Mounir A. I. Salem

Reactions of 5-(p-Anisyl)-2-methyl-7-(p-tolyl)-4H-pyrido[2,3-d][1,3]oxazin-4-one

5-(p-Anisyl)-2-methyl-7-(p-tolyl)-4H-pyrido[2,3-d][1,3]oxazin-4-one (III) was prepared. The reactivity of III towards nucleophilic reagents was investigated. 5-(p-Anisyl)-2-methyl-7-(p-tolyl)-4H-pyrido[2,3-d] pyrimidin-4-one(VI) was synthesised from III by the action of ammonium acetate and zinc chloride. The structure of VI was chemically confirmed by reactions with acetic anhydride, benzoyl chloride, chloroacetic acid, methyl iodide, dimethyl sulphate and ethyl bromoacetate. Compound (VI) reacted with secondary and primary amines under Mannich conditions to afford 5-(p-anisyl)-2-methyl-3-methylene substituted amino-7-(p-tolyl)- 4H-pyrido[2,3-d]pyrimidin-4-ones (XIV) and (XV), respectively. Thiation of VI gave the thione 5-(p-anisyl)-2-methyl-7-(p-tolyl)-4H-pyrido [2,3-d]pyrimidin-4-thione (XIX)

Cationic schiff base amphiphiles and their metal complexes: Surface and biocidal activities against bacteria and fungi

A series of cationic surfactants containing schiff base groups was synthesized by condensation of four fatty amines namely: dodecyl, tetradecyl, hexadecyl and octadecyl amine and 4-diethyl aminobenzaldehyde (1-4), as well as their metal complexes with divalent transition metal ions including Co, Cu and Mn (5-16). The surface activities of the synthesized surfactants were influenced by their chemical structures and the type of the transition metals. The biological activity measurements of the parent cationic schiff bases showed high efficacy against Gram positive and Gram negative bacterial strains and fungi. While on complexation, the biocidal activity was increased remarkably. The biocidal activity of the tested compounds against sulfur reducing bacteria showed promising results in the field of biocide applications.

UTILITY OF 1-(2,4-DIMETHOXYPHENYL)-3-ARYL-PROP-2-ENE-1-ONES AS RING TRANSFORMER IN PREPARING HETEROCYCLIC COMPOUNDS AND THEIR POTENTIAL BIOLOGICAL ACTIVITIES

As an effort to synthesize new heterocyclic compounds, which would be expected to have a pharmacological and biological activities, we report here the reactivity of 1-(2,4-dimethoxyphenyl)-3-aryl-2-propen-1-ones (Ia&b), as Michael acceptors under different conditions, towards different Michael donors namely, pyrazolin-5-one, 2-cyanomethylthiazolidin-4-one, thiobarbituric acid, cyclohexanone, and ethyl cyanoacetate affording the adducts bispyrazolo[5,4-b]-4H-pyranes III, 5-oxopyrazolin-4-yl-propan-1-ones IV, 2-(4-oxothiazolidine-2-yl)-5-oxopentano-carbonitrile XI, 4-oxo-4H-pyranol[2,3-d]tetrahydropyrimidin-2-thiones XVI, cyclohexano[b]-4H-pyran XVII, ethyl-5-oxo-pentanoate XVIII, and 1-aroyl-2-arylcyclopropanes XIX respectively. Fusion of XI with excess ammonium acetate yielded 2-aminopyridine derivative XII and 2-aminotetrahydropyridine derivative XIII. Diazotization of XII by treatment with HNO2 at 0°C produced the diazonium chloride derivative XIV which underwent coupling reaction with phenolic compounds to yield the azo-disperse dyes XV. Alkaline hydrolysis of XVIII afforded the corresponding acid XX which reacted with hydrazines by fusion to yield the diazapinone derivatives XXI. The structures of the products obtained were confirmed by elemental analysis, infrared, 1H-NMR, 13C-NMR, and mass spectra. The biological activity for some synthesized products are screened.

Solubilization Behaviors of Nonpolar Substrates Using Double Tailed Cationic Surfactants

A series of double hydrophobic tails of N-methyl diethanolammonium bromide cationic surface active agents were synthesized. Their chemical structures were elucidated using different analytical tools including elemental analyses, FTIR, mass fragmentation, and 1H-NMR spectroscopy. Their surface parameters including critical micelle concentration (CMC), effectiveness (π CMC ), efficiency (Pc 20), maximum surface excess (Γ max ), and minimum surface area (A min ) were calculated. The behaviors of the synthesized molecules in their solutions were discussed based on the data of surface parameters, micellization and adsorption thermodynamics at 25°, 40°, and 55°C. The experimental data of surface activity showed that these molecules are tends to form micelles in the bulk of their solutions at lower temperatures. On contrarily, they prefer to adsorb at higher temperatures. The synthesized cationic surfactants were used as solubilizing agent for nonpolar substrate (paraffin oil) at 25°C. The results of solubilization measurements showed good ability for the used surfactants towards solubilizing paraffin oil in aqueous medium. The results showed that the chemical structure of the solubilizate plays an important rule in its solubilization. Several factors were found to influence the extent of solubilization including: number of alkyl chains within surfactant molecule, symmetry of molecules and chain length of hydrophobic parts. The results were rationalized by the Kraft point and HLB values of the used surfactants. Furthermore, solubilization curves showed the steady state solubilization of each surfactant used.

A FACILE ONE-POT SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF AZIRIDINES AND THIAZINES FROM 1,3-DIARYLPROP-2-ENONES

Abstract The title compounds 1a,b as examples for acyclic alkenones were utilized for the synthesis of some heterocycles namely, thiazines 2a,b and 3a-d, pyrimidines 4a,b. aziridines 7a,b. The unexpected tribromides 8a,b, obtained from bromination of 1a,b, were readily used to afford the pyrazoles 9a,b and isoxazoles 10 a,b. Biological screening of some selective synthesised compounds was determined in vitro using Gram-negative and Gram-positive bacterial strains.

Synthesis and Characterization of Some New Coumarins with In Vitro Antitumor and Antioxidant Activity and High Protective Effects against DNA Damage

Coumarins are naturally occurring oxygen heterocyclic compounds having multifarious medicinal properties, hence used as lead compounds for designing new potent analogs. The chromene butenoic acid 3 and the benzochromene butenoic acid 4 which are derived from the reaction of glyoxalic acid with 3-acetylcoumarin and 3-acetylbenzocoumarin, respectively, were reacted with different nitrogen and carbon nucleophiles to give new heterocyclic compounds. The structures of the prepared compounds were elucidated by IR, 1H-NMR, and mass spectroscopy. Some of the newly prepared compounds were tested in vitro against a panel of four human tumor cell lines namely; hepatocellular carcinoma (liver) HepG2, colon cancer HCT-116, human prostate cancer PC3, and mammary gland breast MCF-7. Also they were tested as antioxidants. Almost all of the tested compounds showed satisfactory activity.

Antibacterial and Antifungal Activities—Surface Active Properties Relation of Novel Dischiff Base Cationic Gemini Amphiphiles Bearing Homogeneous Hydrophobes

A novel series of cationic Gemini amphiphiles containing Dischiff base species were synthesized and their chemical structures were determined using different analytical tools. Their surface properties were determined using surface tension measurements. The adsorption and micellization thermodynamic parameters were calculated using Gibbs equations at 25°C. The surface parameters were also determined including critical micelle concentration, effectiveness, efficiency, maximum surface excess, minimum surface area, interfacial tension, and emulsification power. The synthesized cationic Gemini surfactants were evaluated as bactericides for gram negative and gram positive bacteria and also against sulfur reducing bacteria (SRB). The results of the cytotoxicity of the synthesized compounds against the targeted bacterial strains were promising and completely dependent on the surface activity of these compounds.

New Phosphono Substituted 3- and 5-Membered Rings Starting from 3(2-Thienyl)acrylonitriles and α-Phosphoryl Carbanions

Abstract A series of phosphono substituted 3- and 5-membered rings were synthesized using the Horner–Wittig reagents 2a–c on 3(2-thienyl)acrylonitriles 1a,b in the presence of different bases. All products are produced according to a sequence that involves an initial Michael reaction between 2 and the exocyclic ethylene linkage of 1a or 1b.

Synthesis of spiro and fused five membered N-heterocycles from alkylidenephosphoranes

Summary. Triketoindan-2-oxime reacted readily with ethoxycarbonylmethylene triphenylphosphorane to give mainly the corresponding spiro-pyrrole (38%) along with the fused 1′-hydroxydihydropyrrole (14%), whereas the spiro-dimer (29%) was obtained from the reaction of the oxime with methoxycarbonylmethylenetriphenyl phosphorane in addition to the corresponding 1′-hydroxydihydropyrrole (31%). Conversely, Wittig products, mono-olefin (52%) and diolefin (<7%) along with the reduced substrate (10%), were observed when the oxime was treated with a cyano ylide. The reactions of the oxime with allyl- and vinyl phosphonium salts proceeded under phase-transfer catalysis to afford fused oxazole (46%) and spiro[2]oxazole (17%), while with the latter the fused 1′-hydroxypyrrole (55%) was produced.

The Reactions of Triphenylphosphine Alkylenes with 3(2-Thienyl)acrylonitriles

Ethyl 3-(2-thienyl)acrylocyanoacetate ( 1b ) reacts with ester ylide phosphoranes 2a , b in toluene, containing triethylamine, affording the Michael addition products 7a , b and the cyclopropanes 6a , b and 8a , b . The reaction of 1b with keto ylide 2c in ethyl acetate containing benzoic acid in addition to the ylide 7c the pyran 12 was obtained. On the other hand, (cyanomethyl)triphenylphosphonium chloride ( 13 ) reacts, under the phase-transfer catalysis conditions, with 1b to give the cyclopropane derivative 15 whereas with 1a , the new ylide 16 along with the propene derivative 17 were obtained.