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Volumn 16, Issue 8, 2006, Pages 2205-2208

An efficient, asymmetric solid-phase synthesis of benzothiadiazine- substituted tetramic acids: Potent inhibitors of the hepatitis C virus RNA-dependent RNA polymerase

Author keywords

HCV polymerase inhibitors; Hepatitis C; Solid phase synthesis

Indexed keywords

BENZOTHIADIAZINE DERIVATIVE; RNA POLYMERASE; TETRAMIC ACID DERIVATIVE;

EID: 33644810532     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.01.034     Document Type: Article
Times cited : (48)

References (18)
  • 1
    • 33644793908 scopus 로고    scopus 로고
    • WHO 1999; CDC/NIH 2002.
    • WHO 1999; CDC/NIH 2002.
  • 5
    • 33644805279 scopus 로고    scopus 로고
    • note
    • In vitro data reported herein were obtained using the Δ21 enzyme.
  • 7
    • 0001246453 scopus 로고
    • For a review on tetramic acids, see: B.J.L. Royles Chem. Rev. 95 1995 1981
    • (1995) Chem. Rev. , vol.95 , pp. 1981
    • Royles, B.J.L.1
  • 11
    • 45949119318 scopus 로고
    • Commercially available resins pre-loaded with l-amino acids were obtained from Polymer Labs (www.polymerlabs.com ), typically 0.86 mmol/g, >99% optical purity. Amino acids can also be loaded onto Wang using standard techniques such as described in P. Sieber Tetrahedron Lett. 28 1987 6147
    • (1987) Tetrahedron Lett. , vol.28 , pp. 6147
    • Sieber, P.1
  • 12
    • 33644801852 scopus 로고    scopus 로고
    • Anti-infectives. WO2004058150, 2004.
    • Fitch, D. M. Anti-infectives. WO2004058150, 2004.
    • Fitch, D.M.1
  • 14
    • 33644799442 scopus 로고    scopus 로고
    • note
    • Reaction progress was monitored using LCMS comparing the UV214 absorbance of the product in solution and a constant internal standard versus time. The residual resin was also cleaved under acidic conditions (trifluoroacetic acid in dichloromethane) to check for any remaining starting material.
  • 16
    • 33644794067 scopus 로고    scopus 로고
    • note
    • A chiral HPLC method was used to determine the enantiomeric excess (Chiralpak AD column with 0.1% TFA in 100% ethanol at 1 mL/min).
  • 17
    • 33644789969 scopus 로고    scopus 로고
    • note
    • All products were subjected to final purification via reverse-phase HPLC before biological analysis. Due to the presence of TFA, products suffered some loss of enantiopurity under the acidic reverse-phase HPLC conditions. Compounds of interest could be resynthesized and repurified using alternative conditions, but the SAR trends discovered for this series remained unchanged.
  • 18


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.