845883-03-6Relevant 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.
In-vitro and in-vivo antimalarial activity of caffeic acid and some of its derivatives
Alson, Sylvain G.,Jansen, Olivia,Cieckiewicz, Ewa,Rakotoarimanana, Hajatiana,Rafatro, Herintsoa,Degotte, Gilles,Francotte, Pierre,Frederich, Michel
, p. 1349 - 1356 (2018/07/31)
Objectives: To explore the in-vitro and in-vivo antimalarial potential of caffeic acid and derivatives. Methods: Two common phenolic acids (caffeic acid and chlorogenic acid) were evaluated for in-vitro and in-vivo antiplasmodial activity in comparison with some semi-synthetic derivatives that were synthesized. An in-vitro assay based on plasmodial lactate dehydrogenase activity, and the classical in-vivo 5-day suppressive test from Peters on an artemisinin-resistant Plasmodium berghei strain was used. Parasitic stage sensitivity to ethyl caffeate was determined in this work. Key findings: Phenolic acid esters derivatives showed better antiplasmodial activity than corresponding phenolic acids. The derivative with the highest in-vitro activity being caffeic acid ethyl ester, exhibiting an IC50?=?21.9?±?9.4?μm. Ethyl caffeate and methyl caffeate were then evaluated for antimalarial activity in?vivo and ethyl caffeate showed a growth inhibition of 55% at 100?mg/kg. Finally, it seems that ethyl caffeate blocks the growth of young parasitic forms. Conclusions: Our study provides evidence for an antimalarial potential of caffeic acid derivatives which are common in several medicinal plants traditionally used against malaria. It also demonstrates the possibility to use such derivatives in the treatment of malaria.
Chemo and regioselective serendipitous electrochemically initiated spirocyclization of caffeic acid esters with barbituric acid derivatives
Alizadeh, Abdolhamid,Khodaei, Mohammad Mehdi,Fakhari, Mitra,Abdi, Gisya,Ghouzivand, Sohrab
, p. 533 - 540 (2015/09/01)
An interesting sequence of oxidation/Michael addition/oxidation/spirocyclization is observed in the electrolysis of caffeic acid esters in the presence of barbituric acid derivatives leading to the synthesis of a series of novel spirocycles. In an experim
