4-(phenoxymethyl)benzenesulfonyl chloride | 1002727-89-0

• 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: 4-(phenoxymethyl)benzenesulfonyl chloride
• CAS: 1002727-89-0
• 化学式: C₁₃H₁₁ClO₃S
• 分子量: 282.748
• InChiKey: ITLWVYCIZYWFNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 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：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(phenoxymethyl)benzenesulfonyl chloride 在 ammonium hydroxide 作用下， 反应 4.0h， 生成 4-(phenoxymethyl)benzenesulfonamide
  参考文献：
  名称：

  SAR by Interligand Nuclear Overhauser Effects (ILOEs) Based Discovery of Acylsulfonamide Compounds Active against Bcl-x_Land Mcl-1

  摘要：

  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.

  DOI：

  10.1021/jm200826s

文献信息

• ANTICANCER COMPOUNDS
  申请人：REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：US20180071258A1

  公开（公告）日：2018-03-15

  The invention provides compounds having the general formula I: and salts thereof, wherein the variables R A , R B , R C , L 1 , L 2 , L 3 , A, B, C, X, Y, Z, E, m, n, and p have the meaning as described herein, and compositions containing such compounds and methods for using such compounds and compositions.

  这项发明提供了具有一般式I的化合物及其盐，其中变量RA、RB、RC、L1、L2、L3、A、B、C、X、Y、Z、E、m、n和p的含义如本文所述，以及含有这种化合物的组合物、使用这种化合物和组合物的方法。
• Anticancer compounds
  申请人：REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：US10357477B2

  公开（公告）日：2019-07-23

  The invention provides compounds having the general formula I: and salts thereof, wherein the variables RA, RB, RC, L1, L2, L3, A, B, C, X, Y, Z, E, m, n, and p have the meaning as described herein, and compositions containing such compounds and methods for using such compounds and compositions.

  本发明提供了具有通式 I 的化合物： 及其盐类，其中变量 RA、RB、RC、L1、L2、L3、A、B、C、X、Y、Z、E、m、n 和 p 的含义如本文所述，以及含有此类化合物的组合物和使用此类化合物及组合物的方法。
• 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.
• 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.