Multicomponent synthesis of new bis(pyranopyrazoles) and their antimicrobial–antioxidant evaluations

Mohamad Yusuf, Saloni Thakur

Abstract


One-pot, three-component reactions were utilized to obtain a series of new symmetrical bis(pyranopyrazoles) built around six rigid linkers in good yields and in the short durations under normal conditions. The structures of the prepared compounds were confirmed using their IR, 1H-NMR, 13C-NMR and ESI-MS spectral parameters. The bis(pyranopyrazoles) 3b and 3f exhibited significant anti­microbial action against Klebsiella pneumoniae, Fusarium oxysporum and Penicil­lium glabrum at a minimum inhibitory concentration (MIC) value of 3.12 µg mL-1, which is equivalent to the MIC of the standard drug. trans-Butene-linked bis(pyranopyrazole) 3f was also associated with a good radical scavenging activity similar to that of ascorbic acid (a standard antioxidant).


Keywords


pyrazole; dibenzaldehydes; rigid chain linkers; atom economy; anti-microbial activity; antioxidant property

References


M. Koohshari, M. Dabiri, P. Salehi, RSC Adv. 4 (2014) 10669

L. A. Wessjohann, B. Voigt, D. G. Rivera, Angew. Chem. Int. Ed. 44 (2005) 4785

(a) N. M. Evdokimov, A. S. Kireev, A. A. Yakovenko, M. Y. Antipin, A. Kornienko, J. Org. Chem. 72 (2007) 3443; (b) H. Bienayme, C. Hulme, G. Oddon, P. Schmitt, Chem. Eur. J. 6 (2000) 3321

A. H. Bedair, N. A. El-Hady, M. S. Abd El-Latif, A. H. Fakery, A. M. El-Agrody, Farmaco 55 (2000) 708

M. J. Perez-Perez, J. Balzarini, J. Rozenski, E. De Clercq, P. Herdewijn, Bioorg. Med. Chem. Lett. 5 (1995) 1115

A. H. Shamroukh, M. E. A. Zaki, E. M. H. Morsy, F. M. Abdel-Motti, F. M. E. Abdel-

-Megeid Arch Pharm. (Weinheim, Ger.) 340 (2007) 345

M. D. Aytemir, U. Calis, M. Ozalp, Arch. Pharm. (Weinheim, Ger.) 337 (2004) 281

E. Melliou, P. Magiatis, S. Mitaku, A. L. Skaltsounis, A. Pierre, G. Atassi, P. Renard, Bioorg. Med. Chem. 9 (2001) 607

F. Chabchoub, M. Messaad, L. Chekir-Ghedira, M. Salem, Eur. J. Med. Chem. 42 (2007) 715

Z.N. Siddiqui, M. Asad, Indian J. Chem., B 48 (2009) 1609

X. L. Ren, H. B. Li, C. Wu, H. Z. Yang, Arkivoc 2005 (xv) (2005) 59

C. Almansa, J. Alfon, A.F. de-Arriba, F.L. Cavalcanti, I. Escamilla, L.A. Gomez, A. Miralles, R. Soliva, J. Bartrolí, E. Carceller, M. Merlos, J. García-Rafanell, J. Med. Chem. 40 (1997) 547t’

H. J. Park, K. Lee, S. J. Park, B. Ahn, J. C. Lee, H. Y. Cho, K. I. Lee, Bioorg. Med. Chem. Lett. 15 (2005) 3307

P. Cali, L. Naerum, S. Mukhija, A. Hjelmencrantz, Bioorg. Med. Chem. Lett. 14 (2004) 5997

Y. R. Prasad, A. L. Rao, L. Prasoona, K. Murali, P. P. Kumar, Bioorg. Med. Chem. Lett. 15 (2005) 5030

G. Vasuki, K. Kumaravel, Tetrahedron Lett. 49 (2008) 5636

S. C. Kuo, L. J. Huang, H. Nakamura, J. Med. Chem. 27 (1984) 539

V. K. Ahluwalia, A. Dahiya, V. Garg, Indian J. Chem., B 36 (1997) 88

J. L. Wang, D. Liu, Z. J. Zheng, S. Shan, X. Han, S. M. Srinivasula, C. M. Croce, E. S. Alnemri, Z. Huang, Proc. Natl. Acad. Sci. U.S.A. 97 (2009) 7124

M. E. A. Zaki, E. M. Morsy, F. M. Abdel-Motti, F. M. E. Abdel-Megei, Heterocycl. Commun. 10 (2004) 97

M. M. M. Ramiz, I. S. Abdel Hafiz, M. A. M. Abdel Reheim, H. M. Gaber, J. Chin. Chem. Soc. 59 (2012) 72

N. Foloppe, L. M. Fisher, R. Howes, A. Potter, A. G. S. Robertson, A. E. Surgenor, Bioorg. Med. Chem. 14 (2006) 4792

a) F. M. Abdelrazek, P. Metz1, O. Kataeva1, A. Jager, S. F. El-Mahrouky, Arch. Pharm. (Weinheim, Ger.) 340 (2007) 543; b) F. M. Abdelrazek, F. A. Michael, A. E. Mohamed, Arch. Pharm. (Weinheim, Ger.) 339 (2006) 305

H. Wamhoff, E. Kroth, K. Strauch, Synthesis 11 (1993) 1129

S. Gogoi, C.-G. Zhao, Tetrahedron Lett. 50 (2009) 2252

K. Kanagaraj, K. Pitchumani, Tetrahedron Lett. 51 (2010) 3312

M. Babaie, H. Sheibani, Arab. J. Chem. 4 (2011) 159

A. Siddekha, A. Nizama, M.A. Pasha, Spectrochim. Acta, A 81 (2011) 431

S. Ambethkar, V. Padmini, N. Bhuvanesh, J. Adv. Res. 6 (2015) 975

A. Moshtaghi Zonouz, D. Moghani, Synth. Commun. 46 (2016) 220

M. B. Madhusudana Reddy, V. P. Jayashankara, Synth. Commun. 40 (2010) 2930

A. S. Waghmare, S. S. Pandit, J. Saudi Chem. Soc. 21 (2017) 286

S. M. Deshmukh, D. P. Hiwarale, Pharma Chem. 9 (2017) 109

K. K. Gangu, S. Maddila, S. Narayana, S. B. Jonnalagadda RSC Adv. 7 (2017) 423

A. D. Rupnar, V. P. Pagore, S. U. Tekale, S. U. Shisodia, R. P. Pawar, Chem. Sinica 8 (2017) 229

M. Mamaghani, R. H. Nia, F. Shirini, K. Tabatabaeian, M. Rassa, Med. Chem. Res. 24 (2015) 1916

M. Yusuf, M. Kaur, H. S. Sohal, J. Heterocycl. Chem. 54 (2017) 706.

R. S. Aliabadi, N. O. Mahmoodi, RSC Adv. 6 (2016) 85877

M. Yusuf, P. Jain, Arab. J. Chem. 5 (2012) 93

M. Yusuf, P. Jain, J. Chem. Sci. 125 (2013) 117

M. Yusuf, P. Jain, J. Heterocycl. Chem. 51 (2014) 1162

M. Yusuf, V. Samdhian, P. Jain, J. Heterocycl. Chem. 52 (2015) 692

M. Yusuf, I. Solanki, J. Saudi Chem. Soc. 21 (2017) 251

M. Yusuf, A. Kaur, M. Abid, J. Heterocycl. Chem. 54 (2017) 2536

M. Yusuf, I. Solanki, P. Jain, J. Chem. Sci. 124 (2012) 703

K. S. Pandey, N. Khan, Arch. Pharm. (Weinheim, Ger.) 341 (2008) 418

M. Alothman, R. Bhat, A. A. Karim, Food Chem. 115 (2009) 785

D. Babu, P. Gurumurthy, S. K. Borra, K. M. Cherian, J. Med. Plant Res. 7 (2013) 2898

H. Ohkawa, N. Ohisini, K. Yagi, Anal. Biochem. 95 (1979) 353.




DOI: https://doi.org/10.2298/10.2298/JSC171107074Y

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