2-trimethylsilylethyl (2R)-2-[(4-bromophenyl)sulfonylamino]-3-methylbutanoate | 959962-85-7

• 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-trimethylsilylethyl (2R)-2-[(4-bromophenyl)sulfonylamino]-3-methylbutanoate
• CAS: 959962-85-7
• 化学式: C₁₆H₂₆BrNO₄SSi
• 分子量: 436.442
• InChiKey: FGTWJAJIZMTWIW-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[4-[(4-Methoxyphenoxy)methyl]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 、 2-trimethylsilylethyl (2R)-2-[(4-bromophenyl)sulfonylamino]-3-methylbutanoate 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成 2-(trimethylsilyl)ethyl ((4'-((4-methoxyphenoxy)methyl)-[1,1'-biphenyl]-4-yl)sulfonyl)-D-valinate
  参考文献：
  名称：

  Synthesis and biological evaluation of ((4-keto)-phenoxy)methyl biphenyl-4-sulfonamides: A class of potent aggrecanase-1 inhibitors

  摘要：

  The prevention of aggrecan (a key component of cartilage) cleavage via the inhibition of aggrecanase-1 may provide a unique opportunity to stop the progression of cartilage degradation in osteoarthritis. The evaluation of a series of biphenylsulfonamides resulted in the identification of the ((4-keto)-phenoxy) methyl biphenyl-4-sulfonamides analogs (19-21 and 24) with improved Agg-1 inhibition and MMP-2, MMP-13 activity. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.056
• 作为产物：
  描述：

  2-(三甲硅基)乙醇 、 (R)-2-(4-bromophenylsulfonamido)-3-methylbutanoic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到2-trimethylsilylethyl (2R)-2-[(4-bromophenyl)sulfonylamino]-3-methylbutanoate
  参考文献：
  名称：

  Synthesis and biological evaluation of ((4-keto)-phenoxy)methyl biphenyl-4-sulfonamides: A class of potent aggrecanase-1 inhibitors

  摘要：

  The prevention of aggrecan (a key component of cartilage) cleavage via the inhibition of aggrecanase-1 may provide a unique opportunity to stop the progression of cartilage degradation in osteoarthritis. The evaluation of a series of biphenylsulfonamides resulted in the identification of the ((4-keto)-phenoxy) methyl biphenyl-4-sulfonamides analogs (19-21 and 24) with improved Agg-1 inhibition and MMP-2, MMP-13 activity. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.056

文献信息

• Synthesis and biological evaluation of ((4-keto)-phenoxy)methyl biphenyl-4-sulfonamides: A class of potent aggrecanase-1 inhibitors
  作者：Darrin W. Hopper、Matthew D. Vera、David How、Joshua Sabatini、Jason S. Xiang、Manus Ipek、Jennifer Thomason、Yonghan Hu、Eric Feyfant、Qin Wang、Katy E. Georgiadis、Erica Reifenberg、Richard T. Sheldon、Cristin C. Keohan、Manas K. Majumdar、Elisabeth A. Morris、Jerauld Skotnicki、Phaik-Eng Sum

  DOI：10.1016/j.bmcl.2009.03.056

  日期：2009.5

  The prevention of aggrecan (a key component of cartilage) cleavage via the inhibition of aggrecanase-1 may provide a unique opportunity to stop the progression of cartilage degradation in osteoarthritis. The evaluation of a series of biphenylsulfonamides resulted in the identification of the ((4-keto)-phenoxy) methyl biphenyl-4-sulfonamides analogs (19-21 and 24) with improved Agg-1 inhibition and MMP-2, MMP-13 activity. (c) 2009 Elsevier Ltd. All rights reserved.