文名称: propargyl 1H-pyrrole-2-carboxylate
• 英文别名: Prop-2-yn-1-yl 1H-pyrrole-2-carboxylate；prop-2-ynyl 1H-pyrrole-2-carboxylate
• CAS: 685563-24-0
• 化学式: C₈H₇NO₂
• mdl: MFCD18830791
• 分子量: 149.149
• InChiKey: YABLZJJMYGHRQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-丙炔-1-基1H-吡咯-2-羧酸酯 在 18-冠醚-6 、 potassium tert-butylate 、 铁粉 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 5.75h， 生成 1-(2-Amino-5-chloro-benzenesulfonyl)-1H-pyrrole-2-carboxylic acid prop-2-ynyl ester
  参考文献：
  名称：

  Anti-HIV-1 activity of pyrryl aryl sulfone (PAS) derivatives: synthesis and SAR studies of novel esters and amides at the position 2 of the pyrrole nucleus

  摘要：

  A SAR study has been performed in order to evaluate how much the ester function could be a determinant for the anti-human immunodeficiency virus type-1 activity of pyrryl aryl sulfones (PASs), a potent family of non-nucleoside reverse transcriptase (RT) inhibitors discovered in the last years. Twenty-three new esters were prepared with the aim to enhance the inhibitory potency of 4a and 4c, two PAS agents endowed with good activity (EC50 = 0.14 microM) and deprived of cytotoxicity up to >200 microM. None of test derivatives was as potent as 4a and 4c and lacked of selectivity due to their higher cytotoxicity (compounds 22-25). Antiviral activity correlate with an ester ramified chain.

  DOI：

  10.1016/j.farmac.2003.11.004
• 作为产物：
  描述：

  2-(三氯乙酰)吡咯 、 2-丙炔-1-醇 在 potassium carbonate 作用下， 反应 17.0h， 以85%的产率得到2-丙炔-1-基1H-吡咯-2-羧酸酯
  参考文献：
  名称：

  Anti-HIV-1 activity of pyrryl aryl sulfone (PAS) derivatives: synthesis and SAR studies of novel esters and amides at the position 2 of the pyrrole nucleus

  摘要：

  A SAR study has been performed in order to evaluate how much the ester function could be a determinant for the anti-human immunodeficiency virus type-1 activity of pyrryl aryl sulfones (PASs), a potent family of non-nucleoside reverse transcriptase (RT) inhibitors discovered in the last years. Twenty-three new esters were prepared with the aim to enhance the inhibitory potency of 4a and 4c, two PAS agents endowed with good activity (EC50 = 0.14 microM) and deprived of cytotoxicity up to >200 microM. None of test derivatives was as potent as 4a and 4c and lacked of selectivity due to their higher cytotoxicity (compounds 22-25). Antiviral activity correlate with an ester ramified chain.

  DOI：

  10.1016/j.farmac.2003.11.004

文献信息

• Anti-HIV-1 activity of pyrryl aryl sulfone (PAS) derivatives: synthesis and SAR studies of novel esters and amides at the position 2 of the pyrrole nucleus
  作者：Romano Silvestri、Marino Artico、Giuseppe La Regina、Gabriella De Martino、Massimiliano La Colla、Roberta Loddo、Paolo La Colla

  DOI：10.1016/j.farmac.2003.11.004

  日期：2004.3

  A SAR study has been performed in order to evaluate how much the ester function could be a determinant for the anti-human immunodeficiency virus type-1 activity of pyrryl aryl sulfones (PASs), a potent family of non-nucleoside reverse transcriptase (RT) inhibitors discovered in the last years. Twenty-three new esters were prepared with the aim to enhance the inhibitory potency of 4a and 4c, two PAS agents endowed with good activity (EC50 = 0.14 microM) and deprived of cytotoxicity up to >200 microM. None of test derivatives was as potent as 4a and 4c and lacked of selectivity due to their higher cytotoxicity (compounds 22-25). Antiviral activity correlate with an ester ramified chain.