tert-butyl {(S)-1-[(S)-2-cyanopyrrolidin-1-yl]-1-oxo-3-[4-(1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl)phenyl]propan-2-yl}carbamate | 1429503-91-2

• 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: tert-butyl {(S)-1-[(S)-2-cyanopyrrolidin-1-yl]-1-oxo-3-[4-(1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl)phenyl]propan-2-yl}carbamate
• CAS: 1429503-91-2
• 化学式: C₂₆H₃₀N₆O₃S
• 分子量: 506.629
• InChiKey: HEGZBTACOJFGQL-UNMCSNQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  113.14
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl {(S)-1-[(S)-2-cyanopyrrolidin-1-yl]-1-oxo-3-[4-(1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl)phenyl]propan-2-yl}carbamate 在 盐酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 以79%的产率得到(S)-1-{(S)-2-amino-3-[4-(1-(thiophen-2-ylmethyl)-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
• 作为产物：
  描述：

  [(S)-2-((S)-2-Cyano-pyrrolidin-1-yl)-1-(4-iodo-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 copper(ll) sulfate pentahydrate 、 四丁基氟化铵 、 sodium ascorbate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 生成 tert-butyl {(S)-1-[(S)-2-cyanopyrrolidin-1-yl]-1-oxo-3-[4-(1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl)phenyl]propan-2-yl}carbamate
  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