Analogs of trehalose are reported that were designed to interfere with mycolylation pathways in the mycobacterial cell wall. Several derivatives of 6,6′-dideoxytrehalose, including N, N′-dialkylamino and 6,6′-bis(sulfonamido) analogs, were prepared and evaluated for antimycobacterial activity against Mycobacterium tuberculosis H37Ra and a panel of clinical isolates of Mycobacterium avium. 6,6′-Diaminotrehalose and its diazido precursor were both inactive, but significant activity apparently related to aliphatic chain length was found among the sulfonamides, N-alkylamines, and one of the amidines. © 2002 Elsevier Science Ltd. All rights reserved.
