2-(3-methoxyphenyl)-4H-benzo[h]chromen-4-one | 71601-13-3

• 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: 2-(3-methoxyphenyl)-4H-benzo[h]chromen-4-one
• 英文别名: 2-(3-Methoxyphenyl)benzo[h]chromen-4-one
• CAS: 71601-13-3
• 化学式: C₂₀H₁₄O₃
• 分子量: 302.329
• InChiKey: PGRWDFOTLBQRCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-methoxyphenyl)-4H-benzo[h]chromen-4-one 在 氢溴酸 、 sodium hydride 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 O-(3-(4-oxo-4H-benzo[h]chromen-2-yl)phenyl)dimethylcarbamothioate
  参考文献：
  名称：

  Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone

  摘要：

  Selective cytochrome P450 (CYP) 1B1 inhibition has potential as an anticancer strategy that is unrepresented in the current clinical arena. For development of a selective inhibitor, we focused on the complexity caused by sp(3)-hybridized carbons and synthesized a series of benzo[h] chromone derivatives linked to a non-aromatic B-ring using alpha-naphthoflavone (ANF) as the lead compound. Ring structure comparison suggested compound 37 as a suitable cyclohexyl-core with improved solubility. Structural evolution of 37 produced the azide-containing cis-49a, which had good properties in three important respects: (1) selectivity for CYP1B1 over CYP1A1 and CYP1A2 (120-times and 150-times, respectively), (2) greater inhibitory potency of > 2 times that of ANF, and (3) improved solubility. The corresponding aromatic B-ring compound 59a showed low selectivity and poor solubility. To elucidate the binding mode, we performed X-ray crystal structure analysis, which revealed the interaction mode and explained the subtype selectivity of cis-49a.

  DOI：

  10.1016/j.bmc.2018.11.045
• 作为产物：
  描述：

  2-乙酰基-1-萘酚 在 4-二甲氨基吡啶 、 硫酸 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-(3-methoxyphenyl)-4H-benzo[h]chromen-4-one
  参考文献：
  名称：

  α-萘黄酮衍生物作为CYP1B1抑制剂的合成及构效关系研究。

  摘要：

  细胞色素P450 1B1（CYP1B1）被公认为是预防癌症和逆转耐药性的重要靶标。为了获得有效和选择性的CYP1B1抑制剂，合成了一系列41种α-萘黄酮（ANF）衍生物，进行了表征，并评估了其对CYP1B1，CYP1A1和CYP1A2的抑制活性。封闭结构对CYP1B1抑制作用的活性关系研究表明，修饰ANF的C环会降低CYP1B1的抑制能力，而在B环的不同位置引入取代基会产生类似的变化CYP1B1的抑制能力。在这些衍生物中，化合物9e和9j被确定为最有效的两种选择性CYP1B1抑制剂，IC50值分别为0.49和0.52 nM，其效力比先导化合物ANF强10倍。此外，进行了分子对接和合理的3D-QSAR（三维定量结构-活性关系）研究，以更好地理解影响CYP1B1抑制活性的关键结构特征。这项研究中获得的结果将为将来开发选择性，有效，低毒和水溶性CYP1B1抑制剂奠定基础。

  DOI：

  10.1016/j.ejmech.2019.111938

文献信息

• Synthesis of methoxybenzoflavones and assignments of their NMR data
  作者：Doseok Hwang、Geunhyeong Jo、Jiye Hyun、Sung Dae Lee、Dongsoo Koh、Yoongho Lim

  DOI：10.1002/mrc.3790

  日期：2012.1

  also is a potent phytotoxin. Six 7,8‐benzoflavones and eight 5,6‐benzoflavones were synthesized in this study. The NMR data for a few of these compounds have been previously reported; however, the NMR data for most of them have not been reported. For reference purposes, the complete NMR data for the 14 benzoflavones are described. Copyright © 2012 John Wiley & Sons, Ltd.

  来自 Acroptilon repens 的植物毒性根系分泌物被鉴定为 7,8-苯黄酮，一种细胞色素 P450 1A2 抑制剂和细胞色素 P450 3A4 激活剂。合成的 5,6-苯并黄酮也是一种有效的植物毒素。本研究合成了 6 种 7,8-苯并黄酮和 8 种 5,6-苯并黄酮。其中一些化合物的 NMR 数据以前已经报道过；然而，其中大部分的核磁共振数据尚未报道。出于参考目的，描述了 14 种苯黄酮的完整 NMR 数据。版权所有 © 2012 John Wiley & Sons, Ltd.
• Fungal metabolism of naphthoflavones
  作者：Jarosław Popłoński、Sandra Sordon、Tomasz Tronina、Agnieszka Bartmańska、Ewa Huszcza

  DOI：10.1016/j.molcatb.2015.04.007

  日期：2015.7

  Naphthoflavones (benzoflavones) are synthetic flavonoids commonly used in drug metabolism studies as selective activators or inhibitors of cytochrome P-450 enzymes. Nowadays they are also used as a component of food supplements for body builders. There is no data regarding naphthoflavone microbial metabolism. In the present studies sixty-three fungal strains have been screened for their ability to transform alpha-naphthoflavone (7,8-benzoflavone) or beta-naphthoflavone (5,6-benzoflavone). Five strains belonging to the genera Penicillium, Cladosporium, Aspergillus and Verticillium transformed alpha-naphthoflavone and beta-naphthoflavone to the corresponding 4'-hydroxy derivatives. These selected fungi have been used in a further study on biotransformation of naphthoflavones with a differently substituted B-ring. Only 4'-methoxy derivatives have been transformed to the related 4'-hydroxy products. Selected strains are good biocatalysts to obtain 4'-hydroxy naphthoflavones in the one step reaction. (C) 2015 Elsevier B.V. All rights reserved.
• Torricelli, Jahrbuch der Philosophischen Fakultaet 2 [Zweite] der Universitaet Bern, 1922, vol. 2, p. 102
  作者：Torricelli

  DOI：——

  日期：——