1,7-(acetone) 3,4-(acetone)-chlorogenic acid diketal

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1,7-(acetone) 3,4-(acetone)-chlorogenic acid diketal
• 英文别名: (3aR,5S)-7c-(3,4-dihydroxy-trans-cinnamoyloxy)-2,2,2',2'-tetramethyl-(3ar,7ac)-tetrahydro-spiro[benzo[1,3]dioxole-5,4'-[1,3]dioxolan]-5'-one；(3aR,5S)-7c-(3,4-Dihydroxy-trans-cinnamoyloxy)-2,2,2',2'-tetramethyl-(3ar,7ac)-tetrahydro-spiro[benzo[1,3]dioxol-5,4'-[1,3]dioxolan]-5'-on；[(3'aR,4S,4'R,7'aR)-2,2,2',2'-tetramethyl-5-oxospiro[1,3-dioxolane-4,6'-4,5,7,7a-tetrahydro-3aH-1,3-benzodioxole]-4'-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₂₂H₂₆O₉
• 分子量: 434.443
• InChiKey: UDVGHVNGBSBPLG-KRJBKCEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,7-(acetone) 3,4-(acetone)-chlorogenic acid diketal 在 盐酸 、 甲醇 、 水 作用下， 反应 1.0h， 以79.6%的产率得到1,7-(acetone)-chlorogenic acid ketal
  参考文献：
  名称：

  Chlorogenic Acid Derivatives with Alkyl Chains of Different Lengths and Orientations: Potent α-Glucosidase Inhibitors

  摘要：

  alpha-Glucosidases play important roles in the digestion of carbohydrates and biosynthesis of viral envelope glycoproteins. Inhibitors of alpha-glucosidase are promising candidates for the development of antitype II diabetics and anti-AIDS drugs. Here, we report the synthesis and cc-glucosidase inhibitory activity of mono- and diketal/acetal derivatives of chlorogenic acid. The diketal derivatives showed more potent inhibitory activity than the monoketals. The 1,7-(5-nonanone) 3,4-(5-nonanone)-chlorogenic acid diketal showed remarkable inhibitory activity against alpha-glucosidases with potency better than that of 1-deoxynojirimycin hydrochloride. Four diasteremers of pelargonaldehyde diacetal and two of monoacetal derivatives of chlorogenic acid were synthesized in this study. They showed significant potent inhibition similar to or more potent than the ketal counterparts. Acetals with the alkyl chain oriented toward position 2 of chlorogenic acid showed more potent activity than those oriented toward position 6.

  DOI：

  10.1021/jm800621x
• 作为产物：
  描述：

  (-)-5-咖啡酰奎宁酸 在 丙酮 、 zinc(II) chloride 作用下， 生成 1,7-(acetone) 3,4-(acetone)-chlorogenic acid diketal
  参考文献：
  名称：

  Fischer; Dangschat, Chemische Berichte, 1932, vol. 65, p. 1037,1038

  摘要：

  DOI：

文献信息

• Chlorogenic Acid Derivatives with Alkyl Chains of Different Lengths and Orientations: Potent α-Glucosidase Inhibitors
  作者：Chao-Mei Ma、Masao Hattori、Mohsen Daneshtalab、Lili Wang

  DOI：10.1021/jm800621x

  日期：2008.10.9

  alpha-Glucosidases play important roles in the digestion of carbohydrates and biosynthesis of viral envelope glycoproteins. Inhibitors of alpha-glucosidase are promising candidates for the development of antitype II diabetics and anti-AIDS drugs. Here, we report the synthesis and cc-glucosidase inhibitory activity of mono- and diketal/acetal derivatives of chlorogenic acid. The diketal derivatives showed more potent inhibitory activity than the monoketals. The 1,7-(5-nonanone) 3,4-(5-nonanone)-chlorogenic acid diketal showed remarkable inhibitory activity against alpha-glucosidases with potency better than that of 1-deoxynojirimycin hydrochloride. Four diasteremers of pelargonaldehyde diacetal and two of monoacetal derivatives of chlorogenic acid were synthesized in this study. They showed significant potent inhibition similar to or more potent than the ketal counterparts. Acetals with the alkyl chain oriented toward position 2 of chlorogenic acid showed more potent activity than those oriented toward position 6.
• Fischer; Dangschat, Chemische Berichte, 1932, vol. 65, p. 1037,1038
  作者：Fischer、Dangschat

  DOI：——

  日期：——