Synthesis of conformationally restricted analogues of the tryptophanyl tRNA synthetase inhibitor indolmycin

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 3067-3070

  Witty, David R ^a   Walker, Graham ^a   Bateson, John H ^a   O'Hanlon, Peter J ^a   Eggleston, Drake S ^a   Haltiwanger, R Curtis ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; INDOLMYCIN; INDOLMYCIN DERIVATIVE; TRYPTOPHAN TRANSFER RNA LIGASE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STAPHYLOCOCCUS AUREUS; STEREOCHEMISTRY;

STAPHYLOCOCCUS AUREUS;

EID: 0029941018     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00471-6     Document Type: Article

References (19)

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14. Over reduction of the intermediate αβ-unsaturated ketone to the saturated alcohol occurs during hydrogenation with the most active palladium catalysts.
15. 2, NMe), 4.10, 4.20 (1H, 2s, OH), 4.61, 4.70, (1H, 2s, CHC=O), 6.65-7.35 (5H, m, Ar-H), 7.65, 7.8 (1H, 2bs, N=CNH), 10.2 (1H, bs, NH indole).
16. Walser, A.; Flynn, T.; Mason, C.; Crowley, H.; Maresca, C; Yaremko, B.; O'Donnell, M. J. Med. Chem. 1991, 34(3), 1209.
17. 2O), 6.68, 6.80 (2H, 2d, Ar-H), 7.12 (1H, t, Ar-H), 7.63 (1H, bs, NH).
18. The coordinates for 2a have been deposited at the Cambridge Crystallographic Data Centre.
19. The authors wish to acknowledge the support of the Analytical Sciences, Microbial Cell Sciences, and Microbial Metabolism and Biochemistry Departments of SmithKline Beecham Pharmaceuticals, Brockham Park.