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Vol. 32 No. 8 (2020): Vol 32 Issue 8, 2020

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Synthesis of Novel Triazolothione, Thiadiazole, Triazole and Oxadiazole Functionalized Tri-fluoromethylnaphthyridine Derivatives and their Anticancer Activity & Antimicrobial Activity

https://doi.org/10.14233/ajchem.2020.22688
Sailu Betala
Department of Chemistry, Telangana University, Dichpally, Nizamabad-503322, India
https://orcid.org/0000-0003-1072-6895
Hanumandlu Racha
Department of Chemistry, Telangana University, Dichpally, Nizamabad-503322, India
https://orcid.org/0000-0001-8850-6476
Chiranjeevi Abba
Department of Chemistry, Telangana University, Dichpally, Nizamabad-503322, India
https://orcid.org/0000-0001-9253-3127

Corresponding Author(s) : Sailu Betala

bethalasailu@gmail.com

Asian Journal of Chemistry, Vol. 32 No. 8 (2020): Vol 32 Issue 8, 2020

Abstract

Novel triazolothione, thiadiazole, triazole and oxadiazole-tagged trifluoromethyl group containing naphthyridine 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 bromoethylacetate and after that reaction with hydrazine hydrate and obtained carbohydrazide derivatives (4), compound 4 on reaction with different substituted phenyl isothiocyanates to obtain phenyl hydrazine carbothiamide derivatives (5). Compound 5 is independently reaction with NaOH, H2SO4 and N2H4·H2O to obtain triazolothione, thiadiazole,  triazole-substituted naphthyridine derivatives (6a-l), respectively. The carbohydrazide compounds 4 on reaction with diverse substituted aromatic acids and obtained oxadiazole  derivatives (7a-d). All the synthesized compounds (6a-l and 7a-d) were tested for anticancer activity 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 molar concentration and found to be non-toxic on normal cell line. And all the products 6a-o and 7a-d were tested against Gram-positive, Gram-negative bacteria and fungal strains. All the compounds, compounds 6e-h showed more activity against Bacillus subtilis (MTCC-121) at < 6.8 micromolar concentration. Compounds (which showed more activity) further  screened for minimum bactericidal concentration against 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 using erythromycin as standard which confirmed the high activity. 

Keywords

Triazolothione Thiadiazole Triazole Oxadiazole Anticancer activity Antimicrobial activity
Betala, S. ., Racha, H. ., & Abba, C. . (2020). Synthesis of Novel Triazolothione, Thiadiazole, Triazole and Oxadiazole Functionalized Tri-fluoromethylnaphthyridine Derivatives and their Anticancer Activity & Antimicrobial Activity. Asian Journal of Chemistry, 32(8), 1931–1940. https://doi.org/10.14233/ajchem.2020.22688
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