4-Hydroxy-2-quinolones 121. Synthesis and biological properties of 1-hydroxy-3-oxo-5,6-dihydro-3h-pyrrolo[3,2,1-ij]quino-line-2-carboxylic acid alkylamides

Abstract

Keywords: alkylamides, 4-hydroxy-2-oxoquinoline-3-carboxylic acids, diuretic activity, anti-inflammatory activity, X-ray structural analysis.For transformation of ethyl 1-hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[3,2,1-ij]quinoline-2-carboxylates (1) to alkyl-, aryl-, or hetarylamides (of interest as potentially biologically active materials) it was proposed to treat them with a 40% excess of the corresponding amine in refluxing bromobenzene over 20 h with subsequent distillation of solvent at reduced pressure and purification of the final reaction products [2]. At the same time, the high reactivity of 1-R-3-ethoxycarbonyl-4-hydroxy-2-oxo-1,2-dihydroquinolines has been noted and this allows them to be amidated quite efficiently [3][4][5]. The obvious structural similarity of ester 1 with these compounds led us to suggest that they will react with amines (at least aliphatic) under milder conditions.i R = C 5 H 11 , j R = i-C 5 H 11 , k R = 2-hydroxyethyl, l R = 3-hydroxypropyl, m R = cyclo-C 3 H 5 ,

Methyl-substituted anilides of 4-hydroxy-1-methyl-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carb-oxylic acid. Synthesis, spectral characteristics and biological properties

“…Из всех теоретически возможных изо-меров здесь внимание на себя обращает только 2,4-диметиланилид 2f, занимающий по уровню анальгетической активности промежуточную по-зицию между 2-и 4-монометильными производ-ными 2а и 2с соответственно. Структурное сходство анилидов 2а-h с обла-дающими высокой диуретической активностью 1-R-4-гидрокси-2-оксо-1,2-дигидрохинолин-3-карбоксанилидами [5][6][7][8][9][10][11] послужило теоретиче-ской предпосылкой для изучения их влияния и на мочевыделительную функцию почек. В дан-ном исследовании использована традиционная методика [12].…”

One-pot synthesis of pyrano[3,2-c]quinoline-2,5-dione derivatives by Fe3O4@SiO2-SO3H as an efficient and reusable solid acid catalyst

“…4-Hydroxyquinolones are among quinolines, which are highly beneficial derivatives and develop activities such as analgesic, anti-inflammatory, and anti-allergy with respect to the existing substituents in the structure [9][10][11]. These compounds as herbicides and dyes have good performance and are used in the synthesis of heterocyclic compounds, for example, oxazinoquinolines, isoxazoloquinolines, and pyranoquinolines [12][13][14].…”

Efficient chemoselective alkylation of quinoline 2,4‐diol derivatives in water

“…These compounds have shown variety of biological activities [1]. The C-3-dialkyl derivative of quinoline 2,4-diol, buchapine 1, was isolated from methanolic extract of the epigeal part of Haplophyllum bucharicum [2], H. tuberculatum [3,4], Euodia roxburghiana.…”