N-{2-[(4-{[3-(tert-butylamino)-6-fluoropyridin-2-yl](methyl)amino}piperidin-1-yl)carbonyl]-1H-indol-5-yl}methanesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-{2-[(4-{[3-(tert-butylamino)-6-fluoropyridin-2-yl](methyl)amino}piperidin-1-yl)carbonyl]-1H-indol-5-yl}methanesulfonamide
• 英文别名: N-[2-[4-[[3-(tert-butylamino)-6-fluoropyridin-2-yl]-methylamino]piperidine-1-carbonyl]-1H-indol-5-yl]methanesulfonamide
• 化学式: C₂₅H₃₃FN₆O₃S
• 分子量: 516.64
• InChiKey: BIMYIIMAPXZIQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-苄基-4-甲氨基哌啶 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 N,N'-羰基二咪唑 、 zinc(II) chloride 作用下， 以 甲醇 、 乙醚 、 乙醇 、 甲苯 、 乙腈 为溶剂， -78.0~25.0 ℃ 、275.79 kPa 条件下， 反应 130.0h， 生成 N-{2-[(4-{[3-(tert-butylamino)-6-fluoropyridin-2-yl](methyl)amino}piperidin-1-yl)carbonyl]-1H-indol-5-yl}methanesulfonamide
  参考文献：
  名称：

  Targeting Delavirdine/Atevirdine Resistant HIV-1:  Identification of (Alkylamino)piperidine-Containing Bis(heteroaryl)piperazines as Broad Spectrum HIV-1 Reverse Transcriptase Inhibitors

  摘要：

  A novel class of bis(heteroaryl)piperazine (BHAP) analogs which possesses the ability to inhibit NNRTI (non-nucleoside reverse transcriptase inhibitor) resistant recombinant HIV-1 reverse transcriptase (RT) and NNRTI resistant variants of HIV-1 has been identified via targeted screening. Further investigation of the structure-activity relationships of close congeners of these novel (alkylamino)piperidine BHAPs (AAP-BHPSs) led to the synthesis of several compounds possessing the desired phenotype (e.g., activity against recombinant RTs carrying the Y181C and P236L substitutions). Further structural modifications were required to inhibit metabolism and modulate solubility in order to obtain compounds with the desired biological profile as well as appropriate pharmaceutical properties. The AAP-BHAPs with the most suitable characteristics were compounds 7, 15, and 36.

  DOI：

  10.1021/jm960158n