Squalene synthase inhibitors 1998

Bibliography

• POULTER CD, RILLING HC: Biosynthesis ollsoprenoid Com-pounds. Porter JVV, Spurgeon SL (Eds.), Wiley, New York (198 1) :413–441.
   Google Scholar
• NADIN A, NICOLAOU KC: Chemistry and biology of the zaragozic acids (squalestatins). Angew. Chem. Intern. Ed. (1996) 35:1622–1656.
   Google Scholar
• BILLER SA, NEUENSCHWANDER K, PONPIPOM MM, POULTER CD: Squalene synthase inhibitors. Curr. Pharm. Des. (1996) 2:1–40.
   Web of Science ®Google Scholar
• ••A comprehensive review article.
   Google Scholar
• BERGSTROM JD, DUFRESNE C, BILLS GF, NALLIN-OMSTEAD M, BYRNE K: Discovery, biosynthesis, and mechanism of action of the zaragozic acids: potent in-hibitors of squalene synthase. Ann. Rev. Microbiol. (1995) 49:607–639.
   Google Scholar
• TANIMOTO T, HAMANO K, ONODERA K: Biological ac-tivities of novel zaragozic acids, the potent inhibitors of squalene synthase, produced by the fungus Mollisia sp. SANK 10294. J. Antibiot. (1997) 50:390–394.
   Google Scholar
• BAXTER A, FITZGERALD BJ, HUTSON JL et al: Squalesta-tin 1, a potent inhibitor of squalene synthase, which serum cholesterol in vivo. J. Biol. Chem. (1992) 267:11705–11708.
   PubMed Web of Science ®Google Scholar
• CHIANG Y-CP, KURTZ MM, BERGSTROM JD,BERGER GD: 3,4-Diesters of zaragozic acid A. Bioorg. Med. Chem. Lett. (1995) 5:1643–1646.
   Google Scholar
• CHAN C, ANDREOTTI D, COX B et al.: The squalestatins: decarboxy and 4-deoxy analogues as potent squalene synthase inhibitors. J. Med. Chem. (1996) 39:207–216.
   PubMed Web of Science ®Google Scholar
• PROCOPIOU PA, COX B, KIRK BE et al: The squal-estatins: inhibitors of squalene synthase. Enzyme in-hibitory activities and in vivo evaluation of C3-modified analogues. J. Med. Chem. (1996) 39:1413–1422.
   Google Scholar
• BAMFORD MJ, CHAN C, CRAVEN AP et al: The squal-estatins: synthesis and biological activity of some C3-modified analogues; replacement of a carboxylic acid or methyl ester with an isoelectronic heterocyclic functionality. J. Med. Chem. (1995) 38:3502–3513.
   PubMed Web of Science ®Google Scholar
• MAGNIN DR, BILLER SA, DICKSON JK, Jr. et al.: 1,1-Bisphosphonate squalene synthase inhibitors: inter-play between the isoprenoid subunit and the diphos-phate surrogate. J. Med. Chem. (1995) 38:2596–2605.
   Google Scholar
• AMIN D, CORNELL SA, PERRONE MH,BILDER GE: 1-Hydroxy-3-(methylpentylamino)-propylidine-1,1-bisphosphonic acis as a potent inhibitor of squalene synthase. Arzneim.-Forsch. Drug Res. (1996) 46(1I)759–762.
   Google Scholar
• MAGNIN DR, BILLER SA, CHEN Y et al.: a-Phosphonosulf-onic acids: potent and selective inhibitors of squalene synthase. J. Med. Chem. (1996) 39:657–660.
   PubMed Web of Science ®Google Scholar
• DICKSON JK, Jr., BILLER SA, MAGNIN DR et al: Orally ac-tive squalene synthase inhibitors: bis((acyloxy)alkyl) prodrugs of the a-phosphonosulfonic acid moiety. J. Med. Chem. (1996) 39:661–664.
   Google Scholar
• •Substrate analogue squalene synthase inhibitors with im-proved bioavailability are described.
   Google Scholar
• TANIMOTO T, ONODERA K, HOSOYA T et al.: Schizosta-tin, a novel squalene synthase inhibitor produced by the mushroom, Schizophyllum commune. I. Taxon-omy, fermentation, isolation, physico-chemical prop-erties and biological activities. J. Antibiot. (Tokyo) (1996) 49:617–623.
   Google Scholar
• KOGEN H, TAGO K, KANEKO S et al: Schizostatin, anovel squalene synthase inhibitor produced by the mushroom, Schizophyllum commune. II. Structure elucidation and total synthesis. J. Antibiot. (Tokyo) (1996) 49:624–630.
   Web of Science ®Google Scholar
• WATTANASIN S, BOETTCHER BR, SCALLEN T: N-hydroxyglycine derivatives as novel inhibitors of squalene synthase. Bioorg. Med. Chem. Lett. (1997) 7:3039–3044.
   Google Scholar
• SHECHTER I, GIU P, ONOFREY TJ, CANN RO, CASTRO A,SPENCER TA: Sulfobetaine zwitterionic inhibitors of squalene synthase. Bioorg. Med. Chem. Lett. (1996) 6:2585–2588.
   Google Scholar
• IWASAWA Y, HAYASHI M, NOMOTO T et al. Synthesis biological activity of J-104,118, a novel, potent of squalene synthase. Bioorg. Med. Chem. Lett. (1995) 5:1989–1994.
   Google Scholar
• IWASAWA Y, SHIBATA J, MITSUYA M et al: J-104,123, a novel and orally active inhibitor of squalene synthase: stereoselective synthesis and cholesterol lowering ef-fects in dogs. Bioorg. Med. Chem. Lett. (1996) 6:463–466.
   Google Scholar
• ••This article describes potent oral hypocholesterolaemic ac-tivity in dogs.
   Google Scholar
• FUNG AK, BAKER WR, FAKHOURY S et al.: (1a,26,36,40-1,2-bis[N-propyl-N-(4-phenoxybenzy0 amino]carbonylicyclobutane-3,4-dicarboxylic acid (A-87049): a novel potent squalene synthase inhibitor. J. Med. Chem. (1997) 40:2123–2125.
   Google Scholar
• BROWN GR, CLARKE DS, FOUBISTER AJ et al.: Synthesis and activity of a novel series of 3-biarylquinuclidine squalene synthase inhibitors. J. Med. Chem. (1996) 39:2971–2979.
   PubMed Web of Science ®Google Scholar
• Ward WHJ, Holdgate GA, Freeman S et al.: Inhibition of synthase in vitro by 3-(biphenyl-4-34)- quinu-. Biochem. Pharmacol. (1996) 51:1489–1501.
   Google Scholar
• •Discussion of the biphasic kinetics of quinuclidine-derived squalene synthase inhibitors.
   Google Scholar
• MCTAGGART F, BROWN GR, DAVIDSON RG et al.: Inhibi- of squalene synthase of rat liver by novel 3' substi-tuted quinuclidines. Biochem. Pharmacol (1996) 5 1:1477–1487.
   Google Scholar
• BROWN GR, FOUBISTER AJ, FREEMAN S et al.: Novel opti-mised quinuclidine squalene synthase inhibitors. Bioorg. Med. Chem. Lett. (1997) 7:597–600.
   Google Scholar
• AMIN D, RUTLEDGE RZ, NEEDLE SN et al.: RPR 107393, a potent squalene synthase inhibitor and orally effec-tive cholesterol-lowering agent: comparison with in-hibitors of HMG-CoA reductase. J. Pharmacol Exp. Ther. (1997) 281:746–752.
   PubMed Web of Science ®Google Scholar
• ••This article describes potent oral hypocholesterolaemic ac-tivity in rat and marmoset.
   Google Scholar
• ALAUPOVIC P, HEINONEN T, SHURZINSKE L, BLACK DM: Effect of a new HMG-CoA reductase inhibitor, atorvas-tatin, on lipids, apolipoproteins and lipoprotein parti-cles in patients with elevated serum cholesterol and triglyceride levels. Atherosclerosis (1997) 133:123–133.
   PubMed Web of Science ®Google Scholar
• DAVIDSON MH, NAWROCKI JW, WEISS SR et al.: Effec-tiveness of atorvastatin for reducing low-density lipo-protein cholesterol to National Cholesterol Education Program treatment goals. Am. J. Cardiol. (1997) 80:347–348.
   Google Scholar
• GONZALEZ-PACANOWSKA D, ARISON B, HAVEL CM, WATSON JA: Isopentenoid synthesis in isolated embry-onic Drosophila cells. Farnesol catabolism and co-oxid-ation. J. Biol. Chem. (1988) 263:1301–1306.
   PubMedGoogle Scholar
• BERGSTROM JD, KURTZ MM, REW DJ et al.: Zaragozic ac-ids: a family of fungal metabolites that are picomolar competitive inhibitors of squalene synthase. Proc. Natl. Acad. ScL USA (1993) 90:80–84.
   PubMed Web of Science ®Google Scholar
• BOSTEDOR RG, KARKAS JD, ARISON BH et al. Farnesol- dicarboxylic acids in the urine of animals with zaragozic acid A or with farnesol. J. Biol. Chem. (1997) 272:9197–9203.
   Google Scholar
• ••Discussion of the metabolic fate of farnesyl diphosphate andpotential toxicity implications.
   Google Scholar