SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY OF NOVEL PYRIMIDINE DERIVATIVES

Main Article Content

Naga Venkata Raghavulu Dusanapudi
Piyush. J. Vyas
Saisuryanarayana Donthukurthi

Keywords

Benzenesulfonohydrazide, Tetrahydropyrimidone, 5-nitro furfural, antimicrobial activity and spectral studies

Abstract

Benzenesulfonohydrazide (1) on reaction with Ethyl acetoacetate (2) yield N'-(3-oxobutanoyl) benzene sulfonohydrazide(3). Then the compound(3) reacted with various aromatic aldehydes (4a-g) and Urea (5) yielded N'-(6-methyl-2-oxo-4-aryl-1,2,3,4-tetrahydropyrimidine-5-carbonyl)benzenesulfonohydrazide (6a-g). The compounds (6a-g) further reacted with 5-nitro furfural (7) yields N'-(3-(hydroxy(5-nitrofuran-2-yl)methyl)-6-methyl-2-oxo-4-aryl-1,2,3,4-tetrahydropyrimidine-5-carbonyl)benzenesulfonohydrazide (8a-g). The  structures of both the series of compounds (6a-g) and (8a-g) were characterized structurally by spectral features. The compounds were also monitored for anti microbial activity.
Abstract 175 | PDF Downloads 32

References

1. X. Bi, X. Meng, G. Chen, and P. Zhao, “Manganese oxide catalyzed synthesis of anti-HIV N-substituted benzimidazoles via a one-pot multistep process”, Catal. Commun., Vol.116,pp.27-31,2018.
2. El Ella Abou, D. A. Ghorab, M. M. Noaman, E., H.I. Heiba, and A.I. Khalil, “Molecular modeling study and synthesis of novel pyrrolo[2,3-d]pyrimidines and pyrrolotriazolo pyrimidines of expected antitumor and radioprotective activities”, Bioorg. Med. Chem. Lett., Vol.16(5),pp.2391-2402,2008.
3. R.Abraham, P. Prakash, K.Mahendran, M.Ramanathan, “A Novel Series of N-acyl Substituted Indole-Linked Benzimidazoles and Naphthoimidazoles as Potential Anti Inflammatory, Anti Biofilm and Anti Microbial Agents”Microb. Pathog., vol.114,409-413,2018.
4. S. M. Ali, S. A. Kadhem, A. Jabar, K. Atia, and R. I. Al-bayti, “Synthesis , Characterization and Antibacterial Studies of Some New Imidazole Derivatives,” Journal of Global Pharma Technology ,vol.3026(1), pp. 123–125, 2018.
5. Y. Deng, Y.Wang, C. Marcos Díaz-Fernández, Saturnino Calvo-Losada, J.-Joaquín Quirante , Francisco Sarabia,Manuel Algarra and M.-Soledad Pino-González, Catalysts 2023, 13, 180.
6. S. A. Kadhem, S. M. Ali, A. Jabar, K. Atia, R. H. Salih, and R. A.Abdulrazaq, “Synthesis and study of biological activities of compounds derived from new Imidazole derivative,” J. Pharm. Sci.Res., vol. 10(11), pp. 2818–2824, 2018.
7. A.Kumar,K.K.Bhagat,A.K.Singh,H.Singh,T.Angre,A.Verma,H.Khalilullah,M.Jaromko,
8. A.H.Emvas and P.Kumar,Medicinal Chemistry perspective of pyrido[2,3-d]pyrimidines as anticancer agents,RSC. Adv.,13,69872-6908(2023).
9. A.U. Nerkar,Use of pyrimidine and its derivative in pharmaceuticals: A review. J. Adv. Chem. Sci., 7, 729–732(2021).
10. F. Wang,; R. Zhang,; Y. Cui,; L. Sheng,; Y. Sun,; W. Tian,; X. Liu,; S. Liang, Design, synthesis and biological evaluation of 3,4-dihydronaphthalen-1(2H)-one derivatives as Bcl-2 inhibitors. Res. Chem. Intermed.,43, 5933–5942(2017).
11. A.H. Ananth,; N. Manikandan,; R.K. Rajan,; R. Elancheran,; K. Lakshmithendral,; M. Ramanathan,; A. Bhattacharjee,; S. Kabilan, Design, Synthesis, and Biological Evaluation of 2-(2-Bromo-3-nitrophenyl)-5-phenyl-1,3,4-oxadiazole Derivatives as Possible Anti-Breast Cancer Agents. Chem. Biodivers.,17(2020).
12. K.D. Katariya,; S.R. Shah,; D. Reddy, Anticancer, antimicrobial activities of quinoline based hydrazone analogues: Synthesis,characterization and molecular docking. Bioorgan. Chem.,94, 103406(2020).
13. P.J.Shah, Synthesis, Characterization and biological study of heterocyclic compounds, Indian Journal of Chemistry, 60B,1223(2021).
14. Z. Weisai , L. Shuai , Organic chemistry frontiers , 2,9-16 ( 2019 ).
15. N. Ozbek , S. Alyar , H. Alyar , E. Sahin , N. Karacan , Spectrochimica Acta Part A, 108,
16. 123-132 ( 2013 )
17. N. Ozbek , S. Alyar , N. Karacan , J. Mol . Str., 938 , 48-53 ( 2009 )
18. H. Zhijuan , A. Akayoshi , Nature communications , 10 , 184-193 ( 2019 ) .
19. P.J. Shah, Indian Journal of Chemistry, 60B,1223(2021).
20. F.Yang , S.Tian , Angew . Chem . Int . Ed . , 52 , 4929 -4932 ( 2013 ) .
21. G. N. Alawandi , M. V. Kulkarni , Indian J. Chem . 45B , 258-66 ( 2006 ) .
22. H. G. Aslan , N. Karacan , E. Aslan , J. Chin . Chem . Soc . 60 , 212-217 ( 2013 ) .
23. H. G. Aslan , S. Ozcan , N. Karacan , Spectrochimica Acta part A , 98 , 329-336(2012).
24. Z.Gisele, M. Lima, L. Pereira, M. Trachez, P. da Costa, J. Souza, E.S. Monteiro, C. Romeiro, D. D'Andrea, T. Sudo, J. Barreiro, Eliezer, Current Topics in Medicinal Chemistry, 12(19),2037-2048(2012).
25. L.R.Venkataravanappa,M.Jyothi,H.A.Khamees,E.Silina,V.Stupin,R.R.Achar,M.Al-Ghorbani and S.A.Khanum, Curr. Issues Mol. Biol., 45(1), 92-109(2023).
26. A.L. Barry,The Antimicrobial Susceptibility Test:Principal and Practices,4th ed., edited
27. by Illuslea and Feger,Philadelphia,180(1976).
28. E.I. Nweze,P.K. Mukherjee and M.A.Ohannoum,J.Clin. Microbiology,48(10), 3750
29. (2019).
30. Laboratary Guide: Methodologies for antimicrobial Susceptibility Testing,APEC-Project: CTI 24,2017A, APEC, Secretariate(2020).SS