N-p-toluenesulfonyl-threo-DL-phenylserine 1-tetradecyl ester

• 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-toluenesulfonyl-threo-DL-phenylserine 1-tetradecyl ester
• 英文别名: tetradecyl (2S,3R)-3-hydroxy-2-[(4-methylphenyl)sulfonylamino]-3-phenylpropanoate
• 化学式: C₃₀H₄₅NO₅S
• 分子量: 531.757
• InChiKey: UTIVHWRGNKJPEC-URLMMPGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  37
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对甲苯磺酰氯 、 threo-DL-phenylserine 1-tetradecyl ester p-toluenesulfonate 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以79%的产率得到N-p-toluenesulfonyl-threo-DL-phenylserine 1-tetradecyl ester
  参考文献：
  名称：

  Synthesis of N-arylsulfonyl dl-phenylserine derivatives exhibiting anti-inflammatory activity in experimental studies

  摘要：

  Synthesis and evaluation of anti-inflammatory activity in rats with adjuvant arthritis of aryl sulfonyl derivatives of nonproteinogenic aromatic amino acids is reported. The studied compounds were synthesized by introducing residues of benzene-, p-toluene-, and p-bromobenzene sulfonic acids into threo-DL-phenylserine and erythro-DL-p-nitrophenylserine structures. From the set of 12 compounds tested in animal screening, N-(p-bromobenzenesulfonyl)-erythro -DL-p-nitrophenylserine ethyl ester 12 demonstrated the most pronounced anti-inflammatory activity. This compound inhibited inflammation process in polyarthritis phase by 53% (P < 0.001) though it was slightly toxic (LD50 > 6000 mg kg(-1) for mice). (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01280-6

文献信息

• Synthesis of N-arylsulfonyl dl-phenylserine derivatives exhibiting anti-inflammatory activity in experimental studies
  作者：Juozapas Straukas、Nijol≐ Dirvianskyt≐、Vytautas Astrauskas、Eugenius Butkus

  DOI：10.1016/s0014-827x(02)01280-6

  日期：2002.9

  Synthesis and evaluation of anti-inflammatory activity in rats with adjuvant arthritis of aryl sulfonyl derivatives of nonproteinogenic aromatic amino acids is reported. The studied compounds were synthesized by introducing residues of benzene-, p-toluene-, and p-bromobenzene sulfonic acids into threo-DL-phenylserine and erythro-DL-p-nitrophenylserine structures. From the set of 12 compounds tested in animal screening, N-(p-bromobenzenesulfonyl)-erythro -DL-p-nitrophenylserine ethyl ester 12 demonstrated the most pronounced anti-inflammatory activity. This compound inhibited inflammation process in polyarthritis phase by 53% (P < 0.001) though it was slightly toxic (LD50 > 6000 mg kg(-1) for mice). (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.