(1"S,2R,4'S,5'S)-[5'-(1",2"-dihydroxy-ethyl)-2',2'-dimethyl-[1,3]dioxolan-4'-yl]-(4-methoxybenzenesulfonylamino)-acetic acid methyl ester | 607707-76-6

• 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: (1"S,2R,4'S,5'S)-[5'-(1",2"-dihydroxy-ethyl)-2',2'-dimethyl-[1,3]dioxolan-4'-yl]-(4-methoxybenzenesulfonylamino)-acetic acid methyl ester
• 英文别名: methyl (2R)-2-[(4S,5S)-5-[(1S)-1,2-dihydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(4-methoxyphenyl)sulfonylamino]acetate
• CAS: 607707-76-6
• 化学式: C₁₇H₂₅NO₉S
• 分子量: 419.453
• InChiKey: NJMNRSRBQATARI-XGUBFFRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (1"S,2R,4'S,5'S)-[5'-(1",2"-dihydroxy-ethyl)-2',2'-dimethyl-[1,3]dioxolan-4'-yl]-(4-methoxybenzenesulfonylamino)-acetic acid methyl ester 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3aS,4R,7S,7aS)-7-hydroxy-5-(4'-methoxybenzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Structure–activity relationships of azasugar-based MMP/ADAM inhibitors

  摘要：

  In order to investigate structure-activity relationships of azasugar series toward metalloprotemases, we synthesized and evaluated several azasugar-based compounds. As a result, it was found that 4-phenoxybenzene derivative 3 having 2R,3R,4R,5S-configurations exhibited most potent inhibitory activities against matrix metalloproteinase-1, -3 and -9 and TACE. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00530-4
• 作为产物：
  描述：

  (2R,4'R,4"S,5'S)-azide-(2',2',2",2"-tetramethyl-[4',4"]bis[[1,3]dioxolanyl]-5'-yl)-acetic acid methyl ester 在 palladium on activated charcoal 4-二甲氨基吡啶 、 Muromac(R) (H⁺-form) 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1"S,2R,4'S,5'S)-[5'-(1",2"-dihydroxy-ethyl)-2',2'-dimethyl-[1,3]dioxolan-4'-yl]-(4-methoxybenzenesulfonylamino)-acetic acid methyl ester
  参考文献：
  名称：

  Structure–activity relationships of azasugar-based MMP/ADAM inhibitors

  摘要：

  In order to investigate structure-activity relationships of azasugar series toward metalloprotemases, we synthesized and evaluated several azasugar-based compounds. As a result, it was found that 4-phenoxybenzene derivative 3 having 2R,3R,4R,5S-configurations exhibited most potent inhibitory activities against matrix metalloproteinase-1, -3 and -9 and TACE. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00530-4

文献信息

• US7223779B2
  申请人：——

  公开号：US7223779B2

  公开（公告）日：2007-05-29