Reda M. Abdel-Rahman

Synthesis of Heterobicyclic Nitrogen Systems Bearing a 1,2,4-Triazine Moiety as Anticancer Drugs: Part IV

Some new isolated and fused heterobicyclic nitrogen systems such as thiazolidinone, imidazolone, pyrimidinone, quinazolone, as-triazolone, as-triazinones, tetrazino-as-triazines, and the related compounds 3,4-diaminotriazine and sulfa derivatives 2–27 have been synthesized via treatment of 4-amino-6-styryl-3-thioxo-1,2,4-triazin-5(2,4H)ones (1) with cyclic and acyclic oxygen and nitrogen compounds. The structures of the products have been established from their elemental and spectral analyses. Some new compounds exhibited significant anticancer activities, where compounds 11j > 2a > 6 and 11I > 14 > 11k showed a moderate activity toward leukemia, ovarian cancer, and non-small cell lung cancer. The authors are very grateful to Prof. Dr. Johan P. Bader, Chief Antiviral Evaluations Branch and Prof. Dr. V. L. Narayanan, Chief Drug Synthesis, Chemistry Branch National Cancer Institute, Bethesda, Maryland, USA for evalution of the vitro antitumor tests as development program. Thanks also are due to the members of the NCl staff.

Synthesis, chemical reactivity and fungicidal activity of pyrido[1,2-b][1,2,4]triazine derivatives

The synthesis of some new pyrido[1,2-b][1,2,4]triazines (2-12) was achieved by cyclocondensation of 4-aryl-1,6-diamino-2-oxo-1,2-dihydropyridine-3,5-dicarbonitriles (1a, b) with α,β-bifunctional compounds. Pyrido[1,2:2´,3´]triazino[5´,6´-f]triazines (13-14) were also prepared. The behavior of 1a, b toward interactions with indole-2,3-dione and its N-acetyl analogue have been studied under different reaction conditions. The structures of the new products have been deduced from elemental analysis and spectral data (UV, IR, 1H NMR, 13C NMR and mass spectra). The new synthesized compounds were screened for their antifungal activities.

FUSED CYANOPYRIMIDINES: PART II SYNTHESIS AND REACTIONS OF FUSED CYANOPYRIMIDINE DERIVATIVES AS AFFECTING ENZYMATIC AGENTS

Abstract Some new fused heterobicyclic systems, such as thiazolo[3,2-a]-pyrimidin-5-one (3), 2,3-tetrahydrothiazolo[3,2-a]pyrimidin-5-one (5), 2,4-tetrahydrothiazino[3,2-a]pyrimidin-3,6-dione (6), 3-dihydrothiazino[3,2-a]pyrimidin-2,4,6-trione (7), 3-arylidenethiazino[3,2-a]pyrimidin-2,4,6-trione (8) and/or the related nitrogen compounds, such as 2,3-tetrahydroimidazolo[3,2-a]-pyrimidin-5-one (9), 1-aryl-2,3-tetra-hydroimidazolo[3,2-a]pyrimidin-5-one (11), quinazolino[3,2-a]-pyrimidin-6,8-dione (12) and 3-mercapto-1,2,4-triazolo[4,3-a]pyrimidin-5-one (14) have been synthesized by the interaction of 2-mercapto-4-arylidene-5-cyanopyrimidin-6(1H)one (1) with α,β-bifunctional nitrogen, oxygen and/or sulfur compounds. The structures have been characterized by elemental analyses, IR, UV, 1H NMR and mass spectral data. Some newly prepared compounds revealed a moderate effect on the activity of cellobiase produced by Aspergillus nidulans.

CHEMISTRY OF UNCONDENSED 1,2,4-TRIAZINES: PART II-SULFUR CONTAINING 5-OXo-1,2,4-TRIAZIN-3-yl MOIETY AN OVERVIEW

Abstract Studies on the chemical constituents of sulfur containing the 5-oxo-1,2,4-triazin-3-yl moiety are reviewed. The synthesis. unique features of the structures and biological significance of these constituents are discussed.

Synthesis and Molluscicidal Activity of Phosphorus-Containing Heterocyclic Compounds Derived from 5,6-Bis (4-bromophenyl)-3-hydrazino-1,2,4-triazine

Novel N1-(phosphoryl moiety)-N2-(1,2,4-triazin-3-yl)hydrazines 4, 6, 8, 9 and 12, iminophosphorane 3, iminophosphane 5, 1,2,4-triazinyldiazaphospholine 7, 1,2,4,3-triazaphospholinotriazines 2, 10, 11, and 1,2,4-triazino[3,2-c][1,2,4,5] triazaphosphine 13 have been obtained via treatment 5,6-bis(4-bromophenyl)-3-hydrazino-1,2,4-triazine (1) with various polyfunctional phosphorus reagents by stirring at room temperature or refluxing for long time in tetrahydrofuran. Structures of these compounds have been deduced upon the basis of elemental and spectral data. Molluscicidal activity of the prepared compounds against Biomphalaria Alexandrina snails (the intermediate host of Schistosoma mansoni) showed considerable activities.

SYNTHESIS AND BIOLOGICAL EVALUATION OF SOME NEW FUSED QUINAZOLINE DERIVATIVES

We report that biologically active fused quinazolines have been synthesized via treatment of 3-(N-acyl/ aroylamino)quinazolin-4(3H)-ones (2) with various nucleophilic reagents; some of the products showed moderate antibacterial activity.