2,4-dihydroxy-β-methoxy-5,6-dimethylacetophenone | 132020-84-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-dihydroxy-β-methoxy-5,6-dimethylacetophenone
• 英文别名: 1-(4,6-Dihydroxy-2,3-dimethylphenyl)-2-methoxyethanone
• CAS: 132020-84-9
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: GFCLMCNADHHWDU-UHFFFAOYSA-N

物化性质

• 沸点：
  372.1±21.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-dihydroxy-β-methoxy-5,6-dimethylacetophenone 在 potassium 3-(benzyloxy)-4-methoxybenzoate 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 3,7-Dimethoxy-2-(4-methoxy-3-phenylmethoxyphenyl)-5,6-dimethylchromen-4-one
  参考文献：
  名称：

  Structure−Activity Requirements for Flavone Cytotoxicity and Binding to Tubulin

  摘要：

  A series of 79 flavones related to centaureidin (3,6,4'-trimethoxy-5,7,3'-trihydroxyflavone 1) was screened for cytotoxicity in the NCI in vitro 60-cell line human tumor screen. The resulting cytotoxicity profiles of these flavones were compared for degree of similarity to the profile of 1. Selected compounds were further evaluated with in vitro assays of tubulin polymerization and [H-3]colchicine binding to tubulin. Maximum potencies for tubulin interaction and production of differential cytotoxicity profiles characteristic of 1 were observed only with compounds containing hydroxyl substituents at C-3' and C-5 and methoxyl groups at C-3 and C-4'.

  DOI：

  10.1021/jm970842h
• 作为产物：
  描述：

  甲氧基乙腈 、 4,5-二甲基间苯二酚 在 盐酸 、 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 以71%的产率得到2,4-dihydroxy-β-methoxy-5,6-dimethylacetophenone
  参考文献：
  名称：

  Structure−Activity Requirements for Flavone Cytotoxicity and Binding to Tubulin

  摘要：

  A series of 79 flavones related to centaureidin (3,6,4'-trimethoxy-5,7,3'-trihydroxyflavone 1) was screened for cytotoxicity in the NCI in vitro 60-cell line human tumor screen. The resulting cytotoxicity profiles of these flavones were compared for degree of similarity to the profile of 1. Selected compounds were further evaluated with in vitro assays of tubulin polymerization and [H-3]colchicine binding to tubulin. Maximum potencies for tubulin interaction and production of differential cytotoxicity profiles characteristic of 1 were observed only with compounds containing hydroxyl substituents at C-3' and C-5 and methoxyl groups at C-3 and C-4'.

  DOI：

  10.1021/jm970842h

文献信息

• 4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity
  作者：Nadine De Meyer、Achiel Haemers、Lallan Mishra、Hrishi Kesh Pandey、L. A. C. Pieters、Dirk A. Vanden Berghe、Arnold J. Vlietinck

  DOI：10.1021/jm00106a039

  日期：1991.2

  4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5-mu-g/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.
• Structure−Activity Requirements for Flavone Cytotoxicity and Binding to Tubulin
  作者：John A. Beutler、Ernest Hamel、Arnold J. Vlietinck、Achiel Haemers、Padinchare Rajan、James N. Roitman、John H. Cardellina、Michael R. Boyd

  DOI：10.1021/jm970842h

  日期：1998.6.1

  A series of 79 flavones related to centaureidin (3,6,4'-trimethoxy-5,7,3'-trihydroxyflavone 1) was screened for cytotoxicity in the NCI in vitro 60-cell line human tumor screen. The resulting cytotoxicity profiles of these flavones were compared for degree of similarity to the profile of 1. Selected compounds were further evaluated with in vitro assays of tubulin polymerization and [H-3]colchicine binding to tubulin. Maximum potencies for tubulin interaction and production of differential cytotoxicity profiles characteristic of 1 were observed only with compounds containing hydroxyl substituents at C-3' and C-5 and methoxyl groups at C-3 and C-4'.