Laccase-catalyzed green synthesis and cytotoxic activity of novel pyrimidobenzothiazoles and catechol thioethers

被引：42

作者：

Abdel-Mohsen, H. T. ^{[1
]}

Conrad, J. ^{[2
]}

Harms, K. ^{[3
]}

Nohr, D. ^{[4
]}

Beifuss, U. ^{[2
]}

机构：

[1] Natl Res Ctr, Pharmaceut Ind Res Div, Chem Nat & Microbial Prod Dept, Cairo, Egypt

[2] Univ Hohenheim, Inst Chem, Bioorgan Chem, Garbenstr 30, D-70599 Stuttgart, Germany

[3] Univ Marburg, Fachbereich Chem, Hans Meerwein Str 4, D-35032 Marburg, Germany

[4] Univ Hohenheim, Inst Biol Chem & Ernahrungswissensch, Garbenstr 30, D-70599 Stuttgart, Germany

来源：

RSC ADVANCES | 2017年 / 7卷 / 28期

关键词：

ONE-POT SYNTHESIS; DOMINO REACTIONS; OXIDATIVE DIMERIZATION; MEDIATED OXIDATION; P-HYDROQUINONES; ENZYME LACCASE; BOND FORMATION; CHEMISTRY; AIR; O-2;

D O I：

10.1039/c6ra28102h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The laccase-catalyzed reaction between unsubstituted catechol and 2-thioxopyrimidin-4(1H)-ones using aerial O-2 as the oxidant delivers novel pyrimidobenzothiazoles with high yields in an aqueous solvent system under mild reaction conditions. With 4-substituted catechols, catechol thioethers are formed exclusively. The synthetic protocols developed provide a sustainable approach for these compound classes. In addition, the cytotoxicity of the products against HepG2 cell line is reported. Most compounds exhibit antiproliferative activities with IC50 values at the micromolar level. A structureactivity relationship study will facilitate the further development of these compounds as cytotoxic agents.

引用

页码：17427 / 17441

页数：15

共 88 条

[11]

[Anonymous], CLIN NURSING SERIES

[12] Green Chemistry Articles of Interest to the Pharmaceutical Industry [J].

Bandichhor, Rakeshwar ;

Bhattacharya, Apurba ;

Bryan, Marian C. ;

Cosbie, Andrew ;

Diaz-Rodriguez, Alba ;

Diorazio, Louis ;

Fei, Zhongbo ;

Fraunhoffer, Kenneth ;

Hayler, John ;

Hickey, Matthew ;

Humphreys, Luke ;

Richardson, Paul ;

Roberts, Scott ;

White, Timothy ;

Wuyts, Stijn ;

Yin, Jingjun .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2016, 20 (07) :1118-1132

[13] Synthesis of 2,3-Dihydro-6-methyl-2-thiopyrimidin-4(1H)-one (6-Methylthiouracil) Derivatives and Their Reactions [J].

Barmaki, Mohammad ;

Valiyeva, Gulgaz ;

Maharramovm, Abel A. ;

Allaverdiyev, Mirze M. .

JOURNAL OF CHEMISTRY, 2013, 2013

[14] Laccase-catalyzed synthesis of 2,3-ethylenedithio-1,4-quinones [J].

Cannatelli, Mark D. ;

Ragauskas, Arthur J. .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2015, 119 :85-89

[15] What is a green solvent?: A comprehensive framework for the environmental assessment of solvents [J].

Capello, Christian ;

Fischer, Ulrich ;

Hungerbuehler, Konrad .

GREEN CHEMISTRY, 2007, 9 (09) :927-934

[16] Laccase-catalyzed carbon-carbon bond formation: oxidative dimerization of salicylic esters by air in aqueous solution [J].

Ciecholewski, S ;

Hammer, E ;

Manda, K ;

Bose, G ;

Nguyen, VTH ;

Langer, P ;

Schauer, F .

TETRAHEDRON, 2005, 61 (19) :4615-4619

[17] Laccases: structure, reactions, distribution [J].

Claus, H .

MICRON, 2004, 35 (1-2) :93-96

[18] Oxidation of amides by laccase-generated aminoxyl radicals [J].

Coniglio, Alessandra ;

Galli, Carlo ;

Gentili, Patrizia ;

Vadala, Raffaella .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2008, 50 (01) :40-49

[19] Key green chemistry research areas - a perspective from pharmaceutical manufacturers [J].

Constable, David J. C. ;

Dunn, Peter J. ;

Hayler, John D. ;

Humphrey, Guy R. ;

Leazer, Johnnie L., Jr. ;

Linderman, Russell J. ;

Lorenz, Kurt ;

Manley, Julie ;

Pearlman, Bruce A. ;

Wells, Andrew ;

Zaks, Aleksey ;

Zhang, Tony Y. .

GREEN CHEMISTRY, 2007, 9 (05) :411-420

[20] Laccase-catalyzed oxidative phenolic coupling of vanillidene derivatives [J].

Constantin, Mihaela-Anca ;

Conrad, Juergen ;

Beifuss, Uwe .

GREEN CHEMISTRY, 2012, 14 (09) :2375-2379

← 1 2 3 4 5 6 7 8 9 →