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Synthesis of sulfur karrikin bioisosteres as potential neuroprotectives

Martin Pošta, Václav Zima, Lenka Poštová Slavětínská, Marika Matoušová and Petr Beier

Beilstein J. Org. Chem. 2022, 18, 549–554. https://doi.org/10.3762/bjoc.18.57

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Synthesis of sulfur karrikin bioisosteres as potential neuroprotectives

Martin Pošta, Václav Zima, Lenka Poštová Slavětínská, Marika Matoušová and Petr Beier

Beilstein J. Org. Chem. 2022, 18, 549–554. https://doi.org/10.3762/bjoc.18.57

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Pošta, M.; Zima, V.; Poštová Slavětínská, L.; Matoušová, M.; Beier, P. Beilstein J. Org. Chem. 2022, 18, 549–554. doi:10.3762/bjoc.18.57

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TY  - JOUR
A1  - Pošta, Martin
A1  - Zima, Václav
A1  - Poštová Slavětínská, Lenka
A1  - Matoušová, Marika
A1  - Beier, Petr
T1  - Synthesis of sulfur karrikin bioisosteres as potential neuroprotectives
JF  - Beilstein Journal of Organic Chemistry
PY  - 2022///
VL  - 18
SP  - 549
EP  - 554
SN  - 1860-5397
DO  - 10.3762/bjoc.18.57
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.18.57
KW  - acetylcholinesterase
KW  - butenolides
KW  - karrikin
KW  - sulfur
N2  - The only known sulfur-containing karrikin, 3-methyl-2H-thiopyrano[3,4-b]furan-2-one, has been recently identified as an extremely efficient neuroprotective butenolide. Herein, we report the targeted synthesis of this compound as well as new synthetic protocols toward a class of compounds derived from 2H-furo[2,3-c]pyran-2-ones (karrikins) via bioisosteric exchange of oxygen with sulfur. In particular, we present synthetic procedures toward bioisosteres of karrikins with one or two sulfur heteroatoms incorporated into the core backbone together with evaluation of their biological activity in inhibition of acetylcholinesterase.
ER  -

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Deepthi, A.; Leena, S. S.; Krishnan, D. Update on thiopyran-fused heterocycle synthesis (2013-2024). Organic & biomolecular chemistry 2024, 22, 5676–5717. doi:10.1039/d4ob00497c
Sharma, S.; Singh, D.; Kumar, S.; Vaishali; Jamra, R.; Banyal, N.; Deepika; Malakar, C. C.; Singh, V. An efficient metal-free and catalyst-free C-S/C-O bond-formation strategy: synthesis of pyrazole-conjugated thioamides and amides. Beilstein journal of organic chemistry 2023, 19, 231–244. doi:10.3762/bjoc.19.22

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