Synthesis of new 6-and 8-Alkenyl-3,7,3′,4′-Tetramethoxyquercetin derivatives by microwave-assisted Heck coupling

被引：3

作者：

Ramos, Ingrid T. L. ^{[1
]}

Silva, Tania M. S. ^{[1
]}

Camara, Celso A. ^{[1
]}

机构：

[1] Univ Fed Rural Pernambuco, Dept Quim, Recife, PE, Brazil

来源：

SYNTHETIC COMMUNICATIONS | 2019年 / 49卷 / 19期

关键词：

Coupling reactions; flavonoids; Heck reaction; microwave; palladium catalytic; quercetin; BIOLOGICAL-ACTIVITIES; FLAVONOIDS; QUERCETIN;

D O I：

10.1080/00397911.2019.1636398

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of flavonoid derivatives were synthesized from 6- and 8-iodo-3,7,3'4'-tetramethoxy-quercetin with terminal alkenes by microwave-assisted palladium-catalyzed Heck coupling. These alkenes include n-butyl acrylate, 2-methyl-3-buten-2-ol, acrylonitrile, and styrene, providing 10 new substituted flavonoid compounds obtained with moderate to good yields. [GRAPHICS] .

引用

页码：2583 / 2589

页数：7

共 21 条

[1] In vitro antileishmanial activity of fisetin flavonoid via inhibition of glutathione biosynthesis and arginase activity in Leishmania infantum [J].

Adinehbeigi, Keivan ;

Jalali, Mohammad Hossein Razi ;

Shahriari, Ali ;

Bahrami, Somayeh .

PATHOGENS AND GLOBAL HEALTH, 2017, 111 (04) :176-185

[2] The antioxidant activity of a prenyl flavonoid alters its antifungal toxicity on Candida albicans biofilms [J].

Andrea Peralta, Mariana ;

Gabriela Orteg, Maria ;

Luis Cabrera, Jose ;

Gabriela Paraje, Maria .

FOOD AND CHEMICAL TOXICOLOGY, 2018, 114 :285-291

[3]

Biajoli AFP, 2014, J BRAZIL CHEM SOC, V25, P2186

[4] Total synthesis of anthocyanidins via Heck reaction [J].

Bianco, A ;

Cavarischia, C ;

Guiso, M .

NATURAL PRODUCT RESEARCH, 2006, 20 (01) :93-97

[5] A systematic review on biological activities of prenylated flavonoids [J].

Chen, Xi ;

Mukwaya, Emmanuel ;

Wong, Man-Sau ;

Zhang, Yan .

PHARMACEUTICAL BIOLOGY, 2014, 52 (05) :655-660

[6] Synthesis of 2,3,6,8-tetrasubstituted chromone scaffolds [J].

Dahlen, Kristian ;

Wallen, Erik A. A. ;

Grotli, Morten ;

Luthman, Kristina .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (18) :6863-6871

[7] Microwave-Assisted Heck Arylations of Non-Activated N-Acyl-3-pyrrolines with Arenediazonium Tetrafluoroborates [J].

Finelli, Fernanda G. ;

Godoi, Marla N. ;

Correia, Carlos R. D. .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2015, 26 (05) :910-915

[8] Antioxidant activity, total phenolics and flavonoids contents: Should we ban in vitro screening methods? [J].

Granato, Daniel ;

Shahidi, Fereidoon ;

Wrolstad, Ronald ;

Kilmartin, Paul ;

Melton, Laurence D. ;

Hidalgo, Francisco J. ;

Miyashita, Kazuo ;

van Camp, John ;

Alasalvar, Cesarettin ;

Ismail, Amin B. ;

Elmore, Stephen ;

Birch, Gordon G. ;

Charalampopoulos, Dimitris ;

Astley, Sian B. ;

Pegg, Ronald ;

Zhou, Peng ;

Finglas, Paul .

FOOD CHEMISTRY, 2018, 264 :471-475

[9]

Hoarau C, 2003, SYNLETT, P127

[10] Synthesis of 8-aryl-3,5,7,3′,4′-penta-O-methylcyanidins from the corresponding quercetin derivatives by reduction with LiAlH4 [J].

Kimura, Yuki ;

Oyama, Kin-Ichi ;

Kondo, Tadao ;

Yoshida, Kumi .

TETRAHEDRON LETTERS, 2017, 58 (10) :919-922

← 1 2 3 →