Synthesis of ferrocene-labeled steroids via copper-catalyzed azide-alkyne cycloaddition. Reactivity difference between 2β-, 6β- and 16β-azido-androstanes

Steroids

Volumn 77, Issue 7, 2012, Pages 738-744

  Fehér, Klaudia ^a   Balogh, János ^a   Csók, Zsolt ^b   Kégl, Tamás ^b   Kollár, László ^b   Skoda Földes, Rita ^a  

^a UNIVERSITY OF PANNONIA   (Hungary)

^b UNIVERSITY OF PÉCS   (Hungary)

Author keywords

Azidosteroid; Copper; Cycloaddition; Ferrocene; Triazole

Indexed keywords

(E) N (PROP 2 YNYL) 2 ETHOXYCARBONYL 3 FERROCENYL 2 PROPENAMIDE; 1 OCTYNE; 16 BETA (4 ((E) ETHYL 3 FERROCENYLACRYLATE 2 METHYLCARBAMOYL) 1,2,3 TRIAZOL 1YL) 17 HYDROXY 5 ANDROSTANE; 16 BETA (4 (ACETOXY METHYL) 1,2,3 TRIAZOL 1 YL) 17 HYDROXY 5 ANDROSTANE; 16 BETA (4 FERROCENYL 1,2,3 TRIAZOL 1 YL) 17 HYDROXY 5 ANDROSTANE; 16 BETA (4 HEXYL 1,2,3 TRIAZOL 1 YL) 17 HYDROXY 5 ANDROSTANE; 16 BETA AZIDO 17 ALPHA HYDROXY 5 ALPHA ANDROSTANE; 16 BETA AZIDO ANDROSTANE DERIVATIVE; 17 HYDROXY 16 BETA (4 (METHOXYCARBONYL) 1,2,3 TRIAZOL 1 YL) 5 ANDROSTANE; 17 HYDROXY 16 BETA (4 PHENYL 1,2,3 TRIAZOL 1 YL) 5 ANDROSTANE; 2 BETA (4 ((E) ETHYL 3 FERROCENYLACRYLATE 2 METHYLCARBAMOYL)) 1,2,3 TRIAZOL 1 YL) 3 HYDROXY 5 ANDROSTAN 17 ONE; 2 BETA (4 (ACETOXY METHYL) 1,2,3 TRIAZOL 1 YL) 3 HYDROXY 5 ANDROSTAN 17 ONE; 2 BETA (4 FERROCENYL 1,2,3 TRIAZOL 1 YL) 3 HYDROXY 5 ANDROSTANE 17 ONE; 2 BETA (4 HEXYL 1,2,3 TRIAZOL 1 YL) 3 HYDROXY 5 ANDROSTAN 17 ONE; 2 BETA AZIDO 3 ALPHA HYDROXY 5 ALPHA ANDROSTAN 17 ONE; 2 BETA AZIDO ANDROSTANE DERIVATIVE; 3 BETA 5 DIHYDROXY 6 BETA (4 METHOXYCARBONYL 1,2,3 TRIAZOL 1 YL) ANDROSTAN 17 ONE; 3 HYDROXY 2 BETA (4 METHOXYCARBONYL 1,2,3 TRIAZOL 1 YL) 5 ANDROSTAN 17 ONE; 3 HYDROXY 2 BETA (4 PHENYL 1,2,3 TRIAZOL 1 YL) 5 ANDROSTAN 17 ONE; 6 BETA (4 ((E) ETHYL 3 FERROCENYLACRYLATE 2 METHYLCARBAMOYL) 1,2,3 TRIAZOL 1 YL) 3,5 DIHYDROXY ANDROSTAN 17 ONE; 6 BETA AZIDO 5 ALPHA 3 BETA DIHYDROXYANDROSTAN 17 ONE; 6 BETA AZIDO ANDROSTANE DERIVATIVE; ALKYNE; ANDROSTANE DERIVATIVE; AZIDE; COPPER; FERROCENE; METHYLPROPIOLATE; PHENYLACETYLENE; PROPARGYLACETATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; SYNTHESIS;

ALKYNES; ANDROSTANES; AZIDES; CATALYSIS; COPPER; CYCLIZATION; FERROUS COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROPHOTOMETRY, INFRARED; STEROIDS;

EID: 84861199309     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2012.04.005     Document Type: Article

References (29)

1. D.R. van Staveren, and N. Metzler-Nolte Bioorganometallic chemistry of ferrocene Chem Rev 104 2004 5931 5985 (Pubitemid 40034049)
2. M.F.R. Fouda, M.M. Abd-Elzaher, R.A. Abdelsamaia, and A.A. Labib On the medicinal chemistry of ferrocene Appl Organomet Chem 21 2007 613 625 (Pubitemid 47122081)
3. D. Osella, C. Nervi, F. Galeotti, G. Cavigiolio, A. Vessieres, and G. Jaouen The ferrocenylethynyl unit: A stable hormone tag Helv Chim Acta 84 2001 3289 3298 (Pubitemid 33151714)
4. J.E. Hein, and V.V. Fokin Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides Chem Soc Rev 39 2010 1302 1315
5. J. Balogh, and R. Skoda-Földesm Transition-metal catalyzed reactions in the synthesis of ferrocene derivatives E.S. Phillips, Ferrocenes: Compounds, Properties and Applications 2011 Nova Publishers 107 148
6. For some recent reviews on click chemistry involving biologically active compounds, see: C.D. Hein, X.M. Liu, and D. Wang Click chemistry, a powerful tool for pharmaceutical sciences Pharm Res 25 2008 2216 2230
7. G.C. Tron, T. Pirali, R.A. Billington, P.L. Canonico, G. Sorba, and A.A. Genazzini Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes Med Res Rev 28 2008 278 308 (Pubitemid 351281190)
8. M.D. Best Click chemistry and bioorthogonal reactions: unprecedented selectivity in the labeling of biological molecules Biochemistry 48 2009 6571 6584
9. F. Amblard, J.H. Cho, and R.F. Schinazi Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide and oligonucleotide chemistry Chem Rev 109 2009 4207 4220
10. S.K. Mamidyala, and M.G. Finn In situ click chemistry: probing the binding landscapes of biological molecules Chem Soc Rev 39 2010 1252 1261
11. V.V. Rostovtsev, L.K. 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. H.Y. Kim, J. Sohn, G.T. Wijewickrama, P. Edirisinghe, T. Gherezghiher, M. Hemachandra, P.Y. Lu, R.E. Chandrasena, M.E. Molloy, D.A. Tonetti, and G.R. Thatcher Click synthesis of estradiol-cyclodextrin conjugates as cell compartment selective estrogens J Bioorg Med Chem 18 2010 809 821
13. J.M. Holub, H. Jang, and K. Kirshenbaum Clickity-click: highly functionalized peptoid oligomers generated by sequential conjugation reactions on solid-phase support Org Biomol Chem 4 2006 1497 1502 (Pubitemid 43797654)
14. J.M. Holub, M.J. Garabedian, and K. Kirshenbaum Peptoids on steroids: precise multivalent estradiol-peptidomimetic conjugates generated via azide-alkyne [3 + 2] cycloaddition reactions QSAR Comb Sci 26 2007 1175 1180
15. N.V. Sokolova, G.V. Latyshev, N.V. Lukashev, and V.G. Nenajdenko Design and synthesis of bile acid-peptide conjugates linked via triazole moiety Org Biomol Chem 9 2011 4921 4926
16. N.S. Vatmurge, B.G. Hazra, V.S. Pore, F. Shirazi, P.S. Chavan, and M.V. Deshpande Synthesis and antimicrobial activity of β-lactam-bile acid conjugates linked via triazole Bioorg Med Chem Lett 18 2008 2043 2047 (Pubitemid 351380871)
17. Z. Li, and R. Bittmann Synthesis and special properties of cholesterol- and FTY720-containing boron dipyrromethene dyes J Org Chem 72 2007 8376 8382 (Pubitemid 350012850)
18. A. Banday, M. Verma, S. Srikakulam, B.D. Gupta, and H.M.S. 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. E. Szánti-Pintér, J. Balogh, Z. Csók, L. Kollár, Á. Gömöry, and R. Skoda-Földes Synthesis of steroid-ferrocene conjugates of steroidal 17-carboxamides via a palladium-catalyzed aminocarbonylation -Copper-catalyzed azide-alkyne cycloaddition reaction sequence Steroids 26 2011 1377 1382
20. K. Pérez-Labrada, I. Brouard, C. Morera, F. Estévez, and J. Bermejo ′Click′ synthesis of Triazole-based spirostan saponins Tetrahedron 67 2011 7713 7727
21. Z. Kádár, D. Kovács, É. Frank, G. Schneider, J. Huber, I. Zupkó, T. Bartók, and J. Wölfling Synthesis and in vitro antiproliferative activity of novel androst-5-ene triazolyl and tetrazolyl derivatives Molecules 16 2011 4786 4806
22. R.C.N.R. Corrales, N.B. de Souza, L.S. Pinheiro, C. Abramo, E.S. Coimbra, and A.D. Da Silva Thiopurine derivatives containing triazole and steroid: synthesis, antimalarial and antileishmanial activities Biomed Pharmacother 65 2011 198 203
23. A.M. Deobald, L.R.S. Camargo, D. Alves, J. Zukerman-Schpector, A.G. Correa, and M.W. Paixāo Click Chemistry: An efficient synthesis of heterocycles substituted with steroids, saponins and digitalis analogues Synthesis 2011 4003 4010
24. É. Frank, J. Molnár, I. Zupkó, Z. Kádár, and J. Wölfling Synthesis of novel steroidal 17α-triazolyl derivatives via Cu(I)-catalyzed azide-alkyne cycloaddition, and an evaluation of their cytotoxic activity in vitro Steroids 76 2011 1141 1148
25. J.P. Perdew, K. Burke, and M. Ernzerhof Generalized gradient approximation made simple Phys Rev Lett 77 1996 3865 3868 (Pubitemid 126631804)
26. W.J. Hehre, R. Ditchfield, and J.A. Pople Self-consistent molecular orbital methods. XII. Further extensions of gaussian-type basis sets for use in molecular orbital studies of organic molecules J Chem Phys 56 1972 2257 2261
27. Granovsky AA, Firefly version 7.1.G, http://classic.chem.msu.su/gran/ firefly/index.html.
28. B. Schönecker, and K. Ponsold Steroids.40. 16,17-Azidoalcohols and 16,17-aminoalcohols of estra-1,3,5(10)-trien-3-methylether Tetrahedron 31 1975 1113 1118
29. J. Balogh, T. Kégl, L. Párkányi, L. Kollár, F. Ungváry, and R. Skoda-Földes Synthesis of (E)-2-(1- ferrocenylmethylidene)malonic acid derivatives by a cobalt-catalyzed domino reaction of ethyl diazoacetate, carbon monoxide and ferrocenylimines J Organomet Chem 696 2011 1394 1403