2-(6-phenoxypyridine-3-sulfonamido)acetic acid | 1430073-08-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(6-phenoxypyridine-3-sulfonamido)acetic acid
• 英文别名: 2-[(6-Phenoxypyridin-3-yl)sulfonylamino]acetic acid；2-[(6-phenoxypyridin-3-yl)sulfonylamino]acetic acid
• CAS: 1430073-08-7
• 化学式: C₁₃H₁₂N₂O₅S
• 分子量: 308.315
• InChiKey: MEHHUVBZIGRUPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(6-phenoxypyridine-3-sulfonamido)acetic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-hydroxy-2-[(6-phenoxypyridin-3-yl)sulfonylamino]acetamide
  参考文献：
  名称：

  Arylsulfonamide inhibitors of aggrecanases as potential therapeutic agents for osteoarthritis: Synthesis and biological evaluation

  摘要：

  Aggrecanases, in particular aggrecanase-2 (ADAMTS-5), are considered the principal proteases responsible for aggrecan degradation in osteoarthritis. For this reason, considerable effort has been put on the discovery and development of aggrecanase inhibitors able to slow down or halt the progression of osteoarthritis. We report herein the synthesis and biological evaluation of a series of arylsulfonamido-based hydroxamates as aggrecanase inhibitors. Compound 18 was found to have a nanomolar activity for ADAMTS-5, ADAMTS-4 and MMP-13 and high selectivity over MMP-1 and MMP-14. Furthermore, this compound proved to be effective in blocking ex vivo cartilage degradation without having effect on cell cytotoxicity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.058
• 作为产物：
  描述：

  6-苯氧基-3-吡啶磺酰氯 在 4-二甲氨基吡啶 、 氨 、 sodium hydride 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 21.67h， 生成 2-(6-phenoxypyridine-3-sulfonamido)acetic acid
  参考文献：
  名称：

  Arylsulfonamide inhibitors of aggrecanases as potential therapeutic agents for osteoarthritis: Synthesis and biological evaluation

  摘要：

  Aggrecanases, in particular aggrecanase-2 (ADAMTS-5), are considered the principal proteases responsible for aggrecan degradation in osteoarthritis. For this reason, considerable effort has been put on the discovery and development of aggrecanase inhibitors able to slow down or halt the progression of osteoarthritis. We report herein the synthesis and biological evaluation of a series of arylsulfonamido-based hydroxamates as aggrecanase inhibitors. Compound 18 was found to have a nanomolar activity for ADAMTS-5, ADAMTS-4 and MMP-13 and high selectivity over MMP-1 and MMP-14. Furthermore, this compound proved to be effective in blocking ex vivo cartilage degradation without having effect on cell cytotoxicity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.058

文献信息

• Arylsulfonamide inhibitors of aggrecanases as potential therapeutic agents for osteoarthritis: Synthesis and biological evaluation
  作者：Elisa Nuti、Salvatore Santamaria、Francesca Casalini、Kazuhiro Yamamoto、Luciana Marinelli、Valeria La Pietra、Ettore Novellino、Elisabetta Orlandini、Susanna Nencetti、Anna Maria Marini、Silvia Salerno、Sabrina Taliani、Federico Da Settimo、Hideaki Nagase、Armando Rossello

  DOI：10.1016/j.ejmech.2012.12.058

  日期：2013.4

  Aggrecanases, in particular aggrecanase-2 (ADAMTS-5), are considered the principal proteases responsible for aggrecan degradation in osteoarthritis. For this reason, considerable effort has been put on the discovery and development of aggrecanase inhibitors able to slow down or halt the progression of osteoarthritis. We report herein the synthesis and biological evaluation of a series of arylsulfonamido-based hydroxamates as aggrecanase inhibitors. Compound 18 was found to have a nanomolar activity for ADAMTS-5, ADAMTS-4 and MMP-13 and high selectivity over MMP-1 and MMP-14. Furthermore, this compound proved to be effective in blocking ex vivo cartilage degradation without having effect on cell cytotoxicity. (C) 2013 Elsevier Masson SAS. All rights reserved.