Stereospecific syntheses of trans-vinyldioxidosqualene and 3-hydroxysulfide derivatives, as potent and time-dependent 2,3-oxidosqualene cyclase inhibitors.

[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.