methyl 2-amino-2-deoxy-3,4;5,6-di-O-isopropylidene-D-gluconate | 170997-51-0

• 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: methyl 2-amino-2-deoxy-3,4;5,6-di-O-isopropylidene-D-gluconate
• 英文别名: methyl (2R)-2-amino-2-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]acetate
• CAS: 170997-51-0
• 化学式: C₁₃H₂₃NO₆
• 分子量: 289.329
• InChiKey: GKXGBGXAYSBCIE-ZYUZMQFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  89.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-amino-2-deoxy-3,4;5,6-di-O-isopropylidene-D-gluconate 在 4-二甲氨基吡啶 、 cerium(III) chloride 、 草酸 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.34h， 生成 (3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4'-methoxybenzenesulfonyl)hexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Azasugar-Based MMP/ADAM Inhibitors as Antipsoriatic Agents

  摘要：

  As a part of synthetic studies on MMP (matrix metalloproteinase)/ADAM (a disintegrin and metalloproteinase) inhibitors, we have preliminarily communicated that azasugar-based compound la exhibited a potential inhibitory activity on some metalloprotease-catalyzed proteolytic reactions. To find promising candidates for the topical treatment of psoriasis, we investigated stability in aqueous solution of compound la and its derivative 1b and then optimized the P1' substuent (2-5). In the present study, we synthesized novel derivatives of compound-la and evaluated their inhibitory activity toward MMP-1, -3, and -9, TACE, and HB-EGF shedding, from a viewpoint of versatility of azasugars as a functional scaffold. As a result, it was found that compound 1b demonstrated desirable inhibitory activity as an antipsoriatic agent, and some of the derivatives showed selective inhibitory activity. In addition, it was found that compound 1b exhibited a significant therapeutic effect on a mouse TPA-induced epidermal hyperplasia. model. Therefore, compound 1b could become a promising candidate as a practical antipsoriatic agent.

  DOI：

  10.1021/jm0304313
• 作为产物：
  描述：

  (2R,4'S,4"R,5'R)-azide-(2',2',2",2"-tetramethyl-[4',4"]bis[[1,3]dioxolanyl]-5'-yl)-acetic acid methyl ester 在 palladium 10% on activated carbon 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 生成 methyl 2-amino-2-deoxy-3,4;5,6-di-O-isopropylidene-D-gluconate
  参考文献：
  名称：

  EP1516872

  摘要：

  公开号：

文献信息

• EP1516872
  申请人：——

  公开号：——

  公开（公告）日：——
• Park, Ki Hun, Heterocycles, 1995, vol. 41, # 8, p. 1715 - 1720
  作者：Park, Ki Hun

  DOI：——

  日期：——
• Azasugar-Based MMP/ADAM Inhibitors as Antipsoriatic Agents
  作者：Hideki Moriyama、Takahiro Tsukida、Yoshimasa Inoue、Kohichi Yokota、Kohichiro Yoshino、Hirosato Kondo、Nobuaki Miura、Shin-Ichiro Nishimura

  DOI：10.1021/jm0304313

  日期：2004.4.1

  As a part of synthetic studies on MMP (matrix metalloproteinase)/ADAM (a disintegrin and metalloproteinase) inhibitors, we have preliminarily communicated that azasugar-based compound la exhibited a potential inhibitory activity on some metalloprotease-catalyzed proteolytic reactions. To find promising candidates for the topical treatment of psoriasis, we investigated stability in aqueous solution of compound la and its derivative 1b and then optimized the P1' substuent (2-5). In the present study, we synthesized novel derivatives of compound-la and evaluated their inhibitory activity toward MMP-1, -3, and -9, TACE, and HB-EGF shedding, from a viewpoint of versatility of azasugars as a functional scaffold. As a result, it was found that compound 1b demonstrated desirable inhibitory activity as an antipsoriatic agent, and some of the derivatives showed selective inhibitory activity. In addition, it was found that compound 1b exhibited a significant therapeutic effect on a mouse TPA-induced epidermal hyperplasia. model. Therefore, compound 1b could become a promising candidate as a practical antipsoriatic agent.