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

doi:10.11944/j.issn.1000-0518.2015.02.140151

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (2): 158-165.DOI: 10.11944/j.issn.1000-0518.2015.02.140151

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

FU Xiaolei^a, ZHAO Chunhui^b, ZHANG Yixuan^a, CHEN Yanhua^a, LI Chang^a, ZHAO Longxuan^{a, b, *}

^aSchool of Chemistry and Chemical Engineering;
^bLiaoning Provincial Key Laboratory of Biotechnology and Drug Discovery,Liaoning Normal University,Dalian,Liaoning 116029,China

Received:2014-04-29 Revised:2014-07-14 Published:2015-02-10 Online:2015-02-10
Contact: Corresponding author:ZHAO Longxuan, professor; E-mail:lxzhao@lnnu.edu.cn; Research interests:pharmaceutical synthesis
Supported by:
Supported by the National Natural Science Foundation of China(No.21102067)

Abstract

Abstract:

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.

Key words: hydroquinone, amino acid, whitening activity, conjugation

CLC Number:

null

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.

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

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