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Open AccessCommunication

Structure-Activity Relationship between Thiol Group-Trapping Ability of Morphinan Compounds with a Michael Acceptor and Anti-Plasmodium falciparum Activities

1
International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8575, Japan
2
Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan
3
School of Medicine, Keio University, 35, Shinanomachi, Shinjuku, Tokyo 160-8582, Japan
4
Kitasato Institute for Life Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan
*
Author to whom correspondence should be addressed.
Academic Editors: Mariana Spetea and Helmut Schmidhammer
Molecules 2020, 25(5), 1112; https://doi.org/10.3390/molecules25051112
Received: 24 January 2020 / Revised: 28 February 2020 / Accepted: 28 February 2020 / Published: 2 March 2020
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. View Full-Text
Keywords: morphinan; BNTX; δ opioid receptor antagonist; 1H-NMR experiments; mechanism elucidation morphinan; BNTX; δ opioid receptor antagonist; 1H-NMR experiments; mechanism elucidation
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Kutsumura, N.; Koyama, Y.; Saitoh, T.; Yamamoto, N.; Nagumo, Y.; Miyata, Y.; Hokari, R.; Ishiyama, A.; Iwatsuki, M.; Otoguro, K.; Ōmura, S.; Nagase, H. Structure-Activity Relationship between Thiol Group-Trapping Ability of Morphinan Compounds with a Michael Acceptor and Anti-Plasmodium falciparum Activities. Molecules 2020, 25, 1112.

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