New 9beta-halogenated Prostaglandine Analogues with an Ester Group at C-6 of the alfa-side Chain

Tanase, Constantin I.; Cocu, Florea G.; Draghici, Constantin; Caproiu, Miron Teodor; Maganu, Maria

Constantin I. Tanase, Florea G. Cocu, Constantin Draghici, Miron Teodor Caproiu, Maria Maganu

New 9beta-halogenated Prostaglandine Analogues with an Ester Group at C-6 of the alfa-side Chain

Abstract:

delta-Lactone prostaglandin intermediates with omega-side chain built were opened with diols in acid catalysis (TsOH) reaction to 9beta-halogeno-15-keto-prostaglandin compounds. As diols, HO(CH2)nOH, with n = 2 to 6 and also 2-butyne-1,4-diol were used. These compounds have an ester group in the position 6 of prostaglandin alfa-side chain and an alcohol group instead of C-1 carboxyl group spaced by two to 6 methylene group from the oxygen of the ester group. The reduction of enone group of the new 9beta-halogeno-prostaglandin analogues with diisobornyloxyaluminium isopropoxide at -70°C was not selective, and the allylic alcohols were obtained pure as oils. Even the reduction of the starting delta-lactone prostaglandin intermediates was not selective. The allylic delta-lactone intermediates were also opened with 1,4-butane-diol and the allylic alcohols had the same structure as those obtained by reduction of 9beta-halogeno-15-keto-prostaglandin compounds. The new prostaglandin analogues were characterized by elemental analysis, optical rotation for optically active compounds, IR, 1H- 13C- and 2D-NMR.

Keywords:
9beta-halogeno-15-keto-prostaglandin analogues; 9beta-halogeno-15-hydroxy-prostaglandin analogues; delta-lactone halogeno-prostaglandin intermediates; X-ray-crystallography; diols; enone reduction; NMR-analysis

Issue: 2016, Volume 67, Issue 3

Pages:

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