(S)-(+)-N-m-methoxybenzyl-5-oxoproline | 213982-69-5

• 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)-(+)-N-m-methoxybenzyl-5-oxoproline
• 英文别名: (2S)-1-[(3-methoxyphenyl)methyl]-5-oxopyrrolidine-2-carboxylic acid
• CAS: 213982-69-5
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: SONSMDNWEQGCHD-NSHDSACASA-N

物化性质

• 沸点：
  503.3±50.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-N-m-methoxybenzyl-5-oxoproline 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Synthesis and identification of chiral aminomethylpiperidine carboxamides as inhibitor of collagen induced platelet activation

  摘要：

  A series of chiral lactam carboxamides of aminomethylpiperidine were synthesized and investigated for the collagen induced in vitro anti-platelet efficacy and collagen plus epinephrine induced in vivo pulmonary thromboembolism. The compound 31a (30 mu M/kg) displayed a remarkable antithrombotic efficacy (60% protection) which was sustained for more than 24 h and points to its excellent bioavailability. The compounds 31a (IC50 = 6.6 mu M) and 32a (IC50 = 37 mu M), as well as their racemic mixture 28i (IC50 = 16 mu M) significantly inhibited collagen-induced human platelet aggregation in vitro. Compound 34c displayed dual mechanism of action against both collagen (IC50 = 3.3 mu M) and U46619 (IC50 = 2.7 mu M) induced platelet aggregation. The pharmacokinetic study of 31a indicated very faster absorption, prolonged and constant systemic exposure and thereby exhibiting better therapeutic response. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.017
• 作为产物：
  描述：

  L-焦谷氨酸甲酯 在 水 、 sodium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.0h， 生成 (S)-(+)-N-m-methoxybenzyl-5-oxoproline
  参考文献：
  名称：

  Synthesis and identification of chiral aminomethylpiperidine carboxamides as inhibitor of collagen induced platelet activation

  摘要：

  A series of chiral lactam carboxamides of aminomethylpiperidine were synthesized and investigated for the collagen induced in vitro anti-platelet efficacy and collagen plus epinephrine induced in vivo pulmonary thromboembolism. The compound 31a (30 mu M/kg) displayed a remarkable antithrombotic efficacy (60% protection) which was sustained for more than 24 h and points to its excellent bioavailability. The compounds 31a (IC50 = 6.6 mu M) and 32a (IC50 = 37 mu M), as well as their racemic mixture 28i (IC50 = 16 mu M) significantly inhibited collagen-induced human platelet aggregation in vitro. Compound 34c displayed dual mechanism of action against both collagen (IC50 = 3.3 mu M) and U46619 (IC50 = 2.7 mu M) induced platelet aggregation. The pharmacokinetic study of 31a indicated very faster absorption, prolonged and constant systemic exposure and thereby exhibiting better therapeutic response. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.017

文献信息

• Remote O, C-dianion chemistry of pyroglutamates: Reaction at C-4 with electrophiles
  作者：Dinesh K. Dikshit、Anjana Maheshwari

  DOI：10.1016/s0040-4039(99)00759-5

  日期：1999.6

  O, C-Di-lithio di-anions derived from N-substituted pyroglutamic acids react with electrophiles to give C-4 α- substituted products.

  由N-取代的焦谷氨酸衍生的O，C-二-二硫代二阴离子与亲电试剂反应，得到C-4α-取代的产物。
• The Improved Synthesis of Enantiopure (S)-N-Arylmethyl-5-Oxoprolines
  作者：Stefan Marchalin、Katarina Kadlecikova、Nathalie Bar、Bernard Decroix

  DOI：10.1080/00397919808004908

  日期：1998.10

  A mild procedure for the preparation of enantiopure N-alkylated (S)-(+)-5-oxoprolines 3a-r is described. The method starting from (S)-glutamic acid appears generally applicable to substrates with a wide range of substituents.