Some pyrimidohexahydroquinoline candidates: synthesis, DFT, cytotoxic activity evaluation, molecular docking, and in silico studies.

Some hexahydroquinoline candidates were prepared by reacting 2-amino-3-cyano-1-cyclohexylhexahydroquinoline with oxalyl chloride and triethyl orthoformate. The computational chemical approach agreed with the product-testing results. The produced substances were examined in vitro for their antiproliferative activity against liver carcinoma (HepG2), breast adenocarcinoma (MCF7), prostate cancer (PC3), and colon cancer (HCT116) cell lines. The highest potency against the four cell lines was exhibited by hydrazide, thiosemicarbazide, and thiazolidinone derivatives. The best docking score was presented by thiosemicarbazide and thiazolidinone derivatives as they showed the highest binding to the Mcl-1 enzyme with binding energies of -8.97 and -8.90 kcal mol-1, respectively, which were higher than that of the co-crystallized ligand (LC3) with a binding energy of -8.74 kcal mol-1. Besides, the modeling pharmacokinetics disclosed their desirable drug-likeness and oral bioavailability characteristics.

Synthesis, SAR studies, and insecticidal activities of certain N-heterocycles derived from 3-((2-chloroquinolin-3-yl)methylene)-5-phenylfuran-2(3H)-one against Culex pipiens L. larvae.

An acid hydrazide derivative was synthesized and transformed into a variety of valuable N-heterocycles such as pyridazinone, oxadiazole, triazolopyridazinone, and triazole derivatives via reactions with certain carbon electrophiles such as 4-methoxybenzaldehyde, indole-3-carbaldehyde, pentan-2,4-dione, and carbon disulfide. The chemical structures of all prepared compounds were verified via their analytical and spectroscopic data. The insecticidal activity of the N-heterocycles was evaluated against field and lab strains of the third larval instar of Culex pipiens. All tested compounds exhibited higher larvicidal activity against the lab strains compared to the field strains, with dissimilar ratios. The obtained results demonstrate that the high toxicity achieved by oxadiazole followed the order of furanone, pyridazinone and hydrazide, with lower LC50 values of the hydrazone and N-acetylpyridazinone derivatives compared to that of imidacloprid. Interestingly, these compounds are promising agents for insect pest control, especially since they are insoluble in water and can overcome the disadvantages of neonicotinoid applications in pest management programs.

Gamma radiation induced preparation of polyampholyte nanocomposite polymers for removal of Co(II).

A series of polyampholyte nanocomposite biopolymers, poly(N,N-diallyldimethylammonium chloride-co-acrylamide) grafted on carboxymethylcellulose/iron(III) oxide [P(DADMAC-AAm)CMC/Fe2O3] and poly(N,N-diallyldimethylammonium chloride-co-sodium acrylate) grafted on carboxymethylcellulose/iron(III) oxide [P(DADMAC-SA)CMC/Fe2O3], was prepared with different molar ratios of anionic groups to cationic groups using gamma irradiation. The grafting properties and swelling behavior were investigated as a function of grafting conditions such as DADMAC, AAm, SA, and CMC concentrations and absorbed dose. Fourier transform infrared spectroscopic analysis (FTIR) confirmed the graft copolymerization. Scanning electron microscope (SEM) was employed to check the morphological structure of CMC, P(DADMAC-AAm)CMC/Fe2O3, and P(DADMAC-SA)CMC/Fe2O3. Thermogravimetric analysis (TGA) and differential thermal analysis (DTA) further characterized the grafted copolymers and showed their high thermal stability. Using batch sorption experiments and 60Co as a radiotracer, P(DADMAC-AAm)CMC/Fe2O3 and P(DADMAC-SA)CMC/Fe2O3 were evaluated for Co(II) removal from aqueous solutions. Experimentally, P(DADMAC-AAm)CMC/Fe2O3 and P(DADMAC-SA)CMC/Fe2O3 show high sorption capacity of Co(II), i.e. 69.67 mg g-1 and 75.17 mg g-1, respectively, which makes them potential sorbents for Co(II) removal from water/wastewater. Finally, the Co(II) sorption was examined using sorption isotherm and kinetic models. Cobalt sorption was best fitted to Langmuir model which suggests the sorption is of chemisorption type. On the other hand, the sorption kinetics was best represented by the pseudo-first-order kinetic model.

Conversion of some 2(3H)-furanones bearing a pyrazolyl group into other heterocyclic systems with a study of their antiviral activity.

3-(1,3-diphenylpyrazol-4-yl-methylene)-5-aryl-2(3H)-furanones 2 were prepared and converted into a variety of heterocyclic systems of synthetic and biological importance. Benzylamine reacted with the furanones 2; the product was found to depend on the reaction conditions. Thus, at room temperature the open-chain N-benzylamides 3 were obtained, whereas under refluxing conditions the 2(3H)-pyrrolones were obtained. Hydrazine hydrate affected ring opening of the furanones to give the corresponding acid hydrazides 5. The latter products were used as key starting materials for the synthesis of pyridazinones 7 and 8, 1,3,4-oxadiazoles 11 and 13 and 1,2,4-triazoles 12 and 14 all bearing pyrazolyl moiety as a side-chain. Evaluation of antiviral activity of selected examples of the compounds obtained was performed using two viruses: HAV and HSV-1. Some of the tested compounds showed promising activities.