6-(3,4,5-trimethoxy)benzyl-5,7-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(3,4,5-trimethoxy)benzyl-5,7-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran
• 英文别名: (5,7-Dihydroxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-(3,4,5-trimethoxyphenyl)methanone；(5,7-dihydroxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-(3,4,5-trimethoxyphenyl)methanone
• 化学式: C₂₁H₂₄O₇
• 分子量: 388.417
• InChiKey: GGGXKCNYUOFVCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-(3,4,5-trimethoxy)benzyl-5,7-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到6-(3,4-dihydroxy-5-methoxy)benzyl-5,7-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran
  参考文献：
  名称：

  Synthesis of natural-like acylphloroglucinols with anti-proliferative, anti-oxidative and tube-formation inhibitory activity

  摘要：

  Two series of natural and natural-like mono- and bicyclic acylphloroglucinols derived from secondary metabolites in the genus Hypericum (Hypericaceae) were synthesised and tested in vitro for anti-proliferative and tube-formation inhibitory activity in human microvascular endothelial cells (HMEC-1). In addition, their anti-oxidative activity was determined via an ORAC-assay. The first series of compounds (4a-e) consisted of geranylated monocyclic acylphloroglucinols with varying aliphatic acyl substitution patterns, which were subsequently cyclised to the corresponding 2-methyl-2-prenylchromane derivatives (5a and 5d). The second series involved compounds containing a 2,2-dimethylchromane skeleton with differing aromatic acyl substitution (6a-d and 7a-e). Compound 7a, (5,7-dihydroxy-2,2-dimethylchroman-6-yl)-(3,4-dihydroxyphenyl)methanone), showed the highest in vitro anti-proliferative activity with an IC50 of 0.88 +/- 0.08 mu M and a remarkable anti-oxidative activity of 2.8 +/- 0.1 TE from the ORAC test. Interestingly, the high anti-proliferative activity of these acylphloroglucinols was not associated with tube-formation inhibition. Compounds (E)-1-(3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4,6-trihydroxyphenyl)-2-methylbutan-1-one (4d) and (5,7-dihydroxy-2,2-dimethylchroman-6-yl)(3,4-dimethoxyphenyl)methanone (6a) exhibited moderate to weak anti-proliferative effects (IC50 11.0 +/- 1 mu M and 48.0 +/- 43 mu M, respectively) and inhibited the capillary-like tube formation of HMEC-1 in vitro, whereas 7a was inactive. The most active compound in the ORAC assay was 7c, which exhibited an anti-oxidative effect of 6.6 +/- 1.0 TE. However, this compound showed only weak activity during the proliferation assay (IC50 53.8 +/- 0.3) and did not inhibit tube-formation. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.017
• 作为产物：
  描述：

  间苯三酚 在 aluminum (III) chloride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 6-(3,4,5-trimethoxy)benzyl-5,7-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran
  参考文献：
  名称：

  Synthesis of natural-like acylphloroglucinols with anti-proliferative, anti-oxidative and tube-formation inhibitory activity

  摘要：

  Two series of natural and natural-like mono- and bicyclic acylphloroglucinols derived from secondary metabolites in the genus Hypericum (Hypericaceae) were synthesised and tested in vitro for anti-proliferative and tube-formation inhibitory activity in human microvascular endothelial cells (HMEC-1). In addition, their anti-oxidative activity was determined via an ORAC-assay. The first series of compounds (4a-e) consisted of geranylated monocyclic acylphloroglucinols with varying aliphatic acyl substitution patterns, which were subsequently cyclised to the corresponding 2-methyl-2-prenylchromane derivatives (5a and 5d). The second series involved compounds containing a 2,2-dimethylchromane skeleton with differing aromatic acyl substitution (6a-d and 7a-e). Compound 7a, (5,7-dihydroxy-2,2-dimethylchroman-6-yl)-(3,4-dihydroxyphenyl)methanone), showed the highest in vitro anti-proliferative activity with an IC50 of 0.88 +/- 0.08 mu M and a remarkable anti-oxidative activity of 2.8 +/- 0.1 TE from the ORAC test. Interestingly, the high anti-proliferative activity of these acylphloroglucinols was not associated with tube-formation inhibition. Compounds (E)-1-(3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4,6-trihydroxyphenyl)-2-methylbutan-1-one (4d) and (5,7-dihydroxy-2,2-dimethylchroman-6-yl)(3,4-dimethoxyphenyl)methanone (6a) exhibited moderate to weak anti-proliferative effects (IC50 11.0 +/- 1 mu M and 48.0 +/- 43 mu M, respectively) and inhibited the capillary-like tube formation of HMEC-1 in vitro, whereas 7a was inactive. The most active compound in the ORAC assay was 7c, which exhibited an anti-oxidative effect of 6.6 +/- 1.0 TE. However, this compound showed only weak activity during the proliferation assay (IC50 53.8 +/- 0.3) and did not inhibit tube-formation. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.017

文献信息

• Synthesis of natural-like acylphloroglucinols with anti-proliferative, anti-oxidative and tube-formation inhibitory activity
  作者：Qiu Sun、Sebastian Schmidt、Martina Tremmel、Jörg Heilmann、Burkhard König

  DOI：10.1016/j.ejmech.2014.08.017

  日期：2014.10

  Two series of natural and natural-like mono- and bicyclic acylphloroglucinols derived from secondary metabolites in the genus Hypericum (Hypericaceae) were synthesised and tested in vitro for anti-proliferative and tube-formation inhibitory activity in human microvascular endothelial cells (HMEC-1). In addition, their anti-oxidative activity was determined via an ORAC-assay. The first series of compounds (4a-e) consisted of geranylated monocyclic acylphloroglucinols with varying aliphatic acyl substitution patterns, which were subsequently cyclised to the corresponding 2-methyl-2-prenylchromane derivatives (5a and 5d). The second series involved compounds containing a 2,2-dimethylchromane skeleton with differing aromatic acyl substitution (6a-d and 7a-e). Compound 7a, (5,7-dihydroxy-2,2-dimethylchroman-6-yl)-(3,4-dihydroxyphenyl)methanone), showed the highest in vitro anti-proliferative activity with an IC50 of 0.88 +/- 0.08 mu M and a remarkable anti-oxidative activity of 2.8 +/- 0.1 TE from the ORAC test. Interestingly, the high anti-proliferative activity of these acylphloroglucinols was not associated with tube-formation inhibition. Compounds (E)-1-(3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4,6-trihydroxyphenyl)-2-methylbutan-1-one (4d) and (5,7-dihydroxy-2,2-dimethylchroman-6-yl)(3,4-dimethoxyphenyl)methanone (6a) exhibited moderate to weak anti-proliferative effects (IC50 11.0 +/- 1 mu M and 48.0 +/- 43 mu M, respectively) and inhibited the capillary-like tube formation of HMEC-1 in vitro, whereas 7a was inactive. The most active compound in the ORAC assay was 7c, which exhibited an anti-oxidative effect of 6.6 +/- 1.0 TE. However, this compound showed only weak activity during the proliferation assay (IC50 53.8 +/- 0.3) and did not inhibit tube-formation. (C) 2014 Elsevier Masson SAS. All rights reserved.