1-Methyl-indol-carbonsaeure-(2)-sulfonsaeure-(3)-imid | 67930-14-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-Methyl-indol-carbonsaeure-(2)-sulfonsaeure-(3)-imid
• 英文别名: 4-methyl-1,1-dioxo-1,4-dihydro-2H-1λ⁶-isothiazolo[4,5-b]indol-3-one；4-methyl-2H-isothiazolo[4,5-b]indol-3(4H)-one 1,1-dioxide；4-methyl-1,1-dioxo-[1,2]thiazolo[4,5-b]indol-3-one
• CAS: 67930-14-7
• 化学式: C₁₀H₈N₂O₃S
• 分子量: 236.251
• InChiKey: CDQBMUVIMYAJQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  76.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Methyl-indol-carbonsaeure-(2)-sulfonsaeure-(3)-imid 在 甲醇 、 sodium hydroxide 、 sodium methylate 、 sodium hydride 作用下， 以 乙醇 、 甲苯 、 xylene 为溶剂， 反应 80.5h， 生成 4-hydroxy-2,5-dimethyl-1,1-dioxo-2,5-dihydro-1H-1λ⁶-[1,2]thiazino[5,6-b]indole-3-carboxylic acid anilide
  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：

  1-Methyl-2-methoxycarbonyl-indol-sulfinsaeure-(3)-amid 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 反应 1.5h， 生成 1-Methyl-indol-carbonsaeure-(2)-sulfonsaeure-(3)-imid
  参考文献：
  名称：

  Reaction of Indole Derivatives with Thionyl and Sulfuryl Chlorides

  摘要：

  DOI：

  10.1021/jo01024a041

文献信息

• US4137313A
  申请人：——

  公开号：US4137313A

  公开（公告）日：1979-01-30
• 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.
• Reaction of Indole Derivatives with Thionyl and Sulfuryl Chlorides
  作者：Jacob Szmuszkovicz

  DOI：10.1021/jo01024a041

  日期：1964.1