Convenient synthesis and evaluation of enzyme inhibitory activity of several N-Alkyl-, N-Phenylalkyl, and cyclic isourea derivatives of 5a-Carba-α-dl-fucopyranosylamine

Synthetic and Crystallographic Insight into Exploiting sp2 Hybridization in the Development of α‐l‐Fucosidase Inhibitors

“…The 1,5-hydroximolactone 12 was aw eak inhibitor (323 AE 12 mm)o ft he enzyme, which demonstrates the potentiali mportance of the phenylc arbamoyl motif. This correlates with what has been observed for some carbasugar inhibitors of GH29 a-l-fucosidases [9,27] and may indicatef ortuitous hydrophobic bindingi nteractions in or aroundt he active site of the enzyme. [26] Some trends were apparent in the relative activities of the carbamates.…”

“…[1] Reflecting the important roles of this carbohydrate motif, there are specific enzymes, termed a-l-fucosidases( which are part of al arger class of enzymes termedg lycoside hydrolases [2] ), that act to cleave a-l-fucose moieties from glycoconjugates. For example, compounds that mimic the chargeo ft he putativet ransition state such as amines 1 [8] (and N-alkyl analogues [9] )a nd 2 [8] have been shown to be potent inhibitors of a-l-fucosidases (Scheme 1C). [3][4][5] As with other glycoside hydrolases, a-l-fucosidases have been classified into families based upon amino acid sequence homologies, with known a-l-fucosidases falling into GH families GH29 and GH95.…”

“…For example, compounds that mimic the chargeo ft he putativet ransition state such as amines 1 [8] (and N-alkyl analogues [9] )a nd 2 [8] have been shown to be potent inhibitors of a-l-fucosidases (Scheme 1C). For example, compounds that mimic the chargeo ft he putativet ransition state such as amines 1 [8] (and N-alkyl analogues [9] )a nd 2 [8] have been shown to be potent inhibitors of a-l-fucosidases (Scheme 1C).…”

Recent Advances in the Chemistry of Aminocyclitols

“…The more classical nonchelating conditions have been widely used for the selective trans ‐diaxial opening of related cyclitol epoxides with different nucleophiles 21,34,73–75…”

Remodeling of N-Heterocyclic Iminato Ligand Frameworks for the Facile Synthesis of Isoureas from Alcohols and Carbodiimides Promoted by Organoactinide (Th, U) Complexes

“…Isoureas, the isomeric analogues of urea, are being vastly exploited as a component of fertilizers as it is an easily accessible source of nitrogen to stimulate the growth of crops. − Besides agriculture, these compounds are also equally important as anti-inflammatory drugs in the pharma industry, a raw material for the manufacture of plastics, surfactants, chemical fire extinguishers, and, last but not least, biocatalysts. − Apparently, to compensate for the skyrocketing demand, many new synthetic methodologies are being designed to synthesize isoureas using ureas, carbodiimides, chloroformamidines, cyanamides, organic cyanates, or isocyanides, as starting materials. , The straightforward synthesis of isoureas via the addition of an alcohol to a carbodiimide (RNCNR′) has drawn great attention for being atom-efficient and utilizing easily available starting materials. For being less electrophilic, the reactions of carbodiimides with alcohols require either very high thermal energy or Lewis acid catalyst activation.…”