New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities
Tài liệu tham khảo
Suginome, 1990, Photoinduced molecular transformations. 107. A versatile substitution of a carbonyl group of steroidal ketones by a heteroatom. The synthesis of Aza-, Oxa-, Thia-, Selena-, and Tellurasteroids, J Org Chem, 55, 2170, 10.1021/jo00294a035
Tietze, 1998, Efficient synthesis of a novel estrone–talaromycin hybrid natural product, Angew Chem Int Ed, 37, 2469, 10.1002/(SICI)1521-3773(19981002)37:18<2469::AID-ANIE2469>3.0.CO;2-M
Tietze, 2000, A novel approach in drug discovery: synthesis of estrone – talaromycin natural product hybrids, Chem Eur J, 6, 3755, 10.1002/1521-3765(20001016)6:20<3755::AID-CHEM3755>3.0.CO;2-L
Wölfling, 2004, Neighboring group participation Part 15. Stereoselective synthesis of some steroidal tetrahydrooxazin-2-ones, as novel presumed inhibitors of human 5α-reductase, Steroids, 69, 451, 10.1016/j.steroids.2004.04.003
Banday, 2010, Studies on novel D-ring substituted steroidal pyrazolines as potential anticancer agents, Steroids, 75, 805, 10.1016/j.steroids.2010.02.014
Hirschmann, 1964, Synthesis and structure of steroidal Pregn-4-eno- and 5α-Pregnano[3,2-c]pyrazoles. A novel class of potent anti-inflammatory steroids, J Am Chem Soc, 86, 1520, 10.1021/ja01062a015
Gupta, 1996, Synthesis and biological activity of azasteroidal [3,2-c]- and [17,16-c]pyrazoles, Eur J Med Chem, 31, 241, 10.1016/0223-5234(96)89140-9
Manson, 1963, Steroidal heterocycles. VII. Androstano[2,3-d]isoxazoles and related compounds, J Med Chem, 6, 1, 10.1021/jm00337a001
Tremblay, 1999, Spironolactone-related inhibitors of Type II 17β-hydroxysteroid dehydrogenase: chemical synthesis, receptor binding affinities, and proliferative/antiproliferative activities, Bioorg Med Chem, 7, 1013, 10.1016/S0968-0896(98)00260-0
Koizumi, 1996, Antiandrogen. IV. C-17 spiro 2-oxasteroids, Chem Pharm Bull, 44, 2162, 10.1248/cpb.44.2162
Gerlt, 1980, Thermochemical identification of the structural factors responsible for the thermodynamic instability of 3′,5′-cyclic nucleotides, J Am Chem Soc, 102, 1655, 10.1021/ja00525a033
Nelson, 1987, The question of chair–twist equilibria for the phosphate rings of nucleoside cyclic 3′,5′-monophosphates. 1H NMR and X-ray crystallographic study of the diastereomers of thymidine phenyl cyclic 3′,5′-monophosphate, J Am Chem Soc, 109, 4058, 10.1021/ja00247a036
Błaszczyk, 1996, Conformation of oxathiaphospholane and dithiaphospholane rings in the solid state, J Mol Struct, 374, 85, 10.1016/0022-2860(95)08929-2
Nawrot, 2008, 1,3,2-Oxathiaphospholane approach to the synthesis of P-chiral stereodefined analogs of oligonucleotides and biologically relevant nucleoside polyphosphates, Pure Appl Chem, 80, 1859, 10.1351/pac200880081859
Błaszczyk, 1996, The synthesis and X-ray structural studies of 2-cholesteryl-2-thio-1,3,2-oxathiaphospholane and 2-cholesteryl-2-thio-1,3,2-dithiaphospholane, J Chem Crystallogr, 26, 33, 10.1007/BF02018694
Foster, 1976, Synthesis of steroidal cyclophosphamides, Steroids, 27, 353, 10.1016/0039-128X(76)90056-8
Frank, 2006, Synthesis of some novel D-ring-fused dioxa- and oxazaphosphorinanes in the estrone series, Tetrahedron Lett, 47, 1105, 10.1016/j.tetlet.2005.12.038
Frank, 2008, Synthesis and conformational study of P-heterocyclic androst-5-ene derivatives, Heteroat Chem, 19, 7, 10.1002/hc.20372
Frank, 2007, New steroid-fused P-heterocycles Part I. Synthesis and conformational study of dioxaphosphorino[16,17-d]estrone derivatives, Steroids, 72, 437, 10.1016/j.steroids.2007.02.002
Frank, 2009, Synthesis and conformational preferences of novel steroidal 16-spiro-1,3,2-dioxaphosphorinanes, Lett Org Chem, 6, 340, 10.2174/157017809788489927
Mohamed, 2003, Studies on organophosphorus compounds VII: transformation of steroidal ketones with Lawesson’s reagent into thioxo and heterofused steroids. Results of antimicrobial and antifungal activity, Phosphorus Sulfur Silicon Relat Elem, 178, 2003, 10.1080/10426500390228693
Mohamed, 2005, Synthesis of biologically active steroid derivatives by the utility of Lawesson’s reagent, Steroids, 70, 131, 10.1016/j.steroids.2004.11.001
Pedersen, 1978, Studies on organophosphorus compounds. XX. Syntheses of thioketones, Bull Soc Chim Belg, 87, 223, 10.1002/bscb.19780870310
Pedersen, 1979, Studies on organophosphorus compounds—XXVIII: Syntheses of 3H–1,2-dithiole-3-thiones and 4H–1,3,2,-oxazaphosphorine derivatives from the dimer of p-methoxyphenyl-thionophosphine sulfide and derivatives of 3-oxo carboxylic acids, Tetrahedron, 35, 2433, 10.1016/S0040-4020(01)93760-3
Cava, 1985, Thionation reaction of Lawesson’s reagent, Tetrahedron, 41, 5061, 10.1016/S0040-4020(01)96753-5
Krstić, 2007, Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities, Steroids, 72, 406, 10.1016/j.steroids.2007.02.005
Krstić, 2010, Thionation of some α, β-unsaturated steroidal ketones, Molecules, 15, 3462, 10.3390/molecules15053462
Kvasnica, 2008, Reaction of lupane and oleanane triterpenoids with Lawesson’s reagent, Tetrahedron, 64, 3736, 10.1016/j.tet.2008.02.023
Sheldrick, 2008, A short history of SHELX, Acta Crystallogr Sect A Found Crystallogr, A64, 112, 10.1107/S0108767307043930
Mosmann, 1983, Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays, J Immunol Methods, 65, 55, 10.1016/0022-1759(83)90303-4
Ohno, 1991, Rapid colorimetric assay for the quantification of leukemia inhibitory factor (LIF) and interleukin-6 (IL-6), J Immunol Methods, 145, 199, 10.1016/0022-1759(91)90327-C
NCCLS (National Committee for Clinical Laboratory Standards): Approval standard document M7–A5, Vilanova, Pa, USA, 2000.
Meyer, 1982, Brine shrimp; a convenient general bioassay for active plant constituents, Planta Med, 45, 31, 10.1055/s-2007-971236
Cahn, 1966, Spezifikation der molekularen Chiralität, Angew Chem, 78, 413, 10.1002/ange.19660780803
Uznanski, 1992, Stereochemistry of base-catalyzed ring opening of 1,3,2-oxathiaphospholanes. Absolute configuration of 2-{N-[(Rc)-1-(α-Naphthyl)ethyl]amino}-2-thiono-1,3,2-oxathiaphospholanes and 0, S-Dimethyl N-[(Rc)-1-(α-Naphthyl)ethyl]phosphoramidothioates, J Am Chem Soc, 114, 10197, 10.1021/ja00052a017
Błaszczyk, 1994, Geometry and conformation of crystalline forms of β-naphthoxy-substituted 2-thio-1,3,2-oxathiaphospholanes and 2-thio-1,3,2-dithiaphospholanes, Heteroat Chem, 5, 519, 10.1002/hc.520050517
Krzyżanowska, 1994, Synthesis and assignment of absolute configuration of enantiomeric dicyclohexylammonium 2-oxo-2-thioxo-1,3,2-oxathiaphospholanes, Heteroat Chem, 5, 533, 10.1002/hc.520050519
Stanojkovic, 2010, Zinc(II) complexes of 2-acetyl pyridine 1-(4-fluorophenyl)-piperazinyl thiosemicarbazone: synthesis, spectroscopic study and crystal structures – Potential anticancer drugs, J Inorg Biochem, 104, 467, 10.1016/j.jinorgbio.2009.12.021