Selective glycosidase inhibitors: A patent review (2012–present)

Wadood, Abdul; Ghufran, Mehreen; Khan, Ajmal; Azam, Syed Sikander; Jelani, Musharraf; Uddin, Reaz

doi:10.1016/j.ijbiomac.2017.12.148

Cited by 40 publications

(32 citation statements)

References 45 publications

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“…57 Among more than 200 naturally occurring iminosugars, deoxynojirimycin, swainsonine and castanospermine have commonly been used as lead compounds in drug development processes. [58][59][60] The enzyme trehalase, in particular, catalyses the hydrolysis of disaccharide trehalose (Fig. 1), a non-reducing disaccharide formed by two molecules of D-glucose linked by an , -1,1-glycosidic bond and which is very important for insects, bacteria, fungi and nematodes as a source of energy (glucose) for their vital functions and in dealing with abiotic stresses.…”

Section: Iminosugarsmentioning

confidence: 99%

“…Because enzyme‐catalysed carbohydrate hydrolysis is widespread biologically, glycosidase inhibitors have many potential applications as agrochemicals and therapeutic agents . Among more than 200 naturally occurring iminosugars, deoxynojirimycin, swainsonine and castanospermine have commonly been used as lead compounds in drug development processes …”

Section: Introductionmentioning

confidence: 99%

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From synthetic control to natural products: a focus on N‐heterocycles

Prandi

Occhiato

2019

Pest Management Science

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Natural products containing a N‐heterocycle motif are widespread in nature and medicinal plants, in particular, have proved to be a source of almost unlimited N‐derived structures with high molecular diversity. Because of their intrinsic potential for use in both biomedical and agricultural applications, there is a general need for new compounds and for the synthesis of ‘natural‐inspired’ analogues. Importantly, transition of a natural product from discovery to a ‘market lead’ is associated with an increasingly challenging demand for more of the compound, which cannot be met by isolation from natural plant sources, often due to low extraction yields and uneven availability of the plant source itself. Synthesis remains the most reliable approach to provide valuable products for the market. In this review, a comprehensive overview of our contribution to synthetic access to N‐derived natural products is given. Major strengths of the proposed methodologies are discussed critically. © 2019 Society of Chemical Industry

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Section: Iminosugarsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

From synthetic control to natural products: a focus on N‐heterocycles

Prandi

Occhiato

2019

Pest Management Science

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“…In recent decades, interest on the synthesis of glycosidase inhibitors has increased, mainly because these enzymes play a central role in many chronic diseases and biological processes [ 31 ]. Most of the glycosidase inhibitors mimic the structures of mono- or disaccharides and thiosugars have been recognized as one of the most popular classes of such inhibitors, with significant therapeutic potential [ 32 ]. Some of them also exhibit anti-diabetic activity [ 33 ] and some others are used in chemotherapy [ 34 ].…”

Section: Thiosaccharidesmentioning

confidence: 99%

Transient Sulfenic Acids in the Synthesis of Biologically Relevant Products

et al. 2018

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Sulfenic acids as small molecules are too unstable to be isolated and their transient nature offers the possibility to involve them in concerted processes that lead to the obtainment of functional groups such as sulfoxides, sulfones, and disulfides. All these functions are present in a number of natural and synthetic drugs and can represent structural motives inducing biologically relevant properties. In this small review the generation and reactions of sulfenic acid bearing naturally occurring residues are described. Carbohydrate and aminoacid-derived sulfenic acids have been used in concerted addition with triple bonds to obtain alliin derivatives and thiosugars in enantiomerically pure form. Glycoconjugates with sulfinyl, sulfonyl, and disulfane functional groups and pyridine-derived disulfides have been obtained from bis- and tris-sulfinyl precursors of sulfenic acids. Small families of such compounds have been subjected to preliminary biological tests. Starting from the evidence that the control of molecular architecture and the presence of suitable functional groups can play a significant role on the exhibition of biological properties, apoptotic effects on malignant cells by glycoconjugates and inhibitory activity against the important human pathogen S. aureus by pyrimidine-derived disulfides have been found.

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“…In the recent decades the interest on the synthesis of glycosidase inhibitors has increased, mainly because these enzymes play a central role in many chronic diseases and biological processes [28]. Most of the glycosidase inhibitors mimic the structures of mono-or disaccharides and thiosugars have been recognized as one of the most popular class of such inhibitors, with significant therapeutic potential [29]. Some of them also exhibit anti-diabetic activity [30] and some others are used in chemotherapy [31].…”

Section: Thiosaccharidesmentioning

confidence: 99%

Transient Sulfenic Acids in the Synthesis of Biologically Relevant Products

Barattucci

Aversa

Mancuso

et al. 2018

Preprint

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Sulfenic acids as small molecules are too unstable to be isolated and their transient nature offers the possibility to involve them in concerted processes that lead to the obtainment of functional groups such as sulfoxides, sulfones and disulfides. All these functions are present in a number of natural and synthetic drugs and can represent structural motives inducing biological relevant properties. In this small review the generation and reactions of sulfenic acid bearing naturally occurring residues are described. Carbohydrate and aminoacid-derived sulfenic acids have been used in concerted addition to triple bonds to obtain alliin derivatives and thiosugars in enantiomerically pure form. Glycoconjugates with sulfinyl, sulfonyl and disulfane functional groups and pyridine-derived disulfides have been obtained from bis and tris-sulfinyl precursors of sulfenic acids. Small families of such compounds have been subjected to preliminary biological tests. Starting from the evidence that the control of molecular architecture and the presence of suitable functional groups can play a significant role on the exhibition of biological properties, apoptotic effects on malignant cells by glycoconjugates and inhibitory activity against the important human pathogen S. aureus by pyrimidine-derived disulfides have been found.

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Selective glycosidase inhibitors: A patent review (2012–present)

Cited by 40 publications

References 45 publications

From synthetic control to natural products: a focus on N‐heterocycles

From synthetic control to natural products: a focus on N‐heterocycles

Transient Sulfenic Acids in the Synthesis of Biologically Relevant Products

Transient Sulfenic Acids in the Synthesis of Biologically Relevant Products

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