(S)-1-{(S)-2-amino-3-[4-(1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl)phenyl]propanoyl}pyrrolidine-2-carbonitrile hydrochloride | 1429503-43-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-1-{(S)-2-amino-3-[4-(1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl)phenyl]propanoyl}pyrrolidine-2-carbonitrile hydrochloride
• 英文别名: (2S)-1-[(2S)-2-amino-3-[4-[1-[(4-chlorophenyl)methyl]triazol-4-yl]phenyl]propanoyl]pyrrolidine-2-carbonitrile;hydrochloride
• CAS: 1429503-43-4
• 化学式: C₂₃H₂₃ClN₆O*ClH
• 分子量: 471.389
• InChiKey: KOURGISIEAPLLJ-GUTACTQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 盐酸 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (S)-1-{(S)-2-amino-3-[4-(1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl)phenyl]propanoyl}pyrrolidine-2-carbonitrile hydrochloride
  参考文献：
  名称：

  Synthesis and biological evaluation of novel benzyl-substituted (S)-phenylalanine derivatives as potent dipeptidyl peptidase 4 inhibitors

  摘要：

  A series of novel benzyl-substituted (S)-phenylalanine derivatives were synthesized and evaluated for their dipeptidyl peptidase 4 (DPP-4) inhibitory activity and selectivity. It was found that most synthesized target compounds were potent DPP-4 inhibitors with IC50 values in 3.79-25.52 nM, which were significantly superior to that of the marketed drug sitagliptin. Furthermore, the 4-fluorobenzyl substituted phenylalanine derivative 6g not only displayed the potent DPP-4 inhibition with an IC50 value of 3.79 nM, but also showed better selectivity against DPP-4 over other related enzymes including DPP-7, DPP-8, and DPP-9. In an oral glucose tolerance test (OGTT) in normal Sprague Dawley rats, compound 6g reduced blood glucose excursion in a dose-dependent manner. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.034

文献信息

• Synthesis and biological evaluation of novel benzyl-substituted (S)-phenylalanine derivatives as potent dipeptidyl peptidase 4 inhibitors
  作者：Yang Liu、Meimei Si、Li Tang、Shihao Shangguan、Haoshu Wu、Jia Li、Peng Wu、Xiaodong Ma、Tao Liu、Yongzhou Hu

  DOI：10.1016/j.bmc.2013.07.034

  日期：2013.9

  A series of novel benzyl-substituted (S)-phenylalanine derivatives were synthesized and evaluated for their dipeptidyl peptidase 4 (DPP-4) inhibitory activity and selectivity. It was found that most synthesized target compounds were potent DPP-4 inhibitors with IC50 values in 3.79-25.52 nM, which were significantly superior to that of the marketed drug sitagliptin. Furthermore, the 4-fluorobenzyl substituted phenylalanine derivative 6g not only displayed the potent DPP-4 inhibition with an IC50 value of 3.79 nM, but also showed better selectivity against DPP-4 over other related enzymes including DPP-7, DPP-8, and DPP-9. In an oral glucose tolerance test (OGTT) in normal Sprague Dawley rats, compound 6g reduced blood glucose excursion in a dose-dependent manner. (C) 2013 Elsevier Ltd. All rights reserved.