112259-26-4

Upstream product

• 91-22-5 quinoline 
• 87707-14-0 1a,7b-dihydrooxireno[2,3-f]quinoline 

Downstream Products

• 135096-28-5 (1aS,7bR)-1a,7b-Dihydro-1-oxa-4-aza-cyclopropa[a]naphthalene 
• 158060-56-1 (1aS,7bR)-1a,2,3,7b-Tetrahydro-1-oxa-4-aza-cyclopropa[a]naphthalene 

Relevant academic research and scientific papers

Metabolites of quinoline, a hepatocarcinogen in a subcellular microsomal system

It was evidenced that quinoline was metabolized to quinoline 1-oxide catalyzed by cytochrome P-450-linked mixed function monooxygenase system and to 5,6-trans-dihydroxy-5,6-dihydroquinoline by cytochrome P-448-linked one. The third metabolite, 3-hydroxyquinoline, may be produced in another course of metabolism, which might be connected with genotoxicity of quinoline, as previously discussed.

Structure and Stereochemistry of cis-Dihydro Diol and Phenol Metabolites of Bicyclic Azaarenes from Pseudomonas putida UV4

Biotransformation of quinoline, isoquinoline, quinoxaline and quinazoline using growing cultures of Pseudomonas putida UV4 yielded cis-dihydro diols from the oxidation of the carbocyclic aromatic ring.Aromatic hydroxylation was observed in both carbocyclic and heterocyclic rings.Ring cleavage of the quinoline skeleton to yield anthranilic acid, and cis-diol formation (with alkene bond reduction) to yield cis-5,6,7,8-tetrahydroquinazoline-5,6-diol from quinazoline were observed.The cis-dihydro diol metabolites of quinoline (5,6- and 7,8-) and quinoxaline (5,6-) were found to be optically pure, while metabolism of isoquinoline gave on e homochiral (5,6-) and one racemic 7,8-) cis-dihydro diol product.The absolute configuration of the cis-dihydro diol metabolites have been determined using 1H NMR analyses, stereochemical correlations and X-ray crystallography methods.

Solvolysis of the Quinoline 5,6- and 7,8-Oxides: Effect of the Ring Nitrogen

pH-rate profiles for the hydrolysis of quinoline arene oxides were measured in 1:9 dioxane-water at 25 deg C (0.1 M NaClO4) and compared with the parent carbocylic compound naphthalene 1,2-oxide.Unlike naphthalene 1,2-oxide whose hydrolysis rate shows a first-order dependence on hydronium ion concentration (kH) below pH 5, rates for the quinoline 5,6- and 7,8-oxides show a kH reaction (0.14 and 1.54 M-1 s-1 for quinoline 5,6- and 7,8-oxides, respectively), but plateau below pH 2-3. pH-independent rate constants in the low-pH plateau are 2.7E-5 and 1.7E-3 s-1for the 5,6- and 7,8-oxides, respectively.On the basis of studies of the N-methyl cation of the 5,6-oxide (kobsd -1 at pH 1.8), it is concluded that the low-pH plateau is due to lack of reactivity for the N-protonated quinoline oxides.Also unlike naphthalene oxide, the quinoline oxides show a reaction with hydroxide ion (kOH rate) that results in the formation of trans dihydrodiols.In acid, quinoline 5,6-oxide, but not quinoline 7,8-oxide, gives a significant yield (20percent) of the trans dihydrodiol product and provides the first example of a benzo-ring arene oxide that forms dihydrodiol product under acidic conditions.Other products of the acid-catalyzed reaction of the 5,6-oxide are 5- (73percent) and 6- (7percent) hydroxyquinolines.The 7,8-oxide upon solvolysis in acid gave exclusively 8-hydroxyquinoline.The 100-1000 fold decrease in reactivity of the quinoline oxides, relative to naphthalene oxide in the pH range of 1-10, can be accounted for in terms of the presence of their ring nitrogens and the differences in the pKa values of these nitrogens.

Metabolism of Bicyclic Aza-arenes by Pseudomonas putida to Yield Vicinal cis-Dihydrodiols and Phenols

Metabolism of the aza-arenes quinoline, isoquinoline, quinazoline, and quinoxaline by a mutant strain of the bacterium Pseudomonas putida resulted in attack at the carbocyclic ring (to yield stable cis-dihydrodiols and phenols) and at the heterocyclic ring (to yield phenols and ring cleavage products).