Synthesis of pregnene and androstane heterocyclic derivatives of potential pharmacological activity

The synthesis of steroidal heterocycles containing the pyrazole, pyrimidine and isoxazole ring attached to pregnene nucleus is reported Progesterone [1] reacted with methoxyphenylthiosemicarbazide [2] to afford the thiosemicarbazoncprogesterone 3, which reacted with either malononitile or ethyl cyanoacetate to afford the condensed products 5a,b. The scope and limitation of compounds 5a,b were studied to form hetemcyclic ring systems. Also, the aminothiophenylandrostene derivatives 14a,b were synthesized and the reactivity of the amino group towards the formation of the biologically active sultam rings was studied.

A new membrane probing steroidal spin label: synthesis and applications.

The applicability of a new steroidal spin label, 3-oxo-androstan-17 beta-yl-(2",2",6",6"-tetramethyl-N-oxyl) piperidyl butan-1',4'-dioate, in studying the phase transition properties of model membrane L-alpha-dipalmitoyl phosphatidyl choline (DPPC) in the presence and absence of drugs has been explored. Its synthesis and characterization has been described herein. Besides, the localization of this spin label in lipid liposomes has been studied using electron spin resonance (ESR), differential scanning calorimetry (DSC) and 1H and 31P NMR spectroscopic techniques. The label has also been used to study the permeability of epinephrine into membrane. The results show that the spin label has a good potential as a spin probe in the study of biomembranes.

Esteroides C-Funcionalizados. III. Participación del grupo 12ß-benzoxy en la reacción de apertura de 9a, 11 a-Epoxiandrostanos / Funcionalized steroids C. III. Participation of the group 12 ß-benzoxy in the opening reaction of 9a, 11 a-epoxyandrostanes

Se describió la síntesis de la 5Ó-androstan-3ß-tetrol-17-onay su acetónico por tratamiento del 9Ó, 11Ó-epoxi-12ß-benzoxiderivado correspondiente con HCIO4 al 70 por ciento. Las estructuras de los productos obtenidos se asignaron empleando RMN-1H y 13C

Esteroides c-funcionalizados: intermedios de sintesis / C-functionalized steroids: synthesis intermediators

Se describe la obtención del 5alfa-androst-9(11)-en-3beta,12beta,12beta-diol-17-ona y su diacetato, intermediarios claves para la síntesis de derivados C-funcionalizados en la serie del androstano. La síntesis se realiza a partir de la delta 9(11)-hecogenina vía reducción del grupo carbonilo, degradación de la cadena lateral hasta la serie del pregnano, formación de la oxima y reordenación de Beckmann de ésta

Esteroides C-funcionalizados: participación del grupo 12 beta-acetoxilo en la reacción de apertura de 9 alfa-11alfa-epoxiandrostanos / C-functionalized steroids: participation of group 12beta-acetoxyl in the reaction of opening of 9alfa-11alfa-epoxyandrostanes

Se describe la síntesis de 5alfa-androst-9alfa-epoxi-3beta, 17beta-dioles 12beta-dioles 12beta-funcionalizados (H,OH,OAc) por reducción (NaBH4) y epoxidación (m-CIPBA) de las 5alfa-androst-9(11(-en-3beta-ol-17-onas correspondientes. Se estudia la reacción de apertura de estos epóxidos con HClO4 70 por ciento en metanol y se corrobora, la importancia del grupo 12beta-OAc en la misma