Synthesis and evaluation of new chromene based [1,8]naphthyridines derivatives as potential antimicrobial agents

Abstract

Novel chromeno[4,3-f][1,8]naphthyridines derivatives were prepared by multicomponent reaction between 2-((sub)amino)quinoline-3-carbaldehyde 1a–f/2a–f, ethyl 2-cyanoacetate 3 and cyclohexane-1,3-dione 4 in ethanol with l-proline as a catalyst.

Efficient Synthesis of Chromeno[4,3,2‐de] [1,6]naphthyridine Derivatives via Pseudo Four‐Component Reaction

“…[21] Gratifyingly, these results showed propionic acid exhibited the highest efficiency to afford 4 a in 67 % yield (Table 1, entry 2). Among several solvents screened, DMF was found to be the best in terms of product yield (Table 1, entries [7][8][9][10][11]. When the usage of EtCO 2 H was decreased to 1.0 or 1.5 equiv., the yield of the product slightly reduced to 58 and 62 %, respectively (Table 1, entries 12 and 13), but further increasing the amount of EtCO 2 H to 2.3 equiv.…”

“…[9] Additionally, as a distinctive π conjugate system, chromenonaphthyr-idine compounds have recently been investigated for their fluorescence properties [10] and corrosive inhibitors. [11] Although chromenonaphthyridine derivatives showed characteristic biological activity and optoelectronic property, relatively few synthetic methods were developed for substituted chromenonaphthyridines, [8,12] for example, Bandyopadhyay et al reported the Ph 3 PHClO 4 -catalysted intramolecular Povarov reaction of 2-(N-Alkenyl-N-aryl) aminochromone-3-carbaldehyde with aromatic amines to produce chromenonaphthyridine derivatives. [13] In 2018, Maji and co-worker dedicated a domino reaction of aminopyridine and different O-propargylated salicylaldehydes in the presence of CuI/InCl 3 to afford chromenonaphthyridine derivatives.…”

“…[7] In 2016, Patel and co-workers found that chromeno [4,3-f][1,8]naphthyridines derivatives possess potential antimicrobial activity. [8] It is noteworthy that the combinations of pharmaceutical moieties often give different pharmacological properties relative to original pharmacoskeletons. [9] Additionally, as a distinctive π conjugate system, chromenonaphthyr-idine compounds have recently been investigated for their fluorescence properties [10] and corrosive inhibitors.…”

Recent Developments and Multiple Biological Activities Available With 1, 8-Naphthyridine Derivatives: A Review

“…Development and advancement in new antimicrobial drugs are yet in the demand of the day due to microbial resistance, whereby 1, 8-Naphthyridines are imperative components in novel antibacterial drug discovery [28][29][30]. Gohil et al [31] synthesize new chromeno [4,3-f] [1,8] naphthyridines analogs (14a-d) by a multicomponent reaction and evaluate for their antimicrobial activity. The compounds with 4-fluorophenyl (14a),3-trifluoromethyl (14b), 6-Amino-8-(4-fluorophenyl) (14c) and 6-Amino-12-methoxy-8-(3-(trifluoro-methyl)phenyl)-(14d) shows excellent antimicrobial activity against both type of bacterial strains with MIC value 50 mg/ml, and also the compounds (14a) and (14c) exhibit excellent antifungal activity with MIC value 250 mg/ml.…”

Design,in silicostudies, and synthesis of new 1,8-naphthyridine-3-carboxylic acid analogues and evaluation of their H1R antagonism effects

“…28,29 In addition, its derivatives are reported to have a broad spectrum of pharmacological activity. Notable amongst these are A1 and A2A adenosine receptor agonist, 30 antibacterial, 31 analgesic and anti-inammatory 32 agents, cannabinoid receptor ligands 33 and phosphodiesterase (PDE 4) inhibitors. 34 A review of the literature also supports that azelastine as an asthma prophylactic has three main pharmacophoric groups: (i) phthalazinone nuclei, (ii) a p-chlorobenzyl moiety and (iii) a basic amino group, N-methyl azepine.…”