2-amino-3-cyano-4-(4'-benzyloxyphenyl)-6-[(2'',3'',6'',2''',3''',4''',6'''-hepta-O-acetyl-β-cellobiosyl)-1''-deoxy-1''-methyl]pyridine | 1345000-32-9

• 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: 2-amino-3-cyano-4-(4'-benzyloxyphenyl)-6-[(2'',3'',6'',2''',3''',4''',6'''-hepta-O-acetyl-β-cellobiosyl)-1''-deoxy-1''-methyl]pyridine
• 英文别名: [(2R,3R,4S,5S,6S)-4,5-diacetyloxy-6-[[6-amino-5-cyano-4-(4-phenylmethoxyphenyl)pyridin-2-yl]methyl]-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1345000-32-9
• 化学式: C₄₆H₅₁N₃O₁₈
• 分子量: 933.92
• InChiKey: ZNOYGNFOOSALCZ-OHYOVNNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  67
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  284
• 氢给体数：
  1
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  2-(4-benzyloxybenzylidene)-malononitrile 、 1-(2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-cellobiosyl)propan-2-one 在 ammonium acetate 作用下， 以 甲苯 为溶剂， 以36%的产率得到2-amino-3-cyano-4-(4'-benzyloxyphenyl)-6-[(2'',3'',6'',2''',3''',4''',6'''-hepta-O-acetyl-β-cellobiosyl)-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