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synthesis of new pyrazole and pyrimidine steroidal derivatives新吡唑并嘧啶的合成甾族的衍生品
Molecules 2003, 8, 444-452
molecules
ISSN 1420-3049
Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives
Daniel G. Rivera 1, Klaus Peseke 2,*, Isabel Jomarrón 1, Alina Montero 3, Reinaldo Molina 3 and
1
Francisco Coll
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 the correspondence should be addressed; Fax +49-381-498-6410, E-mail:
klaus.peseke@chemie.uni-rostock.de; http://www.fb-chemie.uni-rostock.de/organik/peseke/index.html
Received: 16 April 2003; in revised form 8 May 2003 / Accepted: 9 May 2003 / Published: 31 May
2003
__________________________________________________________________________________
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’:16,1
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