6-phenoxypyridine-3-sulfonamide | 1263277-41-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-phenoxypyridine-3-sulfonamide
• CAS: 1263277-41-3
• 化学式: C₁₁H₁₀N₂O₃S
• 分子量: 250.278
• InChiKey: ZOOUZJKOGQEBNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-phenoxypyridine-3-sulfonamide 在 4-二甲氨基吡啶 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 21.17h， 生成 N-((tert-butyldimethylsilyl)oxy)-2-((6-phenoxypyridine)-3-sulfonamido)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 氨 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以94%的产率得到6-phenoxypyridine-3-sulfonamide
  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

• BRIDGED CARBAMATE MACROLIDES
  申请人：Kim Heejin

  公开号：US20080027012A1

  公开（公告）日：2008-01-31

  The present invention discloses compounds of formulae (I) and (II) or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.

  本发明公开了式(I)和(II)的化合物或其药学上可接受的盐、酯或前药：这些化合物具有抗菌性能。本发明还涉及含有上述化合物的药物组合物，用于治疗需要抗生素治疗的受试者。该发明还涉及通过给予含有本发明化合物的药物组合物来治疗受试者的细菌感染的方法。该发明还包括制备本发明化合物的方法。
• SAR by Interligand Nuclear Overhauser Effects (ILOEs) Based Discovery of Acylsulfonamide Compounds Active against Bcl-x_Land Mcl-1
  作者：Michele F. Rega、Bainan Wu、Jun Wei、Ziming Zhang、Jason F. Cellitti、Maurizio Pellecchia

  DOI：10.1021/jm200826s

  日期：2011.9.8

  Overexpression of antiapoptotic members of the Bcl-2 family proteins, such as Bcl-x(L), and Mfl-1, has been shown to be involved in resistance to chemotherapeutic drugs in many forms of cancers. Recent efforts from the Abbott Laboratories resulted in the development of the acylsulfonamide compound and clinical candidate that targets selectively Bcl-2, Bcl-x(L), and Bcl-w while it is not active against Mcl-1 and Bfl-1. However, early clinical and preclinical studies suggest that pan-Bcl-2 antagonists, targeting simultaneously Mcl-1, Bcl-x(L), and possibly all other four antiapoptotic Bcl-2 proteins, may result in more efficacious drugs. Here, following an NMR fragment-based approach, SAR by ILOEs, we report on compounds that exhibit nanomolar affinities for both Bcl-x(L) and Mcl-1 in vitro. We believe that these molecules can be used as useful starting point for the development of novel Bcl-2 antagonists, in particular targeting Mcl-1.
• DERIVATIVES OF 1-AMINO-2-CYCLOPROPYLETHYLBORONIC ACID
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：EP2552216B1

  公开（公告）日：2018-01-24
• US7291602B2
  申请人：——

  公开号：US7291602B2

  公开（公告）日：2007-11-06
• US7312201B2
  申请人：——

  公开号：US7312201B2

  公开（公告）日：2007-12-25