3-amino-4-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester | 201465-26-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-amino-4-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester
• 英文别名: ethyl 3-amino-4-phenyl-1H-pyrrole-2-carboxylate
• CAS: 201465-26-1
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: DLBRQGBKUSUXHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  3-amino-4-phenyl-1H-pyrrole-2-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 102.0h， 生成
  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：

  2-甲酸基-2-苯基乙腈 在 sodium ethanolate 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 49.0h， 生成 3-amino-4-phenyl-1H-pyrrole-2-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

• [EN] DIAZA-INDOLE DERIVATIVES AND THEIR USE AS FUNGICIDES<br/>[FR] DÉRIVÉS DE DIAZAINDOLE ET LEUR EMPLOI EN TANT QUE FONGICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2010046215A2

  公开（公告）日：2010-04-29

  The present invention relates to novel compounds of the formula (I) in which any one of G1, G2 and G3 is N and the other two of G1, G2 and G3 are CR8, CR1 or CR2, such that when G1 is not N, G1 is CR8; when G2 is not N, G2 is CR1; when G3 is not N, G3 is CR2; and X1, X2, R1, R2, R3, R4, R6, R7, and R8 are as defined in the claims. In particular, the invention relates to use of these compounds in methods for the control and/or prevention of fungal infection in plants. The invention also relates to compositions containing these compounds as well as methods for preparing these compounds.
• Synthesis and molecular modeling of 1H-pyrrolopyrimidine-2,4-dione derivatives as ligands for the α1-adrenoceptors
  作者：Valeria Pittalà、Maria A. Siracusa、Maria N. Modica、Loredana Salerno、Alessandro Pedretti、Giulio Vistoli、Alfredo Cagnotto、Tiziana Mennini、Giuseppe Romeo

  DOI：10.1016/j.bmc.2011.06.043

  日期：2011.9

  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.