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硫代卡里金生物电子等排体作为潜在神经保护剂的合成。

Synthesis of sulfur karrikin bioisosteres as potential neuroprotectives.

作者信息

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

机构信息

Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Flemingovo nám. 2, 16610 Prague 6, Czech Republic.

出版信息

Beilstein J Org Chem. 2022 May 16;18:549-554. doi: 10.3762/bjoc.18.57. eCollection 2022.

DOI:10.3762/bjoc.18.57
PMID:35651698
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9127252/
Abstract

The only known sulfur-containing karrikin, 3-methyl-2-thiopyrano[3,4-]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 2-furo[2,3-]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.

摘要

唯一已知的含硫卡里金，即3-甲基-2-硫代吡喃并[3,4 -]呋喃-2-酮，最近被鉴定为一种极其有效的神经保护丁烯内酯。在此，我们报告了该化合物的定向合成以及通过氧与硫的生物电子等排体交换，针对一类源自2-呋喃并[2,3 -]吡喃-2-酮（卡里金）的化合物的新合成方案。特别是，我们展示了合成核心骨架中含有一个或两个硫杂原子的卡里金生物电子等排体的程序，并评估了它们在抑制乙酰胆碱酯酶方面的生物活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/e9c97ca3a2d2/Beilstein_J_Org_Chem-18-549-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/812588229196/Beilstein_J_Org_Chem-18-549-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/a8420303df8e/Beilstein_J_Org_Chem-18-549-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/00ac70e27958/Beilstein_J_Org_Chem-18-549-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/a1daa0dbe47a/Beilstein_J_Org_Chem-18-549-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/5844a29cdf29/Beilstein_J_Org_Chem-18-549-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/39239b184560/Beilstein_J_Org_Chem-18-549-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/25582fc02dd3/Beilstein_J_Org_Chem-18-549-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/e9c97ca3a2d2/Beilstein_J_Org_Chem-18-549-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/812588229196/Beilstein_J_Org_Chem-18-549-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/a8420303df8e/Beilstein_J_Org_Chem-18-549-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/00ac70e27958/Beilstein_J_Org_Chem-18-549-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/a1daa0dbe47a/Beilstein_J_Org_Chem-18-549-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/5844a29cdf29/Beilstein_J_Org_Chem-18-549-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/39239b184560/Beilstein_J_Org_Chem-18-549-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/25582fc02dd3/Beilstein_J_Org_Chem-18-549-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3523/9127252/e9c97ca3a2d2/Beilstein_J_Org_Chem-18-549-g009.jpg

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