(2R)-3-methyl-2-[[4-[4-[[2-(trifluoromethyl)phenyl]methoxy]phenyl]phenyl]sulfonylamino]butanoic acid | 1345961-67-2

• 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: (2R)-3-methyl-2-[[4-[4-[[2-(trifluoromethyl)phenyl]methoxy]phenyl]phenyl]sulfonylamino]butanoic acid
• CAS: 1345961-67-2
• 化学式: C₂₅H₂₄F₃NO₅S
• 分子量: 507.53
• InChiKey: BKXKRQGSEIULQV-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  tert-butyl N-[(4'-hydroxy-1,1'-biphenyl-4-yl)sulfonyl]-D-valinate 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (2R)-3-methyl-2-[[4-[4-[[2-(trifluoromethyl)phenyl]methoxy]phenyl]phenyl]sulfonylamino]butanoic acid
  参考文献：
  名称：

  Continued exploration of biphenylsulfonamide scaffold as a platform for aggrecanase-1 inhibition

  摘要：

  Design, synthesis and structure-activity relationship of a series of biphenylsulfonamido-3-methylbutanoic acid based aggrecanase-1 inhibitors are described. In addition to robust aggrecanase-1 inhibition, these compounds also exhibit potent MMP-13 activity. In cell-based cartilage explants assay compound 48 produced 87% inhibition of proteoglycan degradation at 10 mu g/mL. Good pharmacokinetic properties were demonstrated by 46 with a half-life of 6 h and bioavailability of 23%. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.036

文献信息

• Continued exploration of biphenylsulfonamide scaffold as a platform for aggrecanase-1 inhibition
  作者：Yonghan Hu、Li Xing、Jennifer R. Thomason、Jason Xiang、Manus Ipek、Satenig Guler、Huanqiu Li、Joshua Sabatini、Priya Chockalingam、Erica Reifenberg、Richard Sheldon、Elisabeth A. Morris、Katy E. Georgiadis、Steve Tam

  DOI：10.1016/j.bmcl.2011.09.036

  日期：2011.11

  Design, synthesis and structure-activity relationship of a series of biphenylsulfonamido-3-methylbutanoic acid based aggrecanase-1 inhibitors are described. In addition to robust aggrecanase-1 inhibition, these compounds also exhibit potent MMP-13 activity. In cell-based cartilage explants assay compound 48 produced 87% inhibition of proteoglycan degradation at 10 mu g/mL. Good pharmacokinetic properties were demonstrated by 46 with a half-life of 6 h and bioavailability of 23%. (C) 2011 Elsevier Ltd. All rights reserved.