ethyl 4-(cyclopentylamino)-2-oxo-6-phenethyl-1,2-dihydropyridine-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl 4-(cyclopentylamino)-2-oxo-6-phenethyl-1,2-dihydropyridine-3-carboxylate
• 英文别名: ethyl 4-(cyclopentylamino)-2-oxo-6-(2-phenylethyl)-1H-pyridine-3-carboxylate
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: RPAWITYZTFPGEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-(cyclopentylamino)-2-oxo-6-phenethyl-1,2-dihydropyridine-3-carboxylate 在 盐酸 、 水 作用下， 反应 48.0h， 以75%的产率得到4-(cyclopentylamino)-6-phenethylpyridin-2(1H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of pyridinone analogues as novel potent HIV-1 NNRTIs

  摘要：

  A novel 2-pyridinone scaffold was rationally designed and synthesized based on the active anti-HIV agent 1 (LAM-trans) via an efficient method. The biological results revealed that some target compounds inhibited HIV-1 reverse transcriptase in the lower micromolar concentration range (IC50 0.089-0.68 mu m). Notably, the most promising compound 25b exhibited extremely potent inhibitory activity against HIV-1 replication with an EC50 value of 0.0563 mu M and the viral selectivity index amounted to 3466.8. Molecular modeling studies were performed, and some SARs were rationalized. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.012
• 作为产物：
  描述：

  3-氧代-5-苯基-戊酸乙酯 在 苄基三乙基氯化铵 、 氨 、 sodium 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 202.0h， 生成 ethyl 4-(cyclopentylamino)-2-oxo-6-phenethyl-1,2-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of pyridinone analogues as novel potent HIV-1 NNRTIs

  摘要：

  A novel 2-pyridinone scaffold was rationally designed and synthesized based on the active anti-HIV agent 1 (LAM-trans) via an efficient method. The biological results revealed that some target compounds inhibited HIV-1 reverse transcriptase in the lower micromolar concentration range (IC50 0.089-0.68 mu m). Notably, the most promising compound 25b exhibited extremely potent inhibitory activity against HIV-1 replication with an EC50 value of 0.0563 mu M and the viral selectivity index amounted to 3466.8. Molecular modeling studies were performed, and some SARs were rationalized. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.012