Efficient one-pot synthesis of anti-HIV and anti-tumour β-carbolines

被引:43
作者
Kusurkar, RS [1 ]
Goswami, SK [1 ]
机构
[1] Univ Poona, Dept Chem, Pune 411007, Maharashtra, India
关键词
harman; harmine; beta-carboline; electrocyclisation; 1-aryl-beta-carboline;
D O I
10.1016/j.tet.2004.04.079
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thermal electrocyclisation of the azahexatriene system has been used as a key step for the synthesis of anti-HIV and anti-tumour compounds, harman, derivatives of harman and 1-aryl-beta-carbolines. A one-pot reaction sequence was used to furnish these compounds in good yield. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5315 / 5318
页数:4
相关论文
共 24 条
[1]   SYNTHETIC AND COMPUTER-ASSISTED ANALYSES OF THE PHARMACOPHORE FOR THE BENZODIAZEPINE RECEPTOR INVERSE AGONIST SITE [J].
ALLEN, MS ;
TAN, YC ;
TRUDELL, ML ;
NARAYANAN, K ;
SCHINDLER, LR ;
MARTIN, MJ ;
SCHULTZ, C ;
HAGEN, TJ ;
KOEHLER, KF ;
CODDING, PW ;
SKOLNICK, P ;
COOK, JM .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2343-2357
[3]   GENERAL REACTIVITY OF 2-LITHIOBENZOTHIAZOLE TO VARIOUS ELECTROPHILES AND THE USE AS A FORMYL ANION EQUIVALENT IN THE SYNTHESIS OF ALPHA-HYDROXY CARBONYL-COMPOUNDS [J].
CHIKASHITA, H ;
ISHIBABA, M ;
ORI, K ;
ITOH, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (10) :3637-3648
[4]  
Choshi T, 2000, CHEM PHARM BULL, V48, P108
[5]   The first total synthesis of the novel β-carboline alkaloid oxopropaline G [J].
Choshi, T ;
Matsuya, Y ;
Okita, M ;
Inada, K ;
Sugino, E ;
Hibino, S .
TETRAHEDRON LETTERS, 1998, 39 (16) :2341-2344
[6]   New organolithium addition methodology to diversely functionalized indoles [J].
Coleman, CM ;
O'Shea, DF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) :4054-4055
[7]   Jafrine, a novel and labile β-carboline alkaloid from the flowers of Tagetes patula [J].
Faizi, S ;
Naz, A .
TETRAHEDRON, 2002, 58 (31) :6185-6197
[8]  
HIBINO S, 1987, CHEM PHARM BULL, V35, P2261
[9]   SYNTHESIS AND REACTIONS OF 2-ARYL-1,3-OXATHIOLIUM SALTS [J].
HIRAI, K ;
ISHIBA, T .
HETEROCYCLES, 1975, 3 (03) :217-222
[10]   Anti-AIDS agents.: 46.: Anti-HIV activity of harman, an anti-HIV principle from Symplocos setchuensis, and its derivatives [J].
Ishida, J ;
Wang, HK ;
Oyama, M ;
Cosentino, ML ;
Hu, CQ ;
Lee, KH .
JOURNAL OF NATURAL PRODUCTS, 2001, 64 (07) :958-960