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Volumn 9, Issue 20, 1999, Pages 2977-2982

First systematic chiral syntheses of two pairs of enantiomers with 3,5-dihydroxyheptenoic acid chain, associated with a potent synthetic statin NK-104

Author keywords

[No Author keywords available]

Indexed keywords

7 [2 CYCLOPROPYL 4 (4 FLUOROPHENYL) 3 QUINOLYL] 3,5 DIHYDROXY 6 HEPTENOIC ACID DERIVATIVE; PITAVASTATIN; UNCLASSIFIED DRUG;

EID: 0033581607     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00519-3     Document Type: Article
Times cited : (27)

References (34)
  • 2
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    • (b) New Current 1995, 6, No. 6, 27.
    • (1995) New Current , vol.6 , Issue.6 , pp. 27
  • 3
    • 0009547335 scopus 로고    scopus 로고
    • (c) New Current 1996, 7, No. 15, 2.
    • (1996) New Current , vol.7 , Issue.15 , pp. 2
  • 4
    • 0031764986 scopus 로고    scopus 로고
    • (d) Drugs of the Future 1998, 23(8), 847.
    • (1998) Drugs of the Future , vol.23 , Issue.8 , pp. 847
  • 6
    • 0009504777 scopus 로고    scopus 로고
    • NK-104, a new potent HMG-Co. A reductase inhibitor (2); The effect on cholesterol synthesis and proliferation of smooth muscle cells
    • (f) Sakashita, M.; Toyoda, K.; Kitahara, M.; Wada, Y.; Saito, Y. Ibid., P22: NK-104, a new potent HMG-Co. A reductase inhibitor (2); The effect on cholesterol synthesis and proliferation of smooth muscle cells.
    • Ibid. , pp. 22
    • Sakashita, M.1    Toyoda, K.2    Kitahara, M.3    Wada, Y.4    Saito, Y.5
  • 8
    • 0009481399 scopus 로고    scopus 로고
    • Inhibition of HMG-CoA reductase by NK-104 suppresses intimal thickening via inhibiting smooth muscle cell growth and matrix formation in balloon injured rabbit artery
    • (h) Kitahara, M.; Kanaki, T.; Tanaka, S.; Tamaki, T.; Saito, Y. Ibid.: Inhibition of HMG-CoA reductase by NK-104 suppresses intimal thickening via inhibiting smooth muscle cell growth and matrix formation in balloon injured rabbit artery.
    • Ibid.
    • Kitahara, M.1    Kanaki, T.2    Tanaka, S.3    Tamaki, T.4    Saito, Y.5
  • 9
    • 0022423907 scopus 로고
    • See the review of HMGR inhibitors
    • Nakamura, C. E.; Abeles, R. H. Biochemistry 1985, 24, 1364. See the review of HMGR inhibitors;
    • (1985) Biochemistry , vol.24 , pp. 1364
    • Nakamura, C.E.1    Abeles, R.H.2
  • 19
    • 0000691988 scopus 로고
    • The syntheses and evaluations of the four stereoisomers of 3,5-dihydroxyheptanoic acid type inhibitor, compactin by Wadsworth-Emmons coupling followed by partially syn stereoselective reduction and HPLC separation were reported: (c)
    • The syntheses and evaluations of the four stereoisomers of 3,5-dihydroxyheptanoic acid type inhibitor, compactin by Wadsworth-Emmons coupling followed by partially syn stereoselective reduction and HPLC separation were reported: (c) Heathcock, C.H.; Hadley, C. R.; Rosen, T.; Theisen, P. D.; Hecker, S. J. J.Med.Chem.1987, 30, 1858.
    • (1987) J.Med.Chem. , vol.30 , pp. 1858
    • Heathcock, C.H.1    Hadley, C.R.2    Rosen, T.3    Theisen, P.D.4    Hecker, S.J.5
  • 28
    • 0009506567 scopus 로고    scopus 로고
    • 3CN : MeOH = 100 : 5 : 10, 30°C. (c) The diastereomeric purities of 6a and 6b; Nucleosil 50-5, 4.6 φ × 250 mm × 2, THF : n-hexane = 20 : 80, 35°C. (d) The enantiomeric purities of 7a and 7b; Chiralpack-AS, 4.6 φ × 250 mm, i-PrOH : n-hexane = 4 : 96, 35°C. (e) The enantiomeric purities of 2a and 2b; Chiralpack-AS, 4.6 φ × 250 mm, i-PrOH : n-hexane = 10 : 90, 35°C
    • 3CN : MeOH = 100 : 5 : 10, 30°C. (c) The diastereomeric purities of 6a and 6b; Nucleosil 50-5, 4.6 φ × 250 mm × 2, THF : n-hexane = 20 : 80, 35°C. (d) The enantiomeric purities of 7a and 7b; Chiralpack-AS, 4.6 φ × 250 mm, i-PrOH : n-hexane = 4 : 96, 35°C. (e) The enantiomeric purities of 2a and 2b; Chiralpack-AS, 4.6 φ × 250 mm, i-PrOH : n-hexane = 10 : 90, 35°C.
    • Tetrahedron Letters
  • 32
    • 0023105558 scopus 로고
    • The syntheses of optical active ß -keto- δ -hydroxy esters were originally realized by Claisen condensation reaction with t-butyl acetoacetate.
    • The syntheses of optical active ß -keto- δ -hydroxy esters were originally realized by Claisen condensation reaction with t-butyl acetoacetate. Lynch, J. E.; Volante, R. P.; Wattley, R. V.; Shinkai, I. Tetrahedron Letters, 1987, 28, 1385.
    • (1987) Tetrahedron Letters , vol.28 , pp. 1385
    • Lynch, J.E.1    Volante, R.P.2    Wattley, R.V.3    Shinkai, I.4
  • 33
    • 0009548591 scopus 로고    scopus 로고
    • A practical process for optical resolution of the racemic ß -keto- δ -hydroxy esters (±-2 was achieved by Daicel Chemical Industries, Ltd. through the batch system with Chiralpak-AS, i-propanol : n-hexane = 5 : 95 vol/vol. E. P. Patent 747,341
    • A practical process for optical resolution of the racemic ß -keto- δ -hydroxy esters ((±)-2) was achieved by Daicel Chemical Industries, Ltd. through the batch system with Chiralpak-AS, i-propanol : n-hexane = 5 : 95 vol/vol. Matsumoto, H.; Ohara, Y.; Kanda, H.; Ikeda, H. E. P. Patent 747,341, 1997.
    • (1997) Tetrahedron Letters
    • Matsumoto, H.1    Ohara, Y.2    Kanda, H.3    Ikeda, H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.