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Vol. 31 No. 6 (2019): Vol 31 Issue 6

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Regioselective Synthesis of Novel [N-(4-Oxo-3-(2-phenyl-1,8-naphthyridin-3-yl)-thiazolidin-2-ylidene)]acetamide/benzamides and their Biological Activity

https://doi.org/10.14233/ajchem.2019.21881
Ramalingam Kundenapally
Department of Chemistry and Pharmaceutical Sciences, Mahatma Gandhi University, Nalgonda-508254, India
https://orcid.org/0000-0003-0005-022X
Ramesh Domala
Department of Chemistry and Pharmaceutical Sciences, Mahatma Gandhi University, Nalgonda-508254, India
https://orcid.org/0000-0002-8197-4709
B. Sreenivasulu
Centre for Chemical Sciences and Technology, Insitute of Science & Technology, Jawaharlal Nehru Technological University, Hyderabad-500085, India
https://orcid.org/0000-0003-4688-0691

Corresponding Author(s) : Ramesh Domala

synchemram@gmail.com

Asian Journal of Chemistry, Vol. 31 No. 6 (2019): Vol 31 Issue 6

Abstract

In an attempt to discover the new antibacterial agents to fight the bacterial infections, a series of 1,8-naphthyridine based 2-iminothiazolidin-4-one derivatives was synthesized by a straight-forward regioselective synthesis. 2-Phenyl-1,8-naphthyridin-3-amine (2) was reacted with acetyl or aroyl isothiocyantes to give the corresponding N-[(2-phenyl-1,8-naphthyridin-3-yl)carbamothioyl)]acetamide or benzamides (3a-e). Finally, the target compounds [N-(4-oxo-3-(2-phenyl-1,8-naphthyridin-3-yl)thiazolidin-2-ylidene)]acetamide or benzamides (4a-e) were obtained by the reaction of thiourea (3a-e) with chloroacetyl chloride in presence of pyridine. All the synthesized products were formed in good yields and their structures were characterized by spectral (IR, EI-MS and NMR) and physical data. The biological activity of title compounds was evaluated against the bacterial strains and found to be more potent.

Keywords

1,8-Naphthyrdine Aroyl thiourea Aroyl isothiocyanate Iminothiazolidin-4-one Antibacterial activity
Kundenapally, R., Domala, R., & Sreenivasulu, B. (2019). Regioselective Synthesis of Novel [N-(4-Oxo-3-(2-phenyl-1,8-naphthyridin-3-yl)-thiazolidin-2-ylidene)]acetamide/benzamides and their Biological Activity. Asian Journal of Chemistry, 31(6), 1246–1250. https://doi.org/10.14233/ajchem.2019.21881
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