New tricyclic systems of biological interest. Annelated 1,2,3-triazolo[1,5-a]pyrimidines through domino reaction of 3-azidopyrroles and methylene active nitriles

Tetrahedron

Volumn 58, Issue 48, 2002, Pages 9723-9727

  Lauria, Antonino ^a   Diana, Patrizia ^a   Barraja, Paola ^a   Montalbano, Alessandra ^a   Cirrincione, Girolamo ^a   Dattolo, Gaetano ^a   Almerico, Anna Maria ^a  

^a UNIVERSITY OF PALERMO   (Italy)

Author keywords

Antiproliferative activity; Domino reaction; Heterotricyclic systems; Pyrrolo triazolo pyrimidine

Indexed keywords

1,2,3 TRIAZOLO[1,5 A]PYRIMIDINE; ACETONITRILE; AZIDOPYRROLE; CARBENE; DNA; NITRILE; PYRIMIDINE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ISOMER; MOLECULAR INTERACTION; MOLECULAR MODEL; PRIORITY JOURNAL;

EID: 0037175596     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01245-0     Document Type: Article

References (18)

1. Barraja P., Diana P., Lauria A., Passannanti A., Almerico A.M., Minnei C., Longu S., Congiu D., Musiu C., La Colla P. Bioorg. Med. Chem. 7:1999;1591-1596.
2. Cirrincione G., Almerico A.M., Barraja P., Diana P., Lauria A., Passannanti A., Musiu C., Pani A., Murtas P., Minnei C., Marongiu M.E., La Colla P. J. Med. Chem. 42:1999;2561-2568.
3. Aiello E., Dattolo G., Cirrincione G., Almerico A.M., Diana P., Grimaudo S., Mingoia F., Barraja P. Il Farmaco. 50:1995;365-368.
4. Wakelin L.P.G., Waring M.J. Sammes P.G., Comprehensive Medicinal Chemistry. 2:1990;703-724 Pergamon, Oxford.
5. Lauria A., Diana P., Barraja P., Almerico A.M., Cirrincione G., Dattolo G. J. Heterocycl. Chem. 37:2000;747-750.
6. (a) Westerlund C. J. Heterocycl. Chem. 27:1980;1765-1769.
7. (b) Westerlund C. J. Heterocycl. Chem. 27:1980;1771-1775.
8. (a) Khan M.A., Carreira Freitas A.C. J. Heterocycl. Chem. 17:1980;1603-1604.
9. (b) Freitas A.P., Proenca M.F.J.R.P., Booth B.L. J. Heterocycl. Chem. 32:1995;457-462.
10. See for examples: (a) Jones R.A., Bean G.B. The Chemistry of Pyrroles. 1977;Academic, London, (b) Jones R.A. Katritzky R.A., Rees C.W., Comprehensive Heterocyclic Chemistry. Vol. 4:1984;268-308 Pergamon, Oxford, 1984; Vol 4, pp 268-308.
11. See for examples: (a) Jones R.A., Bean G.B. The Chemistry of Pyrroles. 1977;Academic, London, (b) Jones R.A. Katritzky R.A., Rees C.W., Comprehensive Heterocyclic Chemistry. Vol. 4:1984;268-308 Pergamon, Oxford, 1984; Vol 4, pp 268-308.
12. Lim M.-I., Klein R.S., Fox J.J. J. Org. Chem. 44:1979;3826-3829.
13. Perrin D.D., Pitman I.H. J. Chem. Soc. 1965;7071-7082.
14. 2SO was carried out, by using the software PIMMS (V 1.43) and Vamp (V 6.1), supplied by Oxford Molecular, to obtain the interatomic distances and molecular orbital energies.
15. . In the protocol, each cell line is inoculated and preincubated on a microtiter plate. Test agents are then added at a single concentration and the culture incubated for 48 h. End-point determinations are made with alamar blue Gray G.D., Wickstrom E. Biotechniques. 21:1996;780-782. Results for each test agent are reported as the percent of growth of the treated cells when compared to the untreated control cells. Compounds which reduce the growth of any one of the cell lines to approximately 32% or less (negative numbers indicate cell kill) are passed on for evaluation in the full panel of 60 cell lines over a 5-log dose range.
16. 50) growth inhibition was determined by linear regression analysis.
17. Anderson E.L., Casey J.E., Greene L.C., Lafferty J.J., Reiff H.E. J. Med. Chem. 7:1964;259-268.
18. Viswanadhan V.N., Ghose A.K., Revankar G.R., Robin R.K. J. Chem. Inf. Comput. Sci. 29:1989;163-172.