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Bioorg Med Chem Lett. 2013 Sep 15;23(18):5213-6. doi: 10.1016/j.bmcl.2013.06.091. Epub 2013 Jul 8.

Optimization of diarylazines as anti-HIV agents with dramatically enhanced solubility.

Author information

1
Department of Chemistry, Yale University, New Haven, CT 06520-8107, USA.

Abstract

Non-nucleoside inhibitors of HIV-1 reverse transcriptase are reported that have ca. 100-fold greater solubility than the structurally related drugs etravirine and rilpivirine, while retaining high anti-viral activity. The solubility enhancements come from strategic placement of a morpholinylalkoxy substituent in the entrance channel of the NNRTI binding site. Compound 4d shows low-nanomolar activity similar to etravirine towards wild-type HIV-1 and key viral variants.

KEYWORDS:

Anti-HIV agent; Drug solubility; NNRTI

PMID:
23937980
PMCID:
PMC3759246
DOI:
10.1016/j.bmcl.2013.06.091
[Indexed for MEDLINE]
Free PMC Article

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