• Javarappa Rangaswamy Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore – 570006, Karnataka, India
  • Nagaraja Naik Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore – 570006, Karnataka, India


Objective: Benzofuran and their heterocyclic analogs represent an important class of molecules which have a wide range of pharmacological activities. Therefore, in this study synthesis and antimicrobial activity of benzofuran fused C-2,4,6-substituted pyrimidine derivatives was extensively discussed.

Methods: Benzofuran fused C-2,4,6-substituted pyrimidine derivatives (4a-k) were built by cyclo condensation, Claisen-Schmidt condensation followed by cyclization via coupling of benzoyl fragments, which include benzofuran, a pyrimidine ring and C-6 substituted phenyl residue with various substituents, connected by linker-S-band. The structures of the synthesized compounds were confirmed by analytical and spectral techniques and evaluated their antimicrobial activity.

Results: The results of antibacterial and antifungal activity against various microbes, most of the compounds have shown considerable antimicrobial activity, but compounds 4g and 4e exhibits superior activity compared to standards, this may be due to presence bromo and fluro electron withdrawing substituent on the benzoyl moiety and more lipophilic nature of pyrimidine ring.

Conclusion: According to the activity studies, it is observed that the synthesis and antimicrobial activity of benzofuran fused C-2,4,6-substituted pyrimidine derivatives have been shown better antimicrobial activity. The obtained results suggest that these classes of compounds can be considered as new hits for further structural optimization to obtain better antimicrobial drug development program.

Keywords: Benzofuran incorporating substituted pyrimidines, Substituted benzoyl moieties, Antimicrobial activity


Download data is not yet available.


1. Simpson TJ. Advanc Heterocycl Chem Academic: London; 1984;35:2–81.
2. Mustafa A. Furopyrans and Furopyrones; John Wiley and Sons: Chapter III: Furochromones, New York; 1967.
3. Gammill RB, Hyde BR. Total synthesis of the lipid-altering and antiatherosclerotic furochromone khellin. The furoic acid route to highly functionalized benzofurans. J Org Chem 1983;48:3863-5.
4. Kim S, Salim AA, Swanson SM, Kinghorn AD. Potential of cyclopenta[b]benzofurans from Aglaia species in cancer chemotherapy. Adv Anticancer Agents Med Chem 2006;6:319-45.
5. Lavanya A, Sribalan R, Padmini V. Synthesis and biological evaluation of new benzofuran carboxamide derivatives. J Saudi Chem Soc 2015;1-9. http://dx.doi. org/10.1016/j. jscs. 2015. 06.008.
6. Basawaraj R, Hugar MH, Sangapure SS. Synthesis and biological evaluation of benzofuro [3, 2-d] pyrimidones. Indian J Hetero Chem 2009;18:329-32.
7. Ostrowski S. Approaches to fused pyrimidine derivatives by the pyrimidine construction and their application to synthesis of purines. Pol J Chem 2001;75:1661–87.
8. Kidwai M, Deo Mishra A. An expeditious synthesis of 3,4-dihydrobenzo[2,3 d]pyrimidines using inorganic solid supports. J Serb Chem Soc 2004;69:247–54.
9. Balzarini J, McGuigan C. Bicyclic pyrimidine nucleoside analogues (BCNAs) as highly selective and potent inhibitors of varicella-zoster virus replication. J Antimicrob Chemother 2002;50:5–9.
10. Lednicer D. Strategies for organic drugs synthesis and design, Chapters 8 and 9 Wiley, New York; 1998.
11. Manna F, Chimenti F, Fioravanti R, Bolasco A, Secci D, Chimenti P, et al. Synthesis of some pyrazoles derivatives and preliminary investigation of their affinity binding to p-gylcoprotein. Bioorg Med Chem Lett 2005;15:4632–5.
12. Jantova S, Stankovsky S, Spirkova K. In vitro antibacterial activity of ten series of substituted quinazolines. Biologia Bratislava 2004;59:741–52.
13. Biradar JS, Sasidhar BS, Parveen R. Synthesis, antioxidant and DNA cleavage activities of novel indole derivatives. Eur J Med Chem 2010;45:4074-8.
14. Harinadhababu V, Manna SK, Srinivasan KK, Bhat VG. Synthesis and biological evaluation of 1,3,5-trisubstituted pyrazolines bearing benzofurans. Indian J Heterocycl Chem 2004;13:253–6.
15. Nagaraja GK, Prakash GK, Satyanarayan ND, Vaidya VP, Mahadevan KM. Synthesis of novel 2-aryl-2,3-dihydronaphtho[ 2,1-b]furo[3,2-b]pyridin-4(1H)-ones of biological importance. Arkivoc 2006;15:142–52.
16. Maruyama T, Kozai S, Demizu Y, Witvrouw M, Pannecouque C, Balzarini J, et al. Synthesis and anti-HIV-1 and anti-HCMV activity of 1-substituted 3-(3,5-dimethylbenzyl)uracil derivatives. Chem Pharm Bull Jpn 2006;54:325–33.
17. Naito H, Ohsuki S, Sugimori M, Atsumi R, Minami M, Nakamura Y, et al. Synthesis and antitumor activity of novel pyrimidinyl pyrazole derivatives. II. Optimization of the phenylpiperazine moiety of 1-[5-methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-3-phenyl piperazinyl-1-trans-propenes. Chem Pharm Bull Jpn 2002:50;453–62.
18. Rida SM, EI-Hawash SA, Fahmy HT, Hazza AA, El-Meligy MM. Synthesis and in vitro evaluation of some novel benzofuran derivatives as potential anti-HIV-1, anticancer and antimicrobial agents. Arch Pharm Res 2006;29:16-25.
19. Shankar B, Shailendra S, Navanath K. Synthesis of aryl (5-substituted benzofuran-2-yl) carbamate derivatives as antimicrobial agents. Asian J Pharm Clin Res 2017;10:377-81.
20. Rangaswamy J, Kumar HV, Harini ST, Naik N. Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: as a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility. Bioorg Med Chem Lett 2012;22:4773-7.
21. Rangaswamy J, Kumar HV, Harini ST, Naik N. An easy eccess to benzofurans via DBU Induced condensation reaction of active 2-hydroxy acetophenones with phenacyl chlorides: A novel class of antioxidant agents. J Heterocycl Chem 2015;52:938-43.
22. Arthington-Skaggs BA, Motley M, Warnock DW, Morrison CJ. Comparative evaluation of PASCO and national committee for clinical laboratory standards M27-A broth microdilution methods for antifungal drug susceptibility testing of yeasts. J Clin Microbiol 2000;38:2254-60.
23. Mac Lowry DJ, Jaqua MJ, Selepak ST. Detailed methodology and implementation of a semiautomated serial dilution microtechnique for antimicrobial susceptibility testing. Appl Microbiol 1970;20:46-53.
24. Rangaswamy J, Kumar HV, Harini ST, Naik N. Synthesis of novel benzofuran-gathered C-2,4,6-substituted pyrimidine derivatives conjugated by sulfonyl chlorides: orally bioavailable, selective, effective antioxidants and antimicrobials drug candidates. J Heterocycl Chem 2015;52:1349-60.
25. Atul K, Akanksha. Zirconium chloride catalyzed efficient synthesis of 1,3-diaryl-2-propenones in solvent free conditions via aldol condensation. J Mol Catal A: Chem 2007;274:212-6.
26. Yadav PP, Gupta P, Chaturvedi AK, Skukla PK, Maurya R. Synthesis of 4-hydroxy-1-methylindole and benzo[b]thiophen-4-ol based unnatural flavonoids as new class of antimicrobial agents. Bioorg Med Chem 2005;13:1497-505.
27. Keri RS, Hosamani KM, Hugar MH. Analgesic, anti-pyretic and DNA cleavage studies of novel pyrimidine derivatives of coumarin moiety. Eur J Med Chem 2010;45:2597-605.
28. Andre R, Andrew TP, Sherry FQ. 2,4-diaminothieno[2,3-d]pyrimidine lipophilic antifolates as inhibitors of pneumocystis carinii and toxoplasma gondii dihydrofolate reductase. J Med Chem 1997;40:3694–9.
402 Views | 925 Downloads
How to Cite
Rangaswamy, J., and N. Naik. “SYNTHESIS AND SCREENING OF BENZOFURAN FUSED C-2,4,6-SUBSTITUTED PYRIMIDINE DERIVATIVES AS A NEW ANTIBACTERIAL AND ANTIFUNGAL AGENT”. International Journal of Pharmacy and Pharmaceutical Sciences, Vol. 9, no. 9, Sept. 2017, pp. 27-32, doi:10.22159/ijpps.2017v9i9.17487.
Original Article(s)