(S)-2-amino-3-phenyl-N-(pyridin-2-yl)propanamide | 88932-73-4

• 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)-2-amino-3-phenyl-N-(pyridin-2-yl)propanamide
• 英文别名: 2-amino-3-phenyl-N-(pyridin-2-yl)propanamide；2-(L-phenylalanylamino)pyridine；(2S)-2-amino-3-phenyl-N-pyridin-2-ylpropanamide
• CAS: 88932-73-4
• 化学式: C₁₄H₁₅N₃O
• mdl: MFCD09725335
• 分子量: 241.293
• InChiKey: XTVJYMDZPSHWLC-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氯吲哚-2-羧酸 、 (S)-2-amino-3-phenyl-N-(pyridin-2-yl)propanamide 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-chloro-N-[(2S)-1-oxo-3-phenyl-1-(pyridin-2-ylamino)propan-2-yl]-1H-indole-2-carboxamide
  参考文献：
  名称：

  Discovery of novel dual-action antidiabetic agents that inhibit glycogen phosphorylase and activate glucokinase

  摘要：

  Dual-target-directed agents simultaneously inhibiting glycogen phosphorylase (GP) and activating glucokinase (GK) could decelerate the inflow of glucose from glycogenolysis and accelerate the outflow of glucose in the liver, therefore allow for a better control over hyperglycaemia in a synergetic manner. A series of hybrid compounds were designed by structure-assisted and ligand-based strategies. In vitro bioassays found two novel compounds (1j, 6g) worthy of further optimization on balance of dual action to GP and GK. In addition, for single-target activity, two compounds exhibited more potent GP inhibitory activity and four compounds showed better GK activation than their corresponding references. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.020
• 作为产物：
  描述：

  phthaloyl-L-phenylalanyl chloride 在 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 12.0h， 生成 (S)-2-amino-3-phenyl-N-(pyridin-2-yl)propanamide
  参考文献：
  名称：

  Synthesis and analgesic activities of urea derivatives of α-amino-N-pyridyl benzene propanamide

  摘要：

  New urea L-phenyl alanine derivatives of 4-aminopyridine have been synthesized and evaluated for analgesic activity with the PBQ writhing test in mice and the Randall-Selitto test in rats. Potent oral activity (ID50 < 10 mg/kg) and good tolerance were found in alkyl, arylalkyl and carboxyalkyl urea derivatives. The analgesic activity was found to be totally dependent on the pyridine moiety and was at least partly inhibited by pretreatment with (alpha) methyltyrosine, as was the case for 4-aminopyridine. These compounds are therefore pharmacologically interesting as new analgesic derivatives of 4-aminopyridine. They have a higher oral activity and a better activity/tolerance profile.

  DOI：

  10.1016/0223-5234(94)90070-1
• 作为试剂：
  描述：

  对硝基苯甲醛 、 环己酮 在 silver hexafluoroantimonate 、 (S)-2-amino-3-phenyl-N-(pyridin-2-yl)propanamide 、 copper dichloride 作用下， 反应 24.0h， 生成 (2R)-2-[(S)-hydroxy(4-nitrophenyl)methyl]cyclohexanone 、 (2S,1'R)-2-[1'-hydroxy-1'-(4-nitrophenyl)methyl]cyclohexan-1-one 、 2-[hydroxy(4-nitrophenyl)methyl]cyclohexan-1-one
  参考文献：
  名称：

  基于简单双齿配体的伯胺金属路易斯酸双功能催化剂：直接不对称醛醇缩合反应。

  摘要：

  开发了一种新型的基于双齿配体的伯胺金属路易斯酸双功能催化剂。这些催化剂在催化具有优异立体选择性的酮类的直接不对称醛醇缩合反应中非常高效。醛醇缩合反应需要低的催化剂负载量（2.5mol％），并且与水相容。

  DOI：

  10.1039/c0cc00917b

文献信息

• Design and synthesis of thiol containing inhibitors of matrix metalloproteinases
  作者：Cynthia A. Fink、J.Eric Carlson、Charles Boehm、Patricia McTaggart、Ying Qiao、John Doughty、Vishwas Ganu、Richard Melton、Ronald Goldberg

  DOI：10.1016/s0960-894x(98)00716-1

  日期：1999.1

  A series of thiol containing derivatives was prepared. Several of these compounds were found to inhibit matrix metalloproteinases 1, 3, and 9 with selectivity towards 3 and 9. Compounds 15, 20, and 22 were administered to rats orally at 75 mumol/kg. Drug levels of compounds 20 and 22 in the plasma were found to exceed the IC50 values for MMP 3 and 9 four hours after administration.

  制备了一系列含硫醇的衍生物。发现这些化合物中的几种抑制基质金属蛋白酶1、3和9，对3和9具有选择性。将化合物15、20和22以75μmol/ kg口服给予大鼠。发现给药后四小时血浆中化合物20和22的药物水平超过MMP 3和9的IC50值。
• Synthesis of Chiral Amino Acid Anilides by Ligand-Free Copper-Catalyzed Selective<i>N</i>-Arylation of Amino Acid Amides
  作者：Junyu Dong、Yan Wang、Qinjie Xiang、Xirui Lv、Wen Weng、Qingle Zeng

  DOI：10.1002/adsc.201200752

  日期：2013.3.11

  atom‐economic, practical and cost‐effective protocol for synthesis of chiral amino acid anilides via ligand‐free copper‐catalyzed selective CN cross coupling of chiral amino acid amides and aryl halides, hetereoaryl halides and a vinyl bromide has been developed. No racemization occurred during the CN coupling. A plausible mechanism is proposed.

  为手性氨基酰苯胺的合成中的原子经济性，实用性和成本效益的协议经由无配体的铜-催化的选择性Ç  Ñ手性氨基酸酰胺和芳基卤化物，杂芳卤化物与乙烯基溴化镁的交叉偶联已经研制成功。CN偶联过程中未发生外消旋作用。提出了一个合理的机制。
• A Three-Component Reaction Based on a Remote-Group-Directed Dynamic Kinetic Aza-Michael Addition: Stereoselective Synthesis of Imidazolidin-4-ones
  作者：Zhenghu Xu、Tyler Buechler、Kraig Wheeler、Hong Wang

  DOI：10.1002/chem.200903508

  日期：2010.3.8

  with an aldehyde and a Michael acceptor to form stable imidazolidin‐4‐ones with high stereoselectivity. A dynamic kinetic aza‐Michael addition was discovered and applied to the three‐component reaction to enforce high stereoselectivity. A remote group was incorporated to invert the reaction process and direct the reaction towards the desired product (see scheme).

  对照：α-氨基酰胺与醛和迈克尔受体反应，形成稳定的咪唑烷定-4-酮，立体选择性高。发现了动态动力学的氮杂-迈克尔加成反应，并将其应用于三组分反应以实现高立体选择性。并入一个远程基团以反转反应过程并将反应导向所需的产物（参见方案）。
• US5200408A
  申请人：——

  公开号：US5200408A

  公开（公告）日：1993-04-06
• Discovery of novel dual-action antidiabetic agents that inhibit glycogen phosphorylase and activate glucokinase
  作者：Lei Zhang、Xiaojie Chen、Jun Liu、Qingzhang Zhu、Ying Leng、Xiaomin Luo、Hualiang Jiang、Hong Liu

  DOI：10.1016/j.ejmech.2012.06.020

  日期：2012.12

  Dual-target-directed agents simultaneously inhibiting glycogen phosphorylase (GP) and activating glucokinase (GK) could decelerate the inflow of glucose from glycogenolysis and accelerate the outflow of glucose in the liver, therefore allow for a better control over hyperglycaemia in a synergetic manner. A series of hybrid compounds were designed by structure-assisted and ligand-based strategies. In vitro bioassays found two novel compounds (1j, 6g) worthy of further optimization on balance of dual action to GP and GK. In addition, for single-target activity, two compounds exhibited more potent GP inhibitory activity and four compounds showed better GK activation than their corresponding references. (C) 2012 Elsevier Masson SAS. All rights reserved.