ChemInform Abstract: New Quinolones. Part 1. Synthesis of New Pyrido(3,2‐h)quinoline Derivatives and Their Antibacterial Activities.

Abstract

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Synthesis and in vitro microbial activities of amides of pyridoquinolone

“…6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro- [1,7]phenanthroline-3-carboxylicacid (1a) The parent molecule was prepared from 5-amino-8-chloro quinoline on reaction with diethyl ethoxymethelene malonate and cyclized in diethyl ether; further condensation with chloroethanol gave ester, which finally hydrolyzed to title compounds (Lee et al, 1992). 1 6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro- [1,7]phenanthroline-3-carboxylicacid (1b) The parent molecule was prepared from 5-amino-8-hydroxy quinoline on reaction with diethyl ethoxymethelene malonate and cyclized in diethyl ether; further condensation with chloroethanol gave ester, which finally hydrolyzed to title compounds (Lee et al, 1992).…”

“…1 6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro- [1,7]phenanthroline-3-carboxylicacid (1b) The parent molecule was prepared from 5-amino-8-hydroxy quinoline on reaction with diethyl ethoxymethelene malonate and cyclized in diethyl ether; further condensation with chloroethanol gave ester, which finally hydrolyzed to title compounds (Lee et al, 1992). 1 6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro- [1,7]phenanthroline-3-carbonyl chloride (2a) The mixture of 6-chloro-1-(2-hydroxyethyl)-4-oxo-1, 4-dihydro- [1,7]phenanthroline-3-carboxylic acid (1a) (0.01 mol) and thionyl chloride (0.01 mol) was refluxed using chloroform as a solvent in water bath at 80°C for 5-6 h in anhydrous condition with the help of calcium chloride guard tube, until the HCl gas evolution ceased, and then solvent was removed by distillation.…”

“…Its derivatives possess versatile activity, e.g., carbonic anhydrase inhibitors (Supuran et al, 1998), anticancer (Reddy et al, 2004), anti-inflammatory (Li et al, 1995), anti-HIV (Selvam et al, 2001), COX-2 inhibitors (Dannhardt et al, 2002), selective 5-HT receptor antagonist (Bromidge et al, 2002), antitubercular (Kamal et al, 2007) and antifungal (Briganti et al, 1997) etc. Pyridoquinolones were synthesized and evaluated for antimicrobial activity (Lee et al, 1992;Chang, 1994, 1996), in which pyridine ring was fused with quinazoline ring, and generally known as phenanthroline. The structure-activity relationships of fluoroquinolone have been studied in some reviews (Mitscher, 2005;Bhanot et al, 2001); consideration of the above facts and the presence of fused pyrido ring in nalidixic acid urged us to synthesize structurally similar compounds to fluoroquinolone by replacing fluoro group with chloro and hydroxy groups at C-6 possition with fused pyrido ring; the carboxylic acid group was further converted to amides for enhanced antimicrobial activity.…”

Pyridoquinolones containing azetidinones: synthesis and their biological evaluation

“…Fluorinated pyridoquinolones have been synthesized by Lee and Chang (Lee et al, 1992) and their biological activity has been studied. We have concentrated on nonfluorinated pyridoquinolones, synthesized several compounds by incorporating various substituted urea, thiourea and piperazine compounds at C-3 position and studied their antimicrobial activities (Patel and Chauhan, 2005;Patel et al, 2010a;Patel et al, 2010b), and found that these compounds showed good antimicrobial activities.…”