Open AccessSynthesis of Novel Triazolothione, Thiadiazole, Triazole and Oxadiazole Functionalized Tri-fluoromethylnaphthyridine Derivatives and their Anticancer Activity & Antimicrobial Activity
Author(s) -
Sailu Betala,
Hanumandlu Racha,
Chiranjeevi Abba
Publication year - 2020
Publication title -
asian journal of chemistry/asian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.145
H-Index - 34
eISSN - 0975-427X
pISSN - 0970-7077
DOI - 10.14233/ajchem.2020.22688
Subject(s) - chemistry , hela , trifluoromethyl , carbohydrazide , oxadiazole , bacillus subtilis , triazole , hydrazine (antidepressant) , antimicrobial , 1,2,4 triazole , combinatorial chemistry , medicinal chemistry , nuclear chemistry , stereochemistry , organic chemistry , bacteria , cell , biochemistry , alkyl , genetics , biology
Novel triazolothione, thiadiazole, triazole and oxadiazole-tagged trifluoromethyl group containingnaphthyridine derivatives (6a-l and 7a-d) were synthesized from 2-amino-6-(thiophen-2-yl)-4-(trifluoromethyl)nicotinonitrile (1) on treatment with acetophenone and obtained 2-phenyl-7-(thiophen-2-yl)-5-(trifluoromethyl)-1,8-naphthyridin-4-amine (2), compound 2 on reaction with bromoethylacetateand after that reaction with hydrazine hydrate and obtained carbohydrazide derivatives (4), compound4 on reaction with different substituted phenyl isothiocyanates to obtain phenyl hydrazine carbothiamidederivatives (5). Compound 5 is independently reaction with NaOH, H2SO4 and N2H4·H2O to obtaintriazolothione, thiadiazole, triazole-substituted naphthyridine derivatives (6a-l), respectively. Thecarbohydrazide compounds 4 on reaction with diverse substituted aromatic acids and obtainedoxadiazole derivatives (7a-d). All the synthesized compounds (6a-l and 7a-d) were tested for anticanceractivity against four cancer cell lines such as “HeLa-cervical cancer (CCL-2) COLO 205-colon cancer(CCL-222) HepG2-liver cancer (HB-8065) MCF7-breast cancer (HTB-22) and one normal cell line(HEK 293)”. Compounds 6b, 6d and 6l are known to have good anticancer activity at micro molarconcentration and found to be non-toxic on normal cell line. And all the products 6a-o and 7a-d weretested against Gram-positive, Gram-negative bacteria and fungal strains. All the compounds, compounds6e-h showed more activity against Bacillus subtilis (MTCC-121) at < 6.8 micromolar concentration.Compounds (which showed more activity) further screened for minimum bactericidal concentrationagainst B. subtilis MTCC 121 using ciprofloxacin as standard and known to show optimistic activity.These compounds further tested for biofilm inhibition activity against B. subtilis MTCC 121 usingerythromycin as standard which confirmed the high activity.