Acta Pharm. 49 (1999) 149-158

Synthesis and anticancer activity in vitro of some new pyrimidines

MOHAMED S. ABD EL-AAL EL-GABY,^*1   SAMI G. ABDEL-HAMIDE,²  MOUSTAFA M. GHORAB, ³ and SAMI M. EL-SAYED⁴

¹Department of Chemistry, Faculty of Science, Al-Azhar University at Assiut, Assiut 71524, Egypt  
²Department of Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt
³Department of Drug Radiation Research, National Center for Radiation Research and Technology (NCRRT), Nasr city, Cairo, Egypt
⁴Biology Department, National Center for Radiation Research and Technology (NCRRT), Cairo, Egypt

Ternary condensation of aromatic aldehydes, ethyl acetoacetate and thiourea furnished tetrahydropyrimidines 1a-c. Cyclic thiourea 1a reacts with some electrophiles such as chloroacetic acid and bromomalononitrile to yield thiazolopyrimidines 2a and 8a, respectively. Also, compound 1c undergoes further reactions with dielectrophiles, namely 2,3-dichloromaleic anhydride; 2,3-dichloro-1,4-naphthoquinone and 2,3-dichloroquinoxaline to furnish novel ring systems furo[3',4':4,5]thiazolo[3,2-a]- pyrimidine (14c), naphtho[2',3':4,5]thiazolo[3,2-a]pyrimidine (15c) and pyrimido[2',1':2,3]thiazolo[4,5-b]quinoxaline (16c), respectively. Preliminary testing for the in vitro anticancer activity of some selected compounds against Ehrlich Ascites Carcinoma (EAC) cells was carried out. Most active compounds are those of trifluoroacetyl derivative 13d and pyranothiazolopyrimidine derivative 5a.

Keywords: pyrimidine derivatives, anticancer activity