Synthesis of novel steroidal 17α-triazolyl derivatives via Cu(I)-catalyzed azide-alkyne cycloaddition, and an evaluation of their cytotoxic activity in vitro

Steroids

Volumn 76, Issue 10-11, 2011, Pages 1141-1148

  Frank, Éva ^a   Molnár, Judit ^a   Zupkó, István ^a   Kádár, Zalán ^a   Wölfling, János ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

Author keywords

Cycloaddition; Cytotoxic activity; Regioselectivity; Triazoles

Indexed keywords

17 ALPHA TRIAZOLYL DERIVATIVE; 17 ALPHA[(4 CYCLOHEXYL 1H 1,2,3 TRIAZOL 1 YL)] 5 ALPHA ANDROST 2 ENE; 17 ALPHA[(4 CYCLOPROPYL 1H 1,2,3 TRIAZOL 1 YL)] 5 ALPHA ANDROST 2 ENE; 17 ALPHA[(4 PHENYL 1H 1,2,3 TRIAZOL 1 YL)] 5 ALPHA ANDROST 2 ENE; 17 ALPHA[4 (4 ETHYLPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 5 ALPHA ANDROST 2 ENE; 17 ALPHA[4 (4 METHOXYPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 5 ALPHA ANDROST 2 ENE; 17 ALPHA[4 (4 PROPYLPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 5 ALPHA ANDROST 2 ENE; 17 ALPHA[4 (4 TERT BUTYLPHENYL) 1H 1,2,3 TRIAZOL 1 YL] 5 ALPHA ANDROST 2 ENE; 17 ALPHA[4 (4 TOLYL) 1H 1,2,3 TRIAZOL 1 YL] 5 ALPHA ANDROST 2 ENE; 17 BETA ESTRADIOL 3 BENZYL ETHER 17 TOSYLATE; 3 BENZYLOXY 17 ALPHA[(4 CYCLOHEXYL 1H 1,2,3 TRIAZOL 1 YL)]ESTRA 1,3,5 (10)TRIENE; 3 BENZYLOXY 17 ALPHA[(4 CYCLOPENTYL 1H 1,2,3 TRIAZOL 1 YL)]ESTRA 1,3,5 (10)TRIENE; 3 BENZYLOXY 17 ALPHA[(4 CYCLOPROPYL 1H 1,2,3 TRIAZOL 1 YL)]ESTRA 1,3,5 (10)TRIENE; 3 BENZYLOXY 17 ALPHA[4 (4 ETHYLPHENYL) 1H 1,2,3 TRIAZOL 1 YL]ESTRA 1,3,5 (10)TRIENE; 3 BENZYLOXY 17 ALPHA[4 (4 FLUOROPHENYL) 1H 1,2,3 TRIAZOL 1 YL]ESTRA 1,3,5 (10)TRIENE; 3 BENZYLOXY 17 ALPHA[4 (4 METHOXYPHENYL) 1H 1,2,3 TRIAZOL 1 YL]ESTRA 1,3,5 (10)TRIENE; 3 BENZYLOXY 17 ALPHA[4 (4 PROPYLPHENYL) 1H 1,2,3 TRIAZOL 1 YL]ESTRA 1,3,5 (10)TRIENE; 3 BENZYLOXY 17 ALPHA[4 (4 TERT BUTYLPHENYL) 1H 1,2,3 TRIAZOL 1 YL]ESTRA 1,3,5 (10)TRIENE; 3 BENZYLOXY 17 ALPHA[4 (4 TOLYL) 1H 1,2,3 TRIAZOL 1 YL]ESTRA 1,3,5 (10)TRIENE; 3 BENZYLOXYESTRA 1,3,5 (10)TRIENE 17 ALPHA AZIDE; 7 ALPHA[(4 CYCLOPENTYL 1H 1,2,3 TRIAZOL 1 YL)] 5 ALPHA ANDROST 2 ENE; ALKYNE; AZIDE; COPPER; TETRAZOLIUM; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CELL STRAIN; CELL STRAIN A431; CELL STRAIN MCF 7; CONTROLLED STUDY; CYCLOADDITION; CYTOTOXICITY TEST; HELA CELL; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IN VITRO STUDY; STEROIDOGENESIS;

ALKYNES; AZIDES; CATALYSIS; CELL LINE, TUMOR; CELL PROLIFERATION; HELA CELLS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; STEROIDS; TRIAZOLES;

EID: 79960445267     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2011.05.002     Document Type: Article

References (25)

1. 17,20-lyase Steroids 74 2009 1025 1032
2. 17,20-lyase Steroids 71 2006 809 816 (Pubitemid 44062604)
3. É. Frank, Z. Mucsi, M. Szécsi, I. Zupkó, J. Wölfling, and Gy. Schneider Intramolecular approach to some new D-ring-fused steroidal isoxazolidines by 1,3-dipolar cycloaddition: synthesis, theoretical and in vitro pharmacological studies New J Chem 34 2010 2671 2681
4. J. Wölfling, L. Hackler, E. Mernyák, G. Schneider, I. Tóth, and M. Szécsi Stereoselective synthesis of some steroidal tetrahydrooxazin-2-ones, as novel presumed inhibitors of human 5α-reductase Steroids 69 2004 451 460 (Pubitemid 38891798)
5. 3-catalyzed intramolecular [3 + 2] cycloadditions of olefinic phenylhydrazones J Am Chem Soc 131 2009 3894 3904
6. M.J. Genin, D.A. Allwine, D.J. Anderson, M.R. Barbachyn, D.E. Emmert, and S.A. Garmon 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 43 2000 953 970 (Pubitemid 30152301)
7. D.R. Buckle, C.J. Rockell, H. Smith, and B.A. Spicer 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 29 1986 2262 2267 (Pubitemid 17182304)
8. R. Alvarez, S. Velazquez, A. San-Felix, S. Aquaro, E. De Clercq, and C.F. Perno 1,2,3-Triazole-[2′,5′-bis-O-(tert-butyldimethylsilyl)-beta-d- ribofuranosyl]-3′-spiro-5″-(4″-amino-1″, 2″-oxathiole 2″,2″-dioxide) (TSAO) analogues: synthesis and anti-HIV-1 activity J Med Chem 37 1994 4185 4194 (Pubitemid 24379707)
9. M.N. Sakač, A.R. Gaković, J.J. Csanádi, E.A. Djurendić, O. Klisurić, and V. Kojić An intramolecular one-pot synthesis of steroidal triazoles via 1,3-dipolar cycloadditions of in situ generated diazo compounds Tetrahedron Lett 50 2009 4107 4109
10. 16 steroids; inhibitions of 17α-hydroxylase/17,20-lyase (17α-lyase) Bioorg Med Chem Lett 6 1996 2777 2782 (Pubitemid 26387265)
11. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angew Chem Int Ed 41 2002 2596 2599 (Pubitemid 34803480)
12. C.W. Tornøe, C. Christensen, and M. Meldal 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 67 2002 3057 3064 (Pubitemid 34457265)
13. M. Meldal, and C.W. Tornøe Cu-catalyzed azide-alkyne cycloaddition Chem Rev 108 2008 2952 3015
14. C.D. Hein, X.M. Liu, and D. Wang Click chemistry, a powerful tool for pharmaceutical sciences Pharm Res 25 2008 2216 2230
15. I-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective Eur J Org Chem 2006 51 68
16. H.C. Kolb, M.G. Finn, and K.B. Sharpless Click chemistry: diverse chemical function from a few good reactions Angew Chem Int Ed 40 2001 2005 2021 (Pubitemid 33644307)
17. 2+ ion and their logic gate behaviour Tetrahedron Lett 50 2009 5842 5845
18. A.H. Banday, M. Verma, S. Srikakulam, B.D. Gupta, and H.M. Sampath Kumar D-ring substituted 1,2,3-triazolyl 20-keto pregnenanes as potential anticancer agents: synthesis and biological evaluation Steroids 75 2010 801 804
19. A.O. Mueck, and H. Seeger 2-Metoxyestradiol-biology and mechanism of action Steroids 75 2010 625 631
20. P. Verdier-Pinard, Z. Wang, A.K. Mohanakrishnan, M. Cushman, and E. Hamel A steroid derivative with paclitaxel-like effects on tubulin polymerization Mol Pharmacol 57 2000 568 575 (Pubitemid 30140888)
21. R. Minorics, T. Szekeres, G. Krupitza, P. Saiko, B. Giessrigl, and J. Wölfling Antiproliferative effects of some novel synthetic solanidine analogs on HL-60 human leukemia cells in vitro Steroids 76 2011 156 162
22. A.G. Fragkaki, Y.S. Angelis, M. Koupparis, A. Tsantili-Kakoulidou, G. Kokotos, and C. Georgakopoulos Structural characteristics of anabolic androgenic steroids contributing to binding to the androgen receptor and to their anabolic and androgenic activities. Applied modifications in the steroidal structure Steroids 74 2009 172 197
23. G.M. Anstead, K.E. Carlson, and J.A. Katzenellenbogen The estradiol pharmacophore: ligand structure-estrogen receptor binding affinity relationships and a model fort he receptor binding site Steroids 62 1997 268 303 (Pubitemid 27114399)
24. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J Immunol Methods 65 1983 55 63 (Pubitemid 14203433)
25. M.I. Merlani, LSh. Aminarashvili, E.P. Kemertelidze, K. Papadopoulos, and E. Yannakopoulou Synthesis of 17α-amino-5α-androst-2-ene from epiandrosterone Chem Nat Compd 42 2006 313 315