Non-enzymatic hydration, amine addition, and oxidation reactions of aza-arene oxides

Boyd, Derek R.; Davies, R. Jeremy H.; Dunlop, Rebecca A.; Porter, H. Patricia; Hamilton, Lynne; McCullough, John J.

doi:10.1039/c39890000163

Cited by 6 publications

(5 citation statements)

References 2 publications

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“…The syntheses of racemic quinoline arene oxides (20, 25), trans-dihydrodiols (21, 26), syn-and anti-arene dioxides (28 and 29), and trans-diol epoxides (30 and 31), were previously reported (Agarwal et al, 1986;Boyd et al, 1989Boyd et al, , 1994Bushman et al, 1989;Willems et al, 1992) (Figures 8, 10). These chiral compounds, along with achiral metabolites including N-oxide 24 and phenols 4, 5, 22, and 23, were tested for mutagenicity, using the Ames/Salmonella microsomes method (Willems et al, 1992;Suzuki et al, 2000).…”

Section: Chemoenzymatic Synthesis Of Isolated and Potential Arene Oxide Metabolites Of Quinolinementioning

confidence: 74%

“…In the context of mutagenesis studies of known and possible mammalian metabolites of quinoline 1 (Willems et al, 1992), our multistep chemical synthesis routes to racemic quinoline oxides (20 and 25) and quinoline dioxides (28 and 29), were achieved via tetrahydrobromohydrins (32, 34) and tetrahydroepoxides (33, 35) intermediates (Figure 10) (Agarwal et al, 1986(Agarwal et al, , 1990Boyd et al, 1989Boyd et al, , 1991b.…”

Section: Chemoenzymatic Synthesis Of Isolated and Potential Arene Oxide Metabolites Of Quinolinementioning

confidence: 99%

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Toluene Dioxygenase-Catalyzed cis-Dihydroxylation of Quinolines: A Molecular Docking Study and Chemoenzymatic Synthesis of Quinoline Arene Oxides

Boyd

Sharma

Loke

et al. 2021

Front. Bioeng. Biotechnol.

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Molecular docking studies of quinoline and 2-chloroquinoline substrates at the active site of toluene dioxygenase (TDO), were conducted using Autodock Vina, to identify novel edge-to-face interactions and to rationalize the observed stereoselective cis-dihydroxylation of carbocyclic rings and formation of isolable cis-dihydrodiol metabolites. These in silico docking results of quinoline and pyridine substrates, with TDO, also provided support for the postulated cis-dihydroxylation of electron-deficient pyridyl rings, to give transient cis-dihydrodiol intermediates and the derived hydroxyquinolines. 2-Chloroquinoline cis-dihydrodiol metabolites were used as precursors in the chemoenzymatic synthesis of enantiopure arene oxide and arene dioxide derivatives of quinoline, in the context of its possible mammalian metabolism and carcinogenicity.

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Section: Chemoenzymatic Synthesis Of Isolated and Potential Arene Oxide Metabolites Of Quinolinementioning

confidence: 74%

Section: Chemoenzymatic Synthesis Of Isolated and Potential Arene Oxide Metabolites Of Quinolinementioning

confidence: 99%

Toluene Dioxygenase-Catalyzed cis-Dihydroxylation of Quinolines: A Molecular Docking Study and Chemoenzymatic Synthesis of Quinoline Arene Oxides

Boyd

Sharma

Loke

et al. 2021

Front. Bioeng. Biotechnol.

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“…Construction of the hydroxyethyl portion: the first route :13d We have previously synthesized the dihydroquinoline segment C ( 66 ) of siomycin D 1 , with the hydroxymethyl group instead of the hydroxyethyl group (Scheme ) 13b. Aldehyde 63 derived from 5,6,7,8‐tetrahydroquinoline ( 62 ) was transformed into alcohol 64 , which was subjected to the regioselective epoxide‐opening reaction70 with the L ‐valine derivative 65 in the presence of LiClO 4 71 to afford 66 . The intermediate aldehyde 63 (91 % ee ) was the starting substance for our first route.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Siomycin A: Construction of Synthetic Segments

Mori¹,

Higashibayashi²,

Goto³

et al. 2008

Chemistry An Asian Journal

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The five practical segments for the total synthesis of siomycin A, that is, the dehydropiperidine segment A (5), the pentapeptide segment B (3), the dihydroquinoline segment C (6), and the beta-phenylselenoalanine dipeptide segments D (7) and E (4), were synthesized. Segment A (5) was constructed by the coupling of the azomethine ylide and the chiral sulfinimine, followed by the stereoselective reduction of the six-membered imine function. Segment B (3) was synthesized by the phenylselenylation of the beta-lactone, stereoselective vinylzinc addition to the chiral sulfinimine, and oxazoline-thioamide conversion. Segment C (6) was prepared by the one-pot olefination of the tetrahydroquinoline N-oxide using triflic anhydride and triethylamine, stereoselective reduction of the methyl ketone function, and regioselective Yb(OTf)(3)-catalyzed epoxide opening by the amino group. Segments D (7) and E (4) were synthesized by coupling of the properly protected beta-phenylselenoalanines.

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“…* Prolonged treatment of either alcohol with PPA yielded a mixtue of olefins (7A)/(7B) via an acid-catalysed isomerisation mechanism. The oxides of quinoline (2) and (4) were obtained via the bromo acetate (8) and dibromo acetate ( 9) intermediates (overall yield from (7), 56-7479 and via the tetrahydro epoxide (10) and bromo tetrahydro epoxide (11) intermediates (overall yield from (7), 5 9 4 5 % ) (Scheme 2). The latter synthetic routes to quinoline 5,6-oxide (2) and 7,8-oxide (4) were analogous to the methods previously reported for the synthesis of naphthalene 1,2-oxide and related arene oxide^.^…”

Section: Resultsmentioning

confidence: 99%

Synthesis of arene oxide and trans-dihydrodiol metabolites of quinoline

Agarwal¹,

Boyd²,

Davies³

et al. 1990

J. Chem. Soc., Perkin Trans. 1

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Racemic samples of 5,6-epoxy-5,6-dihydroquinoline (2) (quinoline 5,6-oxide) and 7,8-epoxy-7,8dihydroquinoline (4) (quinoline 7,8-oxide) have been synthesised by two methods from the corresponding di hydroquinol ine precursors. trans-5,6-D i hydroqui noli ne-5,6 -diol (3) and trans-7,8dihydroquinoline-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).Quinoline (1) is a major azapolycyclic aromatic hydrocarbon found in tobacco smoke,' urban particulates,2 and automobile exhaust^.^ The prevalence of quinoline (1) in the en~ironment,'-~ * 1 eV ca. 1.602 x J.

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Non-enzymatic hydration, amine addition, and oxidation reactions of aza-arene oxides

Cited by 6 publications

References 2 publications

Toluene Dioxygenase-Catalyzed cis-Dihydroxylation of Quinolines: A Molecular Docking Study and Chemoenzymatic Synthesis of Quinoline Arene Oxides

Toluene Dioxygenase-Catalyzed cis-Dihydroxylation of Quinolines: A Molecular Docking Study and Chemoenzymatic Synthesis of Quinoline Arene Oxides

Total Synthesis of Siomycin A: Construction of Synthetic Segments

Synthesis of arene oxide and trans-dihydrodiol metabolites of quinoline

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