Synthesis and in vitro antiproliferative activity of novel androst-5-ene triazolyl and tetrazolyl derivatives

Molecules

Volumn 16, Issue 6, 2011, Pages 4786-4806

  Kádár, Zalán ^a   Kovács, Dóra ^a   Frank, Éva ^a   Schneider, Gyula ^a   Huber, Judit ^a   Zupkó, István ^a   Bartók, Tibor ^a,b   Wölfling, János ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

^b Fumizol Ltd   (Hungary)

Author keywords

Click chemistry; CuAAC; Steroid azides; Tetrazoles; Triazoles

Indexed keywords

ANDROSTANE DERIVATIVE; ANTINEOPLASTIC AGENT; TRIAZOLE DERIVATIVE;

ARTICLE; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECT; HELA CELL; HUMAN; SYNTHESIS; TUMOR CELL LINE;

ANDROSTENES; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; HELA CELLS; HUMANS; TRIAZOLES;

EID: 79959627028     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16064786     Document Type: Article

References (31)

1. Rostovtsev, V.V.; Green, L.G.; Fokin, V.V.; Sharpless, K.B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem., Int. Ed. 2002, 41, 2596-2599. (Pubitemid 34803480)
2. Tornøe, C.W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002, 67, 3057-3064. (Pubitemid 34457265)
3. Bock, V.D.; Hiemstra, H.; Van Maarseveen, J.H. CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective. Eur. J. Org. Chem. 2006, 1, 51-68.
4. Wu, P.; Fokin, V.V. Catalytic azide-alkyne cycloaddition: Reactivity and applications. Aldrichim. Acta 2007, 40, 7-17.
5. Hein, C.D.; Liu, X.M.; Wang, D. Click chemistry, a powerful tool for pharmaceutical sciences. Pharm. Res. 2008, 25, 2216-2230.
6. Klaubert, D.H.; Sellstedt, J.H.; Guinosso, C.J.; Bell, S.C.; Capetola, R.J. 5-Tetrazolecarboxamides and their salts: New orally active antiallergy agents. J. Med. Chem. 1981, 24, 748-752. (Pubitemid 11043258)
7. Demko, Z.P.; Sharpless, K.B. A click chemistry approach to tetrazoles by Huisgen 1,3-dipolar cycloaddition: Synthesis of 5-acyltetrazoles from azides and acyl cyanides. Angew. Chem., Int. Ed. 2002, 41, 2113-2116. (Pubitemid 34746919)
8. Demko, Z.P.; Sharpless, K.B. A click chemistry approach to tetrazoles by Huisgen 1,3-dipolar cycloaddition: Synthesis of 5-sulfonyl tetrazoles from azides and sulfonyl cyanides. Angew. Chem., Int. Ed. 2002, 41, 2110-2113. (Pubitemid 34746918)
9. 2-catalyzed and microwave-controlled preparation of tetrazoles from nitriles and organic azides under mild, safe conditions. Angew. Chem., Int. Ed. 2007, 46, 3926-3930. (Pubitemid 46959970)
10. Salomon, R.G.; Kochi, J.K. Copper(I) catalysis in cyclopropanations with diazo compounds. The role of olefin coordination. J. Am. Chem. Soc. 1973, 95, 3300-3310.
11. Pore, V.S.; Aher, N.G.; Kumar, M.; Shukla, P.K. Design and synthesis of fluconazole/bile acid conjugate using click reaction. Tetrahedron 2006, 62, 11178-11186. (Pubitemid 44573333)
12. Aher, N.G.; Pore, V.S.; Patil, S.P. Design, synthesis, and micellar properties of bile acid dimers and oligomers linked with a 1,2,3-triazole ring. Tetrahedron 2007, 63, 12927-12934. (Pubitemid 350116219)
13. Aher, N.G.; Pore, V.S. Synthesis of bile acid dimers linked with 1,2,3-triazole ring at C-3, C-11, and C-24 positions. Synlett 2005, 14, 2155-2158. (Pubitemid 41297693)
14. Zhang, Z.; Ju, Y.; Zhao, Y. Synthesis of 1,2,3-triazole-containing bile acid dimers and properties of inverse micellar mimic. Chem. Lett. 2007, 36, 1450-1452.
15. Banday, A.H.; Shameem, S.A.; Gupta, B.D.; Sampath-Kumar, H.M. D-ring substituted 1,2,3- triazolyl 20-keto pregnenanes as potential anticancer agents: Synthesis and biological evaluation. Steroids 2010, 75, 801-804.
16. Ivanyi, Z.; Wflfling, J.; Gfrbe, T.; Sz?csi, M.; Wittmann, T.; Schneider, G. Synthesis of regioisomeric 17β-N-phenylpyrazolyl steroid derivatives and their inhibitory effect on 17a- hydroxylase/C17,20-lyase. Steroids 2010, 75, 450-456.
17. Ondr?, D.; Wflfling, J.; Tsth, I.; Sz?csi, M.; Julesz, J.; Schneider, G. Steroselective synthesis of some steroidal oxazolines, as novel potential inhibitors of 17a-hydroxylase-C17,20-lyase. Steroids 2009, 74, 1025-1032.
18. Ondr?, D.; Wflfling, J.; Ivanyi, Z.; Schneider, G.; Tsth, I.; Sz?csi, M.; Julesz, J. Neighboring group participation: Part 17 Stereoselective synthesis of some steroidal 2-oxazolidones, as novel potential inhibitors of 17a-hydroxylase-C17,20-lyase. Steroids 2008, 73, 1375-1384.
19. Frank, É.; Mucsi, Z.; Zupkó, I.; Réthy, B.; Falkay, G.; Schneider, G.; Wölfling, J. Efficient approach to androstene-fused arylpyrazolines as potent antiproliferative agents. Experimental and theoretical studies of substituent effects on BF3-catalyzed intramolecular [3+2] cycloadditions of olefinic phenylhydrazones. J. Am. Chem. Soc. 2009, 131, 3894-3904.
20. Genin, M.J.; Allwine, D.A.; Anderson, D.J.; Barbachyn, M.R.; Emmert, D.E.; Garmon, S.A.; Graber, D.R.; Grega, K.C.; Hester, J.B.; Hutchinson, D.K.; et al. Substituent effects on the antibacterial activity of nitrogen-carbon- linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious Gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis. J. Med. Chem. 2000, 43, 953-970. (Pubitemid 30152301)
21. Alvarez, R.; Velazquez, S.; San-Felix, A.; Aquaro, S.; De Clercq, E.; Perno, C.F.; Karlsson, A.; Balzarini, J.; Camarasa, M.J. 1,2,3-Triazole-[2',5'- bis-O-(tert-butyldimethylsilyl)-beta-Dribofuranosyl]- 3'-spiro-5"-(4"- amino-1",2"-oxathiole 2",2"-dioxide) (TSAO) analogues: synthesis and anti-HIV-1 activity. J. Med. Chem. 1994, 37, 4185-4194.
22. Buckle, D.R.; Rockell, C.J.; Smith, H.; Spicer, B.A. Piperazinylalkoxy- [1]benzopyrano[2,3-d]- 1,2,3-triazol-9(1H)-ones with combined H1-antihistamine and mast cell stabilizing properties. J. Med. Chem. 1986, 29, 2262-2267. (Pubitemid 17182304)
23. Palhagen, S.; Canger, R.; Henriksen, O.; van Parys, J.A.; Riviere, M.E.; Karolchyk, M.A. Rufinamide: A double-blind, placebo-controlled proof of principle trial in patients with epilepsy. Epilepsy Res. 2001, 43, 115-124. (Pubitemid 32115522)
24. Reddy, D.M.; Srinivas, J.; Chashoo, G.; Saxena, A.K.; Kumar, H.M.S. 4β-[(4-Alkyl)-1,2,3-triazol- 1-yl] podophyllotoxins as anticancer compounds: Design, synthesis and biological evaluation. Eur. J. Med. Chem. 2011, 46, 1983-1991.
25. Fu, J.; Yang, Y.; Zhang, X.W.; Mao, W.J.; Zhang, Z.M.; Zhu, H.L. Discovery of 1Hbenzo[ d][1,2,3]triazol-1-yl-3,4,5-trimethoxybenzoate as a potential antiproliferative agent by inhibiting histone deacetylase. Bioorg. Med. Chem. 2010, 18, 8457-8462.
26. Gundugola, A.S.; Chandra, K.L.; Perchellet, E.M.; Waters, A.M.; Perchellet, J.P.H.; Rayat, S. Synthesis and antiproliferative evaluation of 5-oxo and 5-thio derivatives of 1,4-diaryl tetrazoles. Bioorg. Med. Chem. Lett. 2010, 20, 3920-3924.
27. Ruzicka, L.; Prelog, V.; Battegay, J. Steroide und sexualhormone. 153. Mitteilung. Über einige Benzo-perhydro-cyclopenteno-phenanthren-derivate. Helv. Chim. Acta 1948, 31, 1296-1301.
28. Schneider, G.; Vincze, I.; Vass, A. Steroids, XIX. Neighbouring group participation, III. (AcO-6) and (PrO-6) neighbouring group participation in the 16-hydroxymethylandrost-5-ene-3,17-diol series. Acta Chim. Acad. Sci. Hung. 1979, 99, 51-67.
29. Meldal, M.; Tornøe, C.W. Cu-catalyzed azide-alkyne cycloaddition. Chem. Rev. 2008, 108, 2952-3015.
30. Lee, B.Y.; Park, S.R.; Jeon, H.B.; Kim, K.S. A new solvent system for efficient synthesis of 1,2,3- triazoles. Tetrahedron Lett. 2006, 47, 5105-5109. (Pubitemid 43867620)
31. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63. (Pubitemid 14203433)