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Cyclic sulfamide HIV-1 protease inhibitors, with sidechains spanning from P2/P2′ to P1/P1′
- Source :
- Bioorganic & Medicinal Chemistry. 13:755-764
- Publication Year :
- 2005
- Publisher :
- Elsevier BV, 2005.
-
Abstract
- Previous studies of HIV protease inhibitors have shown that it is possible to elongate the P1/P1' sidechains to reach the S3/S3' binding sites. By analogy, we expected that it would be possible to design inhibitors reaching between the S1/S1' and S2/S2' binding sites. Molecular modeling suggested that this could be achieved with appropriate ortho-substitution of the P2/P2' benzyl groups in our cyclic sulfamide inhibitors. Four different spacer groups were investigated. The compounds were smoothly prepared from tartaric acid in five steps and exhibit low to moderate activity, the most potent inhibitor possessing a Ki value of 0.53 microM.
- Subjects :
- Models, Molecular
Magnetic Resonance Spectroscopy
Molecular model
Stereochemistry
medicine.medical_treatment
Clinical Biochemistry
Pharmaceutical Science
Biochemistry
chemistry.chemical_compound
HIV-1 protease
Drug Discovery
medicine
Protease inhibitor (pharmacology)
Binding site
Molecular Biology
Sulfamide
chemistry.chemical_classification
Protease
biology
Chemistry
Organic Chemistry
HIV Protease Inhibitors
Enzyme
Enzyme inhibitor
HIV-1
biology.protein
Molecular Medicine
Sulfonic Acids
Subjects
Details
- ISSN :
- 09680896
- Volume :
- 13
- Database :
- OpenAIRE
- Journal :
- Bioorganic & Medicinal Chemistry
- Accession number :
- edsair.doi.dedup.....113faafdceffc9b05afc8c9a9351f4ee