ethyl 4,6-diamino-2-methyl-3-quinolinecarboxylate | 828930-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 4,6-diamino-2-methyl-3-quinolinecarboxylate
• 英文别名: Ethyl 4,6-diamino-2-methylquinoline-3-carboxylate；ethyl 4,6-diamino-2-methylquinoline-3-carboxylate
• CAS: 828930-85-4
• 化学式: C₁₃H₁₅N₃O₂
• 分子量: 245.281
• InChiKey: RGHPSUAAIQUWGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  91.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(4-fluorophenoxy)methyl]benzoyl chloride 、 ethyl 4,6-diamino-2-methyl-3-quinolinecarboxylate 在 吡啶 作用下， 反应 3.0h， 以61%的产率得到Ethyl 4-amino-6-[[2-[(4-fluorophenoxy)methyl]benzoyl]amino]-2-methylquinoline-3-carboxylate
  参考文献：
  名称：

  A new synthetic approach of N-(4-amino-2-methylquinolin-6-yl)-2-(4-ethylphenoxymethyl)benzamide (JTC-801) and its analogues and their pharmacological evaluation as nociceptin receptor (NOP) antagonists

  摘要：

  A series of 4-amino-2-methylquinoline and 4-aminoquinazoline derivatives, including the reference NOP antagonist JTC-801, were synthesized by an alternative pathway and their in vitro pharmacological properties were investigated. 3-Substitution of the quinoline ring resulted very critical for affinity. So 3-methyl derivative 4j showed a similar potency compared with the reference 4h while bulky lipophilic or electron withdrawing groups in the same position strongly decreased affinity. Structural and conformational requirements for affinity were outlined by NOE NMR and computational methods and suggestions for a pharmacophore model design were provided. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.09.009
• 作为产物：
  描述：

  2-氰基-4-硝基苯胺 在 aluminum nickel 、 溶剂黄146 、 tin(ll) chloride 作用下， 以 水 、 甲苯 为溶剂， 反应 5.5h， 生成 ethyl 4,6-diamino-2-methyl-3-quinolinecarboxylate
  参考文献：
  名称：

  A new synthetic approach of N-(4-amino-2-methylquinolin-6-yl)-2-(4-ethylphenoxymethyl)benzamide (JTC-801) and its analogues and their pharmacological evaluation as nociceptin receptor (NOP) antagonists

  摘要：

  A series of 4-amino-2-methylquinoline and 4-aminoquinazoline derivatives, including the reference NOP antagonist JTC-801, were synthesized by an alternative pathway and their in vitro pharmacological properties were investigated. 3-Substitution of the quinoline ring resulted very critical for affinity. So 3-methyl derivative 4j showed a similar potency compared with the reference 4h while bulky lipophilic or electron withdrawing groups in the same position strongly decreased affinity. Structural and conformational requirements for affinity were outlined by NOE NMR and computational methods and suggestions for a pharmacophore model design were provided. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.09.009

文献信息

• A new synthetic approach of N-(4-amino-2-methylquinolin-6-yl)-2-(4-ethylphenoxymethyl)benzamide (JTC-801) and its analogues and their pharmacological evaluation as nociceptin receptor (NOP) antagonists
  作者：Isabella Sestili、Anna Borioni、Carlo Mustazza、Andrea Rodomonte、Luciana Turchetto、Maria Sbraccia、Daniela Riitano、Maria Rosaria Del Giudice

  DOI：10.1016/j.ejmech.2004.09.009

  日期：2004.12

  A series of 4-amino-2-methylquinoline and 4-aminoquinazoline derivatives, including the reference NOP antagonist JTC-801, were synthesized by an alternative pathway and their in vitro pharmacological properties were investigated. 3-Substitution of the quinoline ring resulted very critical for affinity. So 3-methyl derivative 4j showed a similar potency compared with the reference 4h while bulky lipophilic or electron withdrawing groups in the same position strongly decreased affinity. Structural and conformational requirements for affinity were outlined by NOE NMR and computational methods and suggestions for a pharmacophore model design were provided. (C) 2004 Elsevier SAS. All rights reserved.