Open Access

ARTICLE

Synthesis and Antioxidant Activity of (E) ω-Formylcamphene-Based Thiazole Hydrazone Derivatives

by Jiayu Chang¹, Qingying Ding¹, Chong Zhong¹, Yao Long², Zhuanquan Xiao³, Hai Luo¹, Yuling Yang¹, Zongde Wang¹, Shengliang Liao¹, Jinzhu Chen², Shangxing Chen^1,*, Ji Zhang^1,*

1 College of Forestry, Jiangxi Agricultural University, East China Woody Fragrance and Flavor Engineering Research Center of National Forestry and Grassland Administration, Camphor Engineering Research Center of NFGA, Nanchang, 330045, China
2 College of Science, Jiangxi Agricultural University, Nanchang, 330045, China
3 College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, 330027, China

* Corresponding Authors: Shangxing Chen. Email: ; Ji Zhang. Email:

(This article belongs to the Special Issue: Renewable Biomass as a Platform for Preparing Green Chemistry)

Journal of Renewable Materials 2023, 11(1), 379-391. https://doi.org/10.32604/jrm.2023.022535

Received 15 March 2022; Accepted 29 April 2022; Issue published 10 August 2022

Abstract

(E) ω-formylcamphene was synthesized from α-pinene, the main component of turpentine, and then reacted with thiosemicarbazide to obtain (E) ω-formylcamphene thiosemicarbazide 3, which was reacted with 14 α-bromoacetophenone compounds to obtain 14 (E) ω-formylcamphene thiazole hydrazone compounds 5a–5n; the yields were all above 80%. The structures of the target compounds were characterized by IR, ¹H-NMR, ¹³C-NMR, and HR-MS analyses. Then, 500, 250, 125, 62.5, and 31.25 mg/L drug solutions were prepared. Free radical scavenging experiments of 1, 1-diphenyl-2-picrylhydrazyl (DPPH) and 2, 2-bis (3-ethyl-benzothiazole-6-sulfonic acid) diammonium salt (ABTS) were carried out with Trolox and L-ascorbic acid as the control samples. The scavenging rates of 14 compounds for DPPH and ABTS free radicals were obtained; the IC₅₀ values of scavenging free radicals were fitted using SPSS software. The results show that 14 (E) ω-formylcamphene-based thiazole hydrazone compounds exhibited good scavenging effects on the two free radicals, especially when the concentration of the drug solution was 125 and 62.5 mg/L; most compounds exceeded the scavenging efficiency of Trolox and L-ascorbic acid.

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