Enantiodivergent strategy for the synthesis of polyhydroxylated pyrrolizidines and evaluation of their inhibitory activities against glycosidases

Minehira, Daisuke; Okada, Takuya; Iwaki, Ren; Kato, Atsushi; Adachi, Isao; Toyooka, Naoki

doi:10.1016/j.tetlet.2014.11.087

Cited by 4 publications

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“…Based on the occurrence in Scilla species of hydroxylated pyrrolizidines bearing extended side chains at C(5), Toyooka's group developed routes to non-natural hyacinthacine analogues with extended C(3) substituents and tested their glycosidase inhibition. 113 The monoacetate (-)-(2S,5R)-207 (Scheme 36) was prepared from N-Boc pyrrole 206 by double carboxylation, two reductive steps, then enzymatic acylation with CAL-B/vinyl acetate. Protecting group and redox manipulation steps were followed by HWE reaction, dihydroxylation, and a second HWE olefination to provide intermediate 208.…”

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Pyrrolizidine alkaloids: occurrence, biology, and chemical synthesis

2017

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confidence: 99%

Pyrrolizidine alkaloids: occurrence, biology, and chemical synthesis

2017

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Pyrrolizidine Alkaloids

Tamariz,

Burgueño-Tapia,

Vázquez

et al. 2018

The Alkaloids: Chemistry and Biology

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Naturally occurring pyrrolizidine alkaloids (PAs) are isolated from plants and other sources. The interest of the scientific community in these compounds owes itself to their high toxicity and biological activity, as well as to the challenge of synthesizing their pyrrolizidine scaffold. This review encompasses a wide range of topics found in the literature from 1995 to date, including the occurrence, biosynthesis, toxicity (hepatotoxicity, genotoxicity, and tumorigenicity), biological activity, and pharmacological properties (glycosidase inhibitory activity) of these secondary metabolites. Particular attention is given to the chemistry of PAs, addressing general strategies for formal and total syntheses via amino-based substrates, pyrroles, and pyrrolidine-based derivatives.

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Discovery of a Potent α-Galactosidase Inhibitor by in Situ Analysis of a Library of Pyrrolizidine–(Thio)urea Hybrid Molecules Generated via Click Chemistry

et al. 2018

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The parallel synthesis of a 26-membered-library of aromatic/aliphatic-(thio)urea-linked pyrrolizidines followed by in situ biological evaluation toward α-galactosidases has been carried out. The combination of the (thio)urea-forming click reaction and the in situ screening is pioneer in the search for glycosidase inhibitors and has allowed the discovery of a potent coffee bean α-galactosidase inhibitor (IC = 0.37 μM, K = 0.12 μM) that has also showed inhibition against human lysosomal α-galactosidase (α-Gal A, IC = 5.3 μM, K = 4.2 μM).

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Enantiodivergent strategy for the synthesis of polyhydroxylated pyrrolizidines and evaluation of their inhibitory activities against glycosidases

Cited by 4 publications

References 18 publications

Pyrrolizidine alkaloids: occurrence, biology, and chemical synthesis

Pyrrolizidine alkaloids: occurrence, biology, and chemical synthesis

Pyrrolizidine Alkaloids

Discovery of a Potent α-Galactosidase Inhibitor by in Situ Analysis of a Library of Pyrrolizidine–(Thio)urea Hybrid Molecules Generated via Click Chemistry

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