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Volumn 118, Issue 46, 1996, Pages 11668-11669

Enantioselective synthesis of α-phosphono sulfonate squalene synthase inhibitors: Chiral recognition in the interactions of an α-phosphono sulfonate inhibitor with squalene synthase

Author keywords

[No Author keywords available]

Indexed keywords

ANTILIPEMIC AGENT; SQUALENE SYNTHASE; SQUALENE SYNTHASE INHIBITOR;

EID: 10544241192     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962505o     Document Type: Article
Times cited : (40)

References (24)
  • 2
    • 0000691423 scopus 로고
    • For reviews on squalene synthase inhibitors, see: Biller, S. A.; Neuenschwander, K.; Ponpipom, M. M.; Poulter, C. D. Curr. Pharm. Des. 1996, 2, 1-40. Abe, A.; Tomesch, J. C.; Wattanasain, S.; Prestwich, G. D. Nat. Prod. Rep. 1994, 279-302.
    • (1994) Nat. Prod. Rep. , pp. 279-302
    • Abe, A.1    Tomesch, J.C.2    Wattanasain, S.3    Prestwich, G.D.4
  • 5
    • 10544249316 scopus 로고    scopus 로고
    • U.S. Patent 3 657 282, April 18, 1972
    • 2,3 Christensen, B. G.; Beattie, T. R.; Graham. D. W. U.S. Patent 3 657 282, April 18, 1972. An unsubstituted α-phosphono methylsulfonate ester was reported as an adenosine phospho sulfate analog: Callahan, L.; Ng, K.; Geller, D. H.; Agarwal, K.; Schwartz, N. B. Anal. Biochem. 1989, 177, 67-71.
    • Christensen, B.G.1    Beattie, T.R.2    Graham, D.W.3
  • 6
    • 0024550378 scopus 로고
    • 2,3 Christensen, B. G.; Beattie, T. R.; Graham. D. W. U.S. Patent 3 657 282, April 18, 1972. An unsubstituted α-phosphono methylsulfonate ester was reported as an adenosine phospho sulfate analog: Callahan, L.; Ng, K.; Geller, D. H.; Agarwal, K.; Schwartz, N. B. Anal. Biochem. 1989, 177, 67-71.
    • (1989) Anal. Biochem. , vol.177 , pp. 67-71
    • Callahan, L.1    Ng, K.2    Geller, D.H.3    Agarwal, K.4    Schwartz, N.B.5
  • 11
    • 0025348425 scopus 로고
    • Denmark, S. E.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 864-866. Denmark, S. E.; Miller, P. C.; Wilson, S. R. J. Am. Chem. Soc. 1991, 113, 1468-1470.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 864-866
    • Denmark, S.E.1    Dorow, R.L.2
  • 13
    • 10544235993 scopus 로고    scopus 로고
    • Control studies indicate that the reduced diastereoselectivity in the sulfuration is not the result of epimerization of sulfurated phosphonate 10
    • Control studies indicate that the reduced diastereoselectivity in the sulfuration is not the result of epimerization of sulfurated phosphonate 10.
  • 14
    • 10544256006 scopus 로고    scopus 로고
    • note
    • 4 (pH = 4.6), 16% 2-propanol, and 6% methanol. The retention times were 24.5 and 15.7 min, respectively.
  • 16
    • 10544244450 scopus 로고    scopus 로고
    • note
    • Details of the X-ray structural analysis for 5(S) and the related compound i of ref 2 are included as Supporting Information. Atomic coordinates for both compounds have been deposited in the Cambridge Crystallographic Database and can be obtained upon request to the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 IEZ, U.K.
  • 19
    • 10544244890 scopus 로고    scopus 로고
    • note
    • Compound 1(S) was isolated from the 3 and 6 h plasma samples and the 0-12 h bile samples of rats that had received single 40 μmol/kg oral doses of 2(S) and analyzed for 1(R) and 1(S) by HPLC using the assay reported in ref 8. The results showed that the isolated samples contained greater than 99.5% of 1(S).
  • 23
    • 10544230915 scopus 로고    scopus 로고
    • note
    • 10 of the related α-phosphono sulfonate (structure i of ref 2).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.