ChemInform Abstract: PREPARATION AND ISOMERIZATION OF 3S‐BENZYLPENICILLOAMIDES

Herak, J. J.; Kovačević, Miće; Gaspert, B.

doi:10.1002/chin.197914099

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1993

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“…1.52 (s, 3H), 3.55 (m, 3H), 4.1-4.4 (m, 2H), 4.50 (t, 1H,=7=7 Hz), 4.90 (d, 1H, «7=7 Hz), 7.1-7.4 (m, 10H), 8.38 (d, 1H, «7 = 8 Hz), 8.58 (t, 1H, J = 4 Hz); IR (Nujol) 3300,1718,1643 cm-1; [apD +69.4°(c 0.89, MeOH), (lit. 16 [ ]22 +88°(c 1, MeOH)). Anal.…”

Section: Methodsmentioning

confidence: 99%

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

Holmes¹,

Bethell²,

Cammack³

et al. 1993

J. Med. Chem.

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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.

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Section: Methodsmentioning

confidence: 99%