Influence of a Cα-Substitution on the S-Pivaloyl-2-Thioethyl Chain on the Anti-HIV Activity and Stability of the Resulting Zidovudine Mononucleoside Phosphotriester | Zendy

Suzanne Peyrottes | Zendy; Christian Périgaud | Zendy; A.M. Aubertin | Zendy; Gilles Gosselin | Zendy; J-L. Imbach | Zendy

Open Access

Influence of a Cα-Substitution on the S-Pivaloyl-2-Thioethyl Chain on the Anti-HIV Activity and Stability of the Resulting Zidovudine Mononucleoside Phosphotriester

Author(s) -

Suzanne Peyrottes,

Christian Périgaud,

A.M. Aubertin,

Gilles Gosselin,

J-L. Imbach

Publication year - 2001

Publication title -

antiviral chemistry and chemotherapy

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.919

H-Index - 51

eISSN - 2040-2066

pISSN - 0956-3202

DOI - 10.1177/095632020101200403

Subject(s) - zidovudine , substituent , human immunodeficiency virus (hiv) , pharmacology , prodrug , chemistry , stereochemistry , in vitro , biology , biochemistry , virology , viral disease

We report the synthesis, in vitro anti-HIV-1 activity and stability study of a mononucleoside phosphotriester derivative of 3′-azido-2′,3′-dideoxythymidine (AZT) bearing a new biolabile phosphate-protection, namely S-pivaloyl-2-thioisopropyl ( tBuSATP). This transient protection was characterized by the presence of a methyl substituent at the Cα-position of the previously described S-pivaloyl-2-thioethyl ( tBuSATE) group. Results demonstrated that the new phosphotriester entity was able to deliver selectively the corresponding 5′-mononucleotide within the infected cells. The introduction of a methyl group at the Cα-position of the tBuSATE chain decreased the rate of this delivery.

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