2-benzylsulfanyl-N-naphthalen-1-ylpyridine-3-carboxamide | 1026078-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-benzylsulfanyl-N-naphthalen-1-ylpyridine-3-carboxamide
• CAS: 1026078-63-6
• 化学式: C₂₃H₁₈N₂OS
• 分子量: 370.475
• InChiKey: BGFGXKAKPZCEPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzylsulfanyl-N-naphthalen-1-ylpyridine-3-carboxamide 在 磺酰氯 作用下， 以 四氯化碳 为溶剂， 反应 0.75h， 以40%的产率得到2-Naphthalen-1-yl-[1,2]thiazolo[5,4-b]pyridin-3-one
  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-巯基烟酸 在 氢氧化钾 、 三甲基乙酰氯 、 三乙胺 作用下， 以 水 、 异丙醇 为溶剂， 反应 22.5h， 生成 2-benzylsulfanyl-N-naphthalen-1-ylpyridine-3-carboxamide
  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.