5-(4-((2S,5S)-2-(4-chlorobenzyl)-4-isobutyl-5-methylpiperazin-1-yl)piperidin-1-yl)-1H-1,2,4-triazol-3-amine | 2221950-65-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(4-((2S,5S)-2-(4-chlorobenzyl)-4-isobutyl-5-methylpiperazin-1-yl)piperidin-1-yl)-1H-1,2,4-triazol-3-amine
• 英文别名: OAT-2068；1H-1,2,4-Triazol-3-amine, 5-[4-[(2S,5S)-2-[(4-chlorophenyl)methyl]-5-methyl-4-(2-methylpropyl)-1-piperazinyl]-1-piperidinyl]-；3-[4-[(2S,5S)-2-[(4-chlorophenyl)methyl]-5-methyl-4-(2-methylpropyl)piperazin-1-yl]piperidin-1-yl]-1H-1,2,4-triazol-5-amine
• CAS: 2221950-65-6
• 化学式: C₂₃H₃₆ClN₇
• 分子量: 446.039
• InChiKey: WHDYUSOWFWKVTD-UWJYYQICSA-N

物化性质

• 沸点：
  612.0±65.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  77.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  allyl 4-((2S,5S)-2-(4-chlorobenzyl)-5-methylpiperazin-1-yl)piperidine-1-carboxylate hydrochloride 在 四(三苯基膦)钯 、 苯硅烷 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 6.5h， 生成 5-(4-((2S,5S)-2-(4-chlorobenzyl)-4-isobutyl-5-methylpiperazin-1-yl)piperidin-1-yl)-1H-1,2,4-triazol-3-amine
  参考文献：
  名称：

  Discovery of selective, orally bioavailable inhibitor of mouse chitotriosidase

  摘要：

  This article describes our work towards the identification of a potent and selective inhibitor of mouse chitotriosidase (mCHIT1). A series of small molecule inhibitors of mCHIT1 and mAMCase have been developed from early lead compound 1. Examination of synthetized analogues led to discovery of several novel highly potent compounds. Among them compound 9 (OAT-2068) displays a remarkable 143-fold mCHIT1 vs. mAMCase selectivity. To explain the observed SAR molecular docking experiments were performed, which were in line with the experimental data from the enzymatic assays. Inhibitor 9 (OAT-2068) was found to have an excellent pharmacokinetic profile. This, together with high activity and selectivity, makes the compound an ideal and unique tool for studying the role of CHIT1 in biological models. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.12.047