Synthesis of a benzylamidine derived from D-mannose. A potent mannosidase inhibitor

Blériot, Yves; Genre-Grandpierre, Arnaud; Tellier, Charles

doi:10.1016/s0040-4039(00)73182-0

Cited by 35 publications

(16 citation statements)

References 12 publications

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“…Lawesson reagent is normally used for conversion of amide to thioamide. Preparation of an amidine-type mannosidase inhibitor 6 is shown as a representative example [14] (Scheme 3.13). [27].…”

Section: Thioamidementioning

confidence: 99%

“…For example, C 2 -symmetrical chiral bicylic amidine 5 was prepared for studies on molecular recognition and were proven to differentiate analytically between the enantiomers of chiral carboxylic acids [13]. Near the same time, a mannose-based amidine 6 was synthesized as a potential mannosidase inhibitor, but not a chiral auxiliary [14]. Three enantiopure hydroxyl substituted amidines 7 of the DBN-type were synthesized from 5-(phenylsulfonyl)pyrroridine-2-one by an oxazaborolidine-catalysed reductive desymmetrization of meso-imide followed by functionalization through N-acyliminium ion [15] (Figure 3.3 Numerous applications have been found for the uses of imidazole derivatives as ionic liquids and N-heterocyclic carbenes and their use in organic chemistry has been well discussed in books or reviews.…”

Section: Introductionmentioning

confidence: 99%

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Amidines in Organic Synthesis

Ishikawa¹,

Kumamoto²

2009

Superbases for Organic Synthesis

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Section: Thioamidementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Amidines in Organic Synthesis

Ishikawa¹,

Kumamoto²

2009

Superbases for Organic Synthesis

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“…11 Sugar amidines have been investigated as inhibitors of carbohydrate-processing enzymes. [12][13][14][15][16][17][18][19][20][21][22][23] Amidines are strong bases and are usually protonated under physiological conditions.…”

Section: Introductionmentioning

confidence: 99%

Hydrogen Bonding Networks and Solid-State Conversions in Benzamidinium Salts

Kamali

Aljohani

McArdle

et al. 2015

Crystal Growth & Design

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Ten benzamidinium salts of carboxylic acids, amides and sulfonamides have been crystallized from solution. Single-crystal X-ray analyses revealed various hydrogen bonding motifs which are discussed in terms of supramolecular synthons and graph sets. Benzamidinium hydrogen maleate (5a) crystallizes as large needles of up to > 3 cm length. Attempts to influence the crystal habit and size through a change of solvent and the presence of additives yielded a second polymorph (5b). The formation of the benzamidinium salts by mechanochemical reaction was also investigated. Grinding of benzamidine with nicotinic acid, salicylic acid, paminobenzoic acid, cyanuric acid, pimelic acid, saccharin and sulfathiazole with mortar and pestle or using a ball-mill gave compounds identical to those obtained by crystallization from solution. Time-dependent X-ray powder patterns of a stoichiometric benzamidine/cyanuric acid mixture suggested that the mechanochemical salt formation occured via the amorphous state. Ball-milling of benzamidine with sulfamerazine generated amorphous benzamidinium sulfamerazinate that was stable towards crystallization for at least two weeks, when stored at 25 % relative humidity.2

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“…[3][4][5][6] Gluco-and mannoamidines have been reported previously as potent transition state analogs and competitive inhibitors of corresponding glycosidases. [7][8][9][10][11][12] Comparable entities with the galacto-configuration are not described yet. However, the galactoconfiguration is preferable over a gluco-configuration for its intended use as template due to the structural constraints imposed by the axial hydroxyl group at C-4.…”

Section: Introductionmentioning

confidence: 99%