Linked Life Data

2309256

Source:http://linkedlifedata.com/resource/pubmed/id/2309256

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1
pubmed:dateCreated
1990-4-12
pubmed:abstractText
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.
pubmed:keyword
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jan
pubmed:issn
0039-128X
pubmed:author
pubmed:issnType
Print
pubmed:volume
55
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
36-9
pubmed:dateRevised
2006-11-15
pubmed:otherAbstract
PIP: 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).
pubmed:meshHeading
pubmed:year
1990
pubmed:articleTitle
Long-acting contraceptive agents: testosterone esters of unsaturated acids.
pubmed:affiliation
Institute of Organic Natural Products, C.S.I.C., Tenerife, Canary Islands, Spain.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't