Microwave Assisted Synthesis and Evaluation of Toxicity and Antioxidant Activity of Pyrazoline Derivatives

https://doi.org/10.22146/ijc.34285

Jasril Jasril(1), Hilwan Yuda Teruna(2), Aisyah Aisyah(3), Nurlaili Nurlaili(4), Rudi Hendra(5*)

(1) Department of Chemistry, University of Riau, Kampus Binawidya KM 12.5 Simpang Baru Pekanbaru, 28293, Indonesia
(2) Department of Chemistry, University of Riau, Kampus Binawidya KM 12.5 Simpang Baru Pekanbaru, 28293, Indonesia
(3) Department of Chemistry, University of Riau, Kampus Binawidya KM 12.5 Simpang Baru Pekanbaru, 28293, Indonesia
(4) Department of Chemistry, University of Riau, Kampus Binawidya KM 12.5 Simpang Baru Pekanbaru, 28293, Indonesia
(5) Department of Chemistry, University of Riau, Kampus Binawidya KM 12.5 Simpang Baru Pekanbaru, 28293, Indonesia
(*) Corresponding Author

Abstract


Four pyrazoline analogues, 3-(4-methoxyphenyl)-5-naphthalene-1-yl-1-phenyl-4,5-dihydro-pyrazole (3), 3-(4-methoxyphenyl)-5-naphthalene-1-yl-4,5-dihydro-1H-pyrazole (4), 3-(2-methoxyphenyl)-5-naphthalene-1-yl-1-phenyl-4,5-dihydro-pyrazole (5) and 3-(2-methoxyphenyl)-5-naphthalene-1-yl-4,5-dihydro-1H-pyrazole (6) were synthesized via intermolecular cyclization between substituted chalcones and hydrazine derivatives. The compounds were synthesized in two steps. In the first step, the chalcones were synthesized by Claisen-Schmidt reaction. In the second step, they were cyclized with some hydrazine derivatives to form pyrazolines by using glacial acetic acid as a catalyst and assisted by microwave irradiation. The toxicity analysis showed that compound 1 and 2 were toxic with LC50 values of 11.47 and 0.97 μg/mL, respectively. Furthermore, only compound 6 showed high antioxidant activity by using DPPH with an IC50 value of 4.47 μg/mL.

Keywords


microwave-assisted synthesis; chalcone; pyrazoline, toxicity; antioxidant activity

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References

[1] Kendre, M.M., and Baseer, M.A., 2013, Synthesis and evaluation of some new pyrazoline derivatives as antimicrobial agents, Orient. J. Chem., 29 (1), 253–256.

[2] Insuasty, B., Ramírez, J., Becerra, D., Echeverry, C., Quiroga, J., Abonia, R., Robledo, S.M., Vélez, I.D., Upegui, Y., Munoz, J.A., Ospina, V., Nogueras, M., and Cobo, J., 2015, An efficient synthesis of new caffeine-based chalcones, pyrazolines and pyrazolo [3,4-b][1,4]diazepines as potential antimalarial, antitrypanosomal and antileishmanial agents, Eur. J. Med. Chem., 93, 401–413.

[3] Kumar, N., Bhatnagar, A, and Dudhe, R., 2017, Synthesis of 3-(4, 5-dihydro-1-phenyl-5-substituted phenyl-1H-pyrazol-3-yl)-2H-chromen-2-one derivatives and evaluation of their anticancer activity, Arabian J. Chem., 10 (Suppl. 2), S2443–S2452.

[4] Khalil, N.A., Ahmed, E.M., El-Nassan, H.B., Ahmed, O.K., and Al-Abd, A.M., 2012, Synthesis and biological evaluation of novel pyrazoline derivatives as anti-inflammatory and antioxidant agents, Arch. Pharmacal Res., 35 (6), 995–1002.

[5] Barsoum, F.F., Hosni, H.M., and Girgis, A.S., 2006, Novel bis(1-acyl-2-pyrazolines) of potential anti-inflammatory and molluscicidal properties, Bioorg. Med. Chem., 14 (11), 3929–3937.

[6] Jadhav, S.Y., Shirame, S.P., Kulkarni, S.D., Patil, S.B., Pasale, S.K., and Bhosale, R.B., 2013, PEG mediated synthesis and pharmacological evaluation of some fluoro substituted pyrazoline derivatives as antiinflammatory and analgesic agents, Bioorg. Med. Chem. Lett., 23 (9), 2575–2578.

[7] Anderson, J.E., Goetz, C.M., McLaughlin, J.L., and Suffness, M., 1991, A blind comparison of simple bench‐top bioassays and human tumor cell cytotoxicities as antitumor prescreens, Phytochem. Anal., 2 (3), 107–111.

[8] Karthikeyan, M.S., Holla, B.S., and Kumari, N.S., 2007, Synthesis and antimicrobial studies on novel chloro-fluorine containing hydroxy pyrazolines, Eur. J. Med. Chem., 42 (1), 30–36.

[9] Palaska, E., Erol, D., and Demirdamar, R., 1996, Synthesis and antidepressant activities of some 1,3,5-triphenyl-2-pyrazolines, Eur. J. Med. Chem., 31 (1), 43–47.

[10] Ahmad, A., Husain, A., Khan, S.A., Mujeeb, M., and Bhandari, A., 2016, Synthesis, antimicrobial and antitubercular activities of some novel pyrazoline derivatives, J. Saudi Chem. Soc., 20 (5), 577–584.

[11] Mamolo, M.G., Zampieri, D., Falagiani, V., Vio, L., and Banfi, E., 2003, Synthesis and antifungal activity of (±)-1-(5-aryl-3-pyridin-2-yl-4,5-dihydro-pyrazol-1-yl)-2-imidazol-1-yl-ethanone derivatives, Farmaco, 58 (4), 315–322.

[12] Molyneux, P., 2004, The use of the stable free radical diphenylpicrylhydrazyl (DPPH) for estimating antioxidant activity, Songklanakarin J. Sci. Technol., 26 (2), 211–219.

[13] Palaska, E., Aytemir, M., Uzbay, I.T., and Erol, D., 2001, Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines, Eur. J. Med. Chem., 36 (6), 539–543.

[14] Abid, M., and Azam, A., 2005, 1-N-substituted thiocarbamoyl-3-phenyl-2-pyrazolines: Synthesis and in vitro antiamoebic activities, Eur. J. Med. Chem., 40 (9), 935–942.

[15] Abid, M., and Azam, A., 2006, Synthesis, characterization and antiamoebic activity of 1-(thiazolo [4,5-b] quinoxaline-2-yl)-3-phenyl-2-pyrazoline derivatives, Bioorg. Med. Chem. Lett., 16 (10), 2812–2816.

[16] Shaharyar, M., Siddiqui, A.A., Ali, M.A., Sriram, D., and Yogeeswari, P., 2006, Synthesis and in vitro antimycobacterial activity of N1-nicotinoyl-3-(4′-hydroxy-3′-methyl phenyl)-5-[(sub)phenyl]-2-pyrazolines, Bioorg. Med. Chem. Lett., 16 (15), 3947–3949.

[17] Azarifar, D., and Ghasemnejad, H., 2003, Microwave-assisted synthesis of some 3,5-arylated 2-pyrazolines, Molecules, 8 (8), 642–648.

[18] Lu, Y., Hendra, R., Oakley, A.J., and Keller, P.A., 2014, Efficient synthesis and antioxidant activity of coelenterazine analogues, Tetrahedron Lett., 55 (45), 6212–6215.

[19] Bhuiyan, M.M.H., Hossain, M.I., Mahmud, M.M., and Al-Amin, M., 2011, Microwave-assisted efficient synthesis of chalcones as probes for antimicrobial activities, J. Chem., 1 (1), 21–28.



DOI: https://doi.org/10.22146/ijc.34285

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