- Aerial oxidation of the glucocorticoid side-chain under pH control
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The outcome of aerial oxidation of the glucocortico-steroid side-chain (as exemplified by dexamethasone) has been shown to be subject to strict pH control. At pH 7.4 the glyoxal is the only product; at pH values of 8 and 9.2 the etioacid is formed, and at
- Edmonds, John S.,Morita, Masatoshi,Turner, Peter,Skelton, Brian W.,White, Allan H.
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- Corticosteroid decomposition via a mixed anhydride
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Oxidation of dexamethasone in an aqueous suspension by air during prolonged storage produces the 17α-formyloxy-17β-carboxylic acid 4. A pathway to 4 is proposed that involves Baeyer-Villiger-type oxidation of keto aldehyde 1 to mixed anhydride 5, followed by intramolecular formyl transfer. Synthetically, acid 3 was reacted with N,N′-carbonyldiimidazole followed by triethylammonium formate in order to generate the transient anhydride 5 en route to an authentic sample of 4.
- Conrow, Raymond E.,Dillow, Glen W.,Bian, Liangqiao,Xue, Liang,Papadopoulou, Olga,Baker, John K.,Scott, Britt S.
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p. 6835 - 6836
(2007/10/03)
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- General method for determination of configuration of steroid-17-yL methyl glycolates at C-20
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Kinetic examination for methoxycarbonylations of the isomeric steroid-17- yl methyl glycolates at C-20 and plots of the amount of each isomer produced by a reaction of their corresponding steroids with cupric acetate in absolute methanol provide a general and facile method for determination of the configuration of the steroid-17-yl methyl glycolates at C-20.
- Suzuki,Tada,Matsuda,Yang,Unno
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p. 1481 - 1483
(2007/10/02)
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- Synthesis of new local anti-inflammatory thiosteroids based on antedrug concept
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The synthesis and the in vitro pharmacological evaluation of a number of topical corticosteroid derivatives designed on the basis of the antedrug concept are reported.Three series of compounds were synthesized in which sulfur-containing amino acids were incorporated to the steroidal structure in the 21 position.Compounds of series I are diesters of cystine with the 21-hydroxyl groups of the corticosteroids, while series II and III contain 21-amino and 21-thio corticosteroid derivatives, respectively.The new compounds were less potent than the parent corticosteroidsin vitro.The 21-yl--S-acetylamino cysteine 13 was the most interesting compound of the series and is now under further evaluation. topical anti-inflammatory steroids / sulfur amino acids / corticosteroid activity
- Milioni, C,Jung, L,Koch, B
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p. 947 - 951
(2007/10/02)
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- Novel pregnanoic acid derivatives
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Pregnanoic acid derivatives of general formula STR1 wherein is a single bond or a double bond; X is hydrogen, fluorine or methyl; Y is hydrogen, fluorine or chlorine; Z is β-hydroxymethylene, β-acyloxymethylene, β-fluoromethylene, β-chloromethylene, carbonyl or methylene; R1 is hydrogen, methyl in the α- or β-position or methylene and R2 is hydrogen, hydroxy or acyloxy, or R1 and R2 collectively are alkylidendioxy and U1 is halogen, halogenated alkyl of 1-5 carbon atoms or halogenated phenyl, are topically effective anti-inflammatory agents.
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