一种合成6-氨基-7-羟基黄酮的新方法。
A novel approach to the synthesis of 6-amino-7-hydroxy-flavone.
作者信息
Tang Lijun, Zhang Shufen, Yang Jinzong, Gao Wentao, Cui Jian, Zhuang Tianyu
机构信息
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116012, PR China.
出版信息
Molecules. 2004 Sep 30;9(10):842-8. doi: 10.3390/91000842.
Abstract
A novel approach to the synthesis of 6-amino-7-hydroxyflavone (1) is described. Reaction in acetone of 2',4'-dihydroxy-5'-nitroacetophenone and benzoyl chloride in the presence of potassium carbonate affords 3-benzoyl-7-hydroxy-6-nitroflavone, which is cleaved in 5% ethanolic potassium hydroxide to give 1-(2,4-dihydroxy-5-nitrophenyl)-3- phenyl-1,3-propanedione. The 1,3-diketone thus formed is then transformed into 7-hydroxy- 6-nitroflavone, followed by reduction to afford the title compound.
摘要
描述了一种合成6-氨基-7-羟基黄酮（1）的新方法。在碳酸钾存在下，2',4'-二羟基-5'-硝基苯乙酮与苯甲酰氯在丙酮中反应得到3-苯甲酰基-7-羟基-6-硝基黄酮，该化合物在5%乙醇氢氧化钾中裂解得到1-(2,4-二羟基-5-硝基苯基)-3-苯基-1,3-丙二酮。由此形成的1,3-二酮随后转化为7-羟基-6-硝基黄酮，接着还原得到标题化合物。
相似文献
1
A novel approach to the synthesis of 6-amino-7-hydroxy-flavone.一种合成6-氨基-7-羟基黄酮的新方法。
Molecules. 2004 Sep 30;9(10):842-8. doi: 10.3390/91000842.
2
Palladium-catalyzed carbonylation reaction of aryl bromides with 2-hydroxyacetophenones to form flavones.钯催化的芳基溴与 2-羟基苯乙酮的羰基化反应生成黄酮。
Chemistry. 2012 Oct 1;18(40):12595-8. doi: 10.1002/chem.201202141. Epub 2012 Aug 24.
3
Synthesis of antiproliferative flavones from calycopterin, major flavonoid of Calycopteris floribunda Lamk.从 Calycopteris floribunda Lamk. 的主要类黄酮贝壳杉双黄酮合成抗增殖类黄酮
Bioorg Med Chem. 2011 Jan 1;19(1):186-96. doi: 10.1016/j.bmc.2010.11.035. Epub 2010 Nov 20.
4
[Synthesis of chrysin derivatives and their interaction with DNA].白杨素衍生物的合成及其与DNA的相互作用
Yao Xue Xue Bao. 2007 May;42(5):492-6.
5
Nobiletin metabolites: synthesis and inhibitory activity against matrix metalloproteinase-9 production.川陈皮素代谢物的合成及其对基质金属蛋白酶-9 产生的抑制活性。
Bioorg Med Chem Lett. 2011 Aug 1;21(15):4540-4. doi: 10.1016/j.bmcl.2011.05.121. Epub 2011 Jun 12.
6
[Synthesis and antioxidative activity of flavone derivatives containing 1,2,4-triazole structure].含1,2,4-三唑结构黄酮衍生物的合成及其抗氧化活性
Yao Xue Xue Bao. 2015 Jul;50(7):861-7.
7
Concise synthesis of chafurosides A and B.查夫罗苷A和B的简洁合成
Org Lett. 2009 Jun 4;11(11):2233-6. doi: 10.1021/ol900689m.
8
An effective synthesis of 5,4'-disubstituted flavones via a cesium enolate assisted intramolecular ipso-substitution reaction.通过铯烯醇盐辅助的分子内本位取代反应高效合成5,4'-二取代黄酮。
Chem Pharm Bull (Tokyo). 2010 Aug;58(8):1107-10. doi: 10.1248/cpb.58.1107.
9
Regio- and stereospecific synthesis of novel 3-enynyl-substituted thioflavones/flavones using a copper-free palladium-catalyzed reaction.使用无铜钯催化反应实现新型3-烯炔基取代硫代黄酮/黄酮的区域和立体特异性合成。
J Org Chem. 2005 Sep 2;70(18):7179-87. doi: 10.1021/jo050828+.
10
Steroid Sulfatase Inhibitors Based on Phosphate and Thiophosphate Flavone Analogs.
Drug Dev Res. 2015 Dec;76(8):450-62. doi: 10.1002/ddr.21281. Epub 2015 Sep 28.
引用本文的文献
1
Therapeutic Perspectives of Aminoflavonoids-A Review.氨基黄酮类化合物的治疗前景——综述
Int J Mol Sci. 2025 Feb 25;26(5):2014. doi: 10.3390/ijms26052014.
2
Diversity-Oriented Synthesis: Amino Acetophenones as Building Blocks for the Synthesis of Natural Product Analogs.多样性导向合成：以氨基苯乙酮作为天然产物类似物合成的构建模块
Pharmaceuticals (Basel). 2021 Nov 5;14(11):1127. doi: 10.3390/ph14111127.
本文引用的文献
1
Polyphenolic compounds: interactions with the gut and implications for human health.多酚类化合物：与肠道的相互作用及其对人类健康的影响。
Curr Med Chem. 2001 Sep;8(11):1245-55. doi: 10.2174/0929867013372256.
2
Flavonoid antioxidants.类黄酮抗氧化剂。
Curr Med Chem. 2001 Jun;8(7):797-807. doi: 10.2174/0929867013373011.
3
B-ring substituted 5,7-dihydroxyflavonols with high-affinity binding to P-glycoprotein responsible for cell multidrug resistance.
Bioorg Med Chem Lett. 2001 Jan 8;11(1):75-7. doi: 10.1016/s0960-894x(00)00595-3.
4
Flavonoids as antioxidants.类黄酮作为抗氧化剂。
J Nat Prod. 2000 Jul;63(7):1035-42. doi: 10.1021/np9904509.
5
1-Benzopyran-4-one antioxidants as aldose reductase inhibitors.作为醛糖还原酶抑制剂的1-苯并吡喃-4-酮类抗氧化剂。
J Med Chem. 1999 Jun 3;42(11):1881-93. doi: 10.1021/jm980441h.
6
Halogenated chalcones with high-affinity binding to P-glycoprotein: potential modulators of multidrug resistance.与P-糖蛋白具有高亲和力结合的卤代查耳酮：多药耐药性的潜在调节剂。
J Med Chem. 1998 Oct 8;41(21):4161-4. doi: 10.1021/jm9810194.
7
Structure-activity relationships of the 7-substituents of 5,4'-diamino-6,8,3'-trifluoroflavone, a potent antitumor agent.强效抗肿瘤药物5,4'-二氨基-6,8,3'-三氟黄酮7-取代基的构效关系
J Med Chem. 1998 Jun 4;41(12):2056-67. doi: 10.1021/jm970728z.
8
Design and synthesis of potent antitumor 5,4'-diaminoflavone derivatives based on metabolic considerations.
J Med Chem. 1997 Jun 6;40(12):1894-900. doi: 10.1021/jm9700326.
9
Anxioselective properties of 6,3'-dinitroflavone, a high-affinity benzodiazepine receptor ligand.6,3'-二硝基黄酮的抗焦虑选择性特性，一种高亲和力苯二氮䓬受体配体。
Eur J Pharmacol. 1996 Dec 27;318(1):23-30. doi: 10.1016/s0014-2999(96)00784-4.
10
Structure-antioxidant activity relationships of flavonoids and phenolic acids.黄酮类化合物和酚酸的结构-抗氧化活性关系
Free Radic Biol Med. 1996;20(7):933-56. doi: 10.1016/0891-5849(95)02227-9.
Zotero 插件