Whitening Effects of Adamantyl Benzamide Derivatives

Abstract

The structure activity relationship of polyhydroxylated benzamide derivatives for whitening effects was examined. The adamantyl benzamide derivatives with catechol (3,4-dihydroxyphenyl) of B-ring part showed good anti-melanogenesis activity, but the inhibitory activity of mono-hydroxyphenyl (3-OH or 4-OH) or 3,4-dimethoxyphenyl substituted derivatives was decreased or lost. Therefore the catechol unit was appeared to be the crucial factor for the inhibition of melanogenesis. And the existence of 2-OH of A-ring part had minor influence on the activity, the length of carbon chain between A-ring and B-ring was also not the major factor for the anti-melanogenesis activity.

Antimelanogenic activity of a novel adamantyl benzylbenzamide derivative, AP736: a randomized, double‐blind, vehicle‐controlled comparative clinical trial performed in patients with hyperpigmentation during the summer

“…In our previous study, we synthesized various derivatives of N ‐benzylbenzamides as novel skin‐lightening agents and found that AP736 downregulates microphthalmia‐associated transcription factor (MITF) and tyrosinase by inhibiting the elevation in cAMP and activation of cAMP response element binding protein (CREB) and protein kinase A (PKA) …”

“…5,6 In our previous study, we synthesized various derivatives of N-benzylbenzamides as novel skin-lightening agents and found that AP736 downregulates microphthalmia-associated transcription factor (MITF) and tyrosinase by inhibiting the elevation in cAMP and activation of cAMP response element binding protein (CREB) and protein kinase A (PKA). [7][8][9] In this study, we conducted a clinical trial to compare the whitening effects of a topical formulation containing AP736 with that of a vehicle control formulation to verify the findings obtained using the in vitro model.…”