Heteroatom directed photoannulation: synthesis of indoloquinoline alkaloids: cryptolepine, cryptotackieine, cryptosanguinolentine, and their methyl derivatives

被引：89

作者：

Dhanabal, T. ^{[1
]}

Sangeetha, R. ^{[1
]}

Mohan, P. S. ^{[1
]}

机构：

[1] Bharathiar Univ, Dept Chem, Coimbatore 641046, Tamil Nadu, India

来源：

TETRAHEDRON | 2006年 / 62卷 / 26期

关键词：

indoloquinoline alkaloids; photoannulation; cryptolepine; cryptotackieine; cryptosanguinolentine;

D O I：

10.1016/j.tet.2006.04.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A three-step synthesis of indoloquinoline alkaloids is described. The reaction of 2,3 and 4-substituted haloquinolines with anilines afforded the respective anilinoquinolines, which upon photocyclization gave the indoloquinolines. By regioselective methylation on quinoline nitrogen, fumished the alkaloids cryptotackieine, cryptosanguinolentine, cryptolepine, and the synthetic isomer isoneocryptolepine. Their methyl derivatives were also synthesized in search of new antiplasmodial drugs and DNA intercalating agents. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：6258 / 6263

页数：6

共 59 条

[1] H-1-NMR AND C-13-NMR ASSIGNMENTS OF CRYPTOLEPINE, A 3 - 4-BENZ-DELTA-CARBOLINE DERIVATIVE ISOLATED FROM CRYPTOLEPIS-SANGUINOLENTA [J].

ABLORDEPPEY, SY ;

HUFFORD, CD ;

BORNE, RF ;

DWUMABADU, D .

PLANTA MEDICA, 1990, 56 (04) :416-417

[2] SOME 4-(DIALKYLAMINOALKYLAMINO)-3-PHENYLQUINOLINES [J].

ADAMS, WJ ;

HEY, DH .

JOURNAL OF THE CHEMICAL SOCIETY, 1950, (NOV) :3254-3259

[3] 2-ARYL-3-ACETYL-4(1H)-QUINOLONES [J].

ANDERSON, PC ;

STASKUN, B .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (09) :3033-&

[4]

[Anonymous], 1983, P 1 INT SEMINAR CRYP

[5]

BEVER BEP, 1986, MED PLANTS TROPICAL, V131, P18

[6] Ethnobotanical-directed discovery of the antihyperglycemic properties of cryptolepine:: Its isolation from Cryptolepis sanguinolenta, synthesis, and in vitro and in vivo activities [J].

Bierer, DE ;

Fort, DM ;

Mendez, CD ;

Luo, J ;

Imbach, PA ;

Dubenko, LG ;

Jolad, SD ;

Gerber, RE ;

Litvak, J ;

Lu, Q ;

Zhang, PS ;

Reed, MJ ;

Waldeck, N ;

Bruening, RC ;

Noamesi, BK ;

Hector, RF ;

Carlson, TJ ;

King, SR .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (06) :894-901

[7] Quindolinocryptotackieine: the elucidation of a novel indoloquinoline alkaloid structure through the use of computer-assisted structure elucidation and 2D NMR [J].

Blinov, K ;

Elyashberg, M ;

Martirosian, ER ;

Molodtsov, SG ;

Williams, AJ ;

Tackie, AN ;

Sharaf, MMH ;

Schiff, PL ;

Crouch, RC ;

Martin, GE ;

Hadden, CE ;

Guido, JE ;

Mills, KA .

MAGNETIC RESONANCE IN CHEMISTRY, 2003, 41 (08) :577-584

[8]

Boakye-Yiadom K., 2008, Q J CRUDE DRUG RES, V17, P78, DOI [DOI 10.3109/13880207909067453, 10.3109/13880207909067453]

[9] New alkaloids from Cryptolepis sanguinolenta [J].

Cimanga, K ;

DeBruyne, T ;

Pieters, L ;

Claeys, M ;

Vlietinck, A .

TETRAHEDRON LETTERS, 1996, 37 (10) :1703-1706

[10] In vitro and in vivo antiplasmodial activity of cryptolepine and related alkaloids from Cryptolepis sanguinolenta [J].

Cimanga, K ;

DeBruyne, T ;

Pieters, L ;

Vlietinck, AJ .

JOURNAL OF NATURAL PRODUCTS, 1997, 60 (07) :688-691

← 1 2 3 4 5 6 →