2-Mercaptonicotinoyl glycine, a new potent melanogenesis inhibitor, exhibits a unique mode of action while preserving melanocyte integrity.

Research on new ingredients that can prevent excessive melanin production in the skin while considering efficacy, safety but also environmental impact is of great importance to significantly improve the profile of existing actives on the market and avoid undesirable side effects. Here, the discovery of an innovative technology for the management of hyperpigmentation is described. High-throughput screening tests on a wide chemical diversity of molecules and in silico predictive methodologies were essential to design an original thiopyridinone backbone and select 2-mercaptonicotinoyl glycine (2-MNG) as exhibiting the most favorable balance between the impact on water footprint, skin penetration potential and performance. The effectiveness of 2-MNG was confirmed by topical application on pigmented reconstructed epidermis and human skin explants. In addition, experiments have shown that unlike most melanogenesis inhibitors on the market, this molecule is not a tyrosinase inhibitor. 2-MNG binds to certain melanin precursors, preventing their integration into growing melanin and leading to inhibition of eumelanin and pheomelanin synthesis, without compromising the integrity of melanocytes.

Divergent Entry to C-Glycosides from Unprotected Sugars.

An efficient, divergent, and straightforward access to novel C-glycosides has been developed, namely, α-hydroxy carboxamide and carboxylic acid derivatives, via a green and scalable process from unprotected carbohydrates. The method involves condensation of 1,3-dimethylbarbituric acid with unprotected sugars followed by subsequent barbiturate oxidative cleavage in the same pot. Further expanding of the chemistry led to the development of efficient entries to diastereoisomerically pure C-glycosyl-α-hydroxy esters or amides through nucleophilic attack on a readily available and versatile key lactone intermediate.