الفهرس 
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Abstract
The aim of the present work is to design and synthesize some new nitrogenous naphthoquinone, αlapachone analogues, binary, fused and spiro ring compounds which incorporate heterocyclic moieties of anticipated biological value. Thus, in the light of the aforementioned importance of lawsone compound, the present work is planned to investigate the reactivity of lawsone and its annulated compounds towards several reagents and conditions. Part 1: Chemical reactivity studies This part is subdivided into three sections Section one: Adaptable Access for Naphthoquinone Annulations In this section, we performed Claisen-Schmidt reaction of lawsone 1 with DMF/DMA in DMF gave enamine 2. Thus, the reaction of 2 with phenyl hydrazine, hydrazine hydrate, urea, thiourea, guanidine.HCl and 3-methoxyaniline. via transamination reaction in DMF followed by in situ cycloaddition afforded 3-7. In addition, fused polycyclic N-containing ring systems 8-11 were synthesized from the reaction of 2 with different binucleophilic reacgent via Michael addition followed by intramolecular condensation. Furthermore, reaction of 2 with piperazine or diselanyl raegent afforded compounds 12-13. Section two: Concise Synthesis of New α-Lapachone Analogues This section aims to synthesize annulated α-lapachone systems during cyclo-condensation reaction of 1 with diethyl oxalate afforded compound 14. Once more, the reaction of 1 with α,β-unsaturated ketones namely; chalcone, 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one, 1,5-diphenylpenta-1,4-dien-3-one ethyl-2-cyano-5-phenylpenta-2,4-dienoate or ethyl-2-cyano-3-(4-nitrophenyl)acrylate yielded 15-19, respectively. Thus, reaction of 1 with 2-(benzylidene)quinuclidin-3-one, 4-(4-methoxybenzylidene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, 3-benzylid-ene indolin-2-one or 2,5-di(benzylidene)cyclopentan-1-one to yield compounds 20-23, respectively. Also, multicomponent reaction of 1 with resorcinol and 4-methoxybenzaldehyde afforded benzo[b]xanthene-6,11(12H)-dione derivative 24. Section three: Synthesis of Some Novel Spiro Lawsone-Ring Skeletons This section focuses on the synthesis of spiro lawsone ring skeletons by Claisen-Schmidt condensation of 1 with 4-methoxybenzaldehyde yielded α,β-unsatureated ketones 25. Furthermore, Multi-component reaction of 25 with istain and benzyl amine gave Dispiro compound 26. Thus, reaction of 25 with H2O2 then guanidine.HCl afforded spiro 27. However, treatment of 25 with guanidine.HCl then H2O2 yielded benzo[g]quinazoline-5,10-dione derivative 28. Finally, treatment of 1 with isothiocyanatobenzene afforded compound 29. Part II: Geometrical Calculation and Molecular Modeling This part includes geometry optimization of the molecular structures for compounds 1, 2, 5, 12, 13, 17, 18, 23, 25, 26, 28 and 29 using the DFT method via cluster calculations using DMOL3 program in order to investigate the stability of their tautomer whether syn- or anti- relative to each other. Part III: Biological activity This part includes three types of biological screening bioassay are Antioxidant activity for ABTS, Antitumor activity against EAC in vitro and in-vitro cytotoxic activities against cancer cell lines as HePG-2 and MCF-7 was implemented.