8-bromo-7-methoxy chrysin | 92796-54-8

• 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: 8-bromo-7-methoxy chrysin
• 英文别名: 5-hydroxy-7-methoxy-8-bromo-flavone；8-Brom-5-hydroxy-7-methoxy-flavon；8-bromo-5-hydroxy-7-methoxyflavone；8-bromo-5-hydroxy-7-methoxy-2-phenyl-chromen-4-one；8-Brom-5-hydroxy-7-methoxy-2-phenyl-chromen-4-on；8-bromo-5-hydroxy-7-methoxy-2-phenylchromen-4-one
• CAS: 92796-54-8
• 化学式: C₁₆H₁₁BrO₄
• 分子量: 347.165
• InChiKey: SKKNNUBLAVPFTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  柯因二甲醚 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 8-bromo-7-methoxy chrysin
  参考文献：
  名称：

  Synthesis and anticancer effect of chrysin derivatives

  摘要：

  A series of chrysin derivatives, prepared by alkylation, halogenation, nitration, methylation, acetylation and trifluoromethylation, were tested in vitro against human gastric adenocarcinoma cell line (SGC-7901) and colorectal adenocarcinoma (HT-29) cells. Among these derivatives of chrysin, 5,7-dimethoxy-8-iodochrysin 3 and 8-bromo-5-hydroxy-7-methoxychrysin 11 have the strongest activities against SGC-7901 and HT-29 cells, respectively. 5,7-Dihydroxy-8-nitrochrysin 12 were found to have strong activities against both SGC-7901 and HT-29 cells. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01081-8

文献信息

• Role of Some Food-Grade Synthesized Flavonoids on the Control of Ochratoxin A in Aspergillus carbonarius
  作者：Alessandra Ricelli、Martina De Angelis、Ludovica Primitivo、Giuliana Righi、Carla Sappino、Roberto Antonioletti

  DOI：10.3390/molecules24142553

  日期：——

  carbonarius cultured in a conducive liquid medium. The best control effect on OTA biosynthesis was achieved using NEG and DHF. In fungal cultures treated with these compounds at 5, 25, and 50 μg/mL, OTA biosynthesis significantly decreased throughout the 8-day experiment. NEG and DHF appear to have an inhibiting effect also on the activity of LOX, whereas MOS, which did not significantly inhibit OTA production

  赭曲霉毒素 A (OTA) 是一种严重影响人类健康的霉菌毒素。在地中海国家，黑曲霉群，尤其是炭黑曲霉，造成最高的 OTA 污染。在这里，我们描述了三种多酚类黄酮的合成：5-羟基-6,7-二甲氧基-黄酮 (MOS)、5,6-二羟基-7-甲氧基-黄酮 (NEG) 和 5,6-二羟基-黄酮 (DHF) ，以及它们对在有益液体培养基中培养的炭黑炭疽菌中 OTA 生物合成和脂氧合酶 (LOX) 活性的预防作用。NEG和DHF对OTA生物合成的控制效果最好。在用 5、25 和 50 μg/mL 的这些化合物处理的真菌培养物中，OTA 生物合成在整个 8 天实验中显着降低。NEG 和 DHF 似乎也对 LOX 的活性有抑制作用，而 MOS，没有显着抑制 OTA 产生，对 LOX 活性没有影响。分子中儿茶酚位置游离羟基的存在似乎是显着抑制 OTA 生物合成的决定因素。然而，NEG 中 C-7 中甲氧基的存
• Convergent synthesis of mosloflavone, negletein and baicalein from crysin
  作者：Giuliana Righi、Roberto Antonioletti、Ilaria Proietti Silvestri、Nicola D'Antona、Daniela Lambusta、Paolo Bovicelli

  DOI：10.1016/j.tet.2009.12.021

  日期：2010.2

  An expeditious synthesis of three polyoxygenated flavones mosloflavone, negletein and baicalein. starting from crysin, an easily available flavone, by a bromination/methoxylation procedure is reported The convergent synthesis exploits a base induced Wesley-Moser type rearrangement (C) 2009 Elsevier Ltd All rights reserved
• Synthesis of 8-Bromoflavone and Related Compounds¹
  作者：C. T. CHANG、T. S. CHEN、F. C. CHEN

  DOI：10.1021/jo01067a025

  日期：1961.9
• 17. Chalkones: a new synthesis of chrysin, apigenin, and luteolin
  作者：W. A. Hutchins、T. S. Wheeler

  DOI：10.1039/jr9390000091

  日期：——
• Synthesis and anticancer effect of chrysin derivatives
  作者：Xing Zheng、Wei-Dong Meng、Yang-Yan Xu、Jian-Guo Cao、Feng-Ling Qing

  DOI：10.1016/s0960-894x(02)01081-8

  日期：2003.3

  A series of chrysin derivatives, prepared by alkylation, halogenation, nitration, methylation, acetylation and trifluoromethylation, were tested in vitro against human gastric adenocarcinoma cell line (SGC-7901) and colorectal adenocarcinoma (HT-29) cells. Among these derivatives of chrysin, 5,7-dimethoxy-8-iodochrysin 3 and 8-bromo-5-hydroxy-7-methoxychrysin 11 have the strongest activities against SGC-7901 and HT-29 cells, respectively. 5,7-Dihydroxy-8-nitrochrysin 12 were found to have strong activities against both SGC-7901 and HT-29 cells. (C) 2003 Elsevier Science Ltd. All rights reserved.