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A series of novel 2-oxo-2-(arylamino)ethyl 4-formylbenzoates were prepared via the reaction of the potassium salt of p-formylbenzoic acid with 2-chloro-N-aryl-acetamide in DMF at reflux. A new series of 1,4- dihydropyridin-3,5-dicarbonitriles, hexahydroacridine-1,8-diones, decahydropyrimido[4,5-b]quinolines, and hexahydrobenzo[4,5]imidazo[2, 1-b]quinazolines which are linked to N-aryl-benzoyloxyacetamide were obtained through the Hantzsch reaction of various 2-oxo-2-(arylamino)ethyl 4-formylbenzoate with the respective 3-aminocrotononitrile or a mixture of 1,3-dicarbonyl compounds and amine source. The structures of the novel compounds were confirmed using a variety of spectra. [ABSTRACT FROM AUTHOR]

A novel regioselective synthesis of a series of bis(tetrahydrobenzimidazo[2,1-b]quinazolin-1-(2H)-ones) via the reaction of bis-aldehydes with two-mole equivalents of both dimedone and benzimidazole in DMF at reflux or under the effect of microwave heating is reported. [ABSTRACT FROM AUTHOR]

A novel series of 6-acetyl-[1,2,4]triazolo[1,5-a]pyrimidines, hexahydro-[1,2,4] triazolo[5,1-b]quinazolines, tetrahydrobenzo[4,5]imidazo[2,1-b]quinazolin-1-ones, and 3-acetyl-1,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidines linked to phenoxy-N-arylacetamide moieties were prepared via Biginelli-like cyclocondensation reaction of the 2-(4-formylphenoxy)-N-arylacetamides, with the appropriate active methylene containing reagents and nitrogen binucleophiles. Elements and spectroscopic data were used to confirm the compositions of the novel compounds. We proposed a reasonable mechanism for the creation of target products. [ABSTRACT FROM AUTHOR]

A novel synthesis of bis(thiazoles) and bis(thiadiazole), each connected to a thienothiophene moiety, is described. The DFT calculations support the favored synthesis of one of the anticipated bis(thiazole) regioisomers. The B3LYP/6-311G** level of theory was used to optimize quantum mechanical calculations of geometrical characteristics and energy of new compounds under study. The electronic absorption of the new compounds in ethanol solvent was handled and finished using time-dependent-density functional theory (TD-DFT) at the B3LYP/6-31G(d,p) level with the addition of the polarizable continuum solvation technique TD-DFT/PCM. The permissible singlet transitions are identified, and their involvements in the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) are described. Natural bond orbital (NBO) analysis was used to investigate hyper conjugative partnerships, molecular stability, and bond strength. Mean polarizability, total static dipole moment, anisotropy of polarizability, and mean first-order hyperpolarizability have all been computed. The results reveal that the compounds are promising contenders for non-linear optical materials. The molecular docking mechanism between ligands 8a–8c and COVID-19/5epw or SARS/5wrg receptors was done to explore the binding modes of these compounds at the active sites. Molecular docking results have shown that the compounds 8a–8c can be considered as a potential agent against COVID-19/5epw and SARS/5wrg receptors. [ABSTRACT FROM AUTHOR]

A synthesis of novel bis(tetrahydropyrimido[4,5-b]quinoline-4,6-diones) connected to butenyl and butynyl spacers via thioether linkages is reported. Two equivalents of the appropriate aldehyde and dimedone were used in a multicomponent reaction with the corresponding bis(6-aminopyrimidin-4(3H)-ones) to produce the target products. Bis(alkylation) of the appropriate 2-thioxohexahydropyrimido[4,5-b]quinoline-4,6-dione in ethanolic potassium hydroxide with 1,4-dichlorobut-2-ene or 1,4-dibromobut-2-yne also produced the target compounds. Furthermore, bis(tetrahydropyrimido[4,5-b]quinolinetriones) linked to olefinic or acetylenic spacers via ether linkage were synthesized in high yields by a three-component reaction of the appropriate bis(aldehydes) with two equivalents of both 6-aminothiouracil and dimedone. [ABSTRACT FROM AUTHOR]

In this study novel 2-(4-(1-phenyl-1H-pyrazol-3-yl)phenoxy)-N-arylacetamide hybrids with fused 1,4-dihydropyridines such as acridines and tetrahydrodipyrazolo[3,4-b:4',3'-e]pyridines were successfully and efficiently prepared through a one-pot multi-component reaction of 2-(4-(4-formyl-1-phenyl-1H-pyrazol-3-yl)phenoxy)-N-arylacetamide with dimedone, or 5-methyl-2,4-dihydro-3H-pyrazol-3-one at reflux. The tri-substituted methanes (TRSMs) were synthesized through the reaction of the appropriate aldehyde with 6-aminothiouracil and 4-hydroxycoumarin. The structures of novel compounds were confirmed based on spectral data. [ABSTRACT FROM AUTHOR]

A series of bis-chalcones with alkyl linkers incorporating 3-(thiophen-2-yl)pyrazole 5–10 has been prepared by the condensation reaction of two moles of 3-(thiophen-2-yl)pyrazole-4-aldehyde 4 with one mole of bis- o- or p-(acetophenones) 3a-f. The synthesized compounds 5-10 have been fully characterized and tested as novel anti-cancer agents. The in vitro anticancer activities of the compounds 5-10 were evaluated against a panel of human cancer cell lines (A431, A549, and PC3), and a normal human skin fibroblast BJ1. Compound 10 was the most promising in the prepared series with IC50 (48.7 and 74.2 µg/mL) against epidermoid cancer cell line A431 and the lung adenocarcinoma cell line A549, respectively, compared to the reference drug doxorubicin (IC50, 28.3 and 27.9 µg/mL, respectively). The target compound 10 was investigated theoretically using molecular docking study to different domain sets (1dls, 2c6o, 2w3t, 4kmn, and 4wt2) and they illustrated different modes of action with different binding energies. [ABSTRACT FROM AUTHOR]

A synthesis of novel bis-thiazoles, linked to quinoxaline as novel hybrid molecules, was accomplished in good yields by the reaction of the appropriate α-haloketones or α-keto-hydrazonoyl chlorides with the corresponding bis(hydrazinecarbothioamide) in ethanol/dimethylformamide (EtOH/DMF) at reflux in the presence of a few drops of triethylamine (TEA). The reaction of the appropriate thioamide with the corresponding bis(2-bromoethanone) yielded novel bis-thiazoles. Furthermore, by reacting bis(2-bromoethanone) with the appropriate 4-amino-3-mercapto-1,2,4-triazole derivatives, novel bis(5,6-dihydro-s-triazolo[3,4-b]thiadiazines) linked to quinoxaline moiety were obtained in good yields. The starting bis-thiosemicarbazone was obtained by reacting 1,1'-((quinoxaline-2,3-diylbis(oxy))bis(4,1-phenylene))diethanone with thiosemicarbazide in EtOH containing a few drops of acetic acid (AcOH) at reflux. On the other hand, the 1,1'-((quinoxaline-2,3-diylbis(oxy))bis(4,1-phenylene))bis(2-bromoethanone) was obtained from the corresponding bis(acetyl) derivative upon treatment with N-bromosuccinimide (NBS) in the presence of p-toluenesulfonic acid (p-TsOH), respectively. Structures of new compounds were confirmed using elemental analyses and spectral data. [ABSTRACT FROM AUTHOR]

A new series of bis(4H‐chromene), bis (pyrano[3,2‐c]chromene), and bis (pyrano[2,3‐c]pyrazole) each linked to the piperazine core via ether linkages was synthesized. The target compounds are probably formed through a three‐component reaction involving two equivalents of each malononitrile and the corresponding active methylene compounds, such as dimedone, 4‐hydroxycoumarine, or 5‐methyl‐2,4‐dihydro‐3H‐pyrazol‐3‐one. Several spectral methods and elemental analyses were used to deduce the chemical structures of the novel compounds. Furthermore, all synthesized compounds were tested for antimicrobial activity, which revealed promising inhibitory results against a variety of multidrug‐resistant microbial strains. These findings were compared to those obtained in the in silico molecular docking study. The docking results improved the activity of new derivatives as potentially effective antimicrobial agents. [ABSTRACT FROM AUTHOR]

Due to their outstanding physicochemical features, azulene derivatives have been proposed for a wide range of prospective technical applications, including molecular switching, sensors, solar cells, and beneficial biological activities. Transition metal‐catalyzed cross‐coupling reactions are catalytic processes that create carbon–carbon bonds in one of the most straightforward and practical ways possible. These techniques have proven to be a very practical way to functionalize azulene. This study summarizes the progress made in this field by employing Rh, Ir, Ru, Au, Fe, Ni, and Cu catalysts over the last two decades. [ABSTRACT FROM AUTHOR]