| 934525-62-9

• 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
• CAS: 934525-62-9
• 化学式: C₁₈H₂₈N₂O₅
• 分子量: 352.431
• InChiKey: OKTZYBRNXXKPCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  85.89
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-3-(2-(2-cyanopyrrolidin-1-yl)-2-oxoethylamino)-N-(3,4-dimethoxyphenyl)-3-methylbutanamide
  参考文献：
  名称：

  3-[2-((2S)-2-Cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-3-methyl-butyramide analogues as selective DPP-IV inhibitors for the treatment of type-II diabetes

  摘要：

  Based on the structures of NVP-DPP728 (1) and NVP-LAF237 (Vildagliptin, 2), three series of DPP-IV inhibitors were synthesized by linking substituted anilines, benzylamines, and phenylethylamines to (2S)-cyanopyrrolidine through a linker. More than 20 compounds were evaluated for their in vitro DPP-IV inhibition and selectivity profile over DPP-II, DPP8, and FAP enzymes. Selected compounds 5f and 7i showed in vivo plasma DPP-IV inhibition and inhibited glucose excursion in OGTT after oral administration in Wistar rats. Compound 5f (DPP-1V IC50 = 116 nM) has the potential for development as antidiabetic agent. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.019
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 N-羟基丁二酰亚胺 、 potassium hypochlorite 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成
  参考文献：
  名称：

  3-[2-((2S)-2-Cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-3-methyl-butyramide analogues as selective DPP-IV inhibitors for the treatment of type-II diabetes

  摘要：

  Based on the structures of NVP-DPP728 (1) and NVP-LAF237 (Vildagliptin, 2), three series of DPP-IV inhibitors were synthesized by linking substituted anilines, benzylamines, and phenylethylamines to (2S)-cyanopyrrolidine through a linker. More than 20 compounds were evaluated for their in vitro DPP-IV inhibition and selectivity profile over DPP-II, DPP8, and FAP enzymes. Selected compounds 5f and 7i showed in vivo plasma DPP-IV inhibition and inhibited glucose excursion in OGTT after oral administration in Wistar rats. Compound 5f (DPP-1V IC50 = 116 nM) has the potential for development as antidiabetic agent. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.019

文献信息

• (2S,4S)-1-[2-(1,1-Dimethyl-3-oxo-3-pyrrolidin-1-yl-propylamino)acetyl]-4-fluoro-pyrrolidine-2-carbonitrile: A potent, selective, and orally bioavailable dipeptide-derived inhibitor of dipeptidyl peptidase IV
  作者：Teng-Kuang Yeh、Ting-Yueh Tsai、Tsu Hsu、Jai-Hong Cheng、Xin Chen、Jen-Shin Song、Horng-Shing Shy、Mei-Chun Chiou、Chia-Hui Chien、Ya-Ju Tseng、Chung-Yu Huang、Kai-Chia Yeh、Yu-Lin Huang、Chih-Hsiang Huang、Yu-Wen Huang、Min-Hsien Wang、Hung-Kuan Tang、Yu-Sheng Chao、Chiung-Tong Chen、Weir-Torn Jiaang

  DOI：10.1016/j.bmcl.2010.04.124

  日期：2010.6

  A series of 2-[3-[2-[(2S)-2-cyano-1-pyrrolidinyl]-2-oxoethylamino]-3-methyl-1-oxobutyl]-based DPP-IV inhibitors with various monocyclic amines were synthesized. The structure-activity relationships (SAR) led to the discovery of potent DPP-IV inhibitors, having IC(50) values of < 100 nM with excellent selectivity over the closely related enzymes, DPP-II, DPP8, DPP9 and FAP (IC(50) > 20 mu M). Of these compounds, the analogues 12a, 12h and 12i exhibited a long-lasting ex vivo DPP-IV inhibition in rats. (C) 2010 Elsevier Ltd. All rights reserved.