Antiallergic activity of tetracyclic derivatives of quinoline-2-carboxylic acids. 1

Abstract

Substitution of 1,4-dihydro-4-oxoquinoline-2-carboxylic acid by acetyl, benzoyl, and phenylsulfonyl substituents was found to enhance activity in the rat passive cutaneous anaphylaxis assay. A further increase in activity, to equipotency with DSCG, was achieved by incorporation of the 8-benzoyl moiety into a tetracyclic structure to give 1,4-dihydro-4,11(1H,11H)-dioxoindeno[1,2-h]quinoline-2-carboxylic acid (20). In contrast, the reverse isomer 19 was found to have little activity.

Controlling Helix Handedness in Water‐Soluble Quinoline Oligoamide Foldamers

“…Three designs were proposed, all of which are accessible from a common ketone precursor 12 (Scheme ), the synthesis of which has been described previously 20. One face of the Q Phen monomer (Figure 2) is hindered by the steric bulk of a pendant phenoxy group.…”

“…Methyl 8‐Acetyl‐4‐methoxyquinoline‐2‐carboxylate (13): Methyl 8‐acetyl‐4‐hydroxyquinoline‐2‐carboxylate20 (491 mg, 2.00 mmol) was dissolved in acetone (10 mL), and potassium carbonate (553 mg, 4.00 mmol) and dimethyl sulfate (182 μL, 2.00 mmol) were added. The mixture was stirred at reflux for 1 h and then cooled to room temp.…”

Quinolone Analogues 12: Synthesis and Tautomers of 2‐Substituted 4‐Quinolones and Related Compounds

“…The 6‐substituted 4‐quinolone‐2‐carboxylates 4a , 4b were synthesized by the reaction of 4‐fluoroaniline and 4‐trifluoromethylaniline with dimethyl acetylenedicarboxylate, according to a known method in a slight modification , wherein intermediary adducts were not purified before cyclization into compounds 4a , 4b under reflux in diphenyl ether.…”

A simple synthesis of trisubstituted quinolines through transesterification

“…The structural core of quinoline has generally been synthesized by various conventional name reactions [5]. There have been very few reports available on synthesis of 2,3,4-trisubstituted quinoline derivatives by using 2-aminoaryl ketones and dialkyl acetylenedicarboxylate, and these compounds show antiallergic properties [6,7]. However, synthetic protocols reported so far suffer from high temperatures, prolonged reaction times, harsh reaction conditions, and low yields of the products.…”