Synthesis of 1-(6-chloro-1,1-dioxo-1,4,2-benzodithiazin-3-yl)semicarbazides and their transformation into 4-chloro-2-mercapto-N-(4,5-dihydro-5-oxo-4-phenyl-1H-1,2,4-triazol-3-yl) benzenesulfonamides as potential anticancer and anti-HIV agents

Farmaco

Volumn 58, Issue 6, 2003, Pages 423-429

  Pomarnacka, Elzbieta ^a   Kozlarska Kedra, Iwona ^a  

^a MEDICAL UNIVERSITY OF GDANSK   (Poland)

Author keywords

1 (6 Chloro 1,1 dioxo 1,4,2 benzodithiazin 3 yl)semicarbazides; 2 Mercapto N (4,5 dihydro 5 oxo 4 phenyl 1H 1,2,4 triazol 3 yl) benzenesulfonamides; Anti HIV activity; Anticancer activity

Indexed keywords

ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; BENZENESULFONAMIDE DERIVATIVE; SEMICARBAZIDE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; DRUG TRANSFORMATION; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS;

EID: 0037951779     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(03)00071-5     Document Type: Article

References (27)

1. Pikul S., Ohler N.E., Ciszewski G., Lauferweiler M.C., Almstead N.G., Natchus M.G., Hsieh L.C., Janusz M.J., Peng S.X., Branch T.M., King S.L., Taiwo Y.O., Mieling G.E. Potent and selective carboxylic acid-based inhibitors of matrix metalloproteinase. J. Med. Chem. 44:2001;2499-2502.
2. Wada C.K., Holms J.H., Cutin M.L., Dai Y., Florjancic A.S., Garland R.B., Guo Y., Heyman H.R., Stacey J.R., Steinman D.H. Phenoxyphenyl sulfone N-formylhydroxylamines (retrohydroxamates) as potent, selective, orally bioavailable matrix metalloproteinase inhibitors. J. Med. Chem. 45:2002;219-232.
3. Scozzafava A., Menabuoni L., Mincione F., Supuran C.T. Carbonic anhydrase inhibitors. A general approach for the preparation of water-soluble sulfonamides incorporating polyamino-polycarboxylate tails and of their metal complexes possessing long-lasting, topical intraocular pressure-lowering properties. J. Med. Chem. 45:2002;1466-1476.
4. Selvam P., Chandramohan M., De Clercq E., Witvrouw M., Pannecouque C. Synthesis and anti-HIV activity of 4-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene) amino]-N-(4,6-dimethyl-2-pyrimidin-yl)benzene sulfonamide and its derivatives. Eur. J. Pharm. Sci. 14:2001;313-316.
5. Rocheblave L., Bihel F., De Micheelis C., Priem G., Courcambeck J., Bonnet B., Chermann J.C., Kraus J.L. Synthesis and antiviral activity of new anti-HIV amprenavir bioisosteres. J. Med. Chem. 45:2002;3321-3324.
6. Brzozowski Z. 2-Mercapto-N-(azolyl)benzenesulfonamides. II. Syntheses, anti-HIV and anticancer activity of some S-substituted 4-chloro-2-mercapto-5-methyl-N-(5-amino-1,2,4-triazol-3-yl) benzenesulfonamides. Acta Polon. Pharm.-Drug Res. 52:1995;287-292.
7. Brzozowski Z. 2-Mercapto-N-(azolyl)benzenesulfonamides. III. Synthesis of some new 2-mercapto-N-(5-amino-1,2,4-triazol-3-yl)benzenesulfonamide derivatives with potential anti-HIV or anticancer activity. Acta Polon. Pharm.-Drug Res. 53:1996;269-276.
8. Pomarnacka E., Brzozowski Z. 2-Mercapto-N-(azolyl)benzenesulfonamides. IV. Synthesis of some 4-chloro-2-mercapto-5-methyl-N-(benzimidazol-2-yl)benzenesulfonamide derivatives with potential anticancer and anti-HIV activities. Acta Polon. Pharm.-Drug Res. 54:1997;215-221.
9. Brzozowski Z. 2-Mercapto-N-(azolyl)benzenesulfonamides. V. Syntheses, anti-HIV and anticancer activity of some 4-chloro-2-mercapto-5-methyl-N- (1,2,4-triazolo[4,3-a]pyrid-3-yl)benzenesulfonamides. Acta Polon. Pharm.-Drug Res. 55:1998;375-379.
10. Brzozowski Z. 2-Mercapto-N-(azolyl)benzenesulfonamides. VI. Synthesis and anti-HIV activity of some new 2-mercapto-N-(1,2,4-triazol-3-yl)benzenesulfonamide derivatives containing the 1,2,4-triazole moiety fused with a variety of heteroaromatic rings. Acta Polon. Pharm.-Drug Res. 55:1998;473-480.
11. Pomarnacka E. Synthesis, anti-HIV and anticancer activities of new 4-(2-mercaptobenzenesulfonyl)perhydro-1,2,4-triazin-3-ones. Acta Polon. Pharm.-Drug Res. 55:1998;481-486.
12. Brzozowski Z., Kornicka A. Syntheses of some 2-hydroxy-1-[(4-chloro-2-mercaptophenyl)sul-fonyl]imidazole derivatives with potential anticancer activity. Acta Polon. Pharm.-Drug Res. 56:1999;135-142.
13. Pomarnacka E., Kornicka A., Saczewski F. A facile synthesis and chemical properties of 3,4-dihydro-2H-1,5,2-benzo[f]dithiazepin-3-ones with potential anticancer activity. Heterocycles. 55:2001;753-760.
14. Pomarnacka E., Kornicka A. Synthesis and in vitro anticancer and anti-HIV evaluation of new 2-mercaptobenzenesulfonamides. Farmaco. 56:2001;571-577.
15. Brzozowski Z., Saczewski F. A new type of mixed anhydride and its applications to the synthesis of 7-substituted 8-chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazines with in vitro antitumor activity. J. Med. Chem. 45:2002;430-437.
16. Neamati N., Sunder S., Pommier Y. Design and discovery of HIV-1 integrase inhibitors. Drug Discov. Today. 2:1997;487-498.
17. Neamati N., Mazumder A., Owen J.M., Schultz R.J., Sunder S., Pommier Y. 2-Mercaptobenzenesulfonamides as novel inhibitors of human immunodeficiency virus type 1 integrase and replication. Antivir. Chem. Chemother. 8:1997;485-495.
18. Neamati N., Turpin J.A., Winslow H.E., Christensen J.L., Williamson K., Orr A., Rice W.G., Pommier Y., Garofalo A., Brizzi A., Campiani G., Fiorini I., Nacci V. Thiazolothiazepine inhibitors of HIV-1 integrase. J. Med. Chem. 42:1999;3334-3341.
19. Ren S., Wang R., Komatsu K., Bonanz-Krause P., Zyrianov Y., McKenna Ch.E., Csipke C., Tokes Z., Lien E.J. Synthesis, biological evaluation, and quantitative structure-activity relationship analysis of new Schiff bases of hydroxysemicarbazide as potential antitumor agents. J. Med. Chem. 45:2002;410-419.
20. Brzozowski Z., Slawinski J. Synthesis of some 3-mercapto-1,1-dioxo-1,4,2-benzodithiazine derivatives. Acta Polon. Pharm. 41:1984;133-139.
21. 1-3-methylthio-1,1-dioxo-1,4,2-benzodithiazino-7-carboxylic acids. Acta Polon. Pharm.-Drug Res. 50:1993;199-203.
22. Katritzky A.R., Karelson M., Harris P.A. Prototropic tautomerism of heteroaromatic compounds. Heterocycles. 32:1991;329-369.
23. Kurosawa Y., Takada A., Kim H.S. Tautomerism and isomerism of heterocycles. Heterocycles. 41:1995;2057-2091.
24. Alkorta I. Comparison of methods to estimate geometric and electronic properties on sulfur containing compounds. Theor. Chim. Acta. 89:1994;1-12.
25. SPARTAN program, version 5.0, installed on a Silicon Graphics 02 workstation, Wavefunction Inc., Irvine, CA, 1997.
26. Weislow O.W., Kiser R., Fine D.L., Bader J., Shoemaker R.H., Boyd M.R. New soluble-formazan assay for HIV-1 cytophatic effects: application to high-flux screening of synthetic and natural products for AIDS-antiviral activity. J. Natl. Cancer Inst. 81:1989;577-586.
27. Boyd M.R. Status of the NCI preclinical antitumor drug discovery screen. Princ. Pract. Oncol. 3:1989;1-12.