7-chloro-2-methyl-1,1-dioxo-1,4-dihydro-2H-1λ⁶-benzo[e][1,2]thiazin-3-one | 36295-15-5

• 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: 7-chloro-2-methyl-1,1-dioxo-1,4-dihydro-2H-1λ⁶-benzo[e][1,2]thiazin-3-one
• 英文别名: 7-Chlor-3,4-dihydro-2-methyl-1,2-benzothiazin-3(2H)-on-1,1-dioxid；7-chloro-2-methyl-1,1-dioxo-4H-benzo[e]thiazin-3-one；7-chloro-2-methyl-1,1-dioxo-4H-1λ6,2-benzothiazin-3-one
• CAS: 36295-15-5
• 化学式: C₉H₈ClNO₃S
• 分子量: 245.686
• InChiKey: JREMXILPBHJMQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-chloro-2-methyl-1,1-dioxo-1,4-dihydro-2H-1λ⁶-benzo[e][1,2]thiazin-3-one 在 三乙胺 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 4.0h， 生成 7-Chloro-3-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-4-carboxylic acid (5-methyl-thiazol-2-yl)-amide
  参考文献：
  名称：

  Effect of Structural Modification of Enol−Carboxamide-Type Nonsteroidal Antiinflammatory Drugs on COX-2/COX-1 Selectivity

  摘要：

  Meloxicam (5), an NSAID in the enol-carboxamide class, was developed on the basis of its antiinflammatory activity and relative safety in animal models. In subsequent screening in microsomal assays using human COX-1 and COX-2, we discovered that it possessed a selectivity profile for COX-2 superior to piroxicam and other marketed NSAIDs. We therefore embarked on a study of enol-carboxamide type compounds to determine if COX-2 selectivity and potency could be dramatically improved by structural modification. Substitution at the 6- and 7-positions of the 4-oxo-1,2-benzothiazine-3-carboxamide, alteration of the N-methyl substituent, and amide modification were all examined. In addition we explored several related systems including the isomeric 3-oxo-1,2-benzothiazine-4-carboxamides, thienothiazines, indolothiazines, benzothienothiazines, naphthothiazines, and 1,3- and 1,4-dioxoisoquinolines. While a few examples were found with greater potency in the COX-2 assay, no compound tested had a better COX-2/COX-1 selectivity profile than that of 5.

  DOI：

  10.1021/jm9607010
• 作为产物：
  描述：

  4-Chlor-N-methyl-2-sulfamoyl-phenylessigsaeure 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 7-chloro-2-methyl-1,1-dioxo-1,4-dihydro-2H-1λ⁶-benzo[e][1,2]thiazin-3-one
  参考文献：
  名称：

  抗炎3,4-二氢-2-烷基-3-氧代-2H-1,2-苯并噻嗪-4-羧酰胺1,1-二氧化物。

  摘要：

  DOI：

  10.1021/jm00292a022

文献信息

• Effect of Structural Modification of Enol−Carboxamide-Type Nonsteroidal Antiinflammatory Drugs on COX-2/COX-1 Selectivity
  作者：Edward S. Lazer、Clara K. Miao、Charles L. Cywin、Ronald Sorcek、Hin-Chor Wong、Zhaoxing Meng、Ian Potocki、MaryAnn Hoermann、Roger J. Snow、Matt A. Tschantz、Terence A. Kelly、Daniel W. McNeil、Simon J. Coutts、Laurie Churchill、Anne G. Graham、Eva David、Peter M. Grob、Wolfhard Engel、Hans Meier、Günter Trummlitz

  DOI：10.1021/jm9607010

  日期：1997.3.1

  Meloxicam (5), an NSAID in the enol-carboxamide class, was developed on the basis of its antiinflammatory activity and relative safety in animal models. In subsequent screening in microsomal assays using human COX-1 and COX-2, we discovered that it possessed a selectivity profile for COX-2 superior to piroxicam and other marketed NSAIDs. We therefore embarked on a study of enol-carboxamide type compounds to determine if COX-2 selectivity and potency could be dramatically improved by structural modification. Substitution at the 6- and 7-positions of the 4-oxo-1,2-benzothiazine-3-carboxamide, alteration of the N-methyl substituent, and amide modification were all examined. In addition we explored several related systems including the isomeric 3-oxo-1,2-benzothiazine-4-carboxamides, thienothiazines, indolothiazines, benzothienothiazines, naphthothiazines, and 1,3- and 1,4-dioxoisoquinolines. While a few examples were found with greater potency in the COX-2 assay, no compound tested had a better COX-2/COX-1 selectivity profile than that of 5.
• Antiinflammatory 3,4-dihydro-2-alkyl-3-oxo-2H-1,2-benzothiazine-4-carboxamide 1,1-dioxides
  作者：Joseph G. Lombardino、Edward H. Wiseman

  DOI：10.1021/jm00292a022

  日期：1971.10