Synthesis and evaluation of some novel derivatives of 2-propoxybenzylidene isonicotinohydrazide for their potential antimicrobial activity

Abstract

A novel series of Mannich which contained isoniaside were prepared. First by the reaction of 2-propoxybenzaldehyde with isoniazid corresponding hydrazone (2a) was obtained. After that, product 2a after mannich reaction of aminomethylation with formaldehyde and secondary give amines (2b-2k). The inhibitory potencies of the synthesized compounds were assayed in vitro against a panel of microorganisms and against A549 human lung adenocarcinoma cell line. Compounds 2c and 2k displayed moderate to potent antimicrobial activity against all the tested strains and they also exhibited significant cytotoxicity in a dose-dependent manner with an IC50 values ranging from 2.84 to 8.55 (μg) and 0.007-0.030 (μM). The structures of newly synthesized compounds were evaluated by elemental and spectral (IR, 1HNMR, 13C-NMR) methods. The result demonstrates the potential and importance of developing new mannich bases which would be effective against resistant microbial strain and they may be useful leads for anticancer drug development in the future

Mannich bases in medicinal chemistry and drug design

“…29). A few members of this collection having an ethoxy group demonstrated at concentration of 100 mg/mL antibacterial activity superior to that of reference drug amoxicillin at 50 mg/mL [223], whereas candidates having a propoxy group were less potent [224]. Mannich bases 154 derived from 7-methyl-2-(substituted aryl) imidazo[1,2-a]pyridines ( Fig.…”

“…Aminomethylated hydrazidones 153 (R 1 ¼ C 2 H 5 ) derived from isonicotinic acid hydrazide ( Fig. 29) had good anti-Candida activity [223], but their analogues 153 (R 1 ¼ n-C 3 H 7 ) were less active, and their activity against A. niger was even poorer [224]. Several dimethylamine Mannich bases 154 derived from 7-methyl-2-(substituted aryl)imidazo[1,2-a]pyridines (Fig.…”

Mannich Bases: An Important Pharmacophore in Present Scenario

“…In each well MTT in phosphate buffer saline was added and incubated and then DMSO was added to each well and kept in incubator. From all the compounds synthesized, 23c and 23k exhibited potential cytotoxic activity superior to that of the standard drug, gemcitabine [ 50 ].…”

Design, Synthesis, Characterization, and Computational Studies on Benzamide Substituted Mannich Bases as Novel, Potential Antibacterial Agents

“…This mixture was allowed to stand for 2 minutes and then 4 mL water was added to it. The crude product was recrystallized with ethanol [ 10 ].…”