1,7-(acetone)-chlorogenic acid ketal | 1067650-02-5

• 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)-chlorogenic acid ketal
• 英文别名: 1,7-chlorogenic acid acetonide；[(5S,7R,8R,9R)-8,9-dihydroxy-2,2-dimethyl-4-oxo-1,3-dioxaspiro[4.5]decan-7-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 1067650-02-5
• 化学式: C₁₉H₂₂O₉
• 分子量: 394.378
• InChiKey: BGAXFHHCXMTPMW-HGQXDNSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  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

文献信息

• In Vitro Evaluation of Caffeoyl and Cinnamoyl Derivatives as Potential Prolyl Oligopeptidase Inhibitors
  作者：Luciana Adolpho、Daniele Marin、Albert Puigpinos、Laura Mendieta、Teresa Tarragó、Ademir Morel、Ernest Giralt、Ionara Dalcol

  DOI：10.1055/s-0033-1350897

  日期：——

  A screening of the natural product chlorogenic acid, isolated from the Brazilian medicinal plant Hypericum brasiliense, caffeic acid, cinnamic acid, and p-methoxycinnamic acid, and derivatives of caffeoylquinic, caffeoyl, and cinnamoyl against the enzymes prolyl oligopeptidase and dipeptidyl peptidase IV was carried out. Caffeoylquinic, caffeoyl, and cinnamoyl derivatives were prepared using simple derivatization procedures and through coupling reactions with the amino acid proline. The dipeptidyl peptidase IV assay showed inhibitory activity of the tested compounds at a high concentration (500 mu M) in the range of 81.5-7.2%. In contrast, the derivatives methyl ester and 1,7-acetonide obtained from chlorogenic acid, and caffeic acid and its methyl ester derivative showed selectivity and activity as prolyl oligopeptidase inhibitors, with IC50 values of 3 to 14mM.
• 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.