Adel Abou El-Khair

Synthesis of condensed heteroaromatics: novel synthesis of aminoquinolizinone derivatives as anti-HIV agents

Abstract New routes for the synthesis of aminoquinolizinone derivatives with interesting biological activities are reported. Reactions enaminones 2 and 9 with malononitrile affords aminoquinolizinone derivatives 7a and 7b. Fusion of acetylcyclohexanone (1) with DMF DMA and ethyl cyanoacetate affords only product 11. Treatment of the latter product with malononitrile affords the aminoquinolizinone derivative 15. Reaction of chalcone 17 with malononitrile furnished the product 22. Condensation of (1) with arylidenemalononitrile 23a,b affords compounds 28a,b, respectively. The structure of the newly synthesized compounds was elucidated by elemental analyses and 1H NMR spectra and in some cases by 13C NMR investigation.

New route for synthesis, spectroscopy, and X-ray studies of 2-[aryl-(6′-hydroxy-4′,4′-dimethyl-2′-oxocyclohex-6′-enyl)methyl]-3-hydroxy-5,5-dimethylcyclohex-2-enone and 1,8-dioxo-octahydroxanthenes and antitumor evaluation

Treatment of 1-(benzothiazol-2-yl-thio)-acetonitrile 1 with 5,5-dimethyl-1,3-cyclohexanedione-(dimedone) 2 and aromatic aldehyde 3a, b in refluxing ethanol containing a catalytic amount of piperidine lead to bisdimedone derivatives 5a and b in short periods of times with excellent yields and not 4H-chromen-5(6H)-one derivatives 8. The compound 5a was then cyclized to 1,8-dioxo-octahydroxanthene derivative 6. The structures of the synthesized compounds were elucidated by elemental analysis 1H NMR and 13C NMR spectra, COSY, HSQC, HMBC, MS, and X-ray crystallographic investigations. The cytotoxicity of the synthesized compounds 5a, b, and 6 were studied and evaluated. Three human tumor and three normal cell lines, namely as breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268), human fibroblast (WI-38), normal prostate epithelial cells, and normal colon mucosal, NCM 460 cells, respectively. The tested compounds were found to exhibit higher inhibitory effects toward the tumor and normal cell lines than the reference drug, doxorubicin.

Diels-Alder in heterocyclic synthesis : a novel synthesis of cycloalkanopyridazinimine, 1,7-alkanothienopyridazines and 1,8-alkanophthalazines: new ring system

Transformation of the newly synthesized alkano[c]pyridazines and 1,7 propanothienopyridazines into 1,8-propanophthalazinones and 1,9-propanothiepinopyridazinones using [4+2] cycloaddition reaction with electron poor olefins and acetylenedicarboxylate derivatives, respectively is described.

2-(3-Arylhydrazono-3-formyl-2-oxopropyl)-1H-isoindole-1,3(2H)-dione in heterocyclic synthesis. Novel derivatives of pyridazin-6(1H)-one, pyridazin-6(1H)-imine, and pyrazolo[5,1-c][1,2,4]triazine incorporating an N-(2-oxoethyl)phthalimide moiety

A novel series of 2-(3-arylhydrazono-3-formyl-2-oxopropyl)-1H-isoindole-1,3-(2H)-diones has been prepared and their utility as building blocks in the synthesis of novel derivatives of pyridazin-6(1H)-ones, pyridazin-6(1H)-imines, and pyrazolo[5,1-c][1,2,4]triazines incorporating a N-(2-oxoethyl)phthalimide moiety is investigated.

Studies with Polyfunctionally Substituted Heteroaromatics: A Novel Synthesis of Substituted 4,8-Diaminoisoquinolines as Potential Antiparasitic Agents

New routes for the synthesis of 4,8-diaminoisoquinolines and pyridine utilizing a 3,4-diaminobut-3-en-2-one (2) as starting material are reported.

Methylheteroaromatic Carbonitriles as Building Blocks for Synthesis of Condensed Heteroaromatics: Novel Syntheses of [1]Benzo[2,3]pyrano[3,4-c]pyridines, Naphtho[2′,1′:5,6]pyrano[3,4-c]pyridines, Pyrido[3,4-c]quinolines and Other New Condensed Pyridines

A variety of condensed pyridines were prepared via condensing alkylheteroaromatic carbonitriles with N,N-dimethylformamide dimethylacetal and subsequent cyclization of the formed products.

Synthesis of novel thieno [2,3,b][1,6 ]naphthyridine and thieno [2',3':2,3]pyrido[4,5-d]pyrimidine derivatives

Derivatives of novel thieno[2,3-b][1,6]naphthyridines and thieno[2′,3′: 2,3]pyrido[4,5-d]pyrimidines containing an attached benzotriazole ring have been synthesised.