(2S,3R,6S)-10-Acetyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotetradecane-2,6-dicarboxylic acid 2-(benzyloxy-amide) 6-methylamide | 191408-34-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (2S,3R,6S)-10-Acetyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotetradecane-2,6-dicarboxylic acid 2-(benzyloxy-amide) 6-methylamide
• CAS: 191408-34-1
• 化学式: C₃₂H₄₄N₄O₆
• 分子量: 580.725
• InChiKey: LBOORYWDKSUCGQ-ULNSLHSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  42.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  126.07
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,6S)-10-Acetyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotetradecane-2,6-dicarboxylic acid 2-(benzyloxy-amide) 6-methylamide 在 Pd-BaSO₄ 氢气 作用下， 以 甲醇 为溶剂， 以89%的产率得到(2S,3R,6S)-10-Acetyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotetradecane-2,6-dicarboxylic acid 2-hydroxyamide 6-methylamide
  参考文献：
  名称：

  P1, P2′-Linked macrocyclic amine derivatives as matrix metalloproteinase inhibitors

  摘要：

  A novel series of 13- and 14-membered macrocyclic amines was developed by linking the P-1, and P-2, groups. The synthesis entails stereoselective Frater alkylation to install the anti-succinate configuration and macrocyclic amination via nucleophilic displacement. This strategy resulted in a new class of conformationally constrained inhibitors that are potent ind selective for MMP-8 and 9 over MMP-1 and 3. (C) 1999 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00215-2
• 作为产物：
  描述：

  tert-butyl N-[(4S)-4-[[(E,2R)-2-[(1S)-1-hydroxy-2-phenylmethoxyethyl]-5-phenylpent-4-enoyl]amino]-5-(methylamino)-5-oxopentyl]carbamate 在 palladium dihydroxide 、 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 ruthenium trichloride 、 sodium periodate 、 氢气 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2S,3R,6S)-10-Acetyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotetradecane-2,6-dicarboxylic acid 2-(benzyloxy-amide) 6-methylamide
  参考文献：
  名称：

  P1, P2′-Linked macrocyclic amine derivatives as matrix metalloproteinase inhibitors

  摘要：

  A novel series of 13- and 14-membered macrocyclic amines was developed by linking the P-1, and P-2, groups. The synthesis entails stereoselective Frater alkylation to install the anti-succinate configuration and macrocyclic amination via nucleophilic displacement. This strategy resulted in a new class of conformationally constrained inhibitors that are potent ind selective for MMP-8 and 9 over MMP-1 and 3. (C) 1999 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00215-2