Synthesis of some F-heterocyclic compounds of potential anticancer activity using 8-fluoro-1- benzosuberone as a synthon

8-fluoro-1-benzosuberone I condensed with aromatic aldehydes in the presence of potassium hydroxide to yield the arylmethylene derrivatives II, which condensed with phenylhydrazinc and thiourea to give the corresponding pyrazol and pyrimidine derivatives III and IV, respectively Compound IV reacted with chloroctic acid, alpha - bromopropionic acid or beta-bromopropionic acid to afford the thiazolopy-rimidine, methylthiazolopyrimia and thiazinopyrimidine derivatives V, VI and VII, respectively. Compound V condensed with aromatic aldehydes to afford the arylmethycine derivativcs VIII. Also, the pyrano and pyridino-fluorobenzosubcronc derivatives IX and X were synthesized. The obtained products were preliminarily tested as anticancer agents and it was found that the products IIa, IIb, IXa, IXb and X showed promising activity against non-small cell lung cancer

Synthesis of some heterocyclic compounds containing naphthalene nucleus for biological evaluation

In this work, 2 mercapto-4-aryl-4H-1,2,3,4,5,6- hexahydrobenzo[h]quianazolines [1] were condensed with alkyl halide to yield the alkyl derivatives II. 3-chloro acetylacetone condensed with compound I in pyridine to yield the thiazoloquinazolines derivatives III. The aminopyrimidine derivatives V were prepared by condensation of aryl methylene-1-tetralone with guanidine hydrochloride. Alpha- tetralone condensed with malononitrile in ethyl alcohol in the presence of beta-alanine to yield 1,2,3,4-tetrahydronaphtho-alpha- yiledene malononitrile VII. Compound VII added one mole of aromatic aldehyde in ethanol in presence of potassium hydroxide to yield 2-imino-10-aryl-8,9-dihyronaphtho[1,2-d] pyrano-3-carhonitrile VIII. Compounds VIII were reacted with ammonium acetate in acetic acid to yield 2-amino-10-aryl-3,9-dihydronaphtho[l,2-d]-3-carbonitrile IX. Compounds IX were prepared directly from VII by the action of appropriate aromatic aldehyde and ammonium acetate in acetic acid

Reactions with [arylmethylene] cycloalkanones 6 Synthesis and deacetylation of 2-acetyl-5-aryl-2,3,6,7,8, 9-hexahdro-5H-thiazolo [23-b] -quinazolin-3-ones

2-[ARYLMETHYLENE] cycIohexanones condensed with thiourea to give 4-aryl-octahydrcquinazoline-2-thiones II,, which reacted with chloroacetic acid to give the title compounds III. Compounds III suffer deacetylation when reacted with aromatic aldehydes, arene-diazonium salts and also when subjected to Mannich reaction to give the following compounds, respectively; 5-aryl-2-[arylmethlene]-2, 3,6,7,8,9, hexahydro-5H - thiazolo [2,3-b] - quinazolin-3-ones [IV], 5-aryl-2-[arylhydrazono]-2,3, 6,7,8,9-hexahydro-5H-thiazolo [2,3-b] -quinazolin-3-ones [V] and 5-aryl-2 - [aminomethyl] - 23,6,7,8,9-hexahydro-5H-thiazolo[2,3-b] quinazolin-3-ones [VI]