(4S)-3-(7-benzyloxy-1-oxoheptyl)-4-benzyl-2-oxazolidinone | 169269-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S)-3-(7-benzyloxy-1-oxoheptyl)-4-benzyl-2-oxazolidinone
• 英文别名: (4S)-4-benzyl-3-(7-phenylmethoxyheptanoyl)-1,3-oxazolidin-2-one
• CAS: 169269-84-5
• 化学式: C₂₄H₂₉NO₄
• 分子量: 395.499
• InChiKey: CBTQEMKDPQHDEE-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-3-(7-benzyloxy-1-oxoheptyl)-4-benzyl-2-oxazolidinone 在 palladium on activated charcoal lithium hydroxide 、 草酰氯 、 氢气 、 双氧水 、 sodium hexamethyldisilazane 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 50.25h， 生成 tert-butyl (2S)-2-[methyl-[(2S)-3-methyl-2-[methyl-[(2S)-3-methyl-2-[methyl-[(2S)-3-methyl-2-[methyl-[(2S)-2-methyloct-7-ynoyl]amino]butanoyl]amino]butanoyl]amino]butanoyl]amino]-3-phenylpropanoate
  参考文献：
  名称：

  龙酰胺的立体化学的全合成与重分配

  摘要：

  据报道，首次合成了龙酰胺。合成导致该分子的带有炔的片段上的立体中心的构型重新分配。

  DOI：

  10.1016/j.tet.2005.09.040
• 作为产物：
  描述：

  1,7-庚二醇 在 重铬酸吡啶 、 正丁基锂 、 草酰氯 、 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 生成 (4S)-3-(7-benzyloxy-1-oxoheptyl)-4-benzyl-2-oxazolidinone
  参考文献：
  名称：

  Inhibition of Matrix Metalloproteinases by Hydroxamates Containing Heteroatom-Based Modifications of the P1' Group

  摘要：

  In this study, structure-based drug design of matrix metalloproteinase inhibitors [human fibroblast collagenase (HFC), human fibroblast stromelysin (HFS), and human neutrophil collagenase (HNC)] was utilized in the development of potent hydroxamates which contain novel, heteroatom-based modifications of the P-1' group. A series containing a P-1' butyramide group resulted in a nanomolar potent and selective HNC inhibitor as well as a dual HFS/HNC inhibitor. Benzylic others with a four- or five-carbon methylene linker in the P-1' position also produced nanomolar potent HFS/HNC inhibition and micromolar potent HFC inhibition as expected. Surprisingly, the phenolic ethers of the same overall length as the benzylic ethers showed nanomolar potencies against HFC, as well as HFS and HNC. The potency profile of the phenolic ethers was optimized by structure-activity relationships of the phenolic group and the C-terminal amide. These inhibitors may help elucidate the in vivo roles of matrix metalloproteinases in normal and disease states.

  DOI：

  10.1021/jm00014a010

文献信息

• Inhibition of Matrix Metalloproteinases by Hydroxamates Containing Heteroatom-Based Modifications of the P1' Group
  作者：Madhusudhan R. Gowravaram、Jeffrey S. Johnson、Daniel Delecki、Ewell R. Cook、Bruce E. Tomczuk、Arup K. Ghose、Alan M. Mathiowetz、John C. Spurlino、Byron Rubin、Douglas L. Smith、Tricia Pulvino、Robert C. Wahl

  DOI：10.1021/jm00014a010

  日期：1995.7

  In this study, structure-based drug design of matrix metalloproteinase inhibitors [human fibroblast collagenase (HFC), human fibroblast stromelysin (HFS), and human neutrophil collagenase (HNC)] was utilized in the development of potent hydroxamates which contain novel, heteroatom-based modifications of the P-1' group. A series containing a P-1' butyramide group resulted in a nanomolar potent and selective HNC inhibitor as well as a dual HFS/HNC inhibitor. Benzylic others with a four- or five-carbon methylene linker in the P-1' position also produced nanomolar potent HFS/HNC inhibition and micromolar potent HFC inhibition as expected. Surprisingly, the phenolic ethers of the same overall length as the benzylic ethers showed nanomolar potencies against HFC, as well as HFS and HNC. The potency profile of the phenolic ethers was optimized by structure-activity relationships of the phenolic group and the C-terminal amide. These inhibitors may help elucidate the in vivo roles of matrix metalloproteinases in normal and disease states.
• The total synthesis and reassignment of stereochemistry of dragonamide
  作者：Hongliang Chen、Yaqing Feng、Zhengshuang Xu、Tao Ye

  DOI：10.1016/j.tet.2005.09.040

  日期：2005.11

  The first total synthesis of dragonamide is reported. The synthesis has led to a reassignment of the configuration at the stereogenic centre on the alkyne-bearing fragment of the molecule.

  据报道，首次合成了龙酰胺。合成导致该分子的带有炔的片段上的立体中心的构型重新分配。