Synthesis, anticancer and cytostatic activity of some 6H-indolo[2,3-b] quinoxalines

Acta Pharmaceutica

Volumn 59, Issue 4, 2009, Pages 431-440

  Karki, Subhas ^a   Hazare, Rahul ^a   Kumar, Sujeet ^a   Bhadauria, Vivek ^a   Balzarini, Jan ^b   De Clercq, Erik ^b  

^a A Constituent Unit of KLE Academy of Higher Education Research   (India)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Anticancer activity; Cytostatic activity; Indolo 2,3 b quinoxaline

Indexed keywords

6 (4 FLUOROBENZYL) 6H INDOLO[2,3 B]QUINOXALINE; 6 (4 FLUOROBENZYL) 9 METHYL 6H INDOLO[2,3 B]QUINOXALINE; 6 (4 METHYLBENZYL) 6H INDOLO[2,3 B]QUINOXALINE; 6 BENZYL 9 CHLORO 6H INDOLO[2,3 B]QUINOXALINE; 6 BENZYL 9 FLUORO 6H INDOLO[2,3 B]QUINOXALINE; 6 BENZYL 9 METHYL 6H INDOLO[2,3 B]QUINOXALINE; 6H INDOLO[2,3 B]QUINOXALINE DERIVATIVE; 9 BROMO 6 (4 FLUOROBENZYL) 6H INDOLO[2,3 B]QUINOXALINE; 9 BROMO 6 (4 METHYLBENZYL) 6H INDOLO[2,3 B]QUINOXALINE; 9 CHLORO 6 (4 FLUOROBENZYL) 6H INDOLO[2,3 B]QUINOXALINE; 9 CHLORO 6 (4 METHYLBENZYL) 6H INDOLO[2,3 B]QUINOXALINE; 9 FLUORO 6 (4 FLUOROBENZYL) 6H INDOLO[2,3 B]QUINOXALINE; 9 FLUORO 6 (4 METHYLBENZYL) 6H INDOLO[2,3 B]QUINOXALINE; 9 METHYL 6 (4 METHYLBENZYL) 6H INDOLO[2,3 B]QUINOXALINE; QUINOXALINE DERIVATIVE; SARCOLYSIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOSTASIS; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; LEUKEMIA L 1210; NONHUMAN; STRUCTURE ACTIVITY RELATION; T LYMPHOCYTE;

EID: 77949432479     PISSN: 13300075     EISSN: None     Source Type: Journal    
DOI: 10.2478/v10007-009-0040-9     Document Type: Article

References (16)

1. D. J. Brown (Ed.), Quinoxalines, Wiley, New York 2004.
2. G. W. H. Cheeseman and R. F. Cookson (Eds.), Condensed Pyrazines, Wiley, New York 1979.
3. A. Carta, P. Corona and M. Loriga, Quinoxaline 1,4-dioxide: A versatile scaffold end-owed with manifold activities, Curr. Med. Chem. 12 (2005) 2259-2272; DOI: 10.2174/0929867054864831.
4. J. Harrmenberg, B. Wahren, J. Bergman, S. Akerfeldt and L. Lundbland, Antiherpes virus activity and mechanism of action of indolo[2,3-b]quinoxaline and analogs, Antimicrob. Agents Chemother. 32 (1988) 1720-1724.
5. J. O. E. Bergman and S. G. Aakerfeldt, Indoloquinoxalines with Substitutients in 6-Position Containing Cyclic Groups, Eur. Pat. 0, 231, 159, 18 Sep 1987; ref. Chem. Abstr. 108 (1988) 6048s.
6. N. Patel, J. Bergman and A. Graslund, Interaction of the deoxy-oligonucleotide duplex d(CGCGATCGCG)2 and anti-hepres virus active indolo[2,3-b]-quinoxaline derivatives, Nucleos. Nucleot. Nucl. 10 (1991) 699-700; DOI: 10.1080/07328319108046576.
7. B. Zarranz, A. Jaso, I. Aldana, A. Monge, S. Maurel, E. Deharo, V. Jullian and M. Sauvain, Synthesis and antimalarial activity of new 3-arylquinoxaline-2-carbonitrile derivatives, Arzneim. Forsch. 55 (2005) 754-761.
8. G. Moarbess, C. Deleuze-Masquefa, V. Bonnard, S. Gayraud-Paniagua, J. Vidal, F. Bressolle, F. Pinguet and B. Pierre-Antoine, In vitro and in vivo anti-tumoral activities of imidazo[1,2-a]qui- noxaline, imidazo[1,5-a] quinoxaline, and pyrazolo[1,5-a]quinoxaline derivatives, Bioorg. Med. Chem. 16 (2008) 6601-6610; DOI:10.1016/j. bmc.2008.05.022.
9. K. Toshima, T. Ozawa, T. Kimura and S. Matsumura, The significant effect of the carbohydrate structures on the DNA photocleavage of the quinoxaline-carbohydrate hybrids, Bioorg. Med. Chem. Lett. 14 (2004) 2777-2779; DOI: 10.1016/j.bmcl.2004.03.065.
10. G. A. Carter, T. Clark, C. S. James and R. S. T. Loeffler, Fungicidal activities of substituted quinoxalines, Pestic. Sci. 14 (1983) 135-144; DOI: 10.1002/ps.2780140207.
11. P. Sanna, A. Carta, M. Loriga, S. Zanetti and L. Sechi, Preparation and biological evaluation of 6/7-trifluoromethyl(nitro)-, 6,7-difluoro-3-alkyl (aryl)-substituted-quinoxalin-2-ones, Farmaco 54 (1999) 169-177; DOI: 10.1016/S0014-827X (99)00011-17
12. J. P. Dirlam, J. E. Presslitz and B. J. Williams, Synthesis and antibacterial activity of some 3(alkylthio) methyl]quinoxaline-1-oxide derivatives, J. Med. Chem. 26 (1983) 1122-1126; DOI: 10.1021/ jm00362a007.
13. C. S. Marvel and G. S. Hiers, Isatin, in Organic Syntheses Collection (Ed. A. H. Blatt), 2nd ed., Vol 1, Wiley, New York 1941, pp. 327-330.
14. J. Azizian, F. B. Shaidaei and H. Kefayati, A facile one-pot method for the preparation of N-alkyl isatins under microwave irradiation, Synth. Commun. 33 (2003) 789-793; DOI: 10.1081/SCC-120016324.
15. A. Monks, D. Scudiero, P. Skehen, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise and A. Vaigro-Wolff, Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines, J. Natl. Cancer Inst. 83 (1991) 757-766; DOI: 10.1093/ jnci/83.11.757.
16. P. G. Baraldi, M. Del Carmen Nunez, M. A. Tabrizi, E. De Clercq, J. Balzarini, J. Bermejo, F. Estévez and R. Romagnoli, Design, synthesis and biological evaluation of hybrid molecules containing a-methylene-g- butyrolactones and polypyrrole minor groove binders, J. Med. Chem. 47 (2004) 2877-2886; DOI: 10.1021/jm031104y.