Effect of the acyl groups on O → N acyl migration in the water-soluble prodrugs of HIV-1 protease inhibitor
Bioorganic & Medicinal Chemistry Letters, ISSN: 0960-894X, Vol: 13, Issue: 16, Page: 2727-2730
2003
- 30Citations
- 7Captures
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Article Description
To improve the low water-solubility of HIV-1 protease inhibitors KNI-272, -279 and -727, we previously reported the water-soluble prodrugs of these inhibitors based on O → N intramolecular acyl migration reaction. These prodrugs were rapidly converted to the corresponding parent drugs under physiological conditions. To understand the steric and electrostatic effects of O -acyl moiety on the migration rate, we examined several types of prodrug. A remarkably slow migration was observed in the benzoyl-type prodrugs, and Hammett plot of migration rate constants of p -substituted benzoyl-type prodrugs gave a linear free energy relationship.
Bibliographic Details
http://www.sciencedirect.com/science/article/pii/S0960894X03005766; http://dx.doi.org/10.1016/s0960-894x(03)00576-6; http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=0037811300&origin=inward; http://www.ncbi.nlm.nih.gov/pubmed/12873502; http://linkinghub.elsevier.com/retrieve/pii/S0960894X03005766; http://api.elsevier.com/content/article/PII:S0960894X03005766?httpAccept=text/xml; http://api.elsevier.com/content/article/PII:S0960894X03005766?httpAccept=text/plain; https://linkinghub.elsevier.com/retrieve/pii/S0960894X03005766; http://dx.doi.org/10.1016/s0960-894x%2803%2900576-6; https://dx.doi.org/10.1016/s0960-894x%2803%2900576-6
Elsevier BV
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