87707-14-0Relevant academic research and scientific papers
Multi-Functional Oxidase Activity of CYP102A1 (P450BM3) in the Oxidation of Quinolines and Tetrahydroquinolines
Li, Yushu,Wong, Luet L.
, p. 9551 - 9555 (2019/08/06)
Tetrahydroquinoline, quinoline, and dihydroquinolinone are common core motifs in drug molecules. Screening of a 48-variant library of the cytochrome P450 enzyme CYP102A1 (P450BM3), followed by targeted mutagenesis based on mutation-selectivity correlations from initial hits, has enabled the hydroxylation of substituted tetrahydroquinolines, quinolines, and 3,4-dihydro-2-quinolinones at most positions around the two rings in good to high yields at synthetically relevant scales (1.5 g L?1 day?1). Other oxidase activities, such as C?C bond desaturation, aromatization, and C?C bond formation, were also observed. The enzyme variants, with mutations at the key active site residues S72, A82, F87, I263, E267, A328, and A330, provide direct and sustainable routes to oxy-functionalized derivatives of these building block molecules for synthesis and drug discovery.
Synthesis of Arene Oxide and trans-Dihydrodiol Metabolites of Quinoline
Agarwal, Shiv K.,Boyd, Derek R.,Davies, R. Jeremy H.,Hamilton, Lynne,Jerina, Donald M.,et al.
, p. 1969 - 1974 (2007/10/02)
Racemic samples of 5,6-epoxy-5,6-dihydroquinoline (2) (quinoline 5,6-oxide) and 7,8-epoxy-7,8-dihydroquinoline (4) (quinoline 7,8-oxide) have been synthesised by two methods from the corresponding dihydroquinoline precursors. trans-5,6-Dihydroquinoline-5,6-diol (3) and trans-7,8-dihydroquinoline-7,8-diol (5) were obtained both by multi-step synthetic routes from the corresponding dihydroquinolines and by the direct base-catalysed hydration of the corresponding arene oxides (2) and (4).
