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Citation: FU Xiaolei, ZHAO Chunhui, ZHANG Yixuan, CHEN Yanhua, LI Chang, ZHAO Longxuan. Synthesis,Characterization and Whitening Activity of Amino Acid-hydroquinone Conjugates[J]. Chinese Journal of Applied Chemistry, ;2015, 32(2): 158-165. doi: 10.11944/j.issn.1000-0518.2015.02.140151 shu

Synthesis,Characterization and Whitening Activity of Amino Acid-hydroquinone Conjugates

1.
a School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029, China;
2.
b Liaoning Provincial Key Laboratory of Biotechnology and Drug Discovery, Liaoning Normal University, Dalian, Liaoning 116029, China

Corresponding author: ZHAO Longxuan,
Received Date: 29 April 2014
Available Online: 14 July 2014
Fund Project: 国家自然科学基金资助项目(21102067) (21102067)

Based on the piecing together principle in the drug design,we directly couple the hydroxyl group of lead compounds with bioactive compounds in order to get hydroquinone derivatives with high efficiency and low toxicity. 4-(Benzyloxy) phenol was synthesized through the protection of phenolic hydroxyl group,and then coupled with amino acid whose amino group was protected. Moreover,we introduced carboxylic acid moeity into 4-(benzyloxy) phenol and coupled it with amino acid methyl ester hydrochloride. After the removal of the benzyl protecting group,sixteen amino acid-hydroquinone conjugates were synthesized. The sixteen conjugates were characterized by IR,¹H NMR,¹³C NMR and ESI-MS. The study of whitening activity of these conjugates showed that HQ-3b,HQ-3c,HQ-4a,HQ-4b,HQ-7c and HQ-8a had significant inhibition to tyrosinase(IC₅₀=3.60) with the IC₅₀ of HQ-4b as low as 0.15.
- hydroquinone,
- amino acid,
- whitening activity,
- conjugation
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