Synthesis and Antioxidant Activity Study of New Mannich Bases Derived From Vanillic Acid

Abstract

We synthesized five new Mannich bases compounds from vanillic acid and evaluated for their antioxidant activities using a free-radical DPPH and FRAP methods. The compounds' structures were confirmed based on infrared, proton NMR, carbon NMR, and mass spectra. In this study, the compound 5-(pyrrolidin-1-ylmethyl)vanillic acid (2e) showed the best free-radical scavenger activity, while compound 2-[(diethylamino)methyl]vanillic acid (2c) showed the best as a ferric reductant. Mannich bases enhanced the free-radical scavenger activity but decreasing the ferric reduction potential of the parent compounds. The compounds were found to be moderate antioxidant agents.

Identification and Simultaneous HPLC-PDA Quantification of Anti-glycation and α-Glucosidase Inhibitory Compounds From Atractylodes lancea Water Extract

“…Their chemical structures were elucidated using 1 H-NMR, 13 C-NMR, and UHPLC-ESI/LTQ-Orbitrap-HRMS data by comparing them with the results from previous studies (Figure 1). [14][15][16][17][18][19][20][21][22][23][24][25][26] The mass accuracy of 13 compounds was observed within 5 ppm, indicating the credibility of the results (Table 1).…”

Sintesis dan Uji Aktivitas Anti-inflamasi Senyawa 2‐Hidroksi‐N‐(Piridin‐2‐il)Benzamida Tersubstitusi Basa Mannich Morfolin dan N-Metilpiperazin

“…Synthesis of Mannich base derivatives (Compounds 2a-b). The synthesis method refers to the reaction for the formation of the amino-alkylation of vanillic acid which has been reported previously (Hayun et al, 2020). An amount of compound 1 (20 mmol) was dissolved in tetrahydrofuran (18 mL).…”

“…Research from asymmetric mono-carbonyl analogs of curcumin Mannich base of N-methyl piperazine has result higher in vitro anti-inflammatory activity than its parent compound, and diclofenac sodium as a standard. One of study about structural modifications of vanillic acid Mannich bases substituted dimethylamine, diethylamine, morpholine and N-methyl piperazine, showed better antioxidant activity than the parent compound, even the 5-(pyrrolidine-1-yl-methyl)-vanillic acid compound, was able to scavenge free radicals better than quercetin as a standard (Hayun et al, 2020;Rahmawati et al, 2020).…”

تحضير وتشخيص و ودراسة النشاط البيولوجي والالتحام الجزيئي لبعض مشتقات السلفاميثوكسازول الجديدة.

“…Figs. [5][6][7][8][9][10][11][12][13][14][15] show the bonding of some compounds in proteins. Table 5 shows various interactions involved between receptors and compounds, types of bonding, and bond length.…”