4-Hydroxy-2-quinolones 166*. Synthesis, isomerism, and antitubercular activity of 3-arylaminomethylene-quinoline-2,4-(1H,3H)-diones

Abstract

The search for novel biologically active compounds with antitubercular activity has gained special urgency in the last 10-15 years. The reason for increased attention directed towards this problem has been the widespread appearance and global distribution of resistant strains of the tubercular mycobacterium which are stable to current medicinal preparations.An interest in thiazolidin-4-ones has not diminished following the isolation in a pure state, structural identification [2], and then the synthesis [3] of actithiazic acid as an antibiotic having highly specific activity towards the mycobacterium. As a result, compounds based on this heterocycle were produced for the fight against pathogens of different mycobacterial infections [4-6] including tuberculosis [7,8].4-Hydroxyquinol-2-ones posses a high potential for antimycobacterial properties hence their combination with thiazolidin-4-ones in a single molecular system seems quite interesting and promising.Thiazolidin-4-ones are obtained by a well known reaction of thioglycolic acid [9] or its esters [10] with Schiff bases. Often more simple in use is a three component condensation of an aldehyde, thioglycolic acid (alkyl thioglycolate) and primary amine [11]. The yields of the final products vary widely and this is fully

4-Hydroxy-2-quinolones 171*. Synthesis, isomerism, and antitubercular activity of 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid alkylidenehydrazides

“…The experimental data in Table 1 clearly shows that exchange of the benzaldehydes for lower aliphatic ketones causes a very marked fall in the antimicobacterial activity of the 1-R-4-hydroxy-2-oxo-1,2-dihydro-3-quinolinoyl hydrazones derived from them. In addition, the much lower activity for the high solubility acylhydrazones 2 and 3 when compared with their extremely poorly soluble structural analogs (prepared using 3-acetyl-4-hydroxy-2-oxo-1,2-dihydroquinoline [22] as the ketone component) once more confirms the conclusion we have reached before that the antitubercular activity of 4-hydroxy-2-quinolones does not, in practice, depend on solubility.…”

Synthesis and biological activity of pyrimido [1, 2-a] quinoline moiety and its 2-substituted derivatives

“…Despite its relatively low efficacy and tolerability, quinine still plays an important role in the treatment of multi resistant malaria 1 . Quinoline and its derivatives are receiving important due to their due to wide range of biological activities as a drug analgesics 2 ,antiamoebic [3][4][5][6] , tryphocidal 7 , antiseptic 8 and antiserotonin 9 .In addition to these, derivatives also exhibit good antimalarial 10,11 , antitubercular 12 , antibacterial 13 , antihistaminic 14 , antineurodegerative 15 , anticonvulsant 16 , antitumor 17 , anticancers [18][19][20] and antiallergics 21 activities. In view of these observations, such as quinoline fused with pyrimidine ring would exhibit some interesting pharmacological activities, further, the ring anellation to amino groups containing nitrogen heterocycles with ketene dithioacetals as reagent has reported [22][23] .…”

Synthesis and Antimicrobial Activity of 3‐Cyano‐4‐imino‐9‐methoxy‐4H‐pyrimido [2, 1-b] pyrimido [4, 5-b] quinoline and 2‐Substituted Derivatives

“…Quinoline and its derivatives are receiving important due to their wide range of biological activities as a drug analgesics [4], antiamoebic [5][6][7][8], trypanocidal [9], antiseptic [10], and antiserotonin [11]. In addition to these, derivatives also exhibit good antimalarial [12,13], antitubercular [14], antibacterial [15], antihistaminic [16], anti-neurodegerneative [17], anticonvulsant [18], antitumor [19], anticancers [20,21], and antiallergics [22] activities.…”