Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives
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-andros...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2003-05-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/8/5/444/ |
| _version_ | 1811235555884662784 |
|---|---|
| author | Francisco Coll Reinaldo Molina Alina Montero Isabel Jomarrón Klaus Peseke Daniel G. Rivera |
| author_facet | Francisco Coll Reinaldo Molina Alina Montero Isabel Jomarrón Klaus Peseke Daniel G. Rivera |
| author_sort | Francisco Coll |
| collection | DOAJ |
| description | 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). |
| first_indexed | 2024-04-12T11:54:09Z |
| format | Article |
| id | doaj.art-c6767d21c84a463889aaa3bbe7a42405 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-12T11:54:09Z |
| publishDate | 2003-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-c6767d21c84a463889aaa3bbe7a424052022-12-22T03:34:06ZengMDPI AGMolecules1420-30492003-05-018544445210.3390/80500444Synthesis of New Pyrazole and Pyrimidine Steroidal DerivativesFrancisco CollReinaldo MolinaAlina MonteroIsabel JomarrónKlaus PesekeDaniel G. RiveraThe 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).http://www.mdpi.com/1420-3049/8/5/444/Androstenolonesteroidal heterocyclespush-pull alkenespyrazolespyrimidines |
| spellingShingle | Francisco Coll Reinaldo Molina Alina Montero Isabel Jomarrón Klaus Peseke Daniel G. Rivera Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives Molecules Androstenolone steroidal heterocycles push-pull alkenes pyrazoles pyrimidines |
| title | Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives |
| title_full | Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives |
| title_fullStr | Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives |
| title_full_unstemmed | Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives |
| title_short | Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives |
| title_sort | synthesis of new pyrazole and pyrimidine steroidal derivatives |
| topic | Androstenolone steroidal heterocycles push-pull alkenes pyrazoles pyrimidines |
| url | http://www.mdpi.com/1420-3049/8/5/444/ |
| work_keys_str_mv | AT franciscocoll synthesisofnewpyrazoleandpyrimidinesteroidalderivatives AT reinaldomolina synthesisofnewpyrazoleandpyrimidinesteroidalderivatives AT alinamontero synthesisofnewpyrazoleandpyrimidinesteroidalderivatives AT isabeljomarraƒa3n synthesisofnewpyrazoleandpyrimidinesteroidalderivatives AT klauspeseke synthesisofnewpyrazoleandpyrimidinesteroidalderivatives AT danielgrivera synthesisofnewpyrazoleandpyrimidinesteroidalderivatives |