2-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-3-methyl-butyric acid | 287403-09-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-3-methyl-butyric acid
• 英文别名: (2R)-2-[(4-but-2-ynoxyphenyl)sulfonyl-methylamino]-3-methylbutanoic acid
• CAS: 287403-09-2
• 化学式: C₁₆H₂₁NO₅S
• 分子量: 339.412
• InChiKey: DWHDWDKCDIGOTI-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  2-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-3-methyl-butyric acid 在 草酰氯 、 羟胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-N-hydroxy-3-methyl-butyramide
  参考文献：
  名称：

  Acetylenic TACE inhibitors. Part 1. SAR of the acyclic sulfonamide hydroxamates

  摘要：

  The SAR of a series of potent sulfonamide hydroxamate TACE inhibitors, all bearing a butynyloxy P1' group, was explored. In particular, compound 5j has excellent in vitro potency against isolated TACE enzyme and in cells, good selectivity over MMP-1 and MMP-9, and oral activity in an in vivo model of TNF-alpha production and a collagen-induced arthritis model. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00514-6
• 作为产物：
  描述：

  sodium p-hydroxybenzenesulfonate 在 sodium hydroxide 、 草酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-3-methyl-butyric acid
  参考文献：
  名称：

  Acetylenic TACE inhibitors. Part 1. SAR of the acyclic sulfonamide hydroxamates

  摘要：

  The SAR of a series of potent sulfonamide hydroxamate TACE inhibitors, all bearing a butynyloxy P1' group, was explored. In particular, compound 5j has excellent in vitro potency against isolated TACE enzyme and in cells, good selectivity over MMP-1 and MMP-9, and oral activity in an in vivo model of TNF-alpha production and a collagen-induced arthritis model. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00514-6

文献信息

• ACETYLENIC ALPHA-AMINO ACID-BASED SULFONAMIDE HYDROXAMIC ACID TACE INHIBITORS
  申请人：Wyeth Holdings Corporation

  公开号：EP1144368B1

  公开（公告）日：2004-07-14
• Acetylenic TACE inhibitors. Part 1. SAR of the acyclic sulfonamide hydroxamates
  作者：J.I. Levin、J.M. Chen、K. Cheung、D. Cole、C. Crago、E.Delos Santos、X. Du、G. Khafizova、G. MacEwan、C. Niu、E.J. Salaski、A. Zask、T. Cummons、A. Sung、J. Xu、Y. Zhang、W. Xu、S. Ayral-Kaloustian、G. Jin、R. Cowling、D. Barone、K.M. Mohler、R.A. Black、J.S. Skotnicki

  DOI：10.1016/s0960-894x(03)00514-6

  日期：2003.8

  The SAR of a series of potent sulfonamide hydroxamate TACE inhibitors, all bearing a butynyloxy P1' group, was explored. In particular, compound 5j has excellent in vitro potency against isolated TACE enzyme and in cells, good selectivity over MMP-1 and MMP-9, and oral activity in an in vivo model of TNF-alpha production and a collagen-induced arthritis model. (C) 2003 Elsevier Ltd. All rights reserved.