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Query: UMLS:C0338671 (Steroids)
 9,479 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

This paper describes the synthesis of esters of levonorgestrel (13 beta-ethyl-17 beta-ethynyl-17 beta-hydroxygon-4-en-3-one) with a variety of unsaturated carboxylic acids for evaluation as potential longacting injectable contraceptive agents. 1-Cyclohexenylacetic acid was prepared by the hydrolysis of 1-cyclohexenylacetonitrile. The synthesis of E-penta-2,4-dienoic acid was achieved by the condensation of acrolein with malonic acid. Reformatsky reaction between crotonaldehyde and ethyl 2-bromopropionate followed by dehydration of the condensation product was used for the synthesis of E,E-2-methylhexa-2,4-dienoic acid. In the preparation of 5-methyl-2-furylacetic acid, 5-methylfurfural was subjected to condensation reaction with rhodanine followed by hydrolysis. The levonorgestrel esters were synthesized by reaction of the appropriate acid chloride with the thallim salt of levonorgestrel, which was obtained by use of thallous ethoxide. The esters prepared were levonorgestrel 1-cyclohexenylacetate; levonorgestrel 1-cyclopentenylacetate; levonorgestrel E-penta-2,4-dienoate; levonorgestrel E,E-2methylhexa-2,4-dienoate; levonorgestrel 5-methyl-2-furylethaoate; levonorgestrel 3-(5'-methyl-2'-furyl)propanoate; levonorgestrel 3-(5'-ethyl-2'-furyl)propanoate; leveonorgestrel 4-(5'-methyl-2'-furyl)butanoate; levonorgestrel E-non-2-en-4-ynoate; 1-cyclohexenylacetic acid; 1-cyclopentenylacetic acid; E-penta-2,4-dienoic acid; E,E-2-methylhexa-2,4-dienoic acid; 5-methyl-2-furylacetic acid; and E-non-2-en-4-ynoic acid.
Steroids 1983 Mar
PMID:Long-acting contraceptive agents: levonorgestrel esters of unsaturated acids. 641 7

E-2,2,3',3'',5,5,5',5''-octadeuteriodiethylstilbestrol (DES-d8) and Z-2,3'3'',4,5,5,5',5''-octadeuterio-3,4-bis(p-hydroxyphenyl)-2-hexene (psi-DES-d8) were synthesized from E-diethylstilbestrol (DES) by hydrogen/deuterium exchange in a mixture of methanol-d and deuterium chloride in deuterium oxide. The structures, isotopic purity, and positions of uptake of deuterium were determined by nuclear magnetic resonance (NMR) and mass spectrometry (MS). Additional confirmation of the positions of deuterium exchange in stilbestrols was obtained from an analysis of the oxidation of dES-d8 to Z,Z-2,3',3'',5,5',5''-hexadeuteriodienestrol (beta-DIES-d6) and of the hydrogen/deuterium exchange reaction of hexestrol (HEX) to 3',3'',5',5''-hexestrol, (HEX-d4). Structural analysis and the determination of isotopic purity of the latter two compounds were also carried out by NMR and MS. The uptake of eight deuterium atoms by DES is postulated to proceed via two different reactions occurring simultaneously: 1. acid catalyzed deuteration of all four phenolic ortho-positions (3',3'',5',5''); 2. acid catalyzed deuteration of the olefin bridge with subsequent formation of deuterated psi-DES (3 or 4). Due to the equilibration between DES, psi-DES, and Z-diethylstilbestrol (cis-DES) in the acidic reaction mixture at 85 degrees C, the deuterated psi-DES is thought to rapidly rearrange to deuterated DES. Repeated deuteration will eventually form DES-d8 fully labeled in the 2,2,5,5 methylene positions.
Steroids 1982 Dec
PMID:Deuterium labeling of diethylstilbestrol and analogues. 718 18