Synthesis, Characterization and Antimicrobial Activities of 1-((5-Bromobenzofuran-2yl)methyl)-4-substituted phenyl-1H-1,2,3-triazoles

P. Sanjeeva; B. Subba Rao; V. Kamala Prasad; P. Venkata Ramana

doi:10.14233/ajchem.2021.23040

Issue

Vol. 33 No. 3 (2021): Vol 33 Issue 3

Issue Published : February 16, 2021

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Characterization and Antimicrobial Activities of 1-((5-Bromobenzofuran-2yl)methyl)-4-substituted phenyl-1H-1,2,3-triazoles

https://doi.org/10.14233/ajchem.2021.23040

P. Sanjeeva

Department of Chemistry, Sri Krishnadevaraya University, Ananthapuramu-515003, India

B. Subba Rao

Department of Chemistry, Sri Krishnadevaraya University, Ananthapuramu-515003, India

V. Kamala Prasad

Denisco Chemicals Pvt. Ltd., Hyderabad-500055, India

P. Venkata Ramana

Department of Chemistry, Sri Krishnadevaraya University, Ananthapuramu-515003, India

Corresponding Author(s) : P. Venkata Ramana

ramanapv54@gmail.com

Asian Journal of Chemistry, Vol. 33 No. 3 (2021): Vol 33 Issue 3
Article Published : February 16, 2021

Abstract

A synthesis of useful intermediate, 2-(azidomethyl)-5-bromobenzofuran starting from 5-bromobenzofuran-2-carboxylic acid is described. The reaction of 5-bromo-2-(iodomethyl)benzofuran with sodium azide affords 2-(azidomethyl)-5-bromobenzofuran. 5-Bromo-2-(iodomethyl)benzofuran was obtained from a combination of consecutive 5-bromobenzofuran-2-carboxylic acid reactions involving NaBH₄ reduction followed by the iodination of the resulting alcohol. The utility of 2-(azidomethyl)-5-bromobenzofuran has been demonstrated for the preparation of a novel series of 1-((5-bromobenzofuran-2-yl-)methyl)-4-substituted phenyl-1H-1,2,3-triazoles in excellent yields. The newly synthesized compounds have been characterized and evaluated for antimicrobial activities against Gram-negative and Gram-positive bacterial strains.

Keywords

2-(Azidomethyl)-5-bromobenzofuran Substituted benzofuran Triazole Antimicrobial activity Antibacterial activity

Sanjeeva, P., Subba Rao, B., Kamala Prasad, V., & Venkata Ramana, P. (2021). Synthesis, Characterization and Antimicrobial Activities of 1-((5-Bromobenzofuran-2yl)methyl)-4-substituted phenyl-1H-1,2,3-triazoles. Asian Journal of Chemistry, 33(3), 565–569. https://doi.org/10.14233/ajchem.2021.23040

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References

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F. Zálešák, D. Jean-Yves, D. Bon and J. Pospíšil, Pharmacol. Res., 146, 104284 (2019); https://doi.org/10.1016/j.phrs.2019.104284

S.M. Rida, S.A.M. El-Hawash, H.T.Y. Fahmy, A.A. Hazza and M.M.M. El-Meligy, Arch. Pharm. Res., 29, 16 (2006); https://doi.org/10.1007/BF02977463

J.L. Toth, C.A. Price, E.C. Madsen, H.L. Handl, S.J. Hudson, R.B. Hubbard III, J.P. Bowen, K. Kiakos, J.A. Hartley and M. Lee, Bioorg. Med. Chem. Lett., 12, 2245 (2002); https://doi.org/10.1016/S0960-894X(02)00341-4

A. Urzua, J. Echeverria, M.C. Rezende and M. Wilkens, Molecules, 13, 2385 (2008); https://doi.org/10.3390/molecules13102385

M. Wahab Khan, M. Jahangir Alam, M.A. Rashid and R. Chowdhury, Bioorg. Med. Chem., 13, 4796 (2005); https://doi.org/10.1016/j.bmc.2005.05.009

K. Kawasaki, M. Masubuchi, K. Morikami, S. Sogabe, T. Aoyama, H. Ebiike, S. Niizuma, M. Hayase, T. Fujii, K. Sakata, H. Shindoh, Y. Shiratori, Y. Aoki, T. Ohtsuka and N. Shimma, Bioorg. Med. Chem. Lett., 13, 87 (2003); https://doi.org/10.1016/S0960-894X(02)00844-2

K. Hu and J.H. Jeong, Arch. Pharm. Res., 29, 476 (2006); https://doi.org/10.1007/BF02969419

K.M. Dawood, H. Abdel-Gawad, E.A. Rageb, M. Ellithey and H.A. Mohamed, Bioorg. Med. Chem., 14, 3672 (2006);https://doi.org/10.1016/j.bmc.2006.01.033

B. Gabriele, R. Mancuso and G. Salerno, J. Org. Chem., 73, 7336 (2008); https://doi.org/10.1021/jo801444n

E.F.V. Scriven and C.A. Ramsden, Advances in Heterocyclic Chemistry vol. 117, Elsevier, Academic Press: Amsterdam, edn 1 (2015).

M. Mahesh, G. Bheemaraju, G. Manjunath and P.V. Ramana, Ann. Pharm. Fr., 74, 34 (2016); https://doi.org/10.1016/j.pharma.2015.07.002

G. Manjunath, G. Bheemaraju, M. Mahesh and P.V. Ramana, Ann.Pharm. Fr., 73, 452 (2015); https://doi.org/10.1016/j.pharma.2015.06.003

P.V.B. Reddy, V.K. Prasad, G. Manjunath and P.V. Ramana, Ann. Pharm. Fr., 74, 350 (2016); https://doi.org/10.1016/j.pharma.2016.05.002

V.V. Sureshbabu, S.A. Naik, H.P. Hemantha, N. Narendra, U. Das and T.N. Guru Row, J. Org. Chem., 74, 5260 (2009); https://doi.org/10.1021/jo900675s

M. Samarasimhareddy, H.P. Hemantha and V.V. Sureshbabu, Tetrahedron Lett., 53, 3104 (2012); https://doi.org/10.1016/j.tetlet.2012.04.034

M.J. Pelczar Jr., R.D. Reid and E.C.S. Chan, Cultivation of bacteria.In: Microbiology, Tata McGraw Hill Publishing Co. Ltd., New Delhi, India,edn 4, p. 103 (1982).

N. Pankaj, B.R. Nayan Bhalodia, V.J. Shukla and B.M. Nariya, Int. J.Pharm. Tech. Res., 2, 2522 (2010).

Issue

Vol. 33 No. 3 (2021): Vol 33 Issue 3

Synthesis, Characterization and Antimicrobial Activities of 1-((5-Bromobenzofuran-2yl)methyl)-4-substituted phenyl-1H-1,2,3-triazoles

Corresponding Author(s) : P. Venkata Ramana

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