New annelated thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidines, with potent anticancer activity, designed through VLAK protocol

European Journal of Medicinal Chemistry

Volumn 62, Issue , 2013, Pages 416-424

  Lauria, Antonino ^a   Abbate, Ilenia ^a   Patella, Chiara ^a   Martorana, Annamaria ^a   Dattolo, Gaetano ^a   Almerico, Anna Maria ^a  

^a UNIVERSITY OF PALERMO   (Italy)

Author keywords

Annelated thienotriazolopyrimidines; Anticancer agents; Developmental Therapeutics Program (DTP); Domino reactions; VLAK protocol

Indexed keywords

ANTINEOPLASTIC AGENT; BENZOTHIENO[2,3 E][1,2,3]TRIAZOLO[1,5 A]PYRIMIDINE; PYRIDO[3,2 4,5]THIENO[2,3 E][1,2,3]TRIAZOLO[1,5 A]PYRIMIDINE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER SCREENING; CONCENTRATION (PARAMETERS); DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR STRUCTURE; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES; TRIAZOLES;

EID: 84873331496     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.01.019     Document Type: Article

References (30)

1. A.R. Katritzky, I. Tulp, D.C. Fara, A. Lauria, U. Maran, and W.E. Acree A general treatment of solubility. 3. Principal component analysis (PCA) of the solubilities of diverse solutes in diverse solvents J. Chem. Inf. Model. 45 2005 913 923
2. A. Lauria, P. Diana, P. Barraja, A. Montalbano, G. Cirrincione, G. Dattolo, and A.M. Almerico MADoSPRO: a new Approach to molecular modelling studies on a series of DNA minor groove binders QSAR Comb. Sci. 25 2006 252 262
3. A. Lauria, M. Ippolito, and A.M. Almerico Principal component analysis on molecular descriptors as an alternative point of view in the search of new Hsp90 inhibitors J. Comp. Biol. Chem. 33 2009 386 390
4. A. Lauria, M. Ippolito, and A.M. Almerico Combined use of PCA and QSAR/QSPR to predict the drugs mechanism of action. An application to the NCI ACAM Database QSAR Comb. Sci. 28 2009 387 395
5. A. Lauria, M. Tutone, and A.M. Almerico Virtual lock-and-key approach: the in silico revival of Fischer model by means of molecular descriptors Eur. J. Med. Chem. 46 2011 4274 4280
6. E. Fischer Influence of the configuration on the action of the enzymes Ber. Dtsch. Chem. Ges. 27 1894 2985 2993
7. E. Fischer Faraday lecture on "SYNTHETICAL chemistry in its relation to biology" J. Chem. Soc. 91 1907 1747 1765
8. E. Fischer Bedeutung der Stereochemie fur die Physilogie Hoppe-Seyler's Z. Physiol. Chem. 26 1898 82 83
9. A. Lauria, C. Patella, G. Dattolo, and A.M. Almerico Design and synthesis of 4-substituted indolo[3,2-e][1,2,3]triazolo[1,5-a]pyrimidine derivatives with antitumor activity J. Med. Chem. 51 2008 2037 2046
10. A. Lauria, P. Diana, P. Barraja, A. Montalbano, G. Cirrincione, G. Dattolo, and A.M. Almerico 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 58 2002 9723 9727
11. A. Lauria, C. Patella, P. Diana, P. Barraja, A. Montalbano, G. Cirrincione, G. Dattolo, and A.M. Almerico New tetracyclic ring system of biological interest. Indolo[3,2-e][1,2,3]triazolo[1,5-a]pyrimidines through domino reaction of 2-azidoindole Heterocycles 60 2003 2669 2675
12. A. Lauria, C. Patella, P. Diana, P. Barraja, A. Montalbano, G. Cirrincione, G. Dattolo, and A.M. Almerico A synthetic approach to new polycyclic ring system of biological interest through domino reaction: indolo[2,3-e][1,2,3]triazolo[1,5-a]pyrimidine Tetrahedron Lett. 47 2006 2187 2190
13. A. Lauria, I. Abbate, C. Patella, N. Gambino, A. Silvestri, G. Barone, and A.M. Almerico Pyrazolo[3,4-d][1,2,3]triazolo[1,5-a]pyrimidine: a new ring system through Dimroth rearrangement Tetrahedron Lett. 49 2008 5125 5128
14. A. Lauria, M. Bruno, P. Diana, P. Barraja, A. Montalbano, G. Cirrincione, G. Dattolo, and A.M. Almerico Annelated pyrrolo-pyrimidines from amino-cyano-pyrroles and BMMAs as leads for new DNA-interactive ring systems Bioorg. Med. Chem. 13 2005 1545 1553
15. A. Lauria, A. Guarcello, G. Dattolo, and A.M. Almerico Bis-1,2,4-triazolo[4,3-a:3',4'-c]quinoxalines of pharmaceutical interest from 1,3-dipolar cycloaddition Tetrahedron Lett. 49 2008 1847 1850
16. A. Lauria, A. Guarcello, G. Macaluso, G. Dattolo, and A.M. Almerico Reactivity of asymmetric benzo-condensed diazines with nitrilimine dipoles in the 1,3-dipolar cycloaddition reactions Tetrahedron Lett. 50 2009 7333 7336
17. A. Lauria, A. Guarcello, G. Dattolo, and A.M. Almerico Study of reactivity in the 1,3-dipolar cycloaddition reactions leading to new triazolopyrrolopyrazine ring systems Synlett 14 2010 2067 2070
18. N.T. Pokhodylo, V.S. Matiychuk, and N.D. Obushak Synthesis of a new heterocyclic system - pyrido[3',2':4,5]thieno[2,3-e][1,2,3]triazolo[1,5-a] pyrimidine Chem. Heterocycl. Comp. 45 2009 881 883
19. H.D.H. Showalter, A.J. Bridges, H.R. Zhou, A.D. Sercel, A. McMichael, and D.W. Fry Tyrosine kinase inhibitors. 16. 6,5,6-tricyclic benzothieno [3,2-d]pyrimidines and pyrimido[5,4-b]- and -[4,5-b]indoles as potent inhibitors of the epidermal growth factor receptor tyrosine kinase J. Med. Chem. 42 1999 5464 5474
20. A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, M. Gray-Goodrich, H. Campbell, J. Mayo, and M. Boyd Feasibility of a high-flux anticancer drug screen utilizing a diverse panel of human tumor cell lines in culture J. Natl. Cancer Inst. 83 1991 757 766
21. J.N. Weinstein, K.W. Kohn, M.R. Grever, V.N. Viswanadhan, L.V. Rubinstein, A.P. Monks, D.A. Scudiero, L. Welch, A.D. Koutsoukos, A.J. Chiausa, and K.D. Paull Neural computing in cancer drug development: predicting mechanism of action Science 258 1992 447 451
22. W.W. Osdol, T.G. Myers, K.D. Paull, K.W. Kohn, and J.N. Weinstein Use of the Kohonen self-organizing map to study the mechanisms of action of chemotherapeutic agents J. Natl. Cancer Inst. 86 1994 1853 1859
23. A. Lauria, C. Patella, I. Abbate, A. Martorana, and A.M. Almerico Lead optimization through VLAK protocol: new annelated pyrrolo-pyrimidine derivatives as antitumor agents Eur. J. Med. Chem. 55 2012 375 383
24. Y. Hirayama, T. Nakamura, S. Uehara, Y. Sakamoto, K. Yamaguchi, K. Sei, and M. Iwamura Synthesis and characterization of new polyester dendrimers from acetoacetate and acrylate Org. Lett. 7 2005 525 528
25. M.R. Grever, S.A. Schepartz, and B.A. Chabner The National Cancer Institute: cancer drug discovery and development program Semin. Oncol. 19 1992 622 638
26. A. Monks, D. Scudiero, and P. Skehan 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
27. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.R. Warren, H. Bokesch, S. Kenney, and M.R. Boyd New colorimetric cytotoxicity assay for anticancer-drug screening J. Natl. Cancer Inst. 82 1990 1107 1112
28. G.D. Gray, and E. Wickstrom Evaluation of anchorage-independent proliferation in tumorigenic cells using the redox dye alamarblue[TM] BioTechniques 21 1996 780 782
29. LigPrep, Version 2.4 2010 Schrödinger LLC New York, NY
30. A.R. Katrinsky, V.S. Lobanov, and M. Karelson Quantum-chemical descriptors in QSAR/QSPR studies Chem. Rev. 96 1996 1027 1043