(S)-4-isopropyl-3-tosyl-1,3-oxazolidin-5-one | 78797-29-2

• 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)-4-isopropyl-3-tosyl-1,3-oxazolidin-5-one
• 英文别名: (4S)-3-(4-methylphenyl)sulfonyl-4-propan-2-yl-1,3-oxazolidin-5-one
• CAS: 78797-29-2
• 化学式: C₁₃H₁₇NO₄S
• 分子量: 283.348
• InChiKey: GHZHZKFPLYNAMT-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-isopropyl-3-tosyl-1,3-oxazolidin-5-one 在 三乙基硅烷 、 氯化亚砜 、 N,N-diisopropylamino amide 、 三氟乙酸 作用下， 以 四氢呋喃 、 氯仿 、 苯 为溶剂， 反应 48.0h， 生成 (+/-)-2,6-dimethyl-3-isopropyl-1,2-benzothiazin-4(3H)-one 1,1-dioxide
  参考文献：
  名称：

  Synthesis and pharmacological profile of 6-methyl-3-isopropyl-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide derivatives: non-steroidal anti-inflammatory agents with reduced ulcerogenic effects in the rat

  摘要：

  The new anti-inflammatory agents 6-methyl-3-isopropyl-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide 6a and its analogues 6b-f were synthesized from L-valine. All compounds were characterized by physical, chemical and spectral studies. Preliminary pharmacological evaluation of the resulting products showed that compounds 6a-f (5-20 mg/kg, i.p.) are active anti-inflammatory agents in carrageenan-induced rat paw oedema assay in albino rats, and their effects are comparable to that of piroxicam (5 mg/kg, i.p.), used as a reference drug. The nature of the substituents on the sulfonamide nitrogen and those on position three had a pronounced effect on the anti-inflammatory activity. Studies of structure-activity relationships have led to selection of compound 2,6-dimethyl-3-isopropyl-1,2-benzothiazin-3,4-diol 1,1-dioxide 6f which exhibited the most potent activity (61.7% inhibition at 5 mg/kg, i.p. and ED50=4.5 mg/kg, i.p.). Comparison of the gastrointestinal safety of compounds 6a-f with that of piroxicam showed a far better tolerability for our products. This comparison was based on the ulcer index and the pH of gastric content. (C) 2002 Elsevier Science BY. All rights reserved.

  DOI：

  10.1016/s0928-0987(02)00046-5
• 作为产物：
  描述：

  N-(p-toluenesulfonyl)-L-valine 、 alkaline earth salt of/the/ methylsulfuric acid 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 (S)-4-isopropyl-3-tosyl-1,3-oxazolidin-5-one
  参考文献：
  名称：

  Synthesis and pharmacological profile of 6-methyl-3-isopropyl-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide derivatives: non-steroidal anti-inflammatory agents with reduced ulcerogenic effects in the rat

  摘要：

  The new anti-inflammatory agents 6-methyl-3-isopropyl-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide 6a and its analogues 6b-f were synthesized from L-valine. All compounds were characterized by physical, chemical and spectral studies. Preliminary pharmacological evaluation of the resulting products showed that compounds 6a-f (5-20 mg/kg, i.p.) are active anti-inflammatory agents in carrageenan-induced rat paw oedema assay in albino rats, and their effects are comparable to that of piroxicam (5 mg/kg, i.p.), used as a reference drug. The nature of the substituents on the sulfonamide nitrogen and those on position three had a pronounced effect on the anti-inflammatory activity. Studies of structure-activity relationships have led to selection of compound 2,6-dimethyl-3-isopropyl-1,2-benzothiazin-3,4-diol 1,1-dioxide 6f which exhibited the most potent activity (61.7% inhibition at 5 mg/kg, i.p. and ED50=4.5 mg/kg, i.p.). Comparison of the gastrointestinal safety of compounds 6a-f with that of piroxicam showed a far better tolerability for our products. This comparison was based on the ulcer index and the pH of gastric content. (C) 2002 Elsevier Science BY. All rights reserved.

  DOI：

  10.1016/s0928-0987(02)00046-5

文献信息

• A Simple and Rapid Protocol for<i>N</i>-Methyl-<i>α</i>-Amino Acids
  作者：G. Vidyasagar Reddy、D.S. Iyengar

  DOI：10.1246/cl.1999.299

  日期：1999.4

  A two step strategy for optically pure N-Protected-N-methyl-α-amino acids starting from N-protected-α-amino acids via reductive cleavage of oxazolidinones using NaCNBH3/TMSCl is described.

  描述了一种两步策略，从N-保护的α-氨基酸出发，通过使用NaCNBH3/TMSCl对恶唑烷酮进行还原性裂解，制备光学纯的N-保护-N-甲基-α-氨基酸。
• A Novel, Simple and Rapid Protocol For N-Protected-oxazolidine-5-ones
  作者：G. Vidyasagar Reddy、G. Venkat Rao、D. S. Iyengar

  DOI：10.1080/00397919908085881

  日期：1999.12.1

  A simple and efficient method fbr the preparation of N-protected oxazolidine-5-ones using microwave irradiation is described.