(+/-)-2,6-dimethyl-3-isopropyl-3-hydroxy-1,2-benzothiazin-4-one 1,1-dioxide | 512167-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: (+/-)-2,6-dimethyl-3-isopropyl-3-hydroxy-1,2-benzothiazin-4-one 1,1-dioxide
• 英文别名: 3-Hydroxy-2,6-dimethyl-1,1-dioxo-3-propan-2-yl-1lambda6,2-benzothiazin-4-one；3-hydroxy-2,6-dimethyl-1,1-dioxo-3-propan-2-yl-1λ6,2-benzothiazin-4-one
• CAS: 512167-62-3
• 化学式: C₁₃H₁₇NO₄S
• 分子量: 283.348
• InChiKey: ZCZRZTMVGRIMNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-2,6-dimethyl-3-isopropyl-3-hydroxy-1,2-benzothiazin-4-one 1,1-dioxide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以94%的产率得到(+/-)-2,6-dimethyl-3-isopropyl-1,2-benzothiazin-3,4-diol 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：

  (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 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 氯仿 、 苯 为溶剂， 反应 78.0h， 生成 (+/-)-2,6-dimethyl-3-isopropyl-3-hydroxy-1,2-benzothiazin-4-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

文献信息

• 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
  作者：Yakdhane Kacem、Jamil Kraiem、Emna Kerkeni、Abderrahman Bouraoui、Béchir Ben Hassine

  DOI：10.1016/s0928-0987(02)00046-5

  日期：2002.9

  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.