Synthesis and antiinflammatory activity of 4-amino-2-aryl-5-cyano-6-{3- and 4-(N-phthalimidophenyl)} pyrimidines.
Six new 4-amino-5-cyano-2,6-diarylpyrimidines 5a-h has been synthesized in a facile manner by reacting the appropriate arylamidines 4a-d with bisnitriles 3a-e. Reduction of the nitro group of 5a-e using Pd in ethyl acetate furnished 6a-e in good yields. Reaction of 6a-e individually with phthalic anhydride yielded 7a-e in good to excellent yields. The newly synthesized heterocycles were characterized by IR, (1)H-NMR and mass spectral data. Compounds 5f-h and 7a-e were also evaluated against inflammation. Pyrimidines 5g, h exhibited better antiinflammatory activity when compared with acetylsalicylic acid (ASA). Phthalimide derivatives 7a-e also presented antiinflammatory activity, and three of them, viz., 7a-c have been found to be twice more active than aspirin. Cytotoxical evaluations of compounds 7a-e using neoplastic cells (NCI-H(292) and Hep-2) presented 41% of growth inhibition of neoplastic cells NCI-H(292).
Falcão
Emerson Peter da S
EP
Departamento de Antibióticos, Universidade Federal de Pernambuco, 50.670-901 Recife, PE, Brazil.
de Melo
Sebastião J
SJ
Srivastava
Rajendra M
RM
Catanho
Maria Tereza Jansen de A
MT
Do Nascimento
Silene Carneiro
SC
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology; D001241:Aspirin / Q000494:pharmacology; D003601:Cytotoxicity Tests, Immunologic; D051379:Mice; D008826:Microbial Sensitivity Tests; D010797:Phthalimides / Q000494:pharmacology; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000494:pharmacology; D013057:Spectrum Analysis; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000894:Anti-Inflammatory Agents, Non-Steroidal; D010797:Phthalimides; D011743:Pyrimidines; D001241:Aspirin