Microwave Assisted One Pot Synthesis of Tetrazole Based 3-hydroxy-4H-chromen-4-ones by modified Algar-Flynn-Oyamada reaction and their Antimicrobial activity

  • ASHOK DONGAMANTI Osmania University
  • Nagaraju Nalaparaju Osmania University
  • Sarasija Madderla Satavahana University
  • Vijaya Lakshmi Bommidi Osmania University
Keywords: 2-hydroxy acetophenone, 4-(1H-tetrazol-5-yl) benzaldehyde, microwave irradiation, antimicrobial activity.

Abstract

In the present work, we report the one pot synthesis of tetrazole based 3-hydroxy-4H-chromen-4-ones 3(a-g) from  4-(1H-tetrazol-5-yl)benzaldehyde and 2-hydroxy acetophenone using KOH and H2O2 by modified Algar-Flynn-Oyamada reaction under conventional and microwave irradiation conditions. In this technique, flavonols are synthesized without isolating chalcones, in good yields. All the synthesized compounds were characterized by IR, NMR, MS and elemental. All newly synthesized compounds were screened for their in-vitro antimicrobial activity against strains such as Staphylococcus aurous, Bacillus subtilis, Klebsiella pneumonia, Escherichia coli, Aspergillus Niger, Aspergillus flavus, and Fusarium oxysporum. The results of antimicrobial studies revealed that most of the compounds exhibit good activity.

Author Biographies

ASHOK DONGAMANTI, Osmania University

Green and Medicinal Chemistry laboratory, Department of Chemistry

Nagaraju Nalaparaju, Osmania University

Green and Medicinal Chemistry laboratory, Department of Chemistry

Sarasija Madderla, Satavahana University

Department of Chemistry

Vijaya Lakshmi Bommidi, Osmania University

Green and Medicinal Chemistry laboratory

References

1. Genoux, E.; Nicolle, E.; Boumendjel, A. Curr. Org. Chem. 2011, 15, 2608-2615 DOI: https://doi.org/10.2174/138527211796367363

Xiao, Z. P.; Peng, Z. Y.; Peng, M. J.; Yan, W. B.; Ouyang, Y. Z.; Zhu, H. L. Mini-Rev. Med. Chem. 2011, 11, 169-177 DOI: 10.2174/138955711794519546

Franke, A. A.; Cooney, R. V.; Custer, L. J.; Mordan, L. J.; Tanaka, Y. Adv. Exp. Med. Biol. 1998, 439, 237-248 DOI: https://doi.org/10.1007/978-1-4615-5335-9_17

Ashok, D.; Kifah, M. A.; Lakshmi, B. V.; Sarasija, M.; Adam, S. Chem. Heterocycl. Compd. 2016, 52, 172-176 DOI: 10.1007/s10593-016-1852-4

Chohan, Z. H.; Rauf, A.; Naseer, M. M.; Somra, M. A.; Supuran, C. T. J. Enzyme Inhib. Med. Chem. 2006, 21, 173-177 DOI: https://doi.org/10.1080/14756360500533059

Kim, H. P.; Son, K. H.; Chang, H. W.; Kang, S. S., Nat. Prod. Sci., 1996, 2, 1-8

Ercelen, S.; Klymchenko, A. S.; Demchenko, A. P. Anal. Chim. Acta., 2002, 464 (2), 273-287 DOI: 10.1016/S0003-2670(02)00493-2

Algar, J. Flynn, J. P. Proc. Roy. Irish Acad., 1934, 42B, 1-18

Oyamada, T. Bull. Chem. Soc. Jopan, 1935, 10, 182-186 DOI: https://doi.org/10.1246/bcsj.10.182

Murakami, M.; Irie, T. Proc. Imp. Acad. Tokyo 1935, 11, 229

Reichel, L.; Steudel, J. Liebigs Ann. 1942, 553, 83-97

Ostrovskii, V. A.; Koldobskii, G. I.; Trifonov, R. E. Comp. Heterocycl. Chem. III., 2008, 6, 257-423 DOI: https://doi.org/10.1016/B978-008044992-0.00517-4

Srinivas, B.; Kumar, P. V.; Reddy, P. N.; Venu, S.; Shyam, P., Krupadanam, G. D. Russ J Bioorg Chem., 2018, 44, 244 DOI: https://doi.org/10.1134/S1068162018020097

Mulwad, V. V.; Pawar, R. B.; Chaskar, A. C. J. Korean Chem. Soc., 2008, 52, 249-256 DOI: 10.5012/jkcs.2008.52.3.249

Kumar, S. M.; Manjunath, B. C.; Lingaraju, G. S.; Abdoh, M. M. M.; Sadashiva, M. P.; Lokanath, N. K., The FASEB Journal., 2007, 21, 790 DOI:10.4236/csta.2013.23017

Bhaskar, V. H.; Mohite, P. B., J. Optoelectron. Biomed. Mater., 2010, 2, 249-259

Le Bourdonnec, B.; Meulon, E.; Yous, S.; Goossens, J. F.; Houssin, R.; Hénichart, J. P. J. Med. Chem., 2000, 43, 2685 DOI: 10.1021/jm9904147

Adamec, J.; Waisser, K.; Kuneš, J.; Kaustová. J. Archiv der Pharmazie, 2005, 338(8), 385-389 DOI: https://doi.org/10.1002/ardp.200400967

Upadhayaya, R. S.; Jain, S.; Sinha, N.; Kishore, N.; Chandra, R.; Arora, S. K. Eur. J. Med. Chem., 2004, 39, 579 DOI: 10.1016/j.ejmech.2004.03.004

Rajasekaran, A.; Murugesan, S.; Ananda Rajagopal, K. Arch of Pharmacal Res., 2006, 29, 535-540 DOI: https://doi.org/10.1007/BF02969261

Ashok, D.; Rangu, K.; Gundu, S.; Lakkadi, A.; Tigulla, P. Med. Chem. Res., 2017, 26, 1735 DOI: https://doi.org/10.1007/s00044-017-1834-9

Ashok, D.; Vijaya Lakshmi, B.; Ravi, S.; Ganesh, A. Med. Chem. Res., 2015, 24, 1487 DOI: 10.1007/s00044-014-1204-9

Akhlaghinia, B.; Soodabeh Rezazadeh, J. Braz. Chem. Soc., 2012, 23, 2197 DOI: 10.1590/S0103

Ashok, D.; Ravi, S.; Vijaya Lakshmi, B.; Ganesh, A., J. Serb. Chem. Soc., 2015, 80, 1 DOI: 10.2298/JSC141203051A

Serdiuk, I. E.; Roshal, A. D.; Błażejowski, J. Chem. Heterocycl. Compd., 2014, 50, 396 DOI: https://doi.org/10.1007/s10593-014-1487-2

Published
12-09-2019