Quinoline-2,4-dicarboxylic acids: Synthesis and evaluation as inhibitors of the glutamate vesicular transport system

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 17, 1999, Pages 2607-2612

  Carrigan, Christina N ^a   Esslinger, C Sean ^a   Bartlett, Richard D ^a   Bridges, Richard J ^a   Thompson, Charles M ^a  

^a UNIVERSITY OF MONTANA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DICARBOXYLIC ACID DERIVATIVE; GLUTAMIC ACID DERIVATIVE; PROTEIN DERIVATIVE; PROTEIN INHIBITOR; QUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; PHARMACOPHORE; PROTEIN TRANSPORT; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

BIOLOGICAL TRANSPORT; CARRIER PROTEINS; DICARBOXYLIC ACIDS; EVALUATION STUDIES; GLUTAMIC ACID;

EID: 0033530121     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00444-8     Document Type: Article

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15. 4. The solution was concentrated and the crude product was chromatographed on silica gel using EtOAc/hex. Yields of dimethyl quinoline-2,4-dicarboxylates ranged from 5-50%. QDC diesters (1.0 mmol) were dissolved in THF (10 mL), water added (5 mL) and 0.5 mL of 6 M NaOH (or LiOH) added with stirring. When the reaction was complete (typically 6-48 h), the THF/water was removed by rotary evaporation, the semi-solid redissolved in water (2-3 mL), the solution chilled, HCl (concd) added to precipitate the product, and the QDC isolated by centrifugation (2000 x g). All QDC's reported in Table 1 had satisfactory spectral and elemental or mass spectral analyses. Details to be reported elsewhere.
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