3-bromo-6-phenethyl-4-(p-tolylthio)pyridin-2(1H)-one

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-bromo-6-phenethyl-4-(p-tolylthio)pyridin-2(1H)-one
• 英文别名: 3-bromo-6-phenethyl-4-(p-tolylsulfanyl)-1H-pyridin-2-one；3-bromo-4-(4-methylphenyl)sulfanyl-6-(2-phenylethyl)-1H-pyridin-2-one
• 化学式: C₂₀H₁₈BrNOS
• 分子量: 400.339
• InChiKey: IXIITUGKNPPKJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氧代-5-苯基-戊酸乙酯 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 苄基三乙基氯化铵 、 氨 、 水 、 sodium 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 盐酸 、 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 250.0h， 生成 3-bromo-6-phenethyl-4-(p-tolylthio)pyridin-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

文献信息

• Synthesis and biological evaluation of pyridinone analogues as novel potent HIV-1 NNRTIs
  作者：Yuanyuan Cao、Yu Zhang、Shaotong Wu、Quanzhi Yang、Xuefeng Sun、Jianxiong Zhao、Fen Pei、Ying Guo、Chao Tian、Zhili Zhang、Haining Wang、Liying Ma、Junyi Liu、Xiaowei Wang

  DOI：10.1016/j.bmc.2014.11.012

  日期：2015.1

  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.