(3aS,4R,7S,7aR)-7-Hydroxy-5-(4-methoxy-benzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid benzyloxy-amide | 607403-20-3

• 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: (3aS,4R,7S,7aR)-7-Hydroxy-5-(4-methoxy-benzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid benzyloxy-amide
• 英文别名: (3aS,4R,7S,7aR)-7-hydroxy-5-(4-methoxyphenyl)sulfonyl-2,2-dimethyl-N-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridine-4-carboxamide
• CAS: 607403-20-3
• 化学式: C₂₃H₂₈N₂O₈S
• 分子量: 492.55
• InChiKey: WMVDNUCSMVWHEP-BQJUDKOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3aS,4R,7S,7aR)-7-Hydroxy-5-(4-methoxy-benzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid benzyloxy-amide 在 palladium on activated charcoal 氢气 作用下， 以66%的产率得到(3aS,4R,7S,7aR)-7-Hydroxy-5-(4-methoxy-benzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid hydroxyamide
  参考文献：
  名称：

  Design, synthesis and evaluation of novel azasugar-based MMP/ADAM inhibitors

  摘要：

  In order to verify whether azasugar would be a useful scaffold for inhibitory activity against metalloproteinases, we synthesized some azasugar-based compounds. As a result, it is clarified that azasugar moiety could function as successful inhibitor of matrix metalloproteinase-1, -3 and -9 and TACE. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00531-6
• 作为产物：
  描述：

  (3aS,6R,7S,7aS)-7-hydroxy-5-(4'-methoxybenzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carboxylic acid benzyloxyamide 在 Dowex-H⁺ 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (3aS,4R,7S,7aR)-7-Hydroxy-5-(4-methoxy-benzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid benzyloxy-amide
  参考文献：
  名称：

  Design, synthesis and evaluation of novel azasugar-based MMP/ADAM inhibitors

  摘要：

  In order to verify whether azasugar would be a useful scaffold for inhibitory activity against metalloproteinases, we synthesized some azasugar-based compounds. As a result, it is clarified that azasugar moiety could function as successful inhibitor of matrix metalloproteinase-1, -3 and -9 and TACE. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00531-6

文献信息

• US7223779B2
  申请人：——

  公开号：US7223779B2

  公开（公告）日：2007-05-29
• Design, synthesis and evaluation of novel azasugar-based MMP/ADAM inhibitors
  作者：Hideki Moriyama、Takahiro Tsukida、Yoshimasa Inoue、Hirosato Kondo、Kohichiro Yoshino、Shin-Ichiro Nishimura

  DOI：10.1016/s0960-894x(03)00531-6

  日期：2003.8

  In order to verify whether azasugar would be a useful scaffold for inhibitory activity against metalloproteinases, we synthesized some azasugar-based compounds. As a result, it is clarified that azasugar moiety could function as successful inhibitor of matrix metalloproteinase-1, -3 and -9 and TACE. (C) 2003 Elsevier Ltd. All rights reserved.