4-[(Benzyl)(4-nitrophenyl)amino]-1-methylpyrrole-2-carboxylic acid | 1058178-67-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[(Benzyl)(4-nitrophenyl)amino]-1-methylpyrrole-2-carboxylic acid
• 英文别名: 4-(N-benzyl-4-nitroanilino)-1-methylpyrrole-2-carboxylic acid
• CAS: 1058178-67-8
• 化学式: C₁₉H₁₇N₃O₄
• 分子量: 351.362
• InChiKey: UYZMGCAMZWVJGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(Benzyl)(4-nitrophenyl)amino]-1-methylpyrrole-2-carboxylic acid 在 甲基磺酰氯 、 三乙胺 、 氨 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以78%的产率得到4-[(Benzyl)(4-nitrophenyl)amino]-1-methylpyrrole-2-carboxamide
  参考文献：
  名称：

  4-(Anilino)pyrrole-2-carboxamides: Novel non-steroidal/non-anilide type androgen antagonists effective upon human prostate tumor LNCaP cells with mutated nuclear androgen receptor

  摘要：

  Various 4-(anilino)pyrrole-2-carboxamides were designed and synthesized as novel androgen receptor (AR) antagonists without steroidal or anilide structure, based on our strategy for developing full antagonists of nuclear receptors. Introduction of a bulky N-alkyl group, such as a cyclohexylmethyl or benzyl group, increased the binding affinity for wild-type AR and the potency for growth inhibition of androgen-dependent SC-3 cells. Among the compounds obtained, N-[4-[(benzyl)(4-nitrophenyl)amino]-1-methylpyrrole-2-carbonyl]pyrrolidine (22) is as potent an AR antagonist as the typical anilide-type AR antagonists hydroxyflutamide and bicalutamide. Further, compound 22 had potent binding affinity for T877A mutated AR, and dose-dependently inhibited the testosterone-induced production of prostate-specific antigen in LNCaP cells bearing T877A AR. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.063
• 作为产物：
  描述：

  Ethyl 4-[(benzyl)(4-nitrophenyl)amino]-1-methylpyrrole-2-carboxylate 在 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以96%的产率得到4-[(Benzyl)(4-nitrophenyl)amino]-1-methylpyrrole-2-carboxylic acid
  参考文献：
  名称：

  4-(Anilino)pyrrole-2-carboxamides: Novel non-steroidal/non-anilide type androgen antagonists effective upon human prostate tumor LNCaP cells with mutated nuclear androgen receptor

  摘要：

  Various 4-(anilino)pyrrole-2-carboxamides were designed and synthesized as novel androgen receptor (AR) antagonists without steroidal or anilide structure, based on our strategy for developing full antagonists of nuclear receptors. Introduction of a bulky N-alkyl group, such as a cyclohexylmethyl or benzyl group, increased the binding affinity for wild-type AR and the potency for growth inhibition of androgen-dependent SC-3 cells. Among the compounds obtained, N-[4-[(benzyl)(4-nitrophenyl)amino]-1-methylpyrrole-2-carbonyl]pyrrolidine (22) is as potent an AR antagonist as the typical anilide-type AR antagonists hydroxyflutamide and bicalutamide. Further, compound 22 had potent binding affinity for T877A mutated AR, and dose-dependently inhibited the testosterone-induced production of prostate-specific antigen in LNCaP cells bearing T877A AR. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.063