5-bromo-2-[(4-hydroxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester | 287108-60-5

• 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: 5-bromo-2-[(4-hydroxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester
• 英文别名: Methyl 5-bromo-2-[(4-hydroxyphenyl)sulfonyl-methylamino]-3-methylbenzoate
• CAS: 287108-60-5
• 化学式: C₁₆H₁₆BrNO₅S
• 分子量: 414.277
• InChiKey: PXDWRQJOIBLNHY-UHFFFAOYSA-N

物化性质

• 沸点：
  560.5±60.0 °C(Predicted)
• 密度：
  1.558±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-bromo-2-[(4-hydroxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester 在 sodium hydroxide 、 草酰氯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Anthranilate sulfonamide hydroxamate TACE inhibitors. Part 1: Structure-based design of novel acetylenic P1′ groups

  摘要：

  The structure-based design of potent sulfonamide hydroxamate TACE inhibitors bearing novel acetylenic P1' groups has led to compounds with excellent in vitro potency against TACE and selectivity over MMP-1. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00135-x
• 作为产物：
  描述：

  5-bromo-2-[(4-fluoro-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester 在 2-丁炔-1-醇 、 sodium hydride 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-bromo-2-[(4-hydroxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester
  参考文献：
  名称：

  Anthranilate sulfonamide hydroxamate TACE inhibitors. Part 1: Structure-based design of novel acetylenic P1′ groups

  摘要：

  The structure-based design of potent sulfonamide hydroxamate TACE inhibitors bearing novel acetylenic P1' groups has led to compounds with excellent in vitro potency against TACE and selectivity over MMP-1. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00135-x

文献信息

• Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid TACE inhibitors
  申请人：American Cyanamid Company

  公开号：US06277885B1

  公开（公告）日：2001-08-21

  Hydroxamic acids having the formula are useful in treating disease conditions mediated by TNF-&agr;, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.

  具有该公式的羟肟酸在治疗由肿瘤坏死因子-α（TNF-α）介导的疾病状况中是有用的，例如类风湿性关节炎、骨关节炎、败血症、艾滋病、溃疡性结肠炎、多发性硬化症、克罗恩病和退行性软骨损失。
• Anthranilate sulfonamide hydroxamate TACE inhibitors. Part 2: SAR of the acetylenic P1′ group
  作者：J.I Levin、J.M Chen、M.T Du、F.C Nelson、L.M Killar、S Skala、A Sung、G Jin、R Cowling、D Barone、C.J March、K.M Mohler、R.A Black、J.S Skotnicki

  DOI：10.1016/s0960-894x(02)00136-1

  日期：2002.4

  The SAR of a series of potent sulfonamide hydroxamate TACE inhibitors bearing novel acetylenic P1' groups was explored. In particular, compound 4t bearing a butynylox P1' moiety has excellent in vitro potency against isolated TACE enzyme and in cells, good selectivity over MMP-1 and oral activity in an in vitro model of TNF-alpha production. (C) 2002 Elsevier Science Ltd. All rights reserved.
• ACETYLENIC ARYL SULFONAMIDE AND PHOSPHINIC ACID AMIDE HYDROXAMIC ACID TACE INHIBITORS
  申请人：Wyeth Holdings Corporation

  公开号：EP1144369B1

  公开（公告）日：2004-07-21
• US6277885B1
  申请人：——

  公开号：US6277885B1

  公开（公告）日：2001-08-21
• US6762178B2
  申请人：——

  公开号：US6762178B2

  公开（公告）日：2004-07-13