2-amino-5-(1,1'-biphenyl-4-yl)-1H-pyrrole-3-carboxylic acid ethyl ester | 187724-79-4

• 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: 2-amino-5-(1,1'-biphenyl-4-yl)-1H-pyrrole-3-carboxylic acid ethyl ester
• 英文别名: 2-Amino-3-ethoxycarbonyl-5-(biphen-4-yl)-1H-pyrrole；ethyl 2-amino-5-(4-phenylphenyl)-1H-pyrrole-3-carboxylate
• CAS: 187724-79-4
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: VVSMJELQIIQVJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 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：
  68.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-5-(1,1'-biphenyl-4-yl)-1H-pyrrole-3-carboxylic acid ethyl ester 在 碳酸氢钠 、 sodium iodide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 30.0h， 生成 5-[1,1'-biphenyl-4-yl]-2-[[[[2-[4-(2-chlorophenyl)-1-piperazinyl]ethyl]amino]carbonyl]amino]-1H-pyrrole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and molecular modeling of 1H-pyrrolopyrimidine-2,4-dione derivatives as ligands for the α1-adrenoceptors

  摘要：

  Three different series of 1H-pyrrolopyrimidine-2,4-dione derivatives were designed and synthesized as ligands for the alpha(1)-adrenergic receptors (alpha(1)-ARs). A microwave-assisted protocol was developed in order to improve purity and yields of some final products. The majority of the synthesized compounds, tested in binding assays, displayed alpha(1)-AR affinities in the nanomolar range. Highest affinity values were found in derivatives 10b and 10c (K-i = 1.4 nM for both) whereas compound 10e was endowed with the best profile in term of alpha(1)-AR affinity (K-i = 2.71 nM) coupled with high selectivity towards 5-HT1A receptors (K-i > 10,000). Molecular docking studies were performed on human alpha(1)-ARs and human 5-HT1A receptors in order to rationalize the observed experimental affinity and selectivity; these computational studies helped to clarify molecular requirements for the design of high-selective alpha(1)-adrenergic ligands. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.043
• 作为产物：
  描述：

  3-乙氧基-3-亚氨基丙酸乙酯盐酸盐 在 potassium carbonate 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 2-amino-5-(1,1'-biphenyl-4-yl)-1H-pyrrole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and molecular modeling of 1H-pyrrolopyrimidine-2,4-dione derivatives as ligands for the α1-adrenoceptors

  摘要：

  Three different series of 1H-pyrrolopyrimidine-2,4-dione derivatives were designed and synthesized as ligands for the alpha(1)-adrenergic receptors (alpha(1)-ARs). A microwave-assisted protocol was developed in order to improve purity and yields of some final products. The majority of the synthesized compounds, tested in binding assays, displayed alpha(1)-AR affinities in the nanomolar range. Highest affinity values were found in derivatives 10b and 10c (K-i = 1.4 nM for both) whereas compound 10e was endowed with the best profile in term of alpha(1)-AR affinity (K-i = 2.71 nM) coupled with high selectivity towards 5-HT1A receptors (K-i > 10,000). Molecular docking studies were performed on human alpha(1)-ARs and human 5-HT1A receptors in order to rationalize the observed experimental affinity and selectivity; these computational studies helped to clarify molecular requirements for the design of high-selective alpha(1)-adrenergic ligands. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.043

文献信息

• Pyrrolopyrimidines and processes for the preparation thereof
  申请人：Novartis AG

  公开号：US06140332A1

  公开（公告）日：2000-10-31

  Described are 7H-pyrrolo[2,3-d]pyrimidine derivatives of formula I ##STR1## wherein the symbols are as defined in claim 1. Those compounds inhibit tyrosine protein kinase and can be used in the treatment of hyperproliferative diseases, for example tumour diseases.

  本发明涉及式I的7H-吡咯[2,3-d]嘧啶衍生物，其中符号如权利要求1所定义。这些化合物抑制酪氨酸蛋白激酶并可用于治疗过度增殖性疾病，例如肿瘤疾病。