(R)-(−)-2-[(5-Oxido-5-phenyl-5λ4-isoquino[4,3-c][2,1]benzothiazin-12-yl)amino]benzonitrile

Frings, Marcus; Atodiresei, Iuliana; Bolm, Carsten

doi:10.3390/m834

Molbank

2014

DOI: 10.3390/m834

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(R)-(−)-2-[(5-Oxido-5-phenyl-5λ4-isoquino[4,3-c][2,1]benzothiazin-12-yl)amino]benzonitrile

Marcus Frings

Iuliana Atodiresei

Carsten Bolm

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Cited by 2 publications

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References 15 publications

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“…A few known strategies are noteworthy. For example, Harmata and co-workers reported the synthesis of benzothiazine S -oxides through palladium-catalyzed coupling reactions, and we prepared related compounds by rhodium-catalyzed ortho C–H functionalization of S -arylsulfoximines . Applying RCM and RCEYM to sulfoximines with two adjacent unsaturated side chains resulted in the formation of partially hydrogenated cyclic derivatives .…”

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Halocyclizations of Unsaturated Sulfoximines

2016

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A method for halocyclizations of S-alkenylsulfoximines is reported. When unsaturated NH-sulfoximines are treated with a combination of iodobenzene diacetate and potassium iodide, a transformation to the corresponding five- and six-membered cyclic products occurs providing S-oxides of dihydro isothiazoles and tetrahydro-1,2-thiazines, respectively, in moderate to high yields with good diastereoselectivities and excellent regioselectivities.

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Halocyclizations of Unsaturated Sulfoximines

2016

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Evaluation of Chiral Organosulfur Compounds on Their Activity against the Malaria Parasite Plasmodium falciparum

et al. 2022

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Malaria is one of the deadliest tropical diseases, especially causing havoc in children under the age of five in Africa. Although the disease is treatable, the rapid development of drug resistant parasites against frontline drugs requires the search for novel antimalarials. In this study, we tested a series of organosulfur compounds from our internal library for their antiplasmodial effect against Plasmodium falciparum asexual and sexual blood stages. Some active compounds were also obtained in enantiomerically pure form and tested individually against asexual blood stages of the parasite to compare their activity. Out of the 23 tested compounds, 7 compounds (1, 2, 5, 9, 15, 16, and 17) exhibited high antimalarial activity, with IC50 values in the range from 2.2 ± 0.64 to 5.2 ± 1.95 µM, while the the other compounds showed moderate to very low activity. The most active compounds also exhibited high activity against the chloroquine-resistant strain, reduced gametocyte development and were not toxic to non-infected red blood cells and Hela cells, as well as the hematopoietic HEL cell line at concentrations below 50 µM. To determine if the enantiomers of the active compounds display different antimalarial activity, enantiomers of two of the active compounds were separated and their antimalarial activity compared. The results show a higher activity of the (–) enantiomers as compared to their (+) counterparts. Our combined data indicate that organosulfur compounds could be exploited as antimalarial drugs and enantiomers of the active compounds may represent a good starting point for the design of novel drugs to target malaria.

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(R)-(−)-2-[(5-Oxido-5-phenyl-5λ4-isoquino[4,3-c][2,1]benzothiazin-12-yl)amino]benzonitrile

Cited by 2 publications

References 15 publications

Halocyclizations of Unsaturated Sulfoximines

Halocyclizations of Unsaturated Sulfoximines

Evaluation of Chiral Organosulfur Compounds on Their Activity against the Malaria Parasite Plasmodium falciparum

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