2-Chloro-N-(4-methanesulfonylamino-phenyl)-nicotinamide | 1027016-73-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Chloro-N-(4-methanesulfonylamino-phenyl)-nicotinamide
• 英文别名: 2-chloro-N-[4-(methanesulfonamido)phenyl]pyridine-3-carboxamide
• CAS: 1027016-73-4
• 化学式: C₁₃H₁₂ClN₃O₃S
• 分子量: 325.776
• InChiKey: LOZAVDJAPPTIPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  96.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Chloro-N-(4-methanesulfonylamino-phenyl)-nicotinamide 在 potassium tert-butylate 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 叔丁醇 为溶剂， 反应 2.0h， 生成 N-(4-Methanesulfonylamino-phenyl)-2-(2-methyl-propane-2-sulfinyl)-nicotinamide
  参考文献：
  名称：

  Heteroaryl-Fused 2-Phenylisothiazolone Inhibitors of Cartilage Breakdown

  摘要：

  The synthesis, biological evaluation, and structure-activity relationships of a series of N-phenyl heteroaryl-fused isothiazolones are described. These isothiazolones have been shown to exhibit potent, dose-dependent inhibition of IL-1 beta-induced breakdown of proteoglycan in a cartilage organ culture assay. This effect is likely due to inhibition of MMP activation and a consequent reduction in MMP activity following IL-1 beta stimulation. Thus these compounds potentially represent simple, non-peptidic disease-modifying agents for the treatment of arthritic diseases. To examine the effects of structure on in vitro activity, three general features of the molecules were varied, substituents on the pendant N-phenyl group, the position of ring fusion to the isothiazolone, and substituents on the fused ring peri to the isothiazolone sulfur.

  DOI：

  10.1021/jm00045a012
• 作为产物：
  描述：

  2-氯烟酸 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 生成 2-Chloro-N-(4-methanesulfonylamino-phenyl)-nicotinamide
  参考文献：
  名称：

  Heteroaryl-Fused 2-Phenylisothiazolone Inhibitors of Cartilage Breakdown

  摘要：

  The synthesis, biological evaluation, and structure-activity relationships of a series of N-phenyl heteroaryl-fused isothiazolones are described. These isothiazolones have been shown to exhibit potent, dose-dependent inhibition of IL-1 beta-induced breakdown of proteoglycan in a cartilage organ culture assay. This effect is likely due to inhibition of MMP activation and a consequent reduction in MMP activity following IL-1 beta stimulation. Thus these compounds potentially represent simple, non-peptidic disease-modifying agents for the treatment of arthritic diseases. To examine the effects of structure on in vitro activity, three general features of the molecules were varied, substituents on the pendant N-phenyl group, the position of ring fusion to the isothiazolone, and substituents on the fused ring peri to the isothiazolone sulfur.

  DOI：

  10.1021/jm00045a012

文献信息

• Heteroaryl-Fused 2-Phenylisothiazolone Inhibitors of Cartilage Breakdown
  作者：Stephen W. Wright、Joseph J. Petraitis、Matthew M. Abelman、Douglas G. Batt、Lori L. Bostrom、Ronald L. Corbett、Carl P. Decicco、Susan V. Di Meo、Bruce Freimark

  DOI：10.1021/jm00045a012

  日期：1994.9

  The synthesis, biological evaluation, and structure-activity relationships of a series of N-phenyl heteroaryl-fused isothiazolones are described. These isothiazolones have been shown to exhibit potent, dose-dependent inhibition of IL-1 beta-induced breakdown of proteoglycan in a cartilage organ culture assay. This effect is likely due to inhibition of MMP activation and a consequent reduction in MMP activity following IL-1 beta stimulation. Thus these compounds potentially represent simple, non-peptidic disease-modifying agents for the treatment of arthritic diseases. To examine the effects of structure on in vitro activity, three general features of the molecules were varied, substituents on the pendant N-phenyl group, the position of ring fusion to the isothiazolone, and substituents on the fused ring peri to the isothiazolone sulfur.