Substituted 5-aroylpyrazine-2-carboxylic acid derivatives: Synthesis and biological activity

Farmaco

Volumn 58, Issue 11, 2003, Pages 1105-1111

  Dolezal, M ^a   Jampilek J ^a   Osicka, Z ^a   Kunes J ^a   Buchta, V ^a   Vichova P ^a  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

Author keywords

Aroylpyrazines; Homolytic aroylation; In vitro antifungal activity; In vitro antimycobacterial activity; MTT assay; Structure activity relationships

Indexed keywords

5 (4 CHLOROBENZOYL)PYRAZINE 2 CARBOTHIOAMIDE; 5 BENZOYLPYRAZINE 2 CARBOTHIOAMIDE; AMIDE; CARBOXYLIC ACID DERIVATIVE; PYRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CYTOTOXICITY; DISEASE PREDISPOSITION; DRUG ACTIVITY; DRUG EFFECT; DRUG SCREENING; DRUG SYNTHESIS; FUNGAL STRAIN; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; STRUCTURE ACTIVITY RELATION; TRICHOPHYTON MENTAGROPHYTES;

EID: 0142248977     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(03)00163-0     Document Type: Article

References (21)

1. Snider D.E., Castro K.G. The global threat of drug-resistant tuberculosis. New Eng. J. Med. 338:1998;1689-1690.
2. World Health Organisation, Stop TB annual report 2001, (http://www.who.int/gtb/whats-new/new_publication.htm).
3. Rolston K.V.I. The spectrum of pulmonary infections in cancer patients. Curr. Opin. Oncol. 13:2001;218-223.
4. Crabb Ch. Global alliance at full steam for new TB drugs. Bull. World Health Org. 80:2002;517.
5. Zhang Y., Amzel L.M. Tuberculosis drug targets. Curr. Drug Targ. 3:2002;131-154.
6. Dolezal M., Hartl J., Lyčka A., Buchta V., Odlerová Ž. Synthesis and antituberculotic activity of some substituted 3-arylamino-5-cyano-2-pyrazinecarboxamides. Collect. Czech. Chem. Commun. 60:1995;1236-1241.
7. Dolezal M., Hartl J., Lyčka A., Buchta V., Odlerová Ž. Synthesis and antituberculotic properties of some substituted pyrazinecarbothioamides. Collect. Czech. Chem. Commun. 61:1996;1102-1108.
8. Hartl J., Dolezal M., Krinková J., Lyčka A., Odlerová Ž. Synthesis and antituberculotic activity of 5-alkyl-6-chloro-2-pyrazinecarboxamides and corresponding carbothioamides. Collect. Czech. Chem. Commun. 61:1996;1109-1114.
9. Dolezal M., Vicík R., Miletín M., Král'ová K. Synthesis and antimycobacterial, antifungal, and photosynthesis-inhibiting evaluation of some anilides of substituted pyrazine-2-carboxylic acids. Chem. Pap. 54:2000;245-248.
10. Krinková J., Dolezal M., Hartl J., Buchta V., Pour M. Synthesis and biological activity of 5-alkyl-6-alkylsulfanyl- resp. 5- arylsulfanylpyrazine-2-carboxamides and corresponding thioamides. Farmaco. 57:2002;71-78.
11. Dolezal M., Miletín M., Kuneš J., Král'ová K. Synthesis and biological evaluation of some amides of pyrazine-2-carboxylic acids. Molecules. 7:2002;363-373.
12. Houminer Y., Southwick E.W., Wiliams A.D. Substituent-directing effects in the homolytic acylation of pyrazine derivatives. J. Org. Chem. 54:1989;640-643.
13. Sato N., Kadota H. Studies on pyrazine 23. Homolytic acylation of 2-amino-3-cyanopyrazine and the related-compounds with alpha-keto acids - a synthesis of 5-acyl-3-aminopyrazinecarboxylic acid-derivatives. J. Heterocycl. Chem. 29:1992;1685-1688.
14. Heinisch G., Loetsch G. A new, convenient synthesis of monoaroylpyrazines via homolytic substitution. Synthesis. 2:1988;119-121.
15. Collins L., Franzblau S.G. Microplate Alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob. Agents Chemother. 41:1997;1004-1009.
16. National Committee for Clinical Laboratory Standards: Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts: Proposed Standard M 27-P, National Committee for Clinical Laboratory Standards, Villanova, Pa, 1992.
17. Sheehan D.J., Espinel-Ingroff A., Steele M., Webb C.D. Antifungal susceptibility testing of yeast - a brief overview. Clin. Infect. Dis. 17:1993;494-500.
18. Mosmann T. Rapid colorimetric assay for cellular growth and survival-application to proliferation and cytotoxicity assays. J. Immunol. Meth. 65:1983;55-63.
19. Vistica D.T., Skehan P., Scudiero D., Monks A., Pittman A., Boyd M.R. Tetrazolium-based assays for cellular viability - a critical-examination of selected parameters affecting formazan production. Cancer Res. 51:1991;2515-2520.
20. Sheldon R.A., Kochi Y.K. Metal-Catalyzed Oxidations of Organic Compounds. 1981;33-48 Academic Press, New York.
21. Melloni P., DellaTorre A., DeMunari S., Meroni M., Tonani R. Alpha-(aryloxy)benzyl derivatives of piperazine and piperidine. Gazz. Chim. Ital. 115:1985;159-163.