Mostafa Khouili

Synthesis of naphtho[2,3-b][1,4]dioxin, 2-substituted naphtho[2,3-b][1,4]dioxins and 2,3-disubstituted naphtho[2,3-b][1,4]dioxins

Abstract In view of their potential biological properties, various 2,3-disubstituted naphtho[2,3- b ][1,4]dioxins and 2-substituted furo[3,4- b ]naphtho[2,3- e ][1,4]dioxins have been synthesized. These novel compounds are intermediates to further extended heterocyclic systems.

Synthesis of enantiomerically pure 7-hydroxy-2-substituted-2,3-dihydro-1,4-benzodioxin derivatives

Abstract A rapid and simple procedure for the preparation of the two pure enantiomers of 7-hydroxy-2-substituted-2,3-dihydro-1,4-beniodioxin derivatives is described.

Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels–Alder reactions

Summary Substituted 3,4-dihydro-1,8-naphthyridin-2(1H)-ones have been synthesized with the inverse electron-demand Diels–Alder reaction from 1,2,4-triazines bearing an acylamino group with a terminal alkyne side chain. Alkynes were first subjected to the Sonogashira cross-coupling reaction with aryl halides, the product of which then underwent an intramolecular inverse electron-demand Diels–Alder reaction to yield 5-aryl-3,4-dihydro-1,8-naphthyridin-2(1H)-ones by an efficient synthetic route.

Efficient synthesis and first regioselective C-6 direct arylation of imidazo[2,1- c ][1,2,4]triazine scaffold and their evaluation in H 2 O 2 -induced oxidative stress

Oxidative stress and apoptosis are both associated with various acute and chronic disorders. Thus, the aim of the present study is to synthesize imidazo[2,1-c][1,2,4]triazines derivatives and to evaluate their effects in H2O2-induced oxidative stress in human neuroblastoma cell line (SH-SY5Y cells). The effects of the compounds on cell viability were measured by MTT assay and the changes in stress and apoptosis-related proteins were investigated by PathScan® Stress and Apoptosis Signaling Antibody Array kit and Western Blot technique. In particular, four compounds were found to protect SH-SY5Y cells from H2O2-induced toxicity by increasing Bcl-2/Bax ratio, regulating PI3-K/Akt cascade and inhibiting the ERK pathway.

Domino Aza-Michael-ih-Diels–Alder Reaction to Various 3-Vinyl-1,2,4-triazines: Access to Polysubstituted Tetrahydro-1,6-naphthyridines

A straightforward domino aza-Michael-inverse-electron-demand-hetero-Diels-Alder/retro-Diels-Alder reaction between primary and secondary propargylamine derivatives and 3-vinyl-1,2,4-triazines is developed highlighting not only the uniqueness of this dual-heterocyclic platform but also a novel and unprecedented path to polysubstituted tetrahydro-1,6-naphthyridine scaffolds.

Crystal structure of 2-meth-oxy-1-nitro-naphthalene.

The asymmetric unit of the title compound, C11H9NO3, contains two molecules, A and B. In molecule A, the dihedral angle between the planes of the naphthalene ring system (r.m.s. deviation = 0.003 Å) and the nitro group is 89.9 (2)°, and the C atom of the methoxy group deviates from the naphthyl plane by 0.022 (2) Å. Equivalent data for molecule B are 0.008 Å, 65.9 (2)° and −0.198 (2) Å, respectively. In the crystal, molecules are linked by weak C—H⋯O interactions, forming [100] chains of alternating A and B molecules. Weak aromatic π–π stacking contacts, with a range of centroid–centroid distances from 3.5863 (9) to 3.8048 (9) Å, are also observed.

Synthesis and Electrochemical Evaluation of Some Organic Molecules as an Antioxidant Agents

A series of new benzamides were synthesized. The chemicals structures were confirmed by elemental analyses 1H NMR and 13C studies. The antioxidant activity of the synthesized compounds was evaluated by square wave voltammetry. A new approach, for antioxidant capacity determination was proposed. It is based on the using of the xanthine-xanthine oxidase system coupled with H2O2 electrochemical sensor.

Crystal structure of ethyl 2-(4-chloro­anilino)acetate

The title compound, C10H12ClNO2, is close to planar (r.m.s. deviation for the 14 non-H atoms = 0.053 Å). In the crystal, inversion dimers linked by pairs of N—H⋯Oc (c = carboxyl) hydrogen bonds generate R 2 2(10) loops.

3-Methyl-sulfanyl-5-phenyl-1,2,4-triazine.

In the molecule of the title compound, C10H9N3S, the dihedral angle between the triazine and phenyl rings is 11.77 (7)°. In the crystal, molecules are linked by π–π stacking interactions [centroid–centroid distances = 3.7359 (3) and 3.7944 (4) Å], forming layers parallel to the bc plane.

1H-Benzotriazol-1-yl 4-{(E)-[4-(dimethyl­amino)­phen­yl]diazen­yl}benzoate

The title compound, C21H18N6O2, was obtained as a by-product of a reaction between (E)-4-(4-dimethylaminophenylazo)benzoic acid and 2-amino-4-(2-pyridyl)-6-(6-pyridyl)-1,3,5-triazine, which has a very low solubility, under peptidic coupling conditions, using THF as solvent. The condensation reaction occurred between 1-hydroxybenzotriazole and (E)-4-(4-dimethylaminophenylazo)benzoic acid. The dihedral angle between the benzene rings in the (E)-diphenyldiazene fragment is 10.92 (13)° and that between the benzotriazole mean plane and the central benzene ring is 80.57 (7)°. In the crystal, π–π stacking [centroid–centroid distances = 3.823 (2) and 3.863 (2) Å] of similar fragments generates molecular layers parallel to (0-12). The crystal packing also features weak C—H⋯N hydrogen bonds involving N atoms of the benzotriazole ring.