5-Bromo-2-{[4-(4-methoxy-but-2-ynyloxy)-benzenesulfonyl]-methyl-amino}-3-methyl-benzoic acid | 287108-86-5

• 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-(4-methoxy-but-2-ynyloxy)-benzenesulfonyl]-methyl-amino}-3-methyl-benzoic acid
• 英文别名: 5-Bromo-2-[[4-(4-methoxybut-2-ynoxy)phenyl]sulfonyl-methylamino]-3-methylbenzoic acid
• CAS: 287108-86-5
• 化学式: C₂₀H₂₀BrNO₆S
• 分子量: 482.352
• InChiKey: KLJDKCVWELHMPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-Bromo-2-{[4-(4-methoxy-but-2-ynyloxy)-benzenesulfonyl]-methyl-amino}-3-methyl-benzoic acid 在 草酰氯 、 羟胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-bromo-N-hydroxy-2-{[4-(4-methoxy-but-2-ynyloxy)-benzenesulfonyl]-methyl-amino}-3-methyl-benzamide
  参考文献：
  名称：

  Anthranilate sulfonamide hydroxamate TACE inhibitors. Part 2: SAR of the acetylenic P1′ group

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(02)00136-1
• 作为产物：
  描述：

  5-Bromo-2-{[4-(4-methoxy-but-2-ynyloxy)-benzenesulfonyl]-methyl-amino}-3-methyl-benzoic acid methyl ester 在 sodium hydroxide 作用下， 生成 5-Bromo-2-{[4-(4-methoxy-but-2-ynyloxy)-benzenesulfonyl]-methyl-amino}-3-methyl-benzoic acid
  参考文献：
  名称：

  Anthranilate sulfonamide hydroxamate TACE inhibitors. Part 2: SAR of the acetylenic P1′ group

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(02)00136-1

文献信息

• 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
• 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.