Facile synthesis and antimicrobial evaluation of some new heterocyclic compounds incorporating a biologically active sulfamoyl moiety.

A facile and convenient synthesis of new heterocyclic compounds containing a sulfamoyl moiety suitable for use as antimicrobial agents was reported. The precursor 3-oxo-3-phenyl-N-(4-sulfamoylphenyl)propionamide was coupled smoothly with arenediazonium salt producing hydrazones which reacted with malononitrile or triethylorthoformate affording pyridazine and triazine derivatives, respectively. Also, the reactivity of the same precursor with DMF-DMA was followed by aminotriazole; aromatic aldehydes was followed by hydrazine hydrate, triethylorthoformate, or thiourea affording triazolo[1,5-a]pyrimidine, pyrazole, acrylamide, and dihydropyrimidine derivatives, respectively. On the other hand, treatment of the precursor propionamide with phenyl isothiocyanate and KOH in DMF afforded the intermediate salt which was treated with dilute HCl followed by 2-bromo-1-phenylethanone affording carboxamide derivative. While the same intermediate salt reacted in situ with chloroacetone, ethyl 2-chloroacetate, 3-(2-bromoacetyl)-2H-chromen-2-one, methyl iodide, or 2-oxo-N-phenylpropane hydrazonoyl chloride afforded the thiophene, ketene N,S-acetal, and thiadiazole derivatives, respectively. The structure of the new products was established based on elemental and spectral analysis. Antimicrobial evaluation of some selected examples from the synthesized products was carried out whereby four compounds were found to have moderate activities and one compound showed the highest activity.

Synthesis and antimicrobial evaluation of some novel thiazole, pyridone, pyrazole, chromene, hydrazone derivatives bearing a biologically active sulfonamide moiety.

This study aimed for the synthesis of new heterocyclic compounds incorporating sulfamoyl moiety suitable for use as antimicrobial agents via a versatile, readily accessible N-[4-(aminosulfonyl)phenyl]-2-cyanoacetamide (3). The 2-pyridone derivatives were obtained via reaction of cyanoacetamide with acetylacetone or arylidenes malononitrile. Cycloaddition reaction of cyanoacetamide with salicyaldehyde furnished chromene derivatives. Diazotization of 3 with the desired diazonium chloride gave the hydrazone derivatives 13a-e. Also, the reactivity of the hydrazone towards hydrazine hydrate to give Pyrazole derivatives was studied. In addition, treatment of 3 with elemental sulfur and phenyl isothiocyanate or malononitrile furnished thiazole and thiophene derivatives respectively. Reaction of 3 with phenyl isothiocyanate and KOH in DMF afforded the intermediate salt 17 which reacted in situ with 3-(2-bromoacetyl)-2H-chromen-2-one and methyl iodide afforded the thiazole and ketene N,S-acetal derivatives respectively. Finally, reaction of 3 with carbon disulfide and 1,3-dibromopropane afforded the N-[4-(aminosulfonyl) phenyl]-2-cyano-2-(1,3-dithian-2-ylidene)acetamide product 22. All newly synthesized compounds were elucidated by considering the data of both elemental and spectral analysis. The compounds were evaluated for both their in vitro antibacterial and antifungal activities and showed promising results.

Preparation and characterization of chemically cross-linked zwitterionic copolymer hydrogel for direct dye and toxic trace metal removal from aqueous medium.

In this work, a zwitterionic copolymer hydrogel with adsorption affinity toward anionic dye and cationic trace metal was prepared by a free radical copolymerization of cationic ([3-(methacryloylamino)propyl] trimethylammonium chloride (MPTC)) and anionic (sodium 4-vinylbenzenesulfonate (SVBS)) monomers. Bis[2-(methacryloyloxy)ethyl] phosphate was used as a cross-linker and its effect on the adsorption properties of the prepared hydrogel was evaluated. The prepared materials were characterized by FTIR, XRD, SEM, EDX, and N2 adsorption at 77 K analysis. FTIR and EDX analysis demonstrated the successful preparation of poly(MPTC-co-VBS). XRD and SEM analysis showed that the poly (MPTC-co-VBS) is amorphous and has quasi-honeycomb morphology with large pores. Increasing the amount of the cross-linker enhanced the adsorption of direct blue 71 dye (DB71) and Pb(II) ions. The highest removal of DB71 and Pb(II) was achieved after 2 h using 1.5 g/L of poly(MPTC-co-VBS); however, the optimum solution pH was 3 for DB71 and 5 for Pb(II). The kinetics and isotherm studies illustrated that the surface of poly(MPTC-co-VBS) is heterogenous with small-sized homogenous pitches and the DB71 and Pb(II) adsorption onto poly(MPTC-co-VBS) is favorable. Finally, poly(MPTC-co-VBS) is more efficient in removing DB71 and Pb(II) from aqueous solutions than many other reported adsorbents.

One-Step Room-Temperature Synthesis of Bimetallic Nanoscale Zero-Valent FeCo by Hydrazine Reduction: Effect of Metal Salts and Application in Contaminated Water Treatment.

The effect of initial salt composition on the formation of zero-valent bimetallic FeCo was investigated in this work. Pure crystalline zero-valent FeCo nanoparticles (NPs) were obtained using either chloride or nitrate salts of both metals. Smaller NPs can be obtained using nitrate salts. Comparing the features of the FeCo prepared at room temperature and the solvothermal method revealed that both materials are almost identical. However, the room-temperature method is simpler, quicker, and saves energy. Energy-dispersive X-ray (EDX) analysis of the FeCo NPs prepared using nitrate salts at room temperature demonstrated the absence of oxygen and the presence and uniform distribution of Fe and Co within the structure with the atomic ratio very close to the initially planned one. The particles were sphere-like with a mean particle size of 7 nm, saturation magnetization of 173.32 emu/g, and surface area of 30 m2/g. The removal of Cu2+ and reactive blue 5 (RB5) by FeCo in a single-component system was conformed to the pseudo-first-order and pseudo-second-order models, respectively. The isotherm study confirmed the ability of FeCo for the simultaneous removal of Cu2+ and RB5 with more selectivity toward Cu2+. The RB5 has a synergistic effect on Cu2+ removal, while Cu2+ has an antagonistic effect on RB5 removal.

Facile synthesis of heterocycles via 2-picolinium bromide and antimicrobial activities of the products.

The 2-picolinium N-ylide 4, generated in situ from the N-acylmethyl-2-picolinium bromide 3, underwent cycloaddition to N-phenylmaleimide or carbon disulfide to give the corresponding cycloadducts 6 and 8, respectively similar reactions of compound 3 with some electron-deficient alkenes in the presence of MnO(2) yielded the products 11 and 12. In addition, reaction of 4 with arylidene cyanothioacetamide andmalononitrile derivatives afforded the thiophene and aniline derivatives 15 and 17, respectively. Heating of picolinium bromide 3 with triethylamine in benzene furnished 2-(2-thienyl)indolizine (18). The structures of the isolated products were confirmed by elemental analysis as well as by (1)H- and (13)C-NMR, IR, and MS data. Both the stereochemistry and the regioselectivity of the studied reactions are discussed. The biological activity of the newly synthesized compounds was examined and showed promising results.