2(R)-2-(4-bromobenzyl)-1,1-dioxo-λ⁶-[1,2]thiazinane-3-carboxylic acid tert-butyl ester | 409107-83-1

• 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(R)-2-(4-bromobenzyl)-1,1-dioxo-λ⁶-[1,2]thiazinane-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (3R)-2-[(4-bromophenyl)methyl]-1,1-dioxothiazinane-3-carboxylate
• CAS: 409107-83-1
• 化学式: C₁₆H₂₂BrNO₄S
• 分子量: 404.325
• InChiKey: GVTREOYAUUUAAE-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2(R)-2-(4-bromobenzyl)-1,1-dioxo-λ⁶-[1,2]thiazinane-3-carboxylic acid tert-butyl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 、 联硼酸频那醇酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2(R)-1,1-dioxo-2-(4-pyridin-4-ylbenzyl)-λ6-[1,2]thiazinane-3-carboxylic acid benzyloxyamide
  参考文献：
  名称：

  Sultam Hydroxamates as Novel Matrix Metalloproteinase Inhibitors

  摘要：

  In this communication we describe the design, synthesis, and evaluation of novel sultam hydroxamates 4 as MMP-2, -9, and -13 inhibitors. Compound 26 was found to be an active inhibitor (NIMP-2 IC50 = 1 nM) with 1000-fold selectivity over MMP-1 and good oral bioavailability (F = 43%) in mouse. An X-ray crystal structure of 26 in MMP-13 confirms the key hydrogen bonds and prime side binding in the active site.

  DOI：

  10.1021/jm049833g
• 作为产物：
  描述：

  2(R)-2-tert-butoxycarbonylamino-5-chlorosulfonylpentanoic acid tert-butyl ester 在 盐酸 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2(R)-2-(4-bromobenzyl)-1,1-dioxo-λ⁶-[1,2]thiazinane-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Sultam Hydroxamates as Novel Matrix Metalloproteinase Inhibitors

  摘要：

  In this communication we describe the design, synthesis, and evaluation of novel sultam hydroxamates 4 as MMP-2, -9, and -13 inhibitors. Compound 26 was found to be an active inhibitor (NIMP-2 IC50 = 1 nM) with 1000-fold selectivity over MMP-1 and good oral bioavailability (F = 43%) in mouse. An X-ray crystal structure of 26 in MMP-13 confirms the key hydrogen bonds and prime side binding in the active site.

  DOI：

  10.1021/jm049833g

文献信息

• Sultam Hydroxamates as Novel Matrix Metalloproteinase Inhibitors
  作者：Robert J. Cherney、Ruowei Mo、Dayton T. Meyer、Karl D. Hardman、Rui-Qin Liu、Maryanne B. Covington、Mingxin Qian、Zelda R. Wasserman、David D. Christ、James M. Trzaskos、Robert C. Newton、Carl P. Decicco

  DOI：10.1021/jm049833g

  日期：2004.6.1

  In this communication we describe the design, synthesis, and evaluation of novel sultam hydroxamates 4 as MMP-2, -9, and -13 inhibitors. Compound 26 was found to be an active inhibitor (NIMP-2 IC50 = 1 nM) with 1000-fold selectivity over MMP-1 and good oral bioavailability (F = 43%) in mouse. An X-ray crystal structure of 26 in MMP-13 confirms the key hydrogen bonds and prime side binding in the active site.