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Effect of N-Amide Substitution on Antioxidative Activities of Melatonin Derivatives

1
Graduate School, Khon Kaen University, Khon Kaen 40002, Thailand
2
Melatonin Research Group, Faculty of Pharmaceutical Sciences, Khon Kaen University, Khon Kaen 40002, Thailand
3
Division of Regional Innovation, Graduate School of Health Sciences, Hirosaki University, 66-1 Hon-cho, Hirosaki, Aomori 036-8564, Japan
*
Author to whom correspondence should be addressed.
Sci. Pharm. 2020, 88(1), 3; https://doi.org/10.3390/scipharm88010003
Received: 22 November 2019 / Revised: 3 January 2020 / Accepted: 7 January 2020 / Published: 8 January 2020
Five N-amide substituted melatonin (MLT) derivatives were synthesized and evaluated for antioxidative activities, and compounds 912 showed higher electron spin resonance (ESR) response than MLT. 4-Bromobenzoyl and naphthoyl derivatives (10 and 11) presented stronger hydroxyl radical inhibitory effect than MLT in Fenton reaction. The substitution at the N1-position on the MLT core structure with acetyl (8), benzoyl (9), 4-bromobenzoyl (10), and naphthoyl (11) and N2-substitution with 4-bromobenzoyl (12) decreased the reducing power of the derivatives in ferric reducing antioxidant power (FRAP) assay. Compounds 811 also presented lower antioxidant capacity than their parent compound in 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) disodium salt (ABTS) assay; whereas, compound 12 presented radical scavenging activity similarly to MLT. All aryl derivatives (912) showed higher ability to quench peroxyl radicals than MLT about three times, especially the benzoylated derivatives (9 and 10) that presented the highest ability in oxygen radical absorbance capacity (ORAC) assay. View Full-Text
Keywords: melatonin; N-amide derivative; radical scavenging; electron spin resonance melatonin; N-amide derivative; radical scavenging; electron spin resonance
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Panyatip, P.; Pratheepawanit Johns, N.; Priprem, A.; Nakagawa, K.; Puthongking, P. Effect of N-Amide Substitution on Antioxidative Activities of Melatonin Derivatives. Sci. Pharm. 2020, 88, 3.

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