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

Jasril Jasril; Hilwan Yuda Teruna; Aisyah Aisyah; Nurlaili Nurlaili; Rudi Hendra

doi:10.22146/ijc.34285

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