Synthesis and comparing the antibacterial activities of pyrimidine derivatives
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Abstract
A series of 10 derivatives of 5-(5-amino-1,3,4-thiadiazole-2-yl)-3,4-dihydro-6-methyl-4-phenyl-pyrimidin-2(1H)-one and 10 derivatives of 3,4-dihydro-5-(5-mercapto-4H-1,2,4-triazol-3-yl)-6-methyl-4-phenyl pyrimidin-2(1H)-one have been synthesized. Among the synthesized derivatives, triazole substituted compounds have shown higher antibacterial inhibition when compared to the thiadiazole derivatives. All the structures of the newly synthesized compounds have been characterized by IR, 1H and 13C NMR, GC-MS and CHN analysis. Most of the compounds have shown promising antibacterial activity when compared with the standard drug ciprofloxacin.
A series of ten derivatives of 5-(5-amino-1,3,4-thiadiazole-2-yl)-3,4-dihydro-6-methyl-4-phenylpyrimidin-2(1H)-one and ten derivatives of 3,4-dihydro-5-(5-mercapto-4H-1,2,4-triazol-3-yl)-6-methyl-4-phenyl pyrimidin-2(1H)-one have been synthesized and structures characterized. Among the synthesized derivatives, triazole substituted compounds have shown higher antibacterial inhibition when compared to the thiadiazole derivatives.
Keywords
5-amino thiadiazole 5-amino triazole hydrazine carbothioamide pseudomonas aeruginosa; staphylococcus aureus escherichia coli.Notes
Acknowledgements
The authors are thankful to the Principal and Research Department of Chemistry, Islamiah College, Vaniyambadi, Vellore district, Tamil Nadu, India for constant encouragement and providing necessary facilities.
Supplementary material
References
- 1.Mohd A, Kumar A, Ali I and Khan S A 2009 The synthesis of pharmaceutically important 1,3,4-thiadiazole and imidazolinone derivatives: Antimicrobial studies of heterocyclic compounds Indian J. Chem. 48 1288Google Scholar
- 2.Xiang Li, He-Mei Liu, Xui-Zhang and Zhi-Hui 2012 Synthesis and evaluation of antitumor activities of Novel chiral 1,2,4-triazole derivatives: A study of Schiff bases bearing γ-butenolide moiety Org. Med. Chem. Lett. 2 1CrossRefGoogle Scholar
- 3.Karaarslan M, Kopair P, Cansiz A, Orek C and Sap O 2012 Synthesis and antimicrobial activity of some new 5-(Pyridin-4-yl)-3-thioacetamido-1,2,4-triazole derivatives: Antimicrobial studies of substituted triazole Chem. Sci. Trans. 1 226CrossRefGoogle Scholar
- 4.Merchant J R, Suneel Y and Dike 1978 Synthesis of some 2,4-diamino-pyrrolo-pyrimidines: A study of substituted pyrimidine J. Chem. Sci. 87 229Google Scholar
- 5.EI-Sayed R 2006 Synthesis, antibacterial and surface activity of 1,2,4-triazole derivatives: Antibacterial studies of triazole Indian J. Chem. 45 738Google Scholar
- 6.Andrews B and Ahmed M 2013 Novel synthesis and characterization of some pyrimidine derivatives of oxadiazoles, triazoles and thiadiazoles: Synthesis of substituted pyrimidine derivatives Asian J. Chem. 25 2070Google Scholar
- 7.Andrews B and Ahmed M 2015 An efficient synthesis, characterization and anti-bacterial activity of pyrimidine bearing 1,3,4-thiadiazole derivatives: A study of pyrimidine moiety Indian J. Chem. 54 406Google Scholar
- 8.Ilangovan A, Saravanakumar S and Umesh S 2015 T3P as an efficient cyclodehydration reagent for the one-pot synthesis of 2-amino-1,3,4-oxadiazoles: A study of substituted oxadiazole J. Chem. Sci. 127 797CrossRefGoogle Scholar
- 9.Kushal R, Lanjewar M. S and Binda D 2009 Synthesis and antimicrobial activity of 5-(2-aminothiazol-4-yl)-3,4-dihydro-4-phenyl pyrimidin-2(1H)-one: Synthesis of pyrimidine compound Indian J. Chem. 48 1732Google Scholar
- 10.Kape C O 2000 Dihydropyrimidine synthesis Eur. J. Med. Chem. 35 1043CrossRefGoogle Scholar
- 11.Kape C O 1993 Biginelli dihydropyrimidine synthesis Tetrahedron 49 6937CrossRefGoogle Scholar
- 12.Nagarajan S, Tanveer M, Shaikh and Kandasamy E 2015 Synthesis of 1-alkyl triazolium triflate room temperature ionic liquids and their catalytic action: Studies in multi-component Biginelli reaction J. Chem. Sci. 127 1539CrossRefGoogle Scholar
- 13.Manjula A, Rao B V and Neelakantam P 2004 An inexpensive protocol for Biginelli reaction: Synthesis of pyrimidine compound Synth. Commun. 34 2665CrossRefGoogle Scholar
- 14.Andrew J, Zych Hong-Jun Wang, Samuel A and Sakwa 2010 Synthesis and Suzuki-Miyaura reaction: Synthesis of dihydropyrimidine-2(1H)-one Tetrahedron Lett. 51 5103CrossRefGoogle Scholar
- 15.Garima, Srivastava V P and Yadav L D S 2010 Biginelli reaction: Starting directly from alcohol Tetrahedron Lett. 51 6436CrossRefGoogle Scholar
- 16.Reddy Y T, Reddy P N, Kumar B S and Rajitha B 2005 Bismuth oxide perchlorate catalysed: Synthesis of dihydropyrimidine-2 compound Indian J. Chem. 44B 1304Google Scholar
- 17.Bose D S, Fathima L and Mereyala H B 2003 Synthesis of 5-alleoxycarbonyl-4-aryl-3,4-dihydropyrimidine-2(1H)-one: Synthesis of multi-compounds J. Org. Chem. 68 587CrossRefGoogle Scholar
- 18.Sergey V, Ryabukhin Andrey S, Plaskon Semen S, Bondarenko Eugeniy N, Ostapchuk Oleksandr O, Grygorenko Oleg V and Tolmachev 2010 Acyl pyruvates as synthos: Biginelli reaction Tetrahedron Lett. 51 4229CrossRefGoogle Scholar
- 19.Rosenani A, Haque and Salam M A 2015 Synthesis, structural characterization and biological activities of organotin(IV) complexes with methoxybenzaldehyde: Synthesis of thiosemicarbazone J. Chem. Sci. 127 1589CrossRefGoogle Scholar
- 20.Ramchander J, Rameshwar N, Reddy T S, Raju G and Reddy A R 2014 Synthesis and photophysical properties of 1,4-disubstituted naphthloxymethyl-N-alkyl naphthimide-1,2,3-triazole: Synthesis of substituted triazole J. Chem. Sci. 126 1063CrossRefGoogle Scholar
