6-bromomethylflavone | 50400-51-6

• 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-bromomethylflavone
• 英文别名: 6-(Bromomethyl)-2-phenyl-4H-1-benzopyran-4-one；6-(bromomethyl)-2-phenylchromen-4-one
• CAS: 50400-51-6
• 化学式: C₁₆H₁₁BrO₂
• 分子量: 315.166
• InChiKey: DYVROXPBQHJZIN-UHFFFAOYSA-N

物化性质

• 熔点：
  128 °C
• 沸点：
  449.0±45.0 °C(Predicted)
• 密度：
  1.509±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-bromomethylflavone 在 乌洛托品 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 生成 5-[(2'-phenyl-4'H-4'-oxo-1'-benzopyran-6'-yl)methylenyl]-2,4-thiazolidinedione
  参考文献：
  名称：

  Bozdag-Duendar; Waheed; Verspohl, Arzneimittel-Forschung/Drug Research, 2001, vol. 51, # 8, p. 623 - 627

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酸对甲酚酯 在 aluminum (III) chloride 、 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 、 potassium carbonate 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 38.0h， 生成 6-bromomethylflavone
  参考文献：
  名称：

  黄酮类化合物作为有效抗癌药的替代作用研究：结构-活性关系研究

  摘要：

  设计并合成了三个系列的类黄酮类似物，这些类黄酮类似物在C-6，C-7和C-8处被不同的氨甲基取代，作为有效的抗癌药进行结构-活性关系研究。评价了制备的类似物对肝癌细胞HepG2和SMMC-7721生长的体外抑制活性。结构-活性关系表明，不仅具有氨基甲基的化合物比没有相同系列基团的化合物更具活性，而且在C-8位被氨基甲基取代的化合物比在C-6和C-6位的化合物更具活性。 C-7。

  DOI：

  10.1007/s00044-011-9701-6

文献信息

• Rapid synthesis of flavone-based monoamine oxidase (MAO) inhibitors targeting two active sites using click chemistry
  作者：Wei Zhen Jia、Feng Cheng、Yin Jun Zhang、Jin Yan Ge、Shao Q. Yao、Qing Zhu

  DOI：10.1111/cbdd.12841

  日期：2017.1

  flavone MAO inhibitor studied is Az2k19 (1.6 mum for MAO-A, 2.1 mum for MAO-B), while Az1k15 and Az2k15 displayed better selectivity toward MAO-B (SI > 10). Docking studies are in accordance with our hypothesis that these inhibitors are most likely located at both the substrate cavity and the "aromatic cage". Our results show that it is considerable to develop new MAO inhibitors from C6 substitution of flavone

  设计并使用6-N3 -2-苯基苯甲酮（Az1-Az2）和一系列N-苯并二甲基苯并色酮之间的点击化学反应（CuAAC反应）合成了针对单胺氧化酶两个活性位点（“芳香族笼”和底物腔）的黄酮衍生物新库。炔烃（k1-k20）。评价了它们对MAO同工型（MAO-A和MAO-B）的抑制活性。具有氟，酰胺键或氨基键的化合物显示出更好的抑制作用。研究的最有效的黄酮类MAO抑制剂是Az2k19（MAO-A为1.6 mM，MAO-B为2.1 mm），而Az1k15和Az2k15对MAO-B表现出更好的选择性（SI> 10）。对接研究符合我们的假设，即这些抑制剂最有可能位于基质腔和“芳香笼”中。
• Synthesis and calcium antagonistic activity of a series of diethyl benzofuryl, benzothienyl and benzogammapyronyl benzylphosphonates
  作者：G Baziard-Mouysset、GW Tchani、JL Stigliani、M Payard、R Bonnafous、J Tisne-Versailles

  DOI：10.1016/0223-5234(93)90084-r

  日期：1993.1

  In this work we present about 15 original heterocyclic diethyl benzylphosphonate analogues of fostedil, in which we have varied the nature of the heterocycle, the substituents or the phosphonic group, or even the position of this latter. Three diethyl 4-(2-benzofuryl) benzyl phosphonates exhibited slightly higher calcium antagonism than the control. Solely substitution with a fluorine atom was able to maintain activity, whereas the other modifications always decreased it.
• Synthesis and biological activity of some new flavonyl-2,4-thiazolidinediones
  作者：Oya Bozdağ-Dündar、Eugen J. Verspohl、Net Daş-Evcimen、Rebecca M. Kaup、Katrin Bauer、Mutlu Sarıkaya、Begüm Evranos、Rahmiye Ertan

  DOI：10.1016/j.bmc.2008.05.059

  日期：2008.7

  A new series of flavonyl-2,4-thiazolidinediones (Va-c, VIa-c) was prepared by Knoevenagel reaction. The synthesized compounds were tested for their ability to inhibit rat kidney aldose reductase (AR) and for their insulinotropic activities in INS-1 cells. Compound Vb was able to increase insulin release in the presence of 5.6 mmol/l glucose. Compounds VIa-c displayed moderate to high AR inhibitory activity levels. Particularly, compound VIa showed the highest AR inhibitory activity (86.57%). (c) 2008 Elsevier Ltd. All rights reserved.
• Intervention in cyclophosphamide induced oxidative stress and DNA damage by a flavonyl-thiazolidinedione based organoselenocyanate and evaluation of its efficacy during adjuvant therapy in tumor bearing mice
  作者：Somnath Singha Roy、Pramita Chakraborty、Sudin Bhattacharya

  DOI：10.1016/j.ejmech.2013.12.015

  日期：2014.2

  A novel flavonyl-thiazolidinedione based organoselenocyanate compound was synthesized and established as nontoxic at the doses of 2.5 and 5 mg/kg b.w. in mice. Oral administration of the compound in combination with cyclophosphamide (CP) resulted in an improved therapeutic efficacy which was mostly evidenced in terms of tumor burden and protection of normal cells. The adjuvant therapy was proved to be immensely significant in increasing the mean survivability of the tumor bearing hosts. Reduction in the tumor volume was manifested through the induction of apoptosis and generation of ROS in transformed cells. Moreover, the organoselenium compound could efficiently suppress CP-induced DNA damage, chromosomal aberration, hepatic damage and enhanced the activities of various antioxidant enzymes in normal cells. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Tuncbilek; Ayhan-Kilcigil; Ertan, Pharmazie, 2000, vol. 55, # 5, p. 359 - 361
  作者：Tuncbilek、Ayhan-Kilcigil、Ertan、Can-Eke、Iscan

  DOI：——

  日期：——