2-amino-3-cyano-4-(thien-2-yl)-6-[(β-D-glucopyranosyl)-1''-deoxy-1''-methyl]pyridine | 1345000-30-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-3-cyano-4-(thien-2-yl)-6-[(β-D-glucopyranosyl)-1''-deoxy-1''-methyl]pyridine
• 英文别名: 2-amino-4-thiophen-2-yl-6-[[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methyl]pyridine-3-carbonitrile
• CAS: 1345000-30-7
• 化学式: C₁₇H₁₉N₃O₅S
• 分子量: 377.421
• InChiKey: COGOWSNSHDKXHV-FHXAZYNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  181
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2-噻吩亚甲基)甲烷-1,1-二甲腈 在 甲醇 、 ammonium acetate 、 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 15.0h， 生成 2-amino-3-cyano-4-(thien-2-yl)-6-[(β-D-glucopyranosyl)-1''-deoxy-1''-methyl]pyridine
  参考文献：
  名称：

  Synthesis and Enzyme Inhibitory Activities of Highly Functionalized Pyridylmethyl-C-β-D-Glycosides

  摘要：

  Several pyridylmethyl-C-beta-D-glycosides (3a-3l, 6a, and 6h) were synthesized by refluxing 3-(beta-D-glucopyranosyl)/(beta-D-cellobiosyl)-propanones and dicyanobenzylidenes with ammonium acetate in anhydrous toluene in moderate to good yields. The reaction involves a C-C Michael addition of enamine, formed from glycosyl ketone and ammonium acetate, to the dicayanobenzylidene derivative; subsequent dehydrative cyclization; and oxidative aromatization. Two of these prototypes, compounds 3e and 3k, were deacetylated to the respective glucopyranosyl methyl pyridines 4e and 4k with NaOMe/MeOH. The synthesized compounds were screened for their in vitro alpha-glucosidase inhibitory activities and one of the compounds showed 20% inhibition as compared to standard drug acarbose displaying 39% inhibition.

  DOI：

  10.1080/07328303.2011.618280

文献信息

• Synthesis and Enzyme Inhibitory Activities of Highly Functionalized Pyridylmethyl-<i>C</i>-β-D-Glycosides
  作者：Vivek Parashar Pandey、Natasha Jaiswal、A. K. Srivastava、Sanjeev K. Shukla、Rama Pati Tripathi

  DOI：10.1080/07328303.2011.618280

  日期：2011.4

  Several pyridylmethyl-C-beta-D-glycosides (3a-3l, 6a, and 6h) were synthesized by refluxing 3-(beta-D-glucopyranosyl)/(beta-D-cellobiosyl)-propanones and dicyanobenzylidenes with ammonium acetate in anhydrous toluene in moderate to good yields. The reaction involves a C-C Michael addition of enamine, formed from glycosyl ketone and ammonium acetate, to the dicayanobenzylidene derivative; subsequent dehydrative cyclization; and oxidative aromatization. Two of these prototypes, compounds 3e and 3k, were deacetylated to the respective glucopyranosyl methyl pyridines 4e and 4k with NaOMe/MeOH. The synthesized compounds were screened for their in vitro alpha-glucosidase inhibitory activities and one of the compounds showed 20% inhibition as compared to standard drug acarbose displaying 39% inhibition.