N-[2(R)-(tert-butylcarboxymethyl)octanoyl]-(S)-4-benzyl-2-oxazolidinone | 200866-60-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-[2(R)-(tert-butylcarboxymethyl)octanoyl]-(S)-4-benzyl-2-oxazolidinone
• 英文别名: tert-butyl (3R)-3-[(4S)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl]nonanoate
• CAS: 200866-60-0
• 化学式: C₂₄H₃₅NO₅
• 分子量: 417.546
• InChiKey: QTPAITXVKZACAO-UXHICEINSA-N

物化性质

• 沸点：
  546.259±33.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.102±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2(R)-(tert-butylcarboxymethyl)octanoyl]-(S)-4-benzyl-2-oxazolidinone 在 lithium hydroxide 、 双氧水 、 三乙胺 、 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (3R)-3-[[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]carbamoyl]nonanoic acid
  参考文献：
  名称：

  Matrix Metalloproteinase Inhibitors:  A Structure−Activity Study

  摘要：

  Modifications around the dipeptide-mimetic core of a hydroxamic acid based matrix metalloproteinase inhibitor were studied. These variations incorporated a variety of natural, unnatural, and synthetic amino acids in addition to modifications of the P1' and P3' substituents. The results of this study indicate the following structural requirements: (1) Two key hydrogen bonds must be present between the enzyme and potent substrates. (2) Potent inhibitors must possess strong zinc-binding functionalities. (3) The potential importance of the hydrophobic group at position R3 as illustrated by its ability to impart greater relative potency against stromelysin when larger hydrophobic groups are used. (4) Requirements surrounding the nature of the amino acid appear to be more restrictive for stromelysin than for neutrophil collagenase, 72 kDa gelatinase, and 92 kDa gelatinase. These requirements may involve planar fused-ring aryl systems and possibly hydrogen-bonding capabilities.

  DOI：

  10.1021/jm970494j
• 作为产物：
  描述：

  (S)-4-苄基-2-唑烷酮 在 正丁基锂 、 lithium hexamethyldisilazane 作用下， 反应 6.0h， 生成 N-[2(R)-(tert-butylcarboxymethyl)octanoyl]-(S)-4-benzyl-2-oxazolidinone
  参考文献：
  名称：

  Matrix Metalloproteinase Inhibitors:  A Structure−Activity Study

  摘要：

  Modifications around the dipeptide-mimetic core of a hydroxamic acid based matrix metalloproteinase inhibitor were studied. These variations incorporated a variety of natural, unnatural, and synthetic amino acids in addition to modifications of the P1' and P3' substituents. The results of this study indicate the following structural requirements: (1) Two key hydrogen bonds must be present between the enzyme and potent substrates. (2) Potent inhibitors must possess strong zinc-binding functionalities. (3) The potential importance of the hydrophobic group at position R3 as illustrated by its ability to impart greater relative potency against stromelysin when larger hydrophobic groups are used. (4) Requirements surrounding the nature of the amino acid appear to be more restrictive for stromelysin than for neutrophil collagenase, 72 kDa gelatinase, and 92 kDa gelatinase. These requirements may involve planar fused-ring aryl systems and possibly hydrogen-bonding capabilities.

  DOI：

  10.1021/jm970494j

文献信息

• Oxazolidinone to succinamide: a novel rearrangement reaction
  作者：Menyan Cheng、Biswanath De、Christopher T. Wahl、Neil G. Almstead、Michael G. Natchus、Stanislaw Pikul

  DOI：10.1016/s0040-4039(99)01168-5

  日期：1999.8

  disubstituted succinimide was obtained with a high degree of stereoselectivity as the major product. Subsequent investigative work confirmed the structure and further defined the scope of this rearrangement reaction.

  在将单取代的琥珀酸半酯束缚在手性恶唑烷酮上的研究过程中，获得了以高度立体选择性为主要产物的意想不到的二取代琥珀酰亚胺。随后的调查工作证实了该结构，并进一步确定了该重排反应的范围。
• Inhibition of Matrix Metalloproteinases: An examination of the S1′ pocket
  作者：Andrew Miller、Marion Askew、R.Paul Beckett、Claire L. Bellamy、Elisabeth A. Bone、Rachael E. Coates、Alan H. Davidson、Alan H. Drummond、Philip Huxley、Fionna M. Martin、Lydia Saroglou、Alison J. Thompson、Sonja E. van Dijk、Mark Whittaker

  DOI：10.1016/s0960-894x(96)00602-6

  日期：1997.1

  Peptidomimetic carboxylate- and hydroxamate-based inhibitors of matrix metalloproteinases containing extended P1' groups have been prepared. Potent inhibition and good selectivity for MMP-2 has been observed for the compounds produced. (C) 1997, Elsevier Science Ltd.