Abstract
7-Benzylidenenaltrexone (BNTX) and most of its derivatives showed in vitro antimalarial activities against chloroquine-resistant and -sensitive Plasmodium falciparum strains (K1 and FCR3, respectively). In addition, the time-dependent changes of the addition reactions of the BNTX derivatives with 1-propanethiol were examined by 1H-NMR experiments to estimate their thiol group-trapping ability. The relative chemical reactivity of the BNTX derivatives to trap the thiol group of 1-propanethiol was correlated highly with the antimalarial activity. Therefore, the measurements of the thiol group-trapping ability of the BNTX derivatives with a Michael acceptor is expected to become an alternative method for in vitro malarial activity and related assays.
Highlights
Malaria is one of the world’s deadliest infectious diseases and it is widespread in the tropical and subtropical regions located in a broad band around the equator, including Africa, SoutheastAsia, Middle East, and Latin America
We investigated the correlation between the thiol group-trapping ability of 1 and its derivatives and in vitro antimalarial activity
The electron-donating substituted derivatives 16 and 17 tended to exhibit weak activities. These results suggested that inductive effects caused by introducing substituents into the benzylidene site affected antimalarial activity to some extent
Summary
Malaria is one of the world’s deadliest infectious diseases and it is widespread in the tropical and subtropical regions located in a broad band around the equator, including Africa, SoutheastAsia, Middle East, and Latin America. In 2017, an estimated 219 million malaria infections were reported in 87 countries, including about 435,000 deaths from malaria [1]. Malaria causes serious complications, such as cerebral malaria involving encephalopathy [2], blackwater fever [3], and acute respiratory distress syndrome (ARDS) [4]. General drug-resistant type of malaria, such as chloroquine-resistance (CQ-resistance), and artemisinin-resistant malaria has been identified, creating a critical social situation [5,6]. Against such a background, we first reported that a δ opioid receptor (DOR) antagonist
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