564-35-2Relevant academic research and scientific papers
Structure determination of microbial metabolites by the crystalline sponge method
Inokuma, Yasuhide,Ukegawa, Tomoya,Hoshino, Manabu,Fujita, Makoto
, p. 3910 - 3913 (2016/06/09)
The structures of metabolites produced in microgram quantities by enzymatic reductions with baker's yeast were analyzed using the crystalline sponge method. The X-ray data provided reliable structures for trace metabolites including their relative and absolute stereochemistries that are not fully addressed by conventional NMR and LC-MS analyses. Technically, combining two or more chromatographic purification techniques is essential because, unlike abundant synthetic compounds, extracted metabolites contain many low level UV-silent impurities. The crystalline sponge method coupled with HPLC purification (LC-SCD) would thus be a useful method for metabolic analysis and drug discovery.
A simple two-step method for the conversion of [3H]cortisol to [3H]- 11-ketotestosterone
Lokman, P. Mark,Irwin, Jacob L.,Blackwell, Leonard F.,Davie, Peter S.,Thomas, Mervyn,Young, Graham
, p. 655 - 658 (2007/10/03)
Despite the existence of several protocols, problems appear to persist in the small scale chemical synthesis of radiolabeled 11-ketotestosterone from cortisol. We investigated the possibilities of using the mild oxidant pyridinium dichromate for the oxidative cleavage of the dihydroxyacetone side chain of cortisol and 17β-hydroxysteroid dehydrogenase for the subsequent reduction of the resulting 17-keto group. Our protocol has resulted in consistently high yields of both the intermediate, adrenosterone (70-80%), and the product, 11-ketotestosterone (up to 60%). This, taken together with the convenience and relatively low cost of our method, recommends the protocol for its use for the synthesis of [3H]-11-ketotestosterone for endocrine studies.
Synthesis of 11-substituted androstenediones and testosterones as human decidual cell growth inhibitors
Zhao, Qinjian,Li, Zhensu
, p. 190 - 195 (2007/10/02)
11α-Hydroxytestosterone (1a), 11β-hydroxytestosterone (1b), 11α- methoxytestosterone (1c), 11β-methoxytestosterone (1d), 11-ketotestosterone (1e), and Δ(9(11))-testosterone (1f) were synthesized from hydrocortisone (4b) or 11-epi-hydrocortisone (4a). The six target compounds, together with 11α-methoxyandrostenedione (2c), 11β-methoxyandrostenedione, (2d) and their lead compound, testosterone (1), were found to effectively inhibit the growth and differentiation of human decidual cells in culture. There is no observable binding of these compounds to estrogen receptor of rabbit uterus. The introduction of a polar group (e.g., hydroxyl and carbonyl) to C-11 of androstenes decreases both the relative binding affinities to progesterone receptor and the inhibitory effects on human decidual cell growth, while the methylation of 11-hydroxyl group minimizes these effects. The similar effects of a polar group at C-11 of testosterone (1) on the inhibitory effects on human decidual cell growth and the relative binding affinities to progesterone receptor of rabbit uterus may suggest that one of the mechanisms of human decidual cell growth inhibition by these compounds is the anti- progestational activity of these androgens.
INTRAMOLECULAR DIELS-ALDER REACTION WITH FURAN-DIENE. TOTAL SYNTHESIS OF (+/-)-11-KETOTESTOSTERONE AND (+/-)-ADRENOSTERONE.
Royen, Luc A. Van,Mijngheer, Roelant,Clercq, Pierre J. De
, p. 4667 - 4680 (2007/10/02)
A novel D BCD ABCD route to 11-keto steroids is reported involving a high yield stereoselective intramolecular Diels-Alder reaction of furan-diene 12 in water as a key-step.The dienophilic side chain is readily introduced starting from 8 via a sequence involving alkylation with ethyl (E)-3-ethoxy-4-iodo-2-butenoate, reduction and acid hydrolysis.The reduced adduct 14 is further converted into (+/-)-adrenosterone (6) via 24, the dienediolate equivalent of which is a known intermediate in corticosteroid synthesis.
INTRAMOLECULAR DIELS-ALDER REACTION WITH FURAN DIENE. A NEW SYNTHESIS OF 11-KETO STEROIDS
Royen, Luc A. Van,Mijngheer, Roelant,Clercq, Pierre J. De
, p. 3145 - 3148 (2007/10/02)
A novel D BCD ABCD route to 11-keto steroids is reported involving a high yield stereoselective intramolecular Diels-Alder reaction of furan-diene 5a in water as a key-step.The dienophilic side chain is readily introduced starting from 2 via a sequence involving alkylation with ethyl 4-iodo-3-ethoxycrotonate, reduction and acid hydrolysis.The reduced adduct 8a, obtained in 24 percent overall yield from 2-methyl-1,3-cyclopentanedione, is converted into (+/-)-adrenosterone (16) via base-opening to 9 and further transformation to 13, the dienediolate equivalent of which is a known intermediate in corticosteroid synthesis.
4-(Dimethylamino)pyridinium Chlorochromate, a New Selective Reagent for the Oxidation of Allylic and Benzylic Alcohols
Guziec, Frank S.,Luzzio, Frederick A.
, p. 1787 - 1789 (2007/10/02)
4-(Dimethylamino)pyridinium chlorochromate (3) is a mild selective reagent for the oxidation of complex allylic and benzylic alcohols to the corresponding carbonyl compounds.
