Synthesis and anti-microbial activity of pyrazolylbisindoles - Promising anti-fungal compounds

被引:169
作者
Sivaprasad, Ganesabaskaran
Perumal, Paramasivan T. [1 ]
Prabavathy, Vaiyapurl R.
Mathivanan, Narayanasamy
机构
[1] Cent Leather Res Inst, Organ Chem Div, Madras 600020, Tamil Nadu, India
[2] Univ Madras, Ctr Adv Studies Bot, Madras 600025, Tamil Nadu, India
关键词
pyrazolylbisindoles; anti-microbial screening; plant pathogenic fungi; human pathogenic bacteria;
D O I
10.1016/j.bmcl.2006.09.019
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of pyrazolylbisindole derivatives have been synthesized by reacting substituted pyrazole aldehydes with substituted indoles using phosphotungstic acid, a Keggin type heteropoly acid as catalyst. The synthesized pyrazolylbisindoles were evaluated for anti-microbial activities. The effect of pyrazolylbisindoles on the mycelial growth of plant pathogenic fungi is revealed. Entries 3c and 3d emerged as the most interesting compounds in this series exhibiting excellent anti-fungal activity. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6302 / 6305
页数:4
相关论文
共 39 条
[1]   Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3 [J].
Alam, MM ;
Varala, R ;
Adapa, SR .
TETRAHEDRON LETTERS, 2003, 44 (27) :5115-5119
[2]  
AREADI A, 2004, SYNLETT, P944
[3]  
BANIK BK, 2005, TETRAHEDRON LETT, V46, P2577
[4]   The Michael addition of indoles to α,β-unsaturated ketones catalyzed by CeCl3•7H2O-NaI combination supported on silica gel [J].
Bartoli, G ;
Bartolacci, M ;
Bosco, M ;
Foglia, G ;
Giuliani, A ;
Marcantoni, E ;
Sambri, L ;
Torregiani, E .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4594-4597
[5]   STRUCTURE-ACTIVITY-RELATIONSHIPS OF DIETARY INDOLES - A PROPOSED MECHANISM OF ACTION AS MODIFIERS OF XENOBIOTIC METABOLISM [J].
BRADFIELD, CA ;
BJELDANES, LF .
JOURNAL OF TOXICOLOGY AND ENVIRONMENTAL HEALTH, 1987, 21 (03) :311-323
[6]   LEWIS-ACID-INDUCED ELECTROPHILIC SUBSTITUTION IN INDOLES WITH ACETONE .2. [J].
CHATTERJEE, A ;
MANNA, S ;
BANERJI, J ;
PASCARD, C ;
PRANGE, T ;
SHOOLERY, JN .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (02) :553-555
[7]   INVIVO DISPOSITION OF THE NATURAL ANTI-CARCINOGEN INDOLE-3-CARBINOL AFTER PO ADMINISTRATION TO RAINBOW-TROUT [J].
DASHWOOD, RH ;
UYETAKE, L ;
FONG, AT ;
HENDRICKS, JD ;
BAILEY, GS .
FOOD AND CHEMICAL TOXICOLOGY, 1989, 27 (06) :385-392
[8]   Enantioselective indole Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes [J].
Evans, DA ;
Scheidt, KA ;
Fandrick, KR ;
Lam, HW ;
Wu, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10780-10781
[9]   Amberlyst 15 catalyzed synthesis of indole-pyrazole based tri(hetero)arylmethanes [J].
Farhanullah ;
Sharon, A ;
Maulik, PR ;
Ram, VJ .
TETRAHEDRON LETTERS, 2004, 45 (26) :5099-5102
[10]  
FOLDEAK S, 1965, ACTA PHYS CHEM, V11, P115