SYNTHESIS AND ANTI-TYROSINASE ACTIVITY EVALUATION OF FLUORINATED CHALCONE AND PHENYL BENZYL ETHER DERIVATIVES

Authors

  • Kanokwan Singpanna Pharmaceutical Development of Green Innovations Group (PDGIG), Faculty of Pharmacy, Silpakorn University, Sanam Chandra Palace Campus, Nakhon Pathom
  • Sittisak Oekchuae Department of Chemistry, Faculty of Science, Silpakorn University, Sanam Chandra Palace Campus, Nakhon Pathom
  • Kochakorn Jareonkunmetee Department of Chemistry, Faculty of Science, Silpakorn University, Sanam Chandra Palace Campus, Nakhon Pathom
  • Anan Athipornchai Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Burapha University, Bangsean, Chonburi
  • Nopparat Nuntharatanapong Pharmaceutical Development of Green Innovations Group (PDGIG), Faculty of Pharmacy, Silpakorn University, Sanam Chandra Palace Campus, Nakhon Pathom
  • Praneet Opanasopit Pharmaceutical Development of Green Innovations Group (PDGIG), Faculty of Pharmacy, Silpakorn University, Sanam Chandra Palace Campus, Nakhon Pathom
  • Panupun Limpachayaporn Department of Chemistry, Faculty of Science, Silpakorn University, Sanam Chandra Palace Campus, Nakhon Pathom

DOI:

https://doi.org/10.69598/tbps.15.1.81-89

Keywords:

anti-tyrosinase activity, bibenzyl compounds, chalcone, phenyl benzyl ether, whitening agent

Abstract

Pigmentation is a common skin disorder caused by several factors including UV exposure, skin aging, hormonal imbalance and skin irritation.  Ascorbic acid, alpha-arbutin, tranexamic acid, kojic acid, and niacinamide have all been used in skin lightening treatments. This study aimed to develop a new active compound for skin lightening. Ten chalcone and nine phenyl benzyl ether analogues of bibenzyl compounds and bifluranol (9) were synthesized using aldol condensation reaction and Williamson ether synthesis, respectively. Their activity in vitro against tyrosinase, the rate-determining enzyme in melanogenesis, was evaluated at 500 µM. The results revealed that the chalcone analogues were more active than the phenyl benzyl ethers. The p-fluorinated analogues for both chalcone 12d (p-F) and ether 15d (p-F) inhibited tyrosinase in vitro to the highest extent for each series with inhibitory percentages of 38 and 32 at 500 µM respectively. These findings might provide useful guidance for further structural development of the more potent tyrosinase inhibitors used in whitening agents.

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Published

2020-05-13

How to Cite

Singpanna, K. ., Oekchuae, S. ., Jareonkunmetee, K. ., Athipornchai, A., Nuntharatanapong, N. ., Opanasopit, P. ., & Limpachayaporn, P. . (2020). SYNTHESIS AND ANTI-TYROSINASE ACTIVITY EVALUATION OF FLUORINATED CHALCONE AND PHENYL BENZYL ETHER DERIVATIVES . Thai Bulletin of Pharmaceutical Sciences, 15(1), 81–89. https://doi.org/10.69598/tbps.15.1.81-89

Issue

Vol. 15 No. 1 (2020): JANUARY - JUNE 2020

Section

Original Research Articles

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