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Molecules 2003, 8(5), 444-452; doi:10.3390/80500444
Article

Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives

1, 2,* , 1, 3, 3 and 1
1 Centro de Investigaciones de Producto Naturales, Facultad de Quimica, Universidad de La Habana, Zapata y G, Vedado, 10400 Habana, Cuba 2 Fachbereich Chemie der Universität Rostock, D-18051 Rostock, Germany 3 Centro Bioactivos Quimicos, Universidad Central de Las Villas, Santa Clara, Cuba
* Author to whom correspondence should be addressed.
Received: 16 April 2003 / Revised: 8 May 2003 / Accepted: 9 May 2003 / Published: 31 May 2003
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Abstract

The synthesis of steroidal heterocycles containing the pyrazole and pyrimidine ring fused to the 16,17-position of the steroid nucleus is reported. Androstenolone acetate (1) reacted with carbon disulfide, iodomethane and sodium hydride to furnish 3β-acetoxy-16-[bis(methylthio)methylene]-5-androst-5-en-17-one (2). The reactions of 2 with hydrazine hydrate and methylhydrazine afforded the 5’-methylthio- pyrazolo[4’,3’:16,17]androst-5-en-3β-ols 3a and 3b, respectively. Treatment of 2 with amidinium, guanidinium, and isothiuronium salts in the presence of sodium methoxide yielded the 6’-methoxy-pyrimido[5’,4’:16,17]androst-5-en-3β-ols (4a-4e).
Keywords: Androstenolone; steroidal heterocycles; push-pull alkenes; pyrazoles; pyrimidines Androstenolone; steroidal heterocycles; push-pull alkenes; pyrazoles; pyrimidines
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Rivera, D.G.; Peseke, K.; Jomarrón, I.; Montero, A.; Molina, R.; Coll, F. Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives. Molecules 2003, 8, 444-452.

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