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3. ChemInform Abstract: Synthesis and Structure‐Activity Relationships of a Series of Penicillin‐Derived HIV Proteinase Inhibitors Containing a Stereochemically Unique Peptide Isostere.

Author

HOLMES, D. S., primary, BETHELL, R. C., additional, CAMMACK, N., additional, CLEMENS, I. R., additional, KICHIN, J., additional, MCMEEKIN, P., additional, MO, C. L., additional, ORR, D. C., additional, PATEL, B., additional, PATERNOSTER, I. L., additional, and STORER, R., additional

Published
1995
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5. ChemInform Abstract: Synthesis from (‐)‐Aristeromcycin and X‐Ray Structure of (‐)‐Carbovir.

Author

EXALL, A. M., primary, JONES, M. F., additional, MO, C.‐L., additional, MYERS, P. L., additional, PATERNOSTER, I. L., additional, SINGH, H., additional, STORER, R., additional, WEINGARTEN, G. G., additional, WILLIAMSON, C., additional, BRODIE, A. C., additional, COOK, J., additional, LAKE, D. E., additional, MEERHOLZ, C. A., additional, TURNBULL, P. J., additional, and HIGHCOCK, R. M., additional

Published
1992
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10. Synthesis and structure-activity relationships of a series of penicillin-derived HIV proteinase inhibitors containing a stereochemically unique peptide isostere.

Author

Holmes DS, Bethell RC, Cammack N, Clemens IR, Kitchin J, McMeekin P, Mo CL, Orr DC, Patel B, and Paternoster IL

Subjects
Amino Acid Sequence, Antiviral Agents chemistry, Antiviral Agents pharmacology, Binding Sites, HIV Protease Inhibitors chemistry, HIV Protease Inhibitors pharmacology, Models, Molecular, Molecular Sequence Data, Penicillins chemistry, Penicillins pharmacology, Stereoisomerism, Structure-Activity Relationship, Thiazoles chemistry, Thiazoles pharmacology, Antiviral Agents chemical synthesis, HIV Protease Inhibitors chemical synthesis, Penicillins chemical synthesis, Thiazoles chemical synthesis
Abstract

A series of HIV-1 proteinase inhibitors was synthesized based upon a single penicillin derived thiazolidine moiety. Reaction of the C-4 carboxyl group with (R)-phenylalaninol gave amide 10 which was a moderately potent inhibitor of HIV-1 proteinase (IC50 = 0.15 microM). Further modifications based on molecular modeling studies led to compound 48 which contained a stereochemically unique statine-based isostere. This was a potent competitive inhibitor (Ki = 0.25 nM) with antiviral activity against HIV-1 in vitro (5 microM). Neither modification to the benzyl group in an attempt to improve interaction with the S2' pocket, nor introduction of a hydrogen bond donating group to interact with residue Gly48' resulted in improved inhibitory or antiviral activity.

Published
1993
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