83504-42-1Relevant articles and documents
Structure?Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents
Bernal, Freddy A.,Kaiser, Marcel,Wünsch, Bernhard,Schmidt, Thomas J.
, p. 68 - 78 (2019/11/22)
Protozoal infections are still a global health problem, threatening the lives of millions of people around the world, mainly in impoverished tropical and sub-tropical regions. Thus, in view of the lack of efficient therapies and increasing resistances against existing drugs, this study describes the antiprotozoal potential of synthetic cinnamate ester analogues and their structure-activity relationships. In general, Leishmania donovani and Trypanosoma brucei were quite susceptible to the compounds in a structure-dependent manner. Detailed analysis revealed a key role of the substitution pattern on the aromatic ring and a marked effect of the side chain on the activity against these two parasites. The high antileishmanial potency and remarkable selectivity of the nitro-aromatic derivatives suggested them as promising candidates for further studies. On the other hand, the high in vitro potency of catechol-type compounds against T. brucei could not be extrapolated to an in vivo mouse model.
Differential Partitioning of Bioantioxidants in Edible Oil-Water and Octanol-Water Systems: Linear Free Energy Relationships
Freiría-Gándara,Losada-Barreiro,Paiva-Martins,Bravo-Díaz
, p. 2999 - 3007 (2018/08/31)
Partition coefficients, PWO, of antioxidants (AOs) between edible oils and water are scarce in the literature, despite that AOs are widely used to control lipid oxidation and the oxidative stress in cells. PWO values have a great importance to predict the efficiency and distribution of bioactives at different levels of biological organization from binary oil-water systems to living cells. Here, we determined the partition coefficients, PWO, of four series of potent, natural AOs of increasing lipophilicity between vegetable oils (olive, soybean, and corn) and water and, for the sake of comparison, between octanol-water, PWOCT. Results indicate that the contribution of the -CH2 groups to the overall lipophilicity of the AO is the same irrespective of the oil employed. The PWO values were compared with PWOCT values, and linear relationships were obtained for each series of AOs. Results indicate that, in general, PWO values cannot be predicted from the PWOCT values, making necessary to determine the PWO values for each oil and antioxidant.
Structure–activity relations of rosmarinic acid derivatives for the amyloid β aggregation inhibition and antioxidant properties
Taguchi, Riho,Hatayama, Koki,Takahashi, Tomohito,Hayashi, Takafumi,Sato, Yuki,Sato, Daisuke,Ohta, Kiminori,Nakano, Hiroto,Seki, Chigusa,Endo, Yasuyuki,Tokuraku, Kiyotaka,Uwai, Koji
supporting information, p. 1066 - 1075 (2017/08/02)
Amyloid-β aggregation inhibitors are expected to be therapeutic or prophylactic agents for Alzheimer's disease. Rosmarinic acid, which is one of the main aggregation inhibitors derived from Lamiaceae, was employed as a lead compound and its 25 derivatives were synthesized. In this study, the structure–activity relations of rosmarinic acid derivatives for the amyloid-β aggregation inhibitory effect (MSHTS assay), antioxidant properties, and xanthine oxidase inhibition were evaluated. Among the tested compounds, compounds 16d and 19 were found to the most potent amyloid aggregation inhibitors. The SAR revealed that the necessity of the presence of the phenolic hydroxyl on one side of the molecule as well as the lipophilicity of the entire molecule. The importance of these structural properties was also supported by docking simulations.
