The Synthesis of Symmetrical and Unsymmetrical P1/P1' Cyclic Ureas As HIV Protease Inhibitors

Overview

Journal Bioorg Med Chem Lett

Specialty Biochemistry

Date 1999 Jan 1

PMID 9871711

Citations 4

Authors

M Patel

R F Kaltenbach 3rd

D A Nugiel

R J McHugh Jr

P K Jadhav

L T Bacheler

B C Cordova

R M Klabe

S Garber

C Reid

S P Seitz

Affiliations

Soon will be listed here.

Abstract

Cyclic urea SD146, a potent HIV protease inhibitor bearing a flat resistance profile, possessed poor solubility and bioavailability, which precluded further development of the compound. In an effort to improve upon the pharmacokinetic profile of the compound, several analogs modified at the P1/P1' residues were prepared and evaluated. Several of those compounds displayed significant improvement of physical properties.

Citing Articles

Urea Derivatives in Modern Drug Discovery and Medicinal Chemistry.

Ghosh A, Brindisi M J Med Chem. 2019; 63(6):2751-2788.

PMID: 31789518 PMC: 7266097. DOI: 10.1021/acs.jmedchem.9b01541.

Identification of novel HIV 1--protease inhibitors: application of ligand and structure based pharmacophore mapping and virtual screening.

Yadav D, Paliwal S, Yadav R, Pal M, Pandey A PLoS One. 2012; 7(11):e48942.

PMID: 23145032 PMC: 3493599. DOI: 10.1371/journal.pone.0048942.

Multiple receptor conformation docking and dock pose clustering as tool for CoMFA and CoMSIA analysis - a case study on HIV-1 protease inhibitors.

Sivan S, Manga V J Mol Model. 2011; 18(2):569-82.

PMID: 21547550 DOI: 10.1007/s00894-011-1048-x.

Catalytic enantioselective hetero-Diels-Alder reactions of an azo compound.

Kawasaki M, Yamamoto H J Am Chem Soc. 2006; 128(51):16482-3.

PMID: 17177380 PMC: 2546566. DOI: 10.1021/ja066726y.