4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-5-(4-methyl-piperazin-1-ylmethyl)-biphenyl-3-carboxylic acid hydroxyamide | 470662-88-5

• 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: 4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-5-(4-methyl-piperazin-1-ylmethyl)-biphenyl-3-carboxylic acid hydroxyamide
• 英文别名: 2-[(4-but-2-ynoxyphenyl)sulfonyl-methylamino]-N-hydroxy-3-[(4-methylpiperazin-1-yl)methyl]-5-phenylbenzamide
• CAS: 470662-88-5
• 化学式: C₃₀H₃₄N₄O₅S
• 分子量: 562.69
• InChiKey: GJOYIIZEXVEUAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-5-(4-methyl-piperazin-1-ylmethyl)-biphenyl-3-carboxylic acid hydroxyamide 在 盐酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到4-[(4-But-2-ynyloxy-benzenesulfonyl)-methyl-amino]-5-(4-methyl-piperazin-1-ylmethyl)-biphenyl-3-carboxylic acid hydroxyamide dihydro-chloride salt
  参考文献：
  名称：

  ACETYLENIC ARYL SULFONAMIDE AND PHOSPHINIC ACID AMIDE HYDROXAMIC ACID TACE INHIBITORS

  摘要：

  公开号：

  EP1144369B1
• 作为产物：
  描述：

  4-{[4-(tert-Butyl-dimethyl-silanyloxy)-benzenesulfonyl]-methyl-amino}-5-methyl-biphenyl-3-carboxylic acid methyl ester 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 草酰氯 、 羟胺 、 potassium carbonate 、 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 4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-5-(4-methyl-piperazin-1-ylmethyl)-biphenyl-3-carboxylic acid hydroxyamide
  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

• 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