New approaches for the synthesis of novel heterocyclic compounds derived from cyanomethylene and Ý-diketone compounds and determination of their biological effect /
إتجاهات جديدة لتحضير مركبات جديدة غير متجانسة الحلقة مشتقة من مركبات السيانوميثيلين والبيتا ثنائى الكيتون وتعيين تأثيرها البيولوجى
Ibram Refat Boshra Mikhail ; Supervied Rafat Milad Mohareb , Noha M. H. Elnagdi
- Cairo : Ibram Refat Boshra Mikhail , 2020
- 169 P. : charts ; 25cm
Thesis (M.Sc.) - Cairo University - Faculty of Science - Department of Organic Chemistry
Pyrazoles are an important heterocyclic family due to their wide spectrum of biological properties such as the anti-proliferative activities and inhibition toward tyrosine kinases. In the present work we started with pyrazole derivative (3) produced through the reaction of ethyl benzoylacetate (1) with hydrazine hydrate (2) followed by its heterocyclization to produce fused derivatives. The target compounds were synthesized in steps outlined in Schemes 1-6. The reaction of the pyrazole (3) with elemental sulfur and phenylisothiocyanate (4) gave the derivative (5). The molecular structure of compound (5) was confirmed on the basis of its elemental and spectral data. On the other hand, the reaction of compound (3) with ethyl orthoformate gave the 4-ethoxymethyleno derivative (6). The presence of the ketone and the active methylene moieties in compound (3) enhanced the synthesis of thieno[3,2-c]pyrazol derivatives using Gewalds thiophene synthesis. Next, we moved towards the formation of some heterocyclic compounds starting from compound (3). The anti-proliferative activities of the newly synthesized compounds were evaluated against the six cancer cell lines. It is clear that compounds 8b, 9, 12b, 12d, 14b, 15b, 18d, 18f, 19b and 21d were the most active compounds. Several tests as Melting point, IR spectra, ¹H-NMR spectra, Mass spectra and analytical data (element analysis) have been made on all components