PUBLICATIONS
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I.K. Sibilska-Kaminski, R.R. Sicinski, L.A.Plum, H.F. DeLuca. Synthesis and Biological Activity of 2,22-Dimethylene Analogues of 19-Norcalcitriol and Related Compounds. J. Med. Chem. 2020, 63, 7355-7368.
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A. Fabisiak, P. Brzemiński, K. Berkowska, L. Rarova, E. Marcinkowska, R.R. Siciński. Design, synthesis and biological evaluation of novel 2-alkylidene 19-norcalcitriol analogs. Bioorg. Chem. 2020, 101, 104013.
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T.-K. Kim, V. Atigadda, P. Brzemiński, A. Fabisiak, E.K.Y. Tang, R.C. Tuckey, A.T. Slominski. Detection of 7-dehydrocholesterol and vitamin D3 derivatives in honey. Molecules, 2020, 25, 2583.
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P. Brzemiński, A. Fabisiak, K. Berkowska, L. Rarova, E. Marcinkowska, R.R. Siciński. Synthesis of Gemini analogs of 19-norcalcitriol and their platinum(II) complexes. Bioorg. Chem. 2020, 100, 103883.
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B. Seroka, Z. Łotowski, A. Hryniewicka, L. Rarova, R.R. Siciński, A.M. Tomkiel, J.W. Morzycki. Synthesis of new cisplatin derivatives from bile acids. Molecules, 2020, 25, 655.
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A. Zep, K. Pruszkowska, Ł. Dobrzycki, K. Sęktas, P. Szałański, P.H. Marek, M.K. Cyrański, R.R. Siciński. Cholesterol based photo-switchable mesogenic dimers. Strongly bent molecules versus intercalated structure. CrystEngComm, 2019, 21, 2779-2789
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M. Misiak, W. Koźmiński, J. Wójcik, R.R. Siciński, J. Wicha. Structural analysis of 25-hydroxycholesterol stereoisomers differing in configuration in position 17 and 20, by three-dimensional NMR spectra. Steroids, 2019, 143, 49-52
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A. Fabisiak, P. Brzemiński, K. Berkowska, E. Marcinkowska, R.R. Siciński. Synthesis of 19-norcalcitriol analogs with pegylated alkylidene chains at C-2. J. Steroid Biochem. Mol. Biol. 2019, 185, 251-255.
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A. Fabisiak, P. Brzemiński, K. Berkowska, E. Marcinkowska, R.R. Siciński. Synthesis of 19-norcalcitriol analogs with alkylidene moieties at C-2 based on succinic acid and L-methionine. J. Steroid Biochem. Mol. Biol. 2018, 177, 235-239
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P. Brzemiński, A. Fabisiak, K. Sęktas, K. Berkowska, E. Marcinkowska, R.R. Siciński. Synthesis of 19-norcalcitriol analogs with elongated side chain . J. Steroid Biochem. Mol. Biol. 2018, 177, 231-234
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M. Szybiński, P.Brzemiński, A. Fabisiak, K. Berkowska, E. Marcinkowska, R.R. Siciński. Seco-B-ring steroidal dienynes with aromatic D ring: Design, synthesis and biological evaluation. Int. J. Mol. Sci. 2017, 18, 2162
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M. Szybiński, K. Sęktas, R.R. Siciński, L.A.Plum, J. Frelek, H.F. DeLuca. Design, synthesis and biological properties of seco-D-ring modified 1α,25-dihydroxyvitamin D3 analogues. J. Steroid Biochem. Mol. Biol. 2017, 171, 144-154.
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M. Szybiński, K. Sokołowska, R.R. Siciński, L.A. Plum, H.F. DeLuca. D-seco-Vitamin D analogs having reversed configurations at C-13 and C-14: Synthesis, docking studies and biological evaluation. J. Steroid Biochem. Mol. Biol. 2017, 173, 57-63.
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U. Kulesza, L. A. Plum, H. F. DeLuca, A. Mouriño, R. R. Siciński. A new suprasterol by photochemical reaction of 1α ,25-dihydroxy-9-methylene-19-norvitamin D3. Org. Biomol. Chem. 2016,
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I. K. Sibilska, M. Szybiński, R. R. Siciński, L. A. Plum, H. F. DeLuca. Synthesis and biological activity of 2-methylene analogues of calcitriol and related compounds. J. Med. Chem. 2015, 58, 9653-9662.
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U. Kulesza, L. A. Plum, H. F. DeLuca, A. Mouriño, R. R. Siciński. Novel 9-alkyl- and 9-alkylidene-substituted 1α,25-dihydroxyvitamin D3 analogues: Synthesis and biological examinations. J. Med. Chem. 2015, 58, 6237-6247.
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K. Sokołowska, D. Carballa, S. Seoane, R. Perez-Fernandez, A. Mouriño, R. R. Siciński. Synthesis and biological activity of two C-7 methyl analogues of vitamin D. J. Org. Chem. 2015, 80, 165-173.
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I. K. Sibilska, R. R. Siciński, J. T. Ochalek, L. A. Plum, H. F. DeLuca. Synthesis and biological activity of 25-hydroxy-2-methylene-vitamin D3 analogues monohydroxylated in the A-ring. J . Med. Chem. 2014, 57, 8319-8331.
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K. Sokołowska, R. R. Siciński. The unusual course of the reaction of allyl phosphine oxides with the Grundmann ketone. Synthetic Communications 2014, 44, 2943-2954.
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K. Sokołowska, R. R. Siciński. Synthesis of novel vitamin D3 analog with an additional ring annulated to A and seco-B rings. Steroids 2014, 87, 67-75.
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A. Głębocka, R. R. Siciński, L. A. Plum, H. F. DeLuca. Ring-A-seco analogs of 1α ,25-dihydroxy-19-norvitamin D3.
J. Steroid Biochem. Mol. Biol. 2013, 136, 39-43.
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K. Sokołowska, R. R. Siciński, A. Mouriño, L. A. Plum, H. F. DeLuca. Synthesis and biological evaluation of novel 6-substituted analogs of 1α ,25-dihydroxy-19-norvitamin D3. J. Steroid Biochem. Mol. Biol. 2013, 136, 30-33.
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U. Kulesza, A. Mouriño, L. A. Plum, H. F. DeLuca, R. R. Siciński. Synthesis of novel 19-norvitamin D3 analogs with unnatural triene system. J. Steroid Biochem. Mol. Biol. 2013, 136, 23-26.
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I. K. Sibilska, R. R. Siciński, L. A. Plum, H. F. DeLuca. Synthesis and biological activity of 25-hydroxy-2-methylene-vitamin D3 compounds. J. Steroid Biochem. Mol. Biol. 2013, 136, 17-22.
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I. K. Sibilska, M. Szybiński, R. R. Siciński, L. A. Plum, H.F. DeLuca. Highly potent 2-methylene analogs of 1α ,25-dihydroxyvitamin D3: Synthesis and biological evaluation. J. Steroid Biochem. Mol. Biol. 2013, 136, 9-13.
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U. Kulesza, R. Sigüeiro, A. Mouriño, L. A. Plum, H. F. DeLuca, R. R. Siciński. Synthesis of 9-alkylated calcitriol and two 1α ,25-dihydroxy-9-methylene-10.19-dihydrovitamin D3 analogues with a non-natural triene system by thermal sigmatropic rearrangements. J. Org. Chem. 2013, 78, 1444-1450.
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A. Flores, R. R. Siciński, P. Grzywacz, J. B. Thoden, L. A. Plum, M. Clagett-Dame, H. F. DeLuca. A 20S combined with a 22R configuration markedly increases both in vivo and in vitro biological activity of 1α ,25-dihydroxy-22-methyl-2-methylene-19-norvitamin D3. J. Med. Chem. 2012, 55, 4352-4366.
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K. Plońska-Ocypa, I. Sibilska, R. R. Siciński, W. Sicińska, L. A. Plum, H. F. DeLuca, 13,13-Dimethyl-des-C,D-analogues of (20S)-1α ,25-dihydroxy-2-methylene-19-norvitamin D3 (2MD). Bioorg. Med. Chem. 2011, 19, 7205-7220.
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A. Głębocka, R. R. Siciński, L. A. Plum, H. F. DeLuca, Synthesis and biological activity of 2-(3'-hydroxypropylidene)-1α -hydroxy-19-norvitamin D analogs with shortened alkyl side chain. J. Med. Chem. 2011, 54, 6832-6842.
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I. Sibilska, K. M. Barycka, R. R. Siciński, L. A. Plum, H. F. DeLuca, 1-Desoxy analog of 2MD: Synthesis and biological activity of (20S)-25-hydroxy-2-methylene-19-norvitamin D3. J. Steroid Biochem. Mol. Biol. 2010, 121, 51-55.
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A. Głębocka, R. R. Siciński, L. A. Plum, H. F. DeLuca, New 1α ,25-dihydroxy-19-norvitamin D3 analogs with frozen A-ring conformation. J. Steroid Biochem. Mol. Biol. 2010, 121, 46-50.
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K. Sokołowska, A. Mouriño, R. R. Siciński, L. A. Plum, H. F. DeLuca, Synthesis and biological evaluation of 6-alkylated analogs of 1α ,25-dihydroxyvitamin D3. J. Steroid Biochem. Mol. Biol. 2010, 121, 29-33.
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R. Barycki, R. R. Siciński, L. A. Plum, P. Grzywacz, M. Clagett-Dame, H. F. DeLuca. Removal of the 20-methyl group from 2-methylene-19-nor-(20S)-1α ,25-dihydroxyvitamin D3 (2MD) selectively eliminates bone calcium mobilization activity. Bioorg. Med. Chem. 2009, 17, 7658-7669.
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A. Głębocka, K. Sokołowska, R. R. Siciński, L. A. Plum, H. F. DeLuca. New 1α ,25-dihydroxy-19-norvitamin D3 compounds constrained in a single A-ring conformation: synthesis of the analogues by ring-closing metathesis route and their biological evaluation. J. Med. Chem. 2009, 52, 3496-3504.
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K. Płońska-Ocypa, R. R. Siciński, L. A. Plum, P. Grzywacz, J. Frelek, M. Clagett-Dame, H. F. DeLuca. 13-Methyl-substituted des-C,D-analogs of (20S)-1α ,25-dihydroxy-2-methylene-19-norvitamin D3 (2MD): synthesis and biological evaluation. Bioorg. Med. Chem. 2009, 17, 1747-1763.
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R. R. Siciński, A. Głębocka, L. A. Plum, H. F. DeLuca. Design, synthesis, and biological evaluation of a 1α ,25-dihydroxy-19-norvitamin D3 analogue with a frozen A-ring conformation. J. Med. Chem. 2007, 50, 6154-6164.
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A. Głębocka, R. R. Siciński, L. A. Plum, H. F. DeLuca. 2-(3'-Hydroxypropylidene)-1α-hydroxy-19-norvitamin D compounds with truncated side chains. J. Steroid Biochem. Mol. Biol. 2007, 103, 310-315.
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E. Slatopolsky, J. L. Finch, A. J. Brown, C. S. Ritter, M. Mizobuchi, L. A. Plum, M. Clagett-Dame, R. R. Siciński, H. F. DeLuca. Effect of 2-methylene-19-nor-(20S)-1α-hydroxy-bishomopregnacalciferol (2MbisP), an analog of vitamin D, on secondary hyperparathyroidism. J. Bone Min. Res. 2007, 22, 686-694.
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K. Płońska-Ocypa, P. Grzywacz, R. R. Siciński, L. A. Plum, H. F. DeLuca. Synthesis and biological evaluation of a des-C,D-analog of 2-methylene-19-nor-1α,25-(OH)2D3. J. Steroid Biochem. Mol. Biol. 2007, 103, 298-304.
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P. Grzywacz, L. A. Plum, R. R. Siciński, M. Clagett-Dame, H. F. DeLuca. Methyl substitution of the 25-hydroxy group on 2-methylene-19-nor-1α,25-dihydroxyvitamin D3 (2MD) reduces potency but allows bone selectivity. Arch. Biochem. Biophys. 2007, 460, 274-284.
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R. R. Siciński, A. Głębocka, L. A. Plum, H. F. DeLuca. An analog of 1α,25-dihydroxy-19-norvitamin D3 with the 1α-hydroxy group fixed in the axial position lacks biological activity in vitro. J. Steroid Biochem. Mol. Biol. 2007, 103, 293-297.
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R. R. Siciński. 2-Alkylidene analogs of 19-nor-1α,25-(OH)2D3: synthesis and biological activity. Pol. J. Chem. 2006, 80, 573-585.
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P. Ł. Szoka, R. R. Siciński. 19-Methyl analogs of vitamin D3: synthesis and structure elucidation by 1H NMR. Pol. J. Chem. 2006, 80, 1155-1168.
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A. Głębocka, R. R. Siciński, L. A. Plum, M. Clagett-Dame, H. F. DeLuca. New 2-alkylidene 1α,25-dihydroxy-19-norvitamin D3 analogues of high intestinal activity: synthesis and biological evaluation of 2-(3'-alkoxypropylidene)- and 2-(3'-hydroxypropylidene) derivatives. J. Med. Chem. 2006, 49, 2909-2920.
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A. Głębocka, R. R. Siciński, H. F. DeLuca. New derivative of 1α,25-dihydroxy-19-norvitamin D3 with 3'-alkoxypropylidene moiety at C-2: synthesis, biological activity and conformational analysis. J. Steroid Biochem. Mol. Biol. 2004, 89-90, 25-30.
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P. Grzywacz, L. A. Plum, W. Sicińska, R. R. Siciński, J. M. Prahl, H. F. DeLuca. 2-Methylene analogs of 1α-hydroxy-19-norvitamin D3: synthesis, biological activities and docking to the ligand binding domain of the rat vitamin D receptor. J. Steroid Biochem. Mol. Biol. 2004, 89-90, 13-17.
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L. A. Plum, J. M. Prahl, X. Ma, R. R. Siciński, S. Gowlugari, M. Clagett-Dame, H. F. DeLuca. Biologically active noncalcemic analogs of 1α,25-dihydroxyvitamin D with an abbreviated side chain containing no hydroxyl. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 6900-6904.
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P. Grzywacz, R. R. Siciński, H. F. DeLuca. A concise synthesis of an AHR endogenous ligand with the indolecarbonyl-thiazole skeleton. Heterocycles 2003, 60, 1219-1224.
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O. Dmitrenko, R. D. Bach, R. R. Siciński, W. Reischl. Computational insight on the effect of C(19)-substituents on [1,7]-H shift in previtamin D molecule. Theor. Chem. Acc. 2003, 109, 170-175.
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M. Song, M. Clagett-Dame, R. E. Peterson, M. E. Hahn, W. M. Westler, R. R. Siciński, H. F. DeLuca. A ligand for the aryl hydrocarbon receptor isolated from lung. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 14694-14699.
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R. R. Siciński, P. Rotkiewicz, A. Koliński, W. Sicińska, J. M. Prahl, C. M. Smith, H. F. DeLuca. 2-Ethyl and 2-ethylidene analogues of 1α,25-dihydroxy-19-norvitamin D3: synthesis, conformational analysis, biological activities, and docking to the modeled rVDR ligand binding domain. J. Med. Chem. 2002, 45, 3366-3380.
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R. R. Siciński, J. M. Prahl, C. M. Smith, H. F. DeLuca. New highly calcemic 1α,25-dihydroxy-19-norvitamin D3 compounds with modified side chain: 26,27-dihomo- and 26,27-dimethylene analogs in 20S-series. Steroids 2002, 67, 247-256.
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P. Tarnowski, P. Piątek, R. R. Siciński, J. Jurczak. Synthesis of interlocked diazacoronand system. Supramol. Chem. 2000, 12, 217-219.
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R. R. Siciński, H. F. DeLuca. Synthesis and biological activity of 22-iodo- and (E)-20(22)-dehydro analogues of 1α,25-dihydroxyvitamin D3. Bioorg. Med. Chem. 1999, 7, 2877-2889.
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R. R. Siciński, J. M. Prahl, C. M. Smith, H. F. DeLuca. New 1α,25-dihydroxy-19-norvitamin D3 compounds of high biological activity: synthesis and biological evaluation of 2-hydroxymethyl, 2-methyl and 2-methylene analogs. J. Med. Chem. 1998, 41, 4662-4674.
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P. Grzegorzewski, I. Koładkiewicz, J. W. Morzycki, R. R. Siciński. Synthesis and photochemical transformations of 19-phenylsulfonyl provitamin D analogue. Collect. Czech. Chem. Commun. 1998, 63, 1597-1612.
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X. Jia, R. R. Siciński, D. M. Wellik, P. Tadikonda, H. K. Schnoes, H. F. DeLuca. Identification of a new all-trans-retinol metabolite produced through a new retinol metabolic pathway. Biochemistry 1998, 37, 5974-5980.
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Z. Łotowski, J. W. Morzycki, R. R. Siciński. Preparation of 7 - and 7 -methylcholestane derivatives by kinetic separation of the diastereomeric mixture. Tetrahedron: Asymm. 1998, 9, 1627-1633.
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R. R. Siciński, K. L. Perlman, J. Prahl, C. Smith, H. F. DeLuca. Synthesis and biological activity of 1α,25-dihydroxy-18-norvitamin D3 and 1 ,25-dihydroxy-18,19-dinorvitamin D3. J. Med. Chem. 1996, 39, 4497-4506.
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K. L. Perlman, R. R. Siciński, H. M. Darwish, H. F. DeLuca. Synthesis of novel 20-oxo-pregnacalciferol analogs with binding affinity to the progesterone receptor. Bioorg. Med. Chem. Lett. 1995, 5, 2695-2700.
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R. R. Siciński. Synthesis and photoisomerization of provitamin D analog with 11 ,19-oxide bridge. Can. J. Chem. 1995, 73, 865-872.
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R. R. Siciński, H. F. DeLuca. Synthesis of 6,7-diaza-19-norvitamin D compounds. Bioorg. Med. Chem. Lett. 1995, 5, 899-904.
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R. R. Siciński, H. F. DeLuca. Ruthenium tetroxide oxidation of Grundmann's ketone derived from vitamin D3. Bioorg. Med. Chem. Lett. 1995, 5, 159-162.
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R. R. Siciński, K. L. Perlman, H. F. DeLuca. Synthesis and biological activity of 2-hydroxy and 2-alkoxy analogs of 1α,25-dihydroxy-19-norvitamin D3. J. Med. Chem. 1994, 37, 3730-3738.
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R. R. Siciński, H. F. DeLuca. Synthesis, conformational analysis, and biological activity of the 1α,25-dihydroxy-10,19-dihydrovitamin D3 isomers. Bioorg. Chem. 1994, 22, 150-171.
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R. R. Siciński. Photochemical and thermal isomerizations of C-19 functionalized previtamin D analogs in the androstane series. Acta Chim. Hung. 1992, 129, 191-200.
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K. L. Perlman, R. R. Siciński, H. K. Schnoes, H. F. DeLuca. 1α,25-Dihydroxy-19-nor-vitamin D3, a novel vitamin D - related compound with potential therapeutic activity. Tetrahedron Lett. 1990, 31, 1823-1824.
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A. Kutner, K. L. Perlman, A. Lago, R. R. Siciński, H. K. Schnoes, H. F. DeLuca. Novel convergent synthesis of side chain modified analogues of 1α,25-dihydroxycholecalciferol and 1 ,25-dihydroxyergocalciferol. J. Org. Chem. 1988, 53, 3450-3457.
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H. F. DeLuca, M. Nakada, Y. Tanaka, R. R. Siciński, M. Phelps. The plasma binding protein for vitamin D is a site of discrimination against vitamin D2 compounds by the chick. Biochim. Biophys. Acta 1988, 965, 16-21
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H. F. DeLuca, R. R. Siciński, Y. Tanaka, P. H. Stern, C. M. Smith. Biological activity of 1α,25-dihydroxyvitamin D2 and 24-epi-1α,25-dihydroxyvitamin D2. Am. J. Physiol. 1988, 254, E402-E-406.
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R. R. Siciński, W. J. Szczepek. Homoallylic rearrangement in the peracid oxidation of 19-iodo-5-androsten derivative. Tetrahedron Lett. 1987, 28, 5729-5732.
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A. Kutner, K. L. Perlman, R. R. Siciński, M. E. Phelps, H. K. Schnoes, H. F. DeLuca. Vitamin D C-22 aldehydes. New key intermediates for the synthesis of side chain modified vitamin D analogues. Tetrahedron Lett. 1987, 28, 6129-6132.
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R. R. Siciński, H. F. DeLuca, H. K. Schnoes, Y. Tanaka, C. M. Smith. 22-Unsaturated analogs of vitamin D3 and their C(1)-hydroxylated derivatives. Bioorg. Chem. 1987, 15, 152-166.
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R. R. Siciński, Y. Tanaka, M. Phelps, H. K. Schnoes, H. F. DeLuca. Synthesis of 25-hydroxy-[26,27-3H]vitamin D2, 1,25-dihydroxy-[26,27-3H]vitamin D2 and their (24R)-epimers. Analyt. Biochem. 1987, 161, 96-102.
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Y. Tanaka, R. R. Siciński, H. F. DeLuca, H. Sai, N. Ikekawa. Unique rearrangement of ergocalciferol side chain in vitro: production of a biologically highly active homologue of 1α,25-dihydroxyvitamin D3. Biochemistry 1986, 25, 5512-5518.
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J. W. Morzycki, R. R. Siciński. Synthesis of 6,7-diazacholestane derivatives. Acta Chim. Hung. 1985, 120, 239-246.
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R. R. Siciński, Y. Tanaka, H. K. Schnoes, H. F. DeLuca. Synthesis of 1α,25-dihydroxyvitamin D2, its 24 epimer and related isomers, and their binding affinity for the 1α,25-dihydroxyvitamin D3 receptor. Bioorg. Chem. 1985, 13, 158-169.
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J. W. Morzycki, R. R. Siciński. Unusual reactions of 8 -cyano-6,7-diazacholesterol. Heterocycles 1984, 22, 2459-2462.
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J. R. Jaszczyński, R. R. Siciński, W. J. Rodewald. 19-Functionalized steroids. Part IV. Mixed acetals as selective protection in androsta-5,7-diene-3 ,17 ,19-triol derivatives synthesis. Pol. J. Chem. 1984, 58, 711-720.
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W. J. Rodewald, R. R. Siciński. 19-Functionalized steroids. Part V. Conversion of androsta-5,7-diene-3 ,17 ,19-triol derivatives into vitamin D analogs. Pol. J. Chem. 1983, 57, 1267-1274.
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J. J. Jagodziński, R. R. Siciński. The unusual course of the reaction of 3 -acetoxylanost-5-en-7-one with p-toluenesulphonylhydrazine. Tetrahedron Lett. 1982, 23, 1837-1840.
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J. J. Jagodziński, R. R. Siciński. Photoinduced cyclization of 3 -acetoxy-C(14a)-homo-B-norlanosta-8(14a),9(11)-diene as a route towards B(9a)-homo-C-norlanostane derivatives. Tetrahedron Lett. 1981, 22, 3901-3904.
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W. J. Rodewald, R. R. Siciński. 19-Functionalized steroids. Part III. Intramolecular oxidative cyclization of 6 -hydroxyandrostanes with lead tetraacetate. Pol. J. Chem. 1979, 53, 131-137.
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W. J. Rodewald, J. R. Jaszczyński, R. R. Siciński. 19-Functionalized steroids. Part II. Epimeric hemiacetal acetates as disubstitution products of 19-methyl group functionalization. Pol. J. Chem. 1978, 52, 715-719.
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W. J. Rodewald, J. R. Jaszczyński, R. R. Siciński. 19-Functionalized steroids. Part I. An improved synthesis of androst-5-ene-3 ,17 ,19-triol derivatives. Pol. J. Chem. 1978, 52, 501-509.