메뉴 건너뛰기




Volumn 39, Issue 15, 1996, Pages 2971-2979

Synthesis and activity of a novel series of 3-biarylquinuclidine squalene synthase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY 3 [4 (4 PYRIDYL)PHENYL]QUINUCLIDINE; 3 QUINUCLIDINOL; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; LOW DENSITY LIPOPROTEIN CHOLESTEROL; METOPROLOL; MEVALONIC ACID; QUINUCLIDINE DERIVATIVE; SQUALENE SYNTHASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 8944244053     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950907l     Document Type: Article
Times cited : (80)

References (29)
  • 1
    • 85067533753 scopus 로고
    • These results were reported in part at the XIIIth International Symposium on Medicinal Chemistry, Paris, France, Sept. 19-23, 1994, Abstract P79, and the Xth International Symposium on Atherosclerosis, Montreal, Canada, Oct. 9-14, 1994. Abstracts published
    • These results were reported in part at the XIIIth International Symposium on Medicinal Chemistry, Paris, France, Sept. 19-23, 1994, Abstract P79, and the Xth International Symposium on Atherosclerosis, Montreal, Canada, Oct. 9-14, 1994. Abstracts published in Atherosclerosis 1994, 109, 252.
    • (1994) Atherosclerosis , vol.109 , pp. 252
  • 2
    • 0021350001 scopus 로고
    • The Lipid Research Clinics Coronary Primary Prevention Trial Results. J. Am. Med. Assoc. 1984, 257, 351-374.
    • (1984) J. Am. Med. Assoc. , vol.257 , pp. 351-374
  • 4
    • 0000491244 scopus 로고
    • Therapeutic Consequences of the Inhibition of Sterol Metabolism
    • Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: Oxford
    • Adams, J. L.; Metcalf, B. Therapeutic Consequences of the Inhibition of Sterol Metabolism. In Comprehensive Medicinal Chemistry; Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: Oxford, 1990; Vol. 2, pp 333-364.
    • (1990) Comprehensive Medicinal Chemistry , vol.2 , pp. 333-364
    • Adams, J.L.1    Metcalf, B.2
  • 10
    • 85067535832 scopus 로고
    • Chicago, IL, Division of Medicinal Chemistry Abstracts
    • (a) 206th National ACS Meeting, Chicago, IL, 1993; Division of Medicinal Chemistry Abstracts, pp 16-20.
    • (1993) 206th National ACS Meeting , pp. 16-20
  • 12
    • 0011865344 scopus 로고
    • Recent β-Adrenergic Blocking Agents
    • Ellis, G. P., Jr.; West, G. B., Eds.; Elsevier Science Publishers: New York
    • Main, B. G.; Tucker, H. Recent β-Adrenergic Blocking Agents. In Progress in Medicinal Chemistry; Ellis, G. P., Jr.; West, G. B., Eds.; Elsevier Science Publishers: New York, 1985; Vol. 22, pp 122-158.
    • (1985) Progress in Medicinal Chemistry , vol.22 , pp. 122-158
    • Main, B.G.1    Tucker, H.2
  • 13
    • 0345074371 scopus 로고
    • Squalene Synthase Inhibitors. US Appl. 5135935
    • Subsequently patent applications and a communication have been published, claiming quinuclidines as SQS inhibitors, (a) Alberts, A. W.; Berger, G. D.; Meade, B.; Bergstrom, J. D. Squalene Synthase Inhibitors. US Appl. 5135935. Chem. Abstr. 1992, 117, 245613. (b) Amin, D.; Morris, R. L.; Neuenscwander, K.; Scotese, A. C. Preparation of Azabicyclooctyloxymethylbenzenes and Related Compounds as Squalene Synthase Inhibitors. PCT Int. Appl. WO 9215579 AI 920917; Chem. Abstr. 1993, 118, 124402. (c) Brown, G. R.; Harrison, P. J.; Mallion, K. B. Preparation of Biphenylquinuclidines as Squalene Synthase Inhibitors. PCT Int. Appl. WO 9309115 AI 920513; Chem. Abstr. 1993, 119, 117132. (d) Zhao, M.; Kumar, N.; Neuenschwander, K.; Nakanishi, K.; Berova, N. Quaternary Ammonium Salts as Chromophores for Exciton Coupled Circular Dichroism: Absolute Configuration of Hypocholesterolemic Quinuclidines. J. Am. Chem. Soc. 1995, 117, 7844-7845.
    • (1992) Chem. Abstr. , vol.117 , pp. 245613
    • Alberts, A.W.1    Berger, G.D.2    Meade, B.3    Bergstrom, J.D.4
  • 14
    • 0344212096 scopus 로고
    • Preparation of Azabicyclooctyloxymethylbenzenes and Related Compounds as Squalene Synthase Inhibitors. PCT Int. Appl. WO 9215579 AI 920917
    • Subsequently patent applications and a communication have been published, claiming quinuclidines as SQS inhibitors, (a) Alberts, A. W.; Berger, G. D.; Meade, B.; Bergstrom, J. D. Squalene Synthase Inhibitors. US Appl. 5135935. Chem. Abstr. 1992, 117, 245613. (b) Amin, D.; Morris, R. L.; Neuenscwander, K.; Scotese, A. C. Preparation of Azabicyclooctyloxymethylbenzenes and Related Compounds as Squalene Synthase Inhibitors. PCT Int. Appl. WO 9215579 AI 920917; Chem. Abstr. 1993, 118, 124402. (c) Brown, G. R.; Harrison, P. J.; Mallion, K. B. Preparation of Biphenylquinuclidines as Squalene Synthase Inhibitors. PCT Int. Appl. WO 9309115 AI 920513; Chem. Abstr. 1993, 119, 117132. (d) Zhao, M.; Kumar, N.; Neuenschwander, K.; Nakanishi, K.; Berova, N. Quaternary Ammonium Salts as Chromophores for Exciton Coupled Circular Dichroism: Absolute Configuration of Hypocholesterolemic Quinuclidines. J. Am. Chem. Soc. 1995, 117, 7844-7845.
    • (1993) Chem. Abstr. , vol.118 , pp. 124402
    • Amin, D.1    Morris, R.L.2    Neuenscwander, K.3    Scotese, A.C.4
  • 15
    • 85067535075 scopus 로고
    • Preparation of Biphenylquinuclidines as Squalene Synthase Inhibitors. PCT Int. Appl. WO 9309115 AI 920513
    • Subsequently patent applications and a communication have been published, claiming quinuclidines as SQS inhibitors, (a) Alberts, A. W.; Berger, G. D.; Meade, B.; Bergstrom, J. D. Squalene Synthase Inhibitors. US Appl. 5135935. Chem. Abstr. 1992, 117, 245613. (b) Amin, D.; Morris, R. L.; Neuenscwander, K.; Scotese, A. C. Preparation of Azabicyclooctyloxymethylbenzenes and Related Compounds as Squalene Synthase Inhibitors. PCT Int. Appl. WO 9215579 AI 920917; Chem. Abstr. 1993, 118, 124402. (c) Brown, G. R.; Harrison, P. J.; Mallion, K. B. Preparation of Biphenylquinuclidines as Squalene Synthase Inhibitors. PCT Int. Appl. WO 9309115 AI 920513; Chem. Abstr. 1993, 119, 117132. (d) Zhao, M.; Kumar, N.; Neuenschwander, K.; Nakanishi, K.; Berova, N. Quaternary Ammonium Salts as Chromophores for Exciton Coupled Circular Dichroism: Absolute Configuration of Hypocholesterolemic Quinuclidines. J. Am. Chem. Soc. 1995, 117, 7844-7845.
    • (1993) Chem. Abstr. , vol.119 , pp. 117132
    • Brown, G.R.1    Harrison, P.J.2    Mallion, K.B.3
  • 16
    • 0029112015 scopus 로고
    • Quaternary Ammonium Salts as Chromophores for Exciton Coupled Circular Dichroism: Absolute Configuration of Hypocholesterolemic Quinuclidines
    • Subsequently patent applications and a communication have been published, claiming quinuclidines as SQS inhibitors, (a) Alberts, A. W.; Berger, G. D.; Meade, B.; Bergstrom, J. D. Squalene Synthase Inhibitors. US Appl. 5135935. Chem. Abstr. 1992, 117, 245613. (b) Amin, D.; Morris, R. L.; Neuenscwander, K.; Scotese, A. C. Preparation of Azabicyclooctyloxymethylbenzenes and Related Compounds as Squalene Synthase Inhibitors. PCT Int. Appl. WO 9215579 AI 920917; Chem. Abstr. 1993, 118, 124402. (c) Brown, G. R.; Harrison, P. J.; Mallion, K. B. Preparation of Biphenylquinuclidines as Squalene Synthase Inhibitors. PCT Int. Appl. WO 9309115 AI 920513; Chem. Abstr. 1993, 119, 117132. (d) Zhao, M.; Kumar, N.; Neuenschwander, K.; Nakanishi, K.; Berova, N. Quaternary Ammonium Salts as Chromophores for Exciton Coupled Circular Dichroism: Absolute Configuration of Hypocholesterolemic Quinuclidines. J. Am. Chem. Soc. 1995, 117, 7844-7845.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 7844-7845
    • Zhao, M.1    Kumar, N.2    Neuenschwander, K.3    Nakanishi, K.4    Berova, N.5
  • 17
    • 85067534118 scopus 로고
    • Quinuclidine Derivatives Useful as Squalene Synthase Inhibitors and their Preparation. Can. Pat. Appl. CA 2104981
    • Brown, G. R.; Mallion, K. B.; Whittamore, P. R. O.; Brittain, D. R. Quinuclidine Derivatives Useful as Squalene Synthase Inhibitors and their Preparation. Can. Pat. Appl. CA 2104981; Chem. Abstr. 1995, 722, 81124.
    • (1995) Chem. Abstr. , vol.722 , pp. 81124
    • Brown, G.R.1    Mallion, K.B.2    Whittamore, P.R.O.3    Brittain, D.R.4
  • 18
    • 0009268097 scopus 로고
    • Quinuclidine-boranes as Intermediates in Formation and Isolation of Functionalised Quinuclidine Systems
    • Stotter, P. L.; Friedman, M. D.; Dorsey, G. O.; Shiely, R. W.; Williams, R. F.; Minter, D. E. Quinuclidine-boranes as Intermediates in Formation and Isolation of Functionalised Quinuclidine Systems. Heterocycles 1987, 25, 251-258.
    • (1987) Heterocycles , vol.25 , pp. 251-258
    • Stotter, P.L.1    Friedman, M.D.2    Dorsey, G.O.3    Shiely, R.W.4    Williams, R.F.5    Minter, D.E.6
  • 19
    • 0026667035 scopus 로고
    • Analogues of the Muscarinic Agent 2′-Methylspiro[1-azabicyclo[2,2,2]octane-3.4′-[1,3]dioxolane]: Synthesis and Pharmacology
    • Nordvall, G.; Sundquist, S.; Glas, G.; Nilvebrant, L.; Hacksell, U. Analogues of the Muscarinic Agent 2′-Methylspiro[1-azabicyclo[2,2,2]octane-3.4′-[1,3]dioxolane]: Synthesis and Pharmacology. J. Med. Chem. 1992, 35, 1541-1550.
    • (1992) J. Med. Chem. , vol.35 , pp. 1541-1550
    • Nordvall, G.1    Sundquist, S.2    Glas, G.3    Nilvebrant, L.4    Hacksell, U.5
  • 20
    • 0009269072 scopus 로고
    • Facile Synthesis of Styrylquinuclidines
    • Ricciardi, F. J.; Doukas, P. H. Facile Synthesis of Styrylquinuclidines. Heterocycles 1986, 24, 971-977.
    • (1986) Heterocycles , vol.24 , pp. 971-977
    • Ricciardi, F.J.1    Doukas, P.H.2
  • 21
    • 0028939816 scopus 로고
    • Cyclisation of α,ω-Diborylalkanes Via Double Suzuki-Miyaura Couplings
    • Soderquist, J. A.; Leon, G.; Colberg, J. C.; Martinez, I. Cyclisation of α,ω-Diborylalkanes Via Double Suzuki-Miyaura Couplings. Tetrahedron Lett. 1995, 36, 3119-3122.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3119-3122
    • Soderquist, J.A.1    Leon, G.2    Colberg, J.C.3    Martinez, I.4
  • 22
    • 85067536103 scopus 로고
    • Preparation of quinuclidine Derivatives as Squalene Synthase Inhibitors. PCT Intnl. Appl. WO 414803
    • Brown, G. R.; Mallion, K. B. Preparation of quinuclidine Derivatives as Squalene Synthase Inhibitors. PCT Intnl. Appl. WO 414803; Chem. Abstr. 1994, 121, 300782.
    • (1994) Chem. Abstr. , vol.121 , pp. 300782
    • Brown, G.R.1    Mallion, K.B.2
  • 23
    • 0000680126 scopus 로고
    • Conversion of Farnesyl Pyrophosphate to Squalene
    • Porter, J. W. , Spurgeon, W., Eds.; Wiley: New York
    • Poulter, C. D.; Rilling, H. C. Conversion of Farnesyl Pyrophosphate to Squalene. In Biosynthesis of Isoprenoid Compounds; Porter, J. W. , Spurgeon, W., Eds.; Wiley: New York, 1981; Vol. 1, pp 414-441.
    • (1981) Biosynthesis of Isoprenoid Compounds , vol.1 , pp. 414-441
    • Poulter, C.D.1    Rilling, H.C.2
  • 24
    • 33845184490 scopus 로고
    • Squalene Synthase. Inhibition by Ammonium Analogues of Carbocationic Intermediates in the Conversion of Presqualene Diphosphate to Squalene
    • Poulter, C. D.; Capson, T. L.; Thompson, M. D.; Bard, R. S. Squalene Synthase. Inhibition by Ammonium Analogues of Carbocationic Intermediates in the Conversion of Presqualene Diphosphate to Squalene. J. Am. Chem. Soc. 1989, 111, 3734-3739.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 3734-3739
    • Poulter, C.D.1    Capson, T.L.2    Thompson, M.D.3    Bard, R.S.4
  • 25
    • 0027465528 scopus 로고
    • Amidinium Cation as a Mimic of Allylic Carbocation: Synthesis and Squalene Synthase Inhibitory Activity of an Amidinium Analog of a Carbocation Intermediate
    • Prashad, M. Amidinium Cation as a Mimic of Allylic Carbocation: Synthesis and Squalene Synthase Inhibitory Activity of an Amidinium Analog of a Carbocation Intermediate. J. Med. Chem. 1993, 36, 631-632.
    • (1993) J. Med. Chem. , vol.36 , pp. 631-632
    • Prashad, M.1
  • 26
    • 0000837910 scopus 로고
    • Squalene Synthase Inhibitors: Synthesis of Sulfonium Ion Mimics of the Carbocationic Intermediate
    • Oehlschlager, A. C.; Singh, S. M.; Sharma, S. Squalene Synthase Inhibitors: Synthesis of Sulfonium Ion Mimics of the Carbocationic Intermediate. J. Org. Chem. 1991, 56, 3856-3861.
    • (1991) J. Org. Chem. , vol.56 , pp. 3856-3861
    • Oehlschlager, A.C.1    Singh, S.M.2    Sharma, S.3
  • 27
    • 0027152062 scopus 로고
    • N-(Arylalkyl)-farnesylamines: New Potent Squalene Synthase Inhibitors
    • Prashad, M.; Kathawala, F. G.; Scallen, T. N-(Arylalkyl)-farnesylamines: New Potent Squalene Synthase Inhibitors. J. Med. Chem. 1993, 36, 1501-1504.
    • (1993) J. Med. Chem. , vol.36 , pp. 1501-1504
    • Prashad, M.1    Kathawala, F.G.2    Scallen, T.3
  • 28
    • 0027483114 scopus 로고
    • Aromatic Isosteres as Conformational Probes for an Isoprenyl Subunit: Application to Inhibitors of Squalene Synthaae
    • Biller, S. A.; Abt, J. W.; Pudzianowski, A. T.; Rich, L. C.; Slusarchyk, D. A.; Ciosek, C. P. Aromatic Isosteres as Conformational Probes for an Isoprenyl Subunit: Application to Inhibitors of Squalene Synthaae. Bioorg. Med. Chem. Lett. 1993, 3, 595-600.
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 595-600
    • Biller, S.A.1    Abt, J.W.2    Pudzianowski, A.T.3    Rich, L.C.4    Slusarchyk, D.A.5    Ciosek, C.P.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.