A novel synthetic route to cytotoxic 1,4-anthraquinones from 1,4-benzoquinones

被引：12

作者：

Castro, MA ^{[1
]}

del Corral, JMM

Gordaliza, M

García, PA

Gamito, AM

Gualberto, SA

Batista, R

San Feliciano, A

机构：

[1] Univ Salamanca, Fac Farm, Dept Quim Farmaceut, E-37007 Salamanca, Spain

[2] Univ Fed Minas Gerais, Fac Farm, Dept Prod Farmaceut, BR-112 Belo Horizonte, MG, Brazil

来源：

SYNTHESIS-STUTTGART | 2005年 / 19期

关键词：

1,4-naphthoquinones; anthracene-1,4-diones; 1,4-anthraquinones; Diels-Alder addition; cytotoxicity;

D O I：

10.1055/s-2005-918437

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new procedure to obtain anthi-acene-1,4-diones from p-benzoquinones and myrcene, in the presence of acids, is described. The cycloaddition reaction between alpha-myrcene and p-benzoquinones, followed by oxidation, led to 1,4-naphthoquinones or 1,4-anthraquinones depending upon whether the Lewis acid used in the Diels-Alder reaction, was present or absent during oxidation; furthermore, traces of acid in the solvents played an important role in determining the cycloadduct obtained. The quinones synthesized exhibited cytotoxicity towards several tumor cell lines.

引用

页码：3202 / 3208

页数：7

共 29 条

[1] Regioselectivity in the Diels-Alder reaction of 8,8-dimethylnaphthalene-1,4,5(8H)-trione with 2,4-hexadien-1-ol [J].

Araya-Maturana, R ;

Cassels, BK ;

Delgado-Castro, T ;

Valderrama, JA ;

Weiss-López, BE .

TETRAHEDRON, 1999, 55 (03) :637-648

[2] SYNTHESES, ELECTROCHEMISTRY AND MOLECULAR MODELING OF N,N'-DICYANOQUINONEDIIMINE (DCNQI) DERIVATIVES OF SUBSTITUTED 1,4-ANTHRACENEDIONES - PRECURSORS FOR ORGANIC METALS [J].

BARRANCO, E ;

MARTIN, N ;

SEGURA, JL ;

SEOANE, C ;

DELACRUZ, P ;

LANGA, F ;

GONZALEZ, A ;

PINGARRON, JM .

TETRAHEDRON, 1993, 49 (22) :4881-4892

[3] Synthesis of 2,3-dioxy-1,4-anthraquinones related to tetracenomycins C and X [J].

Cameron, DW ;

Griffiths, PG ;

Riches, AG .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1999, 52 (12) :1173-1177

[4] Further antineoplastic terpenylquinones and terpenylhydroquinones [J].

del Corral, JM ;

Gordaliza, M ;

Castro, A ;

Mahiques, MM ;

San Feliciano, A ;

Garcia-Gravalos, MD .

BIOORGANIC & MEDICINAL CHEMISTRY, 1998, 6 (01) :31-41

[5]

del Corral JMM, 2002, ARCH PHARM, V335, P427, DOI 10.1002/1521-4184(200212)335:9<427::AID-ARDP427>3.0.CO

[6]

2-M

[7] New selective cytotoxic diterpenylquinones and diterpenylhydroquinones [J].

del Corral, JMM ;

Gordaliza, M ;

Castro, MA ;

Mahiques, MM ;

Chamorro, P ;

Molinari, A ;

García-Grávalos, MD ;

Broughton, HB ;

San Feliciano, A .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (08) :1257-1267

[8] POLYCYCLIC HYDROXYQUINONES .28. SYNTHESIS AND DIELS-ALDER REACTIONS OF N,N,O-TRIACYL DERIVATIVES OF 10-AMINO-9-HYDROXY-1,4-ANTHRAQUINONES - AN EFFICIENT, REGIOSPECIFIC SYNTHESIS OF (+/-)-5-IMINODAUNOMYCINONE, (+/-)-4-DEMETHOXY-5-IMINODAUNOMYCINONE, AND (+/-)-DAUNOMYCINONE [J].

FARINA, F ;

NOHEDA, P ;

PAREDES, MC .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7406-7415

[9]

Foye W.O., 1995, Cancer Chemotherapeutic Agents

[10] NEW APPROACHES TO ANTHRACYCLINONES - THE [BCD-]ABCD] CYCLOADDITION STRATEGY [J].

LAUGRAUD, S ;

GUINGANT, A ;

DANGELO, J .

TETRAHEDRON LETTERS, 1992, 33 (10) :1289-1290

← 1 2 3 →