SYNTHESIS OF ARYL (5-SUBSTITUTED BENZOFURAN-2-YL) CARBAMATE DERIVATIVES AS ANTIMICROBIAL AGENTS
Objectives: Benzofurans are very interesting heterocycles, which are available in nature and show a wide range of pharmacological activities, viz.,
antifungal, antibacterial, antitumor, antimalarial and antioxidant activity.
Methods: A convenient method for the preparation of aryl (5-substituted benzofuran-2-yl) carbamate derivatives 6a-6j has been developed. The
target compounds 1-(5-nitrobenzofuran-2-yl)-3-arylurea (6a-6e) and 1-(5-bromobenzofuran-2-yl)-3arylurea (6f-6j) have been prepared by reacting
5-nitrobenzofuran-2-carbonyl azide 5a or 5-bromobenzofuran-2-carbonyl azide 5b with substituted phenols in reasonable overall yields. All
the synthesized compounds were characterized using Fourier transform infrared (FTIR), 1H NMR and mass spectrometry and were subjected to
antimicrobial screening against two Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), two Gram-negative bacteria (Escherichia
coli and Pseudomonas aeruginosa), and two fungi (Candida albicans and Aspergillus niger) using two-fold dilution method.
Results and Discussion: All the values of FTIR, 1H NMR and mass spectra were found to be prominent. The results indicate that synthesized compound
6i showed potent antimicrobial activity comparable to standard.
Conclusion: The detailed synthesis, spectroscopic data, and antimicrobial activities of synthesized compounds were reported.
Keywords: Benzofuran, Antibacterial activity, Antifungal activity.
1. Lee SK, Cui B, Mehta RR, Kinghorn AD, Pezzuto JM. Cytostatic mechanism and antitumor potential of novel 1hcyclopenta[b]benzofuran lignans isolated from Aglaia elliptica. Chem Biol Interact 1998;115:215-28.
2. Janprasert J, Satasook C, Sukumalanand P, Champagne DE, Isman MB, Wiriyachitra P. Rocaglamide, a natural benzofuran insecticide from Aglaia odorata. Phytochemistry 1992;32:67-9.
3. Sundaram R, Ganesan R, Murugesan G. In vitro antiplasmodial activity of spiro benzofuran compound from mangrove plant of Southern India. Asian Pac J Trop Med 2012;5:358-61.
4. Yu B, Shi XJ, Zheng YF, Fang Y, Zhang E, Yu DQ. A novel [1,2,4] triazolo [1,5-a] pyrimidine-based phenyl-linked steroid dimer: Synthesis and its cytotoxic activity. Eur J Med Chem 2013;69:323-30.
5. Panno ML, Giordano F, Mastroianni F, Palma MG, Bartella V, Carpino A, et al. Breast cancer cell survival signal is affected by bergapten combined with an ultraviolet irradiation. FEBS Lett 2010;584(11):2321-6.
6. Hsieh MJ, Chen MK, Yu YY, Sheu GT, Chiou HL. Psoralen reverses docetaxel-induced multidrug resistance in A549/D16 human lung cancer cells lines. Phytomedicine 2014;21(7):970-7.
7. Hassan GS, Abou-Seri SM, Kamel G, Ali MM. Celecoxib analogs bearing benzofuran moiety as cyclooxygenase-2 inhibitors: Design, synthesis and evaluation as potential antiinflammatory agents. Eur J Med Chem 2014;76:482-93.
8. Sashidhara KV, Modukuri RK, Sonkar R, Rao KB, Bhatia G. Hybrid benzofuran-bisindole derivatives: New prototypes with promising anti-hyperlipidemic activities. Eur J Med Chem 2013;68:38-46.
9. El-Sawy ER, Ebaid MS, Abo-Salem HM, Al-Sehemi AG, Mandour AH. Synthesis, anti-inflammatory, analgesic and anticonvulsant activities of some new 4,6-dimethoxy-5-(heterocycles)benzofuran starting from naturally occurring visnagin. Arab J Chem 2012. Available from: http://www.dx.doi.org/10.1016/j.arabjc.2012.12.041.
10. Wu J, Li Y, Chen K, Jiang H, Xu MH, Liu D. Identification of benzofuran-3-yl(phenyl)methanones as novel SIRT1 inhibitors: Binding mode, inhibitory mechanism and biological action. Eur J Med Chem 2013;60:441-50.
11. Xiang Y, Hirth B, Asmussen G, Biemann HP, Bishop KA, Good A, et al. The discovery of novel benzofuran-2-carboxylic acids as potent Pim-1 inhibitors. Bioorg Med Chem Lett 2011;21(10):3050-6.
12. Jiang X, Liu W, Zhang W, Jiang F, Gao Z, Zhuang H, et al. Synthesis and antimicrobial evaluation of new benzofuran derivatives. Eur J Med Chem 2011;46(8):3526-30.
13. Shankerrao S, Bodke YD, Santoshkumar S. Synthesis and antimicrobial activity of some imidazothiazole derivatives of benzofuran. Arab J Chem 2012. Available from: http://www.dx.doi.org/10.1016/j.arabjc.2012.10.018.
14. Kirilmis C, Ahmedzade M, Servi S, Koca M, Kizirgil A, Kazaz C. Synthesis and antimicrobial activity of some novel derivatives of benzofuran: Part 2. The synthesis and antimicrobial activity of some novel 1-(1-benzofuran-2-yl)-2-mesitylethanone derivatives. Eur J Med Chem 2008;43(2):300-8.
15. Dawood KM, Abdel-Gawad H, Rageb EA, Ellithey M, Mohamed HA. Synthesis, anticonvulsant and anti-inflammatory evaluation of some new benzotriazole and benzofuran-based heterocycles. Bioorg Med Chem 2006;14:3672-80.
16. Santana L, Teijeira M, Uriarte E, Teran C, LinËœ ares B, Villar R. AM1 theoretical study, synthesis and biological evaluation of some benzofuran analogues of anti-inflammatory arylalkanoic acids. Eur J Pharm Sci 1999;7:161-6.
17. Malpani Y, Achary R, Kim SY, Jeong HC, Kim P, Han SB, et al. Efficient synthesis of 3H,3â€™H-spiro[benzofuran-2,1â€™-isobenzofuran]-3,3â€™-dione as novel skeletons specifically for influenza virus type B inhibition. Eur J Med Chem 2013;62:534-44.
18. 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.
19. Rangaswamy J, Kumar HV, Harini ST, Naik N. Functionalized 3-(benzofuran-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1h-pyrazole scaffolds: A new class of antimicrobials and antioxidants. Arab J Chem 2013. Available from: http://www.dx.doi.org/10.1016/j.arabjc.2013.10.012.
20. Yamuna AJ, Vaidya VP, Shruthi EK, Mahadevan M. Synthesis, characterization and biological activities of some benzofuropyrimidine derivatives. Int J Pharm Pharm Sci 2013;5(2):450-5.
21. Naik NH, Kumar V, Dias SM, Swamy JR. Novel 4-methoxy-2-acetyl benzofuran based chalcones: A new perceptivity into their antioxidant potentials. Int J Pharm Pharm Sci 2013;5(1):242-7.
22. Galal SA, Abd El-All AS, Abdallah MM, El-Diwani HI. Synthesis ofpotent antitumor andantiviral benzofuran derivatives. Bioorg Med Chem Lett 2009;19:2420-8.
23. Hranjec M, Sovic I, Ratkaj I, Pavlovic G, Ilic N, Valjalo L, et al. Antiproliferative potency of novel benzofuran-2-carboxamides on tumour cell lines: Cell death mechanisms and determination of crystal structure. Eur J Med Chem 2013;59(9):111-9.
24. Parekh S, Bhavsar D, Savant M, Thakrar S, Bavishi A, Parmar M. Synthesis of some novel benzofuran-2-yl (4,5-dihyro-3,5-substituted diphenylpyrazol-1-yl) methanones and studies on the antiproliferative effects and reversal of multidrug resistance of human MDR1-gene transfected mouse lymphoma cells in vitro. Eur J Med Chem 2011;46:1942-8.
25. Ono M, Kung MP, Hou C, Kung HF. Benzofuran derivatives as A beta-aggregate-specific imaging agents for Alzheimerâ€™s disease. Nucl Med Biol 2002;29(6):633-42.
26. Sable PN, Ganguly S, Chaudhari PD. An efficient one-pot three-component synthesis and antimicrobial evaluation of tetra substituted thiophene derivatives. Chin Chem Lett 2014;25:1099-103.
27. Madaan P, Tyagi VK. Quaternary pyridinium salts: A review. J Oleo Sci 2008;57(4):197-215.
The publication is licensed under CC By and is open access. Copyright is with author and allowed to retain publishing rights without restrictions.