N-(4-nitropyrrole-2-carbonyl)pyrrolidine | 851589-98-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(4-nitropyrrole-2-carbonyl)pyrrolidine
• 英文别名: (4-nitro-1H-pyrrol-2-yl)-pyrrolidin-1-ylmethanone
• CAS: 851589-98-5
• 化学式: C₉H₁₁N₃O₃
• 分子量: 209.205
• InChiKey: XLUGMURSSKLTGD-UHFFFAOYSA-N

物化性质

• 沸点：
  445.0±30.0 °C(Predicted)
• 密度：
  1.423±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  79.24
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(4-nitropyrrole-2-carbonyl)pyrrolidine 在 palladium on activated charcoal tris(dibenzylideneacetone)dipalladium (0) 、 氢气 、 sodium hydride 、 2-(二叔丁基膦)联苯 、 sodium t-butanolate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 41.0h， 生成 N-[4-(4-cyanophenylamino)-1-methylpyrrole-2-carbonyl]pyrrolidine
  参考文献：
  名称：

  Novel non-steroidal/non-anilide type androgen antagonists: discovery of 4-substituted pyrrole-2-carboxamides as a new scaffold for androgen receptor ligands

  摘要：

  We designed and synthesized novel pyrrole-2-carboxamide derivatives as androgen antagonists. Compounds 10 and 13 bearing benzylamine or aniline at the 4-position of the pyrrole ring showed moderate androgen antagonistic activity, and inhibited the androgen-dependent growth of Shionogi carcinoma cells (SC-3). Study of the structure-activity relationships of compound 13 led to a potent androgen antagonist 36, which has higher affinity than flutamide (4) for androgen nuclear receptor (AR). Thus, pyrrole-2-carboxamide is a new scaffold for developing AR antagonists. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.019
• 作为产物：
  描述：

  4-硝基吡咯-2-羧酸 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.5h， 生成 N-(4-nitropyrrole-2-carbonyl)pyrrolidine
  参考文献：
  名称：

  Novel non-steroidal/non-anilide type androgen antagonists: discovery of 4-substituted pyrrole-2-carboxamides as a new scaffold for androgen receptor ligands

  摘要：

  We designed and synthesized novel pyrrole-2-carboxamide derivatives as androgen antagonists. Compounds 10 and 13 bearing benzylamine or aniline at the 4-position of the pyrrole ring showed moderate androgen antagonistic activity, and inhibited the androgen-dependent growth of Shionogi carcinoma cells (SC-3). Study of the structure-activity relationships of compound 13 led to a potent androgen antagonist 36, which has higher affinity than flutamide (4) for androgen nuclear receptor (AR). Thus, pyrrole-2-carboxamide is a new scaffold for developing AR antagonists. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.019