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Título

Long-acting contraceptive agents: testosterone esters of unsaturated acids

AutorFrancisco, Cosme G. ; Freire, Raimundo ; Gawronski, J.; Hernández, Rosendo ; Kielczewski, M.; Salazar, José A.; Savabi, F.; Shafiee, A.; Strekowski, L.; Suárez, Ernesto
Palabras claveTestosterone esters
Unsaturated acids
Long-acting androgens
Contraceptions
Steroids
Fecha de publicaciónene-1990
EditorElsevier
CitaciónSteroids 55(1): 36-39 (1990)
ResumenThe synthesis of 13 new esters of testosterone is described, with the esterifying acids bearing acetylenic, olefinic, or polyunsaturated functions in the chain, for evaluation as long-acting androgens.
DescripciónPIP: A program of the World Health Organization for developing long-acting esters of testosterone that would exhibit a more constant release rate and maintain testosterone levels in the normal range longer than testosterone enanthate found that these esters had a role in fertility, and gerontology. The synthesis of 13 new esters of testosterone is described, with the esterifying acids bearing acetylenic, olefinic or polyunsaturated functions in the chain, for evaluation as long-acting androgens. The nuclear magnetic resonance (NMR) images were recorded on a spectrometer. The samples were recorded in tubes using CDC13 as solvent. The NMR spectra were recorded with Perkin-Elmer instrument in CDC13, with tetramethylsilane as internal reference. Infrared spectra were measured on the same spectrometer. Mass spectra were also recorded. Thin-layer chromatography was performed on Merck silica gel and the spray reagent was iodine or vanillin. To a solution of testosterone the corresponding acid chloride was added yielding the pure ester after the usual work-up. E-5-methylhexa-2,4-dienoic (IXb), 5- phenylpenta-2-,4-dienoic (Xb), 5-phenyl-4-yn-pent-2-enoic (XIb), and non-4-en-6-ynoic acid (XIIb), were required for the synthesis. Esterification of testosterone with each of the first 12 unsaturated acids was performed by reaction with the corresponding acid chlorides in pyridine. Although the nona-2,3-dienoic acid ethyl ester was easily obtained, this compound could not be hydrolyzed to the acid (XIIIb). Hence, an alternative procedure was tried for the synthesis of the ester XIIIa, by reaction of bromoacetate of testosterone (XIVa) with triphenylphosphine to give the phosphorane (XVa). Reaction of this phosphorane (XVa) with 1-diazoheptan-2-one (XVI) led to the allenic ester (XIIIa).
4 pages, 2 tables, 1 scheme.-- PMID: 2309256 [PubMed].
Versión del editorhttp://dx.doi.org/10.1016/0039-128X(90)90072-J
URIhttp://hdl.handle.net/10261/16431
DOI10.1016/0039-128X(90)90072-J
ISSN0039-128X
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