Main Article Content
Abstract
Present work reports the biologically important benzofuran aryl ureas and carbamates. The benzofuran ring was formed by reacting bromo salicylaldehyde with diethyl bromomalonate in presence of dry acetone and anhydrous potassium carbonate to obtain 5-bromo-2-ethyl carboxylate (1). The obtained ester (1) was converted into corresponding hydrazide (2) by treating with hydrazine hydrate in ethanol. Compound 2 was then converted into 5-bromobenzofuran-2-carbonyl azide (3) by treating it with sodium nitrite in dioxane and acetic acid. The compound 3 is converted into 5-bromobenzofuranyl aryl ureas (4a-e) after treating primary amines and anhydrous toluene. 5-Bromobenzofuranyl aryl carbamate (5) and ethyl carbamate (6) were also synthesized by treating compound 3 with substituted phenol in toluene and ethanol respectively. All the compounds were characterized by NMR, IR and screened for antimicrobial activities.
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References
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- K. Takaoka, Y. Tatsu, N. Yumoto, T. Nakajima and K. Shimamoto, Synthesis of Carbamate-Type Caged Derivatives of a Novel Glutamate Transporter Blocker, Bioorg. Med. Chem., 12, 3687 (2004); https://doi.org/10.1016/j.bmc.2004.04.011.
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- H.M. Naveena Kumara, M.H. Mathada, S. Hugar and K.M. Basavaraja, Synthesis, Characterization, Antibacterial and Antifungal Screening of Various 5-Bromo-7-Methoxy-Benzofuran Schiff Bases, J. Applicable Chem., 8, 165 (2019).
References
Y.-H. Miao, Y.-H. Hu, J. Yang, T. Liu, J. Sun and X.-J. Wang, Natural Source, Bioactivity and Synthesis of Benzofuran Derivatives, RSC Adv., 9, 27510 (2019); https://doi.org/10.1039/C9RA04917G.
B. De, S. Sen and T.S. Easwari, Asian J. Res. Chem., 8, 428 (2015); https://doi.org/10.5958/0974-4150.2015.00069.3.
E.M. Rymbai, A. Chakraborty, R. Choudhury, N. Verma and B. De, Review on Chemistry and Therapeutic Activity of the Derivatives of Furan and Oxazole: The Oxygen Containing Heterocycles, Der Pharm. Chem., 11, 20 (2019).
G. Khodarahmi, P. Asadi, F. Hassanzadeh and E. Khodarahmi Benzofuran as a Promising Scaffold for the Synthesis of Antimicrobial and Antibreast Cancer Agents: A Review, J. Res. Med. Sci., 20, 1094 (2015); https://doi.org/10.4103/1735-1995.172835.
S. Bhargava and D. Rathore, Synthetic Routes and Biological Activities of Benzofuran and its Derivatives: A Review, Lett. Org. Chem., 14, 381 (2017); https://doi.org/10.2174/1570178614666170321125853.
G. Nagalakshmi, Synthesis, Antimicrobial and Antiinflammatory Activity of 2,5-Disubstituted-1,3,4-oxadiazoles, Indian J. Pharm. Sci., 70, 49 (2008); https://doi.org/10.4103/0250-474X.40331.
K. Chand, Rajeshwari, A. Hiremathad, M. Singh, M.A. Santos and R.S.Keri, A Review on Antioxidant Potential of Bioactive Heterocycle Benzofuran: Natural and Synthetic Derivatives, Pharm. Rep., 69, 281 (2017); https://doi.org/10.1016/j.pharep.2016.11.007.
K.M. Basavaraja, M.H. Mathada, H.M. Naveena Kumari, M. Kumar and K.T. Sudha, Synthesis and Characterisation of Biologically Active Benzofuranyl Indolinones, Asian J. Res. Chem. Pharm. Sci., 7, 233 (2019).
K.M. Dawood, Benzofuran Derivatives: A Patent Review, Expert Opin. Therap. Patents, 23, 1133 (2013); https://doi.org/10.1517/13543776.2013.801455.
M. Napiórkowska, M. Cieslak, J. Kazmierczak-Baranska, K. Królewska-Golinska and B. Nawrot, Synthesis of New Derivatives of Benzofuran as Potential Anticancer Agents, Molecules, 24, 1529 (2019); https://doi.org/10.3390/molecules24081529.
H.M. Solomon, P. Jwier, C.M. Jonson, L.M. Posobiec, J.E. Rendemonti, and D.F. Rumberger, Benzofuranyl Ureas with Potent Cardiovascular Teratogenicity in Rats, Teratology, 61, 211 (2000); https://doi.org/10.1002/(SICI)1096-9926(200003)61:3<211::AID-TERA9>3.0.CO;2-E.
K. Takaoka, Y. Tatsu, N. Yumoto, T. Nakajima and K. Shimamoto, Synthesis of Carbamate-Type Caged Derivatives of a Novel Glutamate Transporter Blocker, Bioorg. Med. Chem., 12, 3687 (2004); https://doi.org/10.1016/j.bmc.2004.04.011.
T. Holas, K. Vavrova, M. Sima, J. Klimentova and A. Hravalek, Synthesis and Transdermal Permeation-Enhancing Activity of Carbonate and Carbamate Analogs of Transkarbam 12, Bioorg. Med. Chem., 14, 7671 (2006); https://doi.org/10.1016/j.bmc.2006.08.014.
H.M. Naveena Kumara, M.H. Mathada, S. Hugar and K.M. Basavaraja, Synthesis, Characterization, Antibacterial and Antifungal Screening of Various 5-Bromo-7-Methoxy-Benzofuran Schiff Bases, J. Applicable Chem., 8, 165 (2019).