4'-chloro-biphenyl-4-sulfonic acid (3-hydroxymethyl-phenyl)-amide | 1062213-32-4

• 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: 4'-chloro-biphenyl-4-sulfonic acid (3-hydroxymethyl-phenyl)-amide
• 英文别名: 4-(4-chlorophenyl)-N-[3-(hydroxymethyl)phenyl]benzenesulfonamide
• CAS: 1062213-32-4
• 化学式: C₁₉H₁₆ClNO₃S
• 分子量: 373.86
• InChiKey: JNMANBHAWSQRJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氨基苯甲醇 在 吡啶 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 21.0h， 生成 4'-chloro-biphenyl-4-sulfonic acid (3-hydroxymethyl-phenyl)-amide
  参考文献：
  名称：

  Development of triarylsulfonamides as novel anti-inflammatory agents

  摘要：

  Triaylsulfonamides were identified as novel anti-inflammatory agents, acting by inhibition of RANKL and TNF alpha signaling. Structure-activity studies led to the identification of compounds with in vitro potencies of <100 nM against J774 macrophages and osteoclasts, but with little activity against osteoblasts or hepatocytes (IC50 >50 mu M). A representative compound (4k, ABD455) was able to completely prevent inflammation in vivo in a prevention model and was highly effective at controlling inflammation in a treatment model. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.067

文献信息

• Biphenyl-4-yl-sulfonic acid arylamides and their use as therapeutic agents
  申请人：Greig Iain Robert

  公开号：US20100286266A1

  公开（公告）日：2010-11-11

  The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain aryl sulfonamides and related compounds (collectively referred to herein as ‘BPSAAA compounds’), as described herein, and including, for example, biphenyl-4-sulfonic acid (hydroxyalkyl-phenyl)-amides and related compounds. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, in treatment and/or prevention, for example, of inflammation and/or joint destruction and/or bone loss; of disorders mediated by excessive and/or inappropriate and/or prolonged activation of the immune system; of, inflammatory and autoimmune disorders, for example, rheumatoid arthritis, psoriasis, psoriatic arthritis, chronic obstructive pulmonary disease (COPD), atherosclerosis, inflammatory bowel disease, ankylosing spondylitis, and the like; of disorders associated with bone loss, such as bone loss associated with excessive osteoclast activation in rheumatoid arthritis, osteoporosis, cancer associated bone disease, Paget's disease and the like.

  本发明涉及治疗化合物领域，更具体地涉及某些芳基磺酰胺和相关化合物（统称为“BPSAAA化合物”），如本文所述，包括例如联苯基-4-磺酸（羟基烷基-苯基）-酰胺和相关化合物。本发明还涉及包含这些化合物的制药组合物，以及这些化合物和组合物在体内外治疗和/或预防炎症、关节破坏和/或骨质流失等方面的使用，包括过度和/或不适当和/或持续激活免疫系统介导的疾病，炎症和自身免疫性疾病，例如类风湿性关节炎、银屑病、银屑病性关节炎、慢性阻塞性肺疾病（COPD）、动脉粥样硬化、炎症性肠病、强直性脊柱炎等，以及与骨质流失相关的疾病，例如类风湿性关节炎中过度成骨破骨细胞激活、骨质疏松症、癌症相关骨病、帕吉特病等。
• BIPHENYL-4-YL-SULFONIC ACID ARYLAMIDES AND THEIR USE AS THERAPEUTIC AGENTS
  申请人：The University Court of The University of Aberdeen

  公开号：EP2137141B1

  公开（公告）日：2015-12-02
• US8524778B2
  申请人：——

  公开号：US8524778B2

  公开（公告）日：2013-09-03
• [EN] BIPHENYL-4-YL-SULFONIC ACID ARYLAMIDES AND THEIR USE AS THERAPEUTIC AGENTS<br/>[FR] ARYLAMIDES DE L'ACIDE BIPHÉNYL-4-YL-SULFONIQUE ET LEUR UTILISATION EN TANT QU'AGENTS THÉRAPEUTIQUES
  申请人：UNIV ABERDEEN

  公开号：WO2008114022A1

  公开（公告）日：2008-09-25

  [EN] The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain aryl sulfonamides and related compounds (collectively referred to herein as "BPSAAA compounds"), as described herein, and including, for example, biphenyl-4-sulfonic acid (hydroxyalkyl-phenyl)-amides and related compounds. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, in treatment and/or prevention, for example, of inflammation and/or joint destruction and/or bone loss; of disorders mediated by excessive and/or inappropriate and/or prolonged activation of the immune system; of, inflammatory and autoimmune disorders, for example, rheumatoid arthritis, psoriasis, psoriatic arthritis, chronic obstructive pulmonary disease (COPD), atherosclerosis, inflammatory bowel disease, ankylosing spondylitis, and the like; of disorders associated with bone loss, such as bone loss associated with excessive osteoclast activation in rheumatoid arthritis, osteoporosis, cancer associated bone disease, Paget's disease and the like.
  [FR] La présente invention concerne de manière générale le domaine des composés thérapeutiques et plus précisément certains aryle sulfonamides et des composés apparentés (nommés collectivement dans le présent document = composés BPSAAA =) tels que décrits dans le présent document. Ces composés comprennent, par exemple, les amides de l'acide biphényl-4-sulfonique (hydroxyalkyl-phényl) et des composés apparentés. La présente invention concerne également des compositions pharmaceutiques qui comprennent de tels composés, ainsi que l'utilisation de tels composés et de telles compositions, à la fois in vitro et in vivo, pour le traitement et/ou la prévention, par exemple, de l'inflammation et/ou de la destruction des articulations et/ou de la perte osseuse; de troubles induits par une activation excessive et/ou inappropriée et/ou prolongée du système immunitaire; de troubles inflammatoires et autoimmuns, par exemple la polyarthrite rhumatoïde, le psoriasis, la polyarthrite psoriasique, la maladie pulmonaire obstructive chronique (MPOC), l'athérosclérose, la maladie intestinale inflammatoire, la spondylite ankylosante et des troubles analogues; de troubles associés avec la perte osseuse, tels que la perte osseuse associée avec l'activation excessive des ostéoclastes dans la polyarthrite rhumatoïde, l'ostéoporose, les maladies osseuses associées à un cancer, la maladie de Paget et des troubles analogues.
• Development of triarylsulfonamides as novel anti-inflammatory agents
  作者：Iain R. Greig、Emmanuel Coste、Stuart H. Ralston、Robert J. van ’t Hof

  DOI：10.1016/j.bmcl.2012.11.067

  日期：2013.2

  Triaylsulfonamides were identified as novel anti-inflammatory agents, acting by inhibition of RANKL and TNF alpha signaling. Structure-activity studies led to the identification of compounds with in vitro potencies of <100 nM against J774 macrophages and osteoclasts, but with little activity against osteoblasts or hepatocytes (IC50 >50 mu M). A representative compound (4k, ABD455) was able to completely prevent inflammation in vivo in a prevention model and was highly effective at controlling inflammation in a treatment model. (c) 2012 Elsevier Ltd. All rights reserved.