Next Article in Journal
Synthesis and Catalytic Activity of Two New Cyclic Tetraaza Ligands
Previous Article in Journal
Synthesis of Some Transition Metal Complexes of a Novel Schiff Base Ligand Derived from 2,2'-bis(p-Methoxyphenylamine) and Salicylicaldehyde
Molecules 2003, 8(5), 444-452; doi:10.3390/80500444

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
View Full-Text   |   Download PDF [285 KB, uploaded 18 June 2014]   |   Browse Figure


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) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
MDPI and ACS Style

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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here


[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert