N-p-methyl benzyl thiomorpholinone carboxylic acid | 1615249-65-4

• 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: N-p-methyl benzyl thiomorpholinone carboxylic acid
• CAS: 1615249-65-4
• 化学式: C₁₃H₁₅NO₃S
• 分子量: 265.333
• InChiKey: LEINKFFJGGHZSQ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.61
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  哌啶-3-基甲基-氨基甲酸叔丁基酯 、 N-p-methyl benzyl thiomorpholinone carboxylic acid 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 以65%的产率得到tert-butyl ((S)-1-((R)-4-(4-methylbenzyl)-5-oxothiomorpholine-3-carbonyl)piperidin-3-yl)methylcarbamate
  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：

  (S)-tert butoxy carbonyl methyl cysteine ethyl ester 在 sodium acetate 、 sodium cyanoborohydride 、 potassium carbonate 、 1-羟基苯并三唑 、 三乙胺 、 三氟乙酸 、 potassium hydroxide 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 氘代甲醇-d 为溶剂， 反应 0.17h， 生成 N-p-methyl benzyl thiomorpholinone carboxylic acid
  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