6-bromo-2',4'-dimethoxyflavone | 1119807-90-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-bromo-2',4'-dimethoxyflavone
• 英文别名: Flavonid, 6d；6-bromo-2-(2,4-dimethoxyphenyl)chromen-4-one
• CAS: 1119807-90-7
• 化学式: C₁₇H₁₃BrO₄
• 分子量: 361.192
• InChiKey: DJOKTCJODXHCDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-bromo-2',4'-dimethoxyflavone 、 7-羟基黄酮 在 copper(l) iodide 、 N,N-二甲基甘氨酸 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 2-(2,4-dimethoxyphenyl)-6-(4-oxo-2-phenyl-4H-chromen-7-yloxy)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis of biflavones having a 6-O-7’’ linkage and effects on cyclooxygenase-2 and inducible nitric oxide synthase

  摘要：

  In order to establish anti-inflammatory potential of biflavonoids, 17 biflavone derivatives having a 6-O-7 '' linkage were synthesized and their effects on cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) were evaluated. The basic molecule (6-O-7 '' biflavone) potently inhibited COX-2-mediated PGE(2) production (IC50: < 2 mu M), being less active on iNOS-mediated NO production (IC50: > 50 mu M) from lipopolysaccharide-treated RAW 264.7 cells, a mouse macrophage cell line. Generally, the hydroxyl/methoxyl substitution(s) on the basic biflavone (6-O-7 '') reduced the inhibitory activity of PGE(2) production, while the effects on NO production were varied. It is suggested that the basic biflavone (6-O-7 '') may have a potential for new anti-inflammatory agent. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.017
• 作为产物：
  描述：

  5'-bromo-2'-hydroxy-2,4-dimethoxychalcone 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 0.33h， 以75%的产率得到6-bromo-2',4'-dimethoxyflavone
  参考文献：
  名称：

  作为有效的组织蛋白酶V抑制剂的Chalcones和Flavones组合文库的溶液相合成

  摘要：

  组织蛋白酶V是一种木瓜蛋白酶样半胱氨酸蛋白酶。它参与人类T细胞的控制（负责细胞免疫），并在蛋白水解酶中表现出最大的弹性。因此，组织蛋白酶V是治疗动脉粥样硬化的潜在分子靶标。在目前的工作中，针对组织蛋白酶V筛选了天然类黄酮，并确定了两种黄酮是组织蛋白酶V的有效抑制剂。基于此结果，在溶液相中使用清道夫试剂制备了查尔酮和黄酮的组合文库，并经过充分评估。

  DOI：

  10.1021/cc100076k

文献信息

• Solution Phase Synthesis of a Combinatorial Library of Chalcones and Flavones as Potent Cathepsin V Inhibitors
  作者：Joel Alvim、Richele P. Severino、Emerson F. Marques、Ariane M. Martinelli、Paulo C. Vieira、João B. Fernandes、M. Fatima das G. F. da Silva、Arlene G. Corrêa

  DOI：10.1021/cc100076k

  日期：2010.9.13

  Cathepsin V is a papain-like cysteine protease. It is involved in the control of human T cells (responsible for cell immunity), and presents the largest elastolytic activity among the proteolytic enzymes. Therefore, cathepsin V is a potential molecular target for the treatment of atherosclerosis. In the present work, natural flavonoids were screened against cathepsin V, and two flavones were identified

  组织蛋白酶V是一种木瓜蛋白酶样半胱氨酸蛋白酶。它参与人类T细胞的控制（负责细胞免疫），并在蛋白水解酶中表现出最大的弹性。因此，组织蛋白酶V是治疗动脉粥样硬化的潜在分子靶标。在目前的工作中，针对组织蛋白酶V筛选了天然类黄酮，并确定了两种黄酮是组织蛋白酶V的有效抑制剂。基于此结果，在溶液相中使用清道夫试剂制备了查尔酮和黄酮的组合文库，并经过充分评估。
• Synthesis of biflavones having a 6-O-7’’ linkage and effects on cyclooxygenase-2 and inducible nitric oxide synthase
  作者：Haiyan Che、Byung Kyu Park、Hyun Lim、Hyun Pyo Kim、Hyeun Wook Chang、Jin-Hyun Jeong、Haeil Park

  DOI：10.1016/j.bmcl.2008.11.017

  日期：2009.1

  In order to establish anti-inflammatory potential of biflavonoids, 17 biflavone derivatives having a 6-O-7 '' linkage were synthesized and their effects on cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) were evaluated. The basic molecule (6-O-7 '' biflavone) potently inhibited COX-2-mediated PGE(2) production (IC50: < 2 mu M), being less active on iNOS-mediated NO production (IC50: > 50 mu M) from lipopolysaccharide-treated RAW 264.7 cells, a mouse macrophage cell line. Generally, the hydroxyl/methoxyl substitution(s) on the basic biflavone (6-O-7 '') reduced the inhibitory activity of PGE(2) production, while the effects on NO production were varied. It is suggested that the basic biflavone (6-O-7 '') may have a potential for new anti-inflammatory agent. (C) 2008 Elsevier Ltd. All rights reserved.