title: Synthesis and biological evaluation of trehalose analogs as potential inhibitors of mycobacterial cell wall biosynthesis.
abstract: 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 H(37)Ra 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.
authors.affiliation: Southern Research Institute, Drug Discovery Division, 2000 Ninth Avenue South, PO Box 55305, Birmingham, AL 35255-5305, USA.
authors.forename: Jerry D
authors.initials: JD
authors.lastname: Rose
authors.forename: Joseph A
authors.initials: JA
authors.lastname: Maddry
authors.forename: Robert N
authors.initials: RN
authors.lastname: Comber
authors.forename: William J
authors.initials: WJ
authors.lastname: Suling
authors.forename: Larry N
authors.initials: LN
authors.lastname: Wilson
authors.forename: Robert C
authors.initials: RC
authors.lastname: Reynolds
mesh_terms: D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002473:Cell Wall / Q000187:drug effects / Q000378:metabolism*; D003311:Cord Factors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects* / Q000378:metabolism; D013449:Sulfonamides / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000995:Antitubercular Agents; D003311:Cord Factors; D013449:Sulfonamides; C021099:trehalose monomycolate