Neu5Ac2en, mimetics

Acetamido 2,4-dideoxy-p-D-t/ eo-hex-4-enopyranosiduronic acids (113) exhibit structural similarities to Neu5Ac2en (5), a feature that has been exploited in the design of a number of Neu5Ac2en mimetics.100,102 104 The use of the relatively... 

Prompted by the success achieved with simple carbocyclic compounds (e.g., 35), which are potent inhibitors of influenza neuraminidase, several other Neu5Ac2en mimetics of this kind were studied. The isomeric carbocyclic derivatives 37 and 38 are selective for influenza A sialidase, but only 38 showed signihcant inhibition (IC50 = 2 X 10 M) [87]. Other carbocyclic neuraminidase inhibitors include the guanidino substituted cyclohexene 39 [88] and amine derivatives [89] such as 40, which was found to be an inhibitor of influenza B neuraminidase comparable with oseltamivir 35, but was not as potent against influenza A virus [89a]. 

The proposed transition state mimetic of the sialidase hydrolysis reaction, 2-dcoxy-2,3-didehydro- -A--acetylneuraminic acid (Neu5Ac2en, 2), was found to be a... 

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