5-hydroxy-7-isopropoxy-2-phenyl-4H-chromen-4-one

• 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: 5-hydroxy-7-isopropoxy-2-phenyl-4H-chromen-4-one
• 英文别名: 5-hydroxy-7-isopropoxyflavone；5-hydroxy-2-phenyl-7-(propan-2-yloxy)-4H-chromen-4-one；5-hydroxy-2-phenyl-7-propan-2-yloxychromen-4-one
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: NLWLYTJIXINFTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxy-7-isopropoxy-2-phenyl-4H-chromen-4-one 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到6-bromo-5-hydroxy-7-isopropoxy-2-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  类黄酮烷基醚的区域选择性单溴化和脱保护方案合成6或8溴类黄酮

  摘要：

  C-6和C-8单溴类黄酮是合成类黄酮天然产物及其衍生物的重要组成部分。用N-溴琥珀酰亚胺在二氯甲烷（DCM）中溴化适当烷基化的类黄酮，然后用BCl 3脱保护，从而以高收率和高区域选择性获得C-6或C-8单溴类黄酮，具体取决于该化合物的保护方式C-5和C-7 OH基团。温和和中性条件对于酸不稳定底物的区域选择性溴化特别有用。

  DOI：

  10.1002/bkcs.10286
• 作为产物：
  描述：

  2-碘代丙烷 、 白杨素 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以88%的产率得到5-hydroxy-7-isopropoxy-2-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  类黄酮烷基醚的区域选择性单溴化和脱保护方案合成6或8溴类黄酮

  摘要：

  C-6和C-8单溴类黄酮是合成类黄酮天然产物及其衍生物的重要组成部分。用N-溴琥珀酰亚胺在二氯甲烷（DCM）中溴化适当烷基化的类黄酮，然后用BCl 3脱保护，从而以高收率和高区域选择性获得C-6或C-8单溴类黄酮，具体取决于该化合物的保护方式C-5和C-7 OH基团。温和和中性条件对于酸不稳定底物的区域选择性溴化特别有用。

  DOI：

  10.1002/bkcs.10286

文献信息

• 6,8-Dibromo- and 6,8-Diiodo-5,7-dihydroxyflavones as New Potent Antibacterial Agents
  作者：Krongkan Kingkaew、Ritbey Ruga、Warinthorn Chavasiri

  DOI：10.1246/cl.171089

  日期：2018.3.5

  highest activity against all bacteria with MIC 31.25–62.5 µM. For Propionibacterium acnes and Staphylococcus aureus, these compounds were bacteriostatic agents, while for Streptococcus sobrinus, S. mutans, and Salmonella typhi, they were bactericidal agents. The combination of 11 and 12 with known antibiotics displayed synergistic effect. The combination of 11 with streptomycin (16) revealed the most synergistic

  检查了包括白杨素、三种天然化合物和九种合成化合物在内的 13 种黄酮的抗菌活性。6,8-二溴- (11) 和 6,8-二碘-5,7-二羟基黄酮 (12) 对所有细菌的活性最高，MIC 为 31.25–62.5 µM。对于痤疮丙酸杆菌和金黄色葡萄球菌，这些化合物是抑菌剂，而对于远缘链球菌、变形链球菌和伤寒沙门氏菌，它们是杀菌剂。11和12与已知抗生素的组合显示出协同作用。11 与链霉素 (16) 的组合显示出与增加链霉素组合的抗菌活性的速率最大的协同效应是对痤疮丙酸杆菌、S. sobrinus 和 S. mutans 的 16 倍。
• [EN] FLAVANOID COMPOUNDS AND PROCESS FOR PREPARATION THEREOF<br/>[FR] COMPOSÉS FLAVANOÏDES ET LEUR PROCÉDÉ DE PRÉPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2010097816A1

  公开（公告）日：2010-09-02

  The present invention relates to flavanoid compounds of general formula (X1) wherein: R1 is selected from a group consisting of morpholinyl, N-methyl piperizinyl, piperidinyl and N,N'-dimethylamino groups, and n ranges from 3 to 6, and process for preparation thereof. The present invention relates to the demonstration of anti Helicobacter pylori activity and gastric antisecretory activity of semisynthetically designed flavonoid compounds, to be used for the prevention and treatment of gastroduodenal disorders in general and peptic ulcer diseases in particular. The present invention also relates to a hetero-dimeric bi-functional molecule that can be used as monotherapy substituting/replacing/overcoming currently used triple/quadruple therapy, thereby implicating/ anticipating/envisaging its commercial applicability.

  本发明涉及一般式为（X1）的黄酮类化合物，其中：R1从包括吗啡啶基、N-甲基哌嗪基、哌啶基和N,N'-二甲基氨基等基团中选择，n的范围为3至6，并涉及其制备方法。本发明涉及半合成设计的黄酮类化合物展示抗幽门螺杆菌活性和胃分泌抑制活性，可用于预防和治疗胃十二指肠疾病，特别是消化性溃疡。本发明还涉及一种异源二聚体双功能分子，可用作单疗法替代/取代/克服目前使用的三联/四联疗法，从而暗示/预期/设想其商业适用性。
• <i>C</i>-Isoprenylation of Flavonoids Enhances Binding Affinity toward P-Glycoprotein and Modulation of Cancer Cell Chemoresistance
  作者：Gilles Comte、Jean-Baptiste Daskiewicz、Christine Bayet、Gwenaëlle Conseil、Armelle Viornery-Vanier、Charles Dumontet、Attilio Di Pietro、Denis Barron

  DOI：10.1021/jm991128y

  日期：2001.3.1

  Previous studies have shown that flavones bind to P-glycoprotein (Pgp) with higher affinity than isoflavones, flavanones, and glycosylated derivatives. In the present work, a series of C- or O-substituted hydrophobic derivatives of chrysin were synthesized to further investigate structural requirements of the A ring toward Pgp modulation. Increasing hydrophobicity at either position 6, 8, or 7 increased the affinity of in vitro binding to a purified cytosolic domain of Pgp, but only benzyl and 3,3-dimethylallyl C-substitution produced a high maximal quenching of the protein intrinsic fluorescence. Inhibition of membrane Pgp within leukemic cells, characterized by intracellular drug accumulation, was specifically produced by isoprenylated derivatives, with 8-(3,3-dimethylallyl)chrysin being even more efficient than the commonly used cyclosporin A.
• Synthesis of 6- or 8-Bromo Flavonoids by Regioselective Mono-Bromination and Deprotection Protocol from Flavonoid Alkyl Ethers
  作者：Guojun Pan、Ke Yang、Yantao Ma、Xia Zhao、Kui Lu、Peng Yu

  DOI：10.1002/bkcs.10286

  日期：2015.5

  C‐6 and C‐8 monobromo flavonoids are important building blocks for the synthesis of flavonoid natural products and their derivatives. Bromination of suitably alkylated flavonoids with N‐bromosuccinimide in dichloromethane (DCM), followed by deprotection with BCl3 , gives either a C‐6 or a C‐8 monobromo flavonoid in high yield and with high regioselectivity, depending on the protection pattern of the

  C-6和C-8单溴类黄酮是合成类黄酮天然产物及其衍生物的重要组成部分。用N-溴琥珀酰亚胺在二氯甲烷（DCM）中溴化适当烷基化的类黄酮，然后用BCl 3脱保护，从而以高收率和高区域选择性获得C-6或C-8单溴类黄酮，具体取决于该化合物的保护方式C-5和C-7 OH基团。温和和中性条件对于酸不稳定底物的区域选择性溴化特别有用。