Synthesis of Coumarins Linked With 1,2,3-Triazoles under Microwave Irradiation and Evaluation of their Antimicrobial and Antioxidant Activity

Authors

  • Nibin Joy Muthipeedika Centre for Chemical and Pharmaceutical Technology Ural Federal University19 Mira Street, Yekaterinburg, 620002.
  • Yadav D Bodke
  • Sandeep Telkar
  • Vasily A Bakulev

DOI:

https://doi.org/10.29356/jmcs.v64i1.1116

Keywords:

Coumarin, 1,2,3-triazole, click chemistry, antimicrobial, antioxidant

Abstract

A series of coumarin derivatives linked with 1,2,3-triazoles has been synthesized by utilizing the copper catalyzed azide-alkyne cycloaddition reaction and were screened for their antimicrobial and antioxidant properties. Some of the compounds displayed promising antibacterial activities (MIC ranging from 5-150 µg/mL) and moderate antifungal activities as compared to the respective standards. The compounds 4k and 4g displayed good antibacterial activity when compared with the standard, Ciprofloxacin, and 4n exhibited better antifungal activity when compared to other synthesized compounds. The in silico docking studies of the active compounds were carried out against the gyrase enzyme and from those studies, it was acknowledged that 4k possessed significant hydrogen bonding and hydrophobic interactions which could be the plausible reason for its superior activity as compared to the other synthesized compounds. The compounds 4h and 4q showed promising antioxidant activity when compared with the standard, BHT, which could be attributed to the presence of electron donating substituents.

                                              

Resumen. Una serie de derivados de cumarina enlazados con 1,2,3-triazoles fue sintetizada empleando la reacción de cicloadición azida-alquino catalizada con cobre y fue evaluada en sus propiedades antimicrobianas y antioxidantes. Algunos de los compuestos exhibieron actividad antimicrobiana promisoria (intervalo MIC de 5-150 µg/mL) y actividad antifúngica moderada con respecto a los estándares respectivos. Los compuestos 4g y 4k mostraron buena actividad antibacterial con relación al estándar. Fluconazole y 4n exhibieron mejor actividad antifúngica en comparación con el resto de los compuestos. Se llevaron a cabo estudios in silico de modelado molecular e interacción de los compuestos activos con la enzima girasa ADN. De estos estudios se observó que 4k posee enlaces puentes de hidrógeno e interacciones hidrofóbicas significativos, los cuales podrían ser una causa plausible de su actividad mayor a aquélla mostrada por los otros compuestos sintetizados. Los compuestos 4h y 4q mostraron una importante actividad antioxidante comparada con el estándar (BHT), lo cual podría atribuirse a la presencia de sustituyentes electro-donadores

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References

Moellering, R. C. Am. J. Med. 1995, 99, 11S–18S.

Singh, P.; Anand, A.; Kumar, V. Eur. J. Med. Chem. 2014, 85, 758–777.

Peet, N. P. Drug. Discov. Today 2010, 15, 583–586.

Sugamura, Jr. K.; Keaney, J. F. Free Radical Biol. Med. 2011, 51, 978–992.

Yang, Y.; Liu, Q. W.; Shi, Y.; Song, Z. G.; Jin, Y. H.; Liu, Z. Q. Eur. J. Med. Chem. 2014, 84, 1–7.

Borges, F.; Roleira, F.; Milhazes, N.; Santana, L.; Uriarte, E. Curr. Med. Chem. 2005, 12, 887–916.

Al-Haiza, M. A.; Mostafa, M. S. Molecules 2003, 8, 275–286.

Fylaktakidou, K. C.; Litina, D. H. J. Curr. Pharm. Des. 2004, 10, 3813–3833.

Lall, N.; Hussein, A. A.; Meyer, J. J. M. Fitoterapia 2006, 77, 230–232.

Kostova, I.; Raleva, S.; Genova, P.; Argirova, R. Bioinorg. Chem. Appl. 2006, 1–9.

Hinman, J. W.; Hoeksema, H.; Caron, E. L.; Jackson, W. G. J. Am. Chem. Soc. 1956, 78, 1072–1074.

Kawaguchi, H.; Tsukiura, H.; Okanishi, M.; Miyaki, T.; Ohmori, T.; Fujisawa, K.; Koshiyama, H. J. Antibiotics, Ser A. 1965, 18, 1–10.

Kumbhare, R. M.; Kosurkar, U. B.; Ramaiah, M. J.; Dadmal, T. L.; Pushpavalli, S. N. C. V. L.; Pal-Bhadra, M. Bioorg. Med. Chem. Lett. 2012, 22, 5424–5427.

Pawelec, G.; Ehninger, G.; Rehbein, A.; Schaudt, K.; Jaschonek, K. Int. J. Immunopharmacol. 1991, 13, 299–304.

Genin, M. J.; Allwine, D. A.; Anderson, D. J.; Barbachyn, M. R.; Emmert, D. E.; Garmon, S. A.; Graber, D. R.; Grega, K. C.; Hester, J. B.; Hutchinson, D. K.; Morris, J.; Reischer, R. J.; Ford, C. W.; Zurenco, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapertand, D.; Yagi, B. H. J. Med. Chem. 2000, 43, 953–970.

Jordao, A. K.; Afonso, P. P.; Ferreira, V. F.; de Souza, M. C.; Almeida, M. C.; Beltrame, C. O.; Paiva, D. P.; Wardell, S. M.; Wardell, J. L.; Tiekink, E. R.; Damaso, C. R.; Cunha, A. C. Eur. J. Med. Chem. 2009, 44, 3777–3783.

Buckle, D. R.; Outred, D. J.; Rockell, C. J. M.; Smith, H.; Spicer, B. A. J. Med. Chem. 1983, 26, 251–254.

Hager, C.; Miethchen, R.; Reinke, H. J. Fluor. Chem. 2000, 104, 135–142.

Kolb, H. C.; Sharpless, K. B. Drug. Discov. Today 2003, 8, 1128–1137.

Singh, P.; Raj, R.; Kumar, V.; Mahajan, M. P.; Bedi, P. M. S.; Kaur, T.; Saxena, A. K. Eur. J. Med. Chem. 2012, 47, 594–600.

Zhou, C. H.; Wang, Y. Curr. Med. Chem. 2012, 19, 239–280.

Kappe, C. O.; Dallinger, D. Mol. Diversity 2009, 13, 71–193.

Hoz, A.; Ortiz, A. D.; Moreno, A. Chem. Soc. Rev. 2005, 34, 164–178.

Meunier, B. Acc. Chem. Res. 2008, 41, 69–77.

Tietze, L. F.; Bell, H. P.; Chandrasekhar, S. Angew. Chem. Int. Ed. 2003, 42, 3996–4028.

Li, W.T.; Wu, W.H.; Tang, C.H.; Tai, R.; Chen, S.T. ACS Comb. Sci. 2011, 13, 72–78.

Olesen, P. H.; Sørensen, A. R.; Ursø, B.; Kurtzhals, P.; Bowler, A. N.; Ehrbar, U.; Hansen, B. F. J. Med. Chem. 2003, 46, 3333?3341.

Sajith, A. M.; Khader, K. K. A.; Joshi, N.; Reddy, M. N.; Padusha, M. S. A.; Nagaswarupa, H. P.; Joy, M. N.; Bodke, Y. D.; Karuvalam, R. P.; Banerjee, R.; Muralidharan, A.; Rajendra, P. Eur. J. Med. Chem. 2015, 89, 21–31.

Joy, M. N.; Bakulev, V. A. AIP Conference Proceedings 2019, 2063, 030015.

Savitha, B.; Reddy, E. K.; Kumar, C. S. A.; Karuvalam, R. P.; Padusha, M. S. A.; Bakulev, V. A.; Narasimhamurthy, K. H.; Sajith, A. M.; Joy, M. N. Tetrahedron Lett. 2019, 60, 151332.

Kenchappa, R.; Bodke, Y. D.; Aswathanarayanappa, C.; Telkar, S.; Manjunatha, K. S.; Sindhe, A. M. Ara. J. Chem. 2017, 10, S1336–S1344.

Yadav, N.; Agarwal, D.; Kumar, S.; Dixit, A. K.; Gupta, R. D.; Awasthi, S. K. Eur. J. Med. Chem. 2018, 145, 735–745.

Shaikh, M. H.; Subhedar, D. D.; Shingate, B. B.; Khan, F. A. K.; Sangshetti, J. N.; Khedkar, V. M.; Nawale, L.; Sarkar, D.; Navale, G. R.; Shinde, S. S. Med. Chem. Res. 2016, 25, 790–804.

Kumari, S.; Joshi, S.; Shakoor, S. M. A.; Agarwal, D. S.; Panda, S. S.; Pant, D. D.; Sakhuja, R. Aus. J. Chem. 2015, 68, 1415–1426.

Pramitha, P.; Bahulayan, D. Bioorg. Med. Chem. Lett. 2012, 22, 2598–2603.

Potdar, M. K.; Mohile, S. S.; Salunkhe, M. M. Tetrahedron Lett. 2001, 42, 9285–9287.

Sheikh, J.; Parvez, A.; Juneja, H.; Ingle, V.; Chohan, Z.; Youssoufi, M.; Hadda, T. B. Eur. J. Med. Chem. 2011, 46, 1390–1399.

Alonso, R.; Fernandez-Aranquiz, A.; Colom, K.; Herreras, A.; Cisterna, R. Rev. Esp. Quimioter. 2000, 13, 384–393.

Sader, H. S.; Jones, R. N.; Silva, J. B. Diagn. Microbiol. Infect. Dis. 2002, 44, 281–288.

Parker, M. A.; Kurrasch, D. M.; Nichols, D. E. Bioorg. Med. Chem. 2008, 16, 4661–4669.

Niki, E. Chem. Phys. Lipids 1987, 44, 227–253.

Matos, M. J.; Pérez-Cruz, F.; Vazquez-Rodriguez, S.; Uriarte, E.; Santana, L.; Borges, F.; Olea-Azar, C. Bioorg. Med. Chem. 2013, 21, 3900–3906.

Yamagami, C.; Akamatsu, M.; Motohashi, N.; Hamada, S.; Tanahashi, T. Bioorg. Med. Chem. Lett. 2005, 15, 2845–2850.

Sivakumar, P. M.; Prabhakar, P. K.; Doble, M. Med. Chem. Res. 2011, 20, 482–492.

Wigley, D. B.; Davies, G. J.; Dodson E. J.; Maxwell, A.; Dodson, G. Nature 1991, 351, 624–629.

Cabral, J. H. M.; Jackson, A. P.; Smith, C. V.; Shikotra, N.; Maxwell, A.; Liddington, R. C. Nature 1997, 388, 903–906.

Bradbury, B. J.; Pucci, M. J. Curr. Opin. Pharmacol. 2008, 8, 574–581.

Ehmann, D. E.; Lahiri, S. D. Curr. Opin. Pharmacol. 2014, 18, 76–83.

Tse-Dinh, Y. C. Infect. Disord. Drug Targets 2007, 7, 3–9.

Collin, F.; Karkare, S.; Maxwell, A. Appl. Microbiol. Biotechnol. 2011, 92, 479–497.

http://www.citeulike.org/group/340/article/240061 accessed in October 2014.

Sander, T.; Freyss, J.; Korff, M. V.; Reich, J. R.; Rufener, C. J. Chem. Inf. Model 2009, 49, 232–246.

Trott, O.; Olson, A. J. J. Comput. Chem. 2010, 31, 455–461.

Bax, B. D.; Chan, P. F.; Eggleston, D. S.; Fosberry, A.; Gentry, D. R.; Gorrec, F. Nature 2010, 466, 935–940.

Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K. J. Comput. Chem. 1998, 19, 1639–1662.

Laskowski, R. A.; Swindells, M. B. J. Chem. Inf. Model 2011, 51, 2778–2786.

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Published

2019-12-12

Issue

Vol. 64 No. 1 (2020): Regular Issue

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Regular Articles

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