Fatty acid analogs and prodrugs

Details Fatty acid analogs and prodrugs Fatty acid analogs and prodrugs

1996-11-04

1997-09-23

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

554 35, 560 41, 560129, 560155, 562455, 562512, 564 78, 564201, 564202, C07C 54124, C07C 6902, C07C22906, C07C23331

Patent

active

056706502

ABSTRACT:
Novel derivatives of fatty acid analogs that have from one to three heteroatoms in the fatty acid moiety which can be oxygen, sulfur or nitrogen, are disclosed in which the carboxy-terminus has been modified to form various amides, esters, ketones, alcohols, alcohol esters and nitriles thereof.
These compounds are useful as substrates for N-myristoyltransferase (NMT) and/or its acyl coenzyme, and as anti-viral and anti-fungal agents or pro-drugs of such agents. Illustrative of the disclosed compounds are fatty acid amino acid analogs of the structure ##STR1## in which X is the ethyl or t-butyl ester of an amino acid such as Gly, L-Ala, L-Ile, L-Phe, L-Trp, L-Thr or an amide such as NHCH.sub.2 C.sub.6 H.sub.5 or NH(CH.sub.2).sub.2 C.sub.6 H.sub.5.

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Bryant et al., Proc. Natl. Acad. Sci. USA 86, 8655-8659 (1989).
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Doering et al., Science 252, 1851-1854 (1991).
Bryant et al., Proc. Natl. Acad. Sci. USA 88, 2055-2059 (1991).
Devadas et al., J. Biol. Chem. 267, 7224-7239 (1992).

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