2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-methylquinolin-3-yl)acetic acid

• 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: 2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-methylquinolin-3-yl)acetic acid
• 英文别名: 2-Tert-butoxy-2-[4-(4-chlorophenyl)-2-methyl-3-quinolyl]acetic acid；2-[4-(4-chlorophenyl)-2-methylquinolin-3-yl]-2-[(2-methylpropan-2-yl)oxy]acetic acid
• 化学式: C₂₂H₂₂ClNO₃
• 分子量: 383.875
• InChiKey: BCLKGXWEVQRUHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟基-2-甲基喹啉 在 盐酸 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 lithium chloro-isopropyl-magnesium chloride 、 四(三苯基膦)钯 、 高氯酸 、 copper(I) bromide dimethylsulfide complex 、 水 、 potassium carbonate 、 溶剂黄146 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-methylquinolin-3-yl)acetic acid
  参考文献：
  名称：

  Synthesis and Evaluation of Aryl Quinolines as HIV-1 Integrase Multimerization Inhibitors

  摘要：

  HIV-1 integrase multimerization inhibitors have recently been established as an effective class of antiretroviral agents due to their potent ability to inhibit viral replication. Specifically, quinoline-based inhibitors have been shown to effectively impair HIV-1 replication, highlighting the importance of these heterocyclic scaffolds. Pursuant of our endeavors to further develop a library of quinoline-based candidates, we have implemented a structure activity relationship study of trisubstituted 4-arylquinoline scaffolds that examined the integrase multimerization properties of substitution patterns at the 4 position of the quinoline. Compounds consisting of substituted phenyl rings, heteroaromatics, or polycyclic moieties were examined utilizing an integrase aberrant multimerization in vitro assay. para-Chloro-4-phenylquinoline 11b and 2,3-benzo[b][1,4]dioxine 15f showed noteworthy EC50 values of 0.10 and 0.08 mu M, respectively.

  DOI：

  10.1021/acsmedchemlett.8b00269

文献信息

• Synthesis and Evaluation of Aryl Quinolines as HIV-1 Integrase Multimerization Inhibitors
  作者：Nicholas G. Jentsch、Alison P. Hart、Jared D. Hume、Jian Sun、Kaitlin A. McNeely、Chiyang Lama、Julie A. Pigza、Matthew G. Donahue、Jacques J. Kessl

  DOI：10.1021/acsmedchemlett.8b00269

  日期：2018.10.11

  HIV-1 integrase multimerization inhibitors have recently been established as an effective class of antiretroviral agents due to their potent ability to inhibit viral replication. Specifically, quinoline-based inhibitors have been shown to effectively impair HIV-1 replication, highlighting the importance of these heterocyclic scaffolds. Pursuant of our endeavors to further develop a library of quinoline-based candidates, we have implemented a structure activity relationship study of trisubstituted 4-arylquinoline scaffolds that examined the integrase multimerization properties of substitution patterns at the 4 position of the quinoline. Compounds consisting of substituted phenyl rings, heteroaromatics, or polycyclic moieties were examined utilizing an integrase aberrant multimerization in vitro assay. para-Chloro-4-phenylquinoline 11b and 2,3-benzo[b][1,4]dioxine 15f showed noteworthy EC50 values of 0.10 and 0.08 mu M, respectively.