2R,3S-Methyl 4-benzyloxy-3-hydroxy-2-(2E-3-phenyl-2-propen-1-yl)butyrate | 191408-24-9

• 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: 2R,3S-Methyl 4-benzyloxy-3-hydroxy-2-(2E-3-phenyl-2-propen-1-yl)butyrate
• 英文别名: methyl (E,2R)-2-[(1S)-1-hydroxy-2-phenylmethoxyethyl]-5-phenylpent-4-enoate
• CAS: 191408-24-9
• 化学式: C₂₁H₂₄O₄
• 分子量: 340.419
• InChiKey: SSLBNYJRKWBTEN-ZCBOBATRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2R,3S-Methyl 4-benzyloxy-3-hydroxy-2-(2E-3-phenyl-2-propen-1-yl)butyrate 在 sodium hydroxide 、 sodium hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成
  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：

  (R)-苄氧甲基环氧乙烷 在 六甲基磷酰三胺 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 四甲基乙二胺 、 碳酸氢钠 、 lithium diisopropyl amide 作用下， 反应 4.5h， 生成 2R,3S-Methyl 4-benzyloxy-3-hydroxy-2-(2E-3-phenyl-2-propen-1-yl)butyrate
  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

文献信息

• Macrocyclic compounds as metalloprotease inhibitors
  申请人：DuPont Pharmaceuticals Company

  公开号：US06281352B1

  公开（公告）日：2001-08-28

  This invention relates to macrocyclic molecules which inhibit metalloproteinases, including aggrecanase, and the production of tumor necrosis factor (TNF). In particular, the compounds are inhibitors of metalloproteinases involved in tissue degradation and inhibitors of the release of tumor necrosis factor. The present invention also relates to pharmaceutical compositions comprising such compounds and to methods of using these compounds for the treatment of inflammatory diseases.

  这项发明涉及抑制金属蛋白酶（包括聚集素酶）和肿瘤坏死因子（TNF）产生的大环分子。具体来说，这些化合物是涉及组织降解的金属蛋白酶的抑制剂，也是肿瘤坏死因子释放的抑制剂。本发明还涉及包括这些化合物的药物组合物，以及使用这些化合物治疗炎症性疾病的方法。
• P1, P2′-Linked macrocyclic amine derivatives as matrix metalloproteinase inhibitors
  作者：James J.-W. Duan、Lihua Chen、Chu-Biao Xue、Zelda R. Wasserman、Karl D. Hardman、Maryanne B. Covington、Robert R. Cope、Elizabeth C. Arner、Carl P. Decicco

  DOI：10.1016/s0960-894x(99)00215-2

  日期：1999.5

  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.