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Identification of a novel oxazolidinone (U-100480) with potent antimycobacterial activity.

Abstract：

:During the course of our investigations in the oxazolidinone antibacterial agent area, we have identified a subclass with especially potent in vitro activity against mycobacteria. The salient structural feature of these oxazolidinone analogues, 6 (U-100480), 7 (U-101603), and 8 (U-101244), is their appended thiomorpholine moiety. The rational design, synthesis, and evaluation of the in vitro antimycobacterial activity of these analogues is described. Potent activity against a screening strain of Mycobacterium tuberculosis was demonstrated by 6 and 7 (minimum inhibitory concentrations or MIC's < or = 0.125 micrograms/mL). Oxazolidinones 6 and 8 exhibit MIC90 values of 0.50 micrograms/mL or less against a panel of organisms consisting of five drug-sensitive and five multidrug-resistant strains of M. tuberculosis, with 6 being the most active congener. Potent in vitro activity against other mycobacterial species was also demonstrated by 6. For example, 6 exhibited excellent in vitro activity against multiple clinical isolates of Mycobacterium avium complex (MIC's = 0.5-4 micrograms/mL). Orally administered 6 displays in vivo efficacy against M. tuberculosis and M. avium similar to that of clinical comparators isoniazid and azithromycin, respectively. Consideration of these factors, along with a favorable pharmaco-kinetic and chronic toxicity profile in rats, suggests that 6 (U-100480) is a promising antimycobacterial agent.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Barbachyn MR,Hutchinson DK,Brickner SJ,Cynamon MH,Kilburn JO,Klemens SP,Glickman SE,Grega KC,Hendges SK,Toops DS,Ford CW,Zurenko GE

doi

10.1021/jm950956y

subject

Has Abstract

pub_date

1996-02-02 00:00:00

pages

680-5

issue

3

eissn

0022-2623

issn

1520-4804

pii

jm950956y

journal_volume

39

pub_type

杂志文章

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