Stereospecific syntheses of trans-vinyldioxidosqualene and 3-hydroxysulfide derivatives, as potent and time-dependent 2,3-oxidosqualene cyclase inhibitors.
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[1] K. Koike,et al. 9β,19-Cyclosterol Analysis by 1H and 13C NMR, Crystallographic Observations, and Molecular Mechanics Calculations , 1998 .
[2] F. Viola,et al. 29-Methylidene-2,3-oxidosqualene derivatives as stereospecific mechanism-based inhibitors of liver and yeast oxidosqualene cyclase. , 1998, Journal of medicinal chemistry.
[3] E. Parish,et al. BIOCHEMISTRY and FUNCTION of STEROLS , 1997 .
[4] E. Corey,et al. Studies on the Substrate Binding Segments and Catalytic Action of Lanosterol Synthase. Affinity Labeling with Carbocations Derived from Mechanism-Based Analogs of 2,3-Oxidosqualene and Site-Directed Mutagenesis Probes , 1997 .
[5] G. Prestwich,et al. Potency and inactivation rates of analogues of an irreversible inhibitor of vertebrate oxidosqualene cyclase , 1997 .
[6] G. Prestwich,et al. Synthesis and inhibition studies of sulfur-substituted squalene oxide analogues as mechanism-based inhibitors of 2,3-oxidosqualene-lanosterol cyclase. , 1997, Journal of medicinal chemistry.
[7] F. Sánchez-Baeza,et al. 2,3,18,19-Dioxidosqualene Stereoisomers: Characterization and Activity as Inhibitors of Purified Pig Liver 2,3-Oxidosqualene-Lanosterol Cyclase. , 1996, The Journal of organic chemistry.
[8] G. Prestwich,et al. Mechanism-Based Active Site Modification of Oxidosqualene Cyclase by Tritium-Labeled 18-Thia-2,3-Oxidosqualene , 1996 .
[9] A. Rahier,et al. Inhibition of higher plant 2,3-oxidosqualene cyclases by nitrogen-containing oxidosqualene analogues , 1996 .
[10] E. Corey,et al. New Insights Regarding the Cyclization Pathway for Sterol Biosynthesis from (S)-2,3-Oxidosqualene , 1995 .
[11] O. Boutaud,et al. Inhibition of 2,3-oxidosqualene cyclase and sterol biosynthesis by 10- and 19-azasqualene derivatives. , 1995, Biochemical pharmacology.
[12] D. Viterbo,et al. Polyene Cyclizations Related to Oxidosqualene Cyclization. A Model for the Anti-Markovnikov Closure of Ring C , 1995 .
[13] Y. Zheng,et al. Synthesis of vinyl sulfide analogs of 2,3-oxidosqualene and their inhibition of 2,3-oxidosqualene lanosterol-cyclases☆ , 1995 .
[14] N. Georgopapadakou,et al. Synthesis of Sulfur- and Sulfoxide-Substituted 2,3-Oxidosqualenes and Their Evaluation as Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase , 1995 .
[15] P. Hartman,et al. Synthesis of (6E)-8-thia, and (14E)-13-thia-2,3-oxidosqualene : inhibitors of 2,3-oxidosqualene-lanosterol cyclase , 1994 .
[16] G. Prestwich,et al. Asymmetric Synthesis of a Mechanism-Based Inhibitor of Oxidosqualene Cyclase , 1994 .
[17] F. Schuber,et al. Effects of a 2,3-oxidosqualene-lanosterol cyclase inhibitor 2,3:22,23-dioxidosqualene and 24,25-epoxycholesterol on the regulation of cholesterol biosynthesis in human hepatoma cell line HepG2. , 1994, Biochemical pharmacology.
[18] G. Prestwich,et al. A specific amino acid repeat in squalene and oxidosqualene cyclases. , 1994, Trends in biochemical sciences.
[19] G. Prestwich,et al. Inhibitors of squalene biosynthesis and metabolism. , 1994, Natural product reports.
[20] A. Messeguer,et al. Epoxidation of 6,7- and 10,11-oxidosqualenes by the squalene epoxidase present in rat liver microsomes , 1993 .
[21] G. Prestwich,et al. ENZYMATIC CYCLIZATION OF SQUALENE AND OXIDOSQUALENE TO STEROLS AND TRITERPENES , 1993 .
[22] F. Sánchez-Baeza,et al. Dioxidosqualenes : characterization and activity as inhibitors of 2,3-oxidosqualene-lanosterol cyclase , 1993 .
[23] F. Viola,et al. Differential inhibition of fungal oxidosqualene cyclase by 6E and 6Z isomers of 2,3‐epoxy‐10‐aza‐10,11‐dihydrosqualene , 1993, FEBS letters.
[24] E. Guittet,et al. Novel results on the biocyclisation of 2,3-oxidosqualene analogs by sterol cyclase , 1993 .
[25] F. Viola,et al. Synthesis and biological activity of 19-azasqualene 2,3-epoxide as inhibitor of 2,3-oxidosqualene cyclase , 1993 .
[26] N. Georgopapadakou,et al. Synthesis of inhibitors of 2,3-oxidosqualene-lanosterol cyclase. 2. Cyclocondensation of .gamma.,.delta.-unsaturated-.beta.-keto esters with imines , 1992 .
[27] O. Boutaud,et al. Preferential cyclization of 2,3(S):22(S),23-dioxidosqualene by mammalian 2,3-oxidosqualene-lanosterol cyclase. , 1992, Biochemical and biophysical research communications.
[28] F. Sánchez-Baeza,et al. 2,3:18,19-dioxidosqualene: synthesis and activity as a potent inhibitor of 2,3-oxidosqualene-lanosterol cyclase in rat liver microsomes , 1992 .
[29] A. Rahier,et al. Inhibition of 2,3-oxidosqualene cyclases. , 1992, Biochemistry.
[30] G. Prestwich,et al. Affinity labeling of vertebrate oxidosqualene cyclases with a tritiated suicide substrate. , 1992, Biochemical and biophysical research communications.
[31] F. Viola,et al. 2,3-Epoxy-10-aza-10,11-dihydrosqualene, a high-energy intermediate analogue inhibitor of 2,3-oxidosqualene cyclase. , 1992, Journal of medicinal chemistry.
[32] G. Prestwich,et al. Epoxidation of 2,3-oxidosqualene to 2,3;22,23-squalene dioxide by squalene epoxidase. , 1992, Biochemical and biophysical research communications.
[33] A. Oehlschlager,et al. Synthesis of inhibitors of 2,3-oxidosqualene-lanosterol cyclase: conjugate addition of organocuprates to N-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone. , 1992 .
[34] G. Patterson. Physiology and Biochemistry of Sterols , 1992 .
[35] G. Prestwich,et al. 29-Methylidene-2, 3-oxidosqualene : a potent mechanism-based inactivator of oxidosqualene cyclase , 1991 .
[36] E. Corey,et al. New mechanistic and stereochemical insights on the biosynthesis of sterols from 2,3-oxidosqualene , 1991 .
[37] E. Corey,et al. Purification of the 2,3-oxidosqualene-lanosterol cyclase from Saccharomyces cerevisiae , 1991 .
[38] E. Corey,et al. An experimental demonstration of the stereochemistry of enzymic cyclization of 2,3-oxidosqualene to the protosterol system, forerunner of lanosterol and cholesterol , 1991 .
[39] I. Abe,et al. Purification and some properties of squalene-2,3-epoxide: lanosterol cyclase from rat liver. , 1991, Chemical and pharmaceutical bulletin.
[40] P. Pasau,et al. Comparison of the behavior of oxidosqualene cyclases from pig liver and yeast toward epoxy-squalene analogues possessing a Δ 18–19 Z or E C, C Double bond. , 1991 .
[41] F. Viola,et al. 22,23-Epoxy-2-aza-2,3-dihydrosqualene derivatives: potent new inhibitors of squalene 2,3-oxide-lanosterol cyclase. , 1990, Farmaco.
[42] G. Prestwich,et al. Vinyl oxirane analog of (3S)-2,3-epoxysqualene: A substrate for oxldosqualene cyclases from yeast and from hog liver , 1990 .
[43] A. Rahier,et al. Potent inhibition of cholesterol biosynthesis in 3T3 fibroblasts by N-[(1,5,9)-trimethyldecyl]-4α, 10-dimethyl-8-AZA-trans-decal-3β-OL, a new 2,3-oxidosqualene cyclase inhibitor , 1988 .
[44] F. Viola,et al. Inhibition of sterol biosynthesis in Saccharomyces cerevisiae by N,N-diethylazasqualene and derivatives. , 1988, Biochimica et biophysica acta.
[45] E. Guittet,et al. About the mechanism of sterol biosynthesis , 1987 .
[46] J. Steele,et al. Rate enhancement of biomimetic polyene cyclizations by a cation-stabilizing auxiliary , 1987 .
[47] F. Viola,et al. Synthesis and biological activity of azasqualenes, bis-azasqualenes and derivatives , 1987 .
[48] U. Schubert,et al. Cation-stabilizing auxiliaries: a new concept in biomimetic polyene cyclization , 1987 .
[49] K. Furuta,et al. Selective Condensation of [3-(Alkylthio)allyl]titanium Reagent with Carbonyl Compounds , 1984 .
[50] T. Molinski,et al. Dilithium tetrabromonickelate (II) as a source of soft nucleophilic bromide : Reaction with epoxides , 1984 .
[51] E. E. Tamelen. BIOORGANIC CHARACTERIZATION AND MECHANISM OF THE 2,3-OXIDOSQUALENE → LANOSTEROL CONVERSION , 1983 .
[52] E. E. Tamelen,et al. Action of 2,3-oxidosqualene lanosterol cyclase on 15'-nor-18,19-dihydro-2,3-oxidosqualene , 1982 .
[53] K. Maruyama,et al. Heterosubstituted allylic carbanion based stereocontrol, regio- and stereo- selective reaction of O and S substituted allylic carbanions with aldehydes , 1982 .
[54] F. Sato,et al. A stereo- and regio-specific addition of η3-trimethylsilylallyltitanium compound with aldehydes. A facile and stereocontrolled synthesis of E- and Z-terminal dienes , 1982 .
[55] J. Nelson,et al. Biosynthesis of 24,25-epoxycholesterol from squalene 2,3;22,23-dioxide. , 1981, The Journal of biological chemistry.
[56] S. Shibuya,et al. General synthesis of oxirans , 1978 .
[57] D. Seebach,et al. Umpolung of the Reactivity of Carbonyl Compounds Through Sulfur-Containing Reagents , 1977 .
[58] R. B. Field,et al. Isolation of 2,3;22,23-dioxidosqualene and 24,25-oxidolanosterol from yeast. , 1977, Archives of biochemistry and biophysics.
[59] Carl R. Johnson,et al. Chemistry of sulfoxides and related compounds. XLIII. Conversion of ketones to epoxides via .beta.-hydroxy sulfides , 1973 .
[60] B. Trost,et al. Preparation and chemistry of vinyl sulfonium ylides. New synthetic intermediates , 1971 .
[61] K. B. Sharpless,et al. Squalene-2,3oxide, an intermediate in the enzymatic conversion of squalene to lanosterol and cholesterol. , 1967, The Journal of biological chemistry.
[62] E. Corey,et al. 2,3-oxidosqualene, an intermediate in the biological synthesis of sterols from squalene. , 1966, Journal of the American Chemical Society.
[63] Y. Shimizu,et al. THE MIGRATION AND ELIMINATION OF HYDROGEN DURING BIOSYNTHESIS OF CHOLESTEROL FROM SQUALENE. , 1965, Journal of the American Chemical Society.