PubMed · 14679924
A new antiretroviral was approved July 2--the 19th now approved in the U.S. It is chemically related to 3TC.
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John S James. 2003-07-25. FTC (Emtriva) approved.. https://pubmed.ncbi.nlm.nih.gov/14679924/
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New bi- and tricyclic deoxycytidine derivatives (dChpd, dCmpp, dCtpp, dCppp) were synthesized as analogues of a fluorescent nucleoside, dChpp, previously reported. The carbamoyl group of dChpd and the 5-position of the cytosine ring are bridged via an ethylene linker so that the modified group forms a nonplanar structure with the cytosine ring. The fluorescent study of dChpd indicated that the coplanar structure between the carbamoyl group and the cytosine ring is of importance. N-Methylation of the carbamoyl group (dCmpp) weakened the intensity of the fluorescence of dChpp, and the derivative (dCtpp), which had a thiocarbamoyl group, lost its fluorescent property. Moreover, addition of a pyrrolo-ring (dCppp) to dChpp enhanced the intensity of fluorescence, and an emission light was observed with a marked Stokes shift of 120 nm.
The syntheses of four pyrimidine C-nucleosides are described. These derivatives are designed as mimics of dC and dU, and in that respect, each can form two hydrogen bonds with complementary dG or dA residues. The minor groove O2 carbonyl in each derivative is replaced by a fluorine or a methyl group. The key carbon-carbon bond connecting the heterocycle to the carbohydrate is formed using a Heck-type palladium-mediated coupling reaction.
Room temperature mid-infrared experiments between 600 and 1600 cm(-1) have been performed on crystalline deoxycytidine as a function of pressure up to about 10 GPa. The wavenumbers of most vibrational modes shift to higher values with increasing pressures except for a mode near 840 cm(-1). Assignments for the observed modes are made on the basis of work published in the literature. Several anomalies are noted near 4.7 GPa, suggesting a phase transition. Our results for deoxycytidine are compared to similar measurements on cytidine.