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An efficient metal-free four-component approach for the synthesis of piperazine derivatives tethered to an isothiourea group through an ethylene link was developed. 1,4-Diazabicyclo[2.2.2]octane (DABCO) salts, generated in situ through the reactions of DABCO with various alkyl bromides, reacted with phenylisothiocyanate (PITC) and amines in a one-pot manner to give the target products. Initially, through two parallel nucleophilic paths, DABCO and the secondary amine adds to the alkyl bromide and PITC, respectively. The process is followed by the combination of the two respective intermediates to produce the final products by forming a new C-S bond with the expense of a C-N bond cleavage. Consequently, various DABCO salts and secondary amines were tolerated well in this protocol to afford the isothiourea-ethylene-tethered-piperazine compounds in good to high yields., Competing Interests: There are no conflicts to declare., (This journal is © The Royal Society of Chemistry.)

In this study, the surface of the polylactic acid/ethyl cellulose (PLA/EC) blend film was modified by dielectric barrier discharge (DBD) plasma treatment to facilitate the spin-coating of chitosan (CH) and wheat germ bioactive peptides (PEP) obtained from enzymatic hydrolysis of defatted wheat germ protein isolate on the surface of the film. The suitable plasma treatment condition was 5 min at 20 kV according to ATR-FTIR, AFM, SEM, water angle contact, and water solubility results. Increasing the surface roughness and oxygen-containing functional groups (CO and -OH) improved coating by PEP and CH. The PEP-coated film had better antioxidant activity than CH-PEP and CH-coated films. The results of antimicrobial activity demonstrated that PEP-coated film could reduce the growth of gram-negative bacteria (Escherichia coli) and gram-positive bacteria (Staphylococcus aureus). The PEP-coated film had competitive antibacterial properties with CH-coated. Hence, the obtained PEP-coated PLA/EC film could be a promising candidate for antioxidant and antibacterial food packaging., (Copyright © 2022 Elsevier B.V. All rights reserved.)

A novel calix[4]arene-bonded silica gel (C4BS) is prepared by covalent attachment of a calix[4]arene derivative to silica gel through a thiol-ene process. The structure and properties of C4BS were studied by Fourier Transform Infra-Red (FTIR) spectroscopy, thermal gravimetric analysis (TGA), elemental analysis (CHN), scanning electron microscopy (SEM), and surface area analysis (BET). In addition, the binding affinity of some antidiabetic drugs towards C4BS was investigated, by quantitative measurement of the drugs in aqueous solution using UV-visible spectroscopy. Results showed that C4BS has higher affinities than plain silica gel for binding to empagliflozin, dapagliflozin and linagliptin at neutral pH, while metformin hydrochloride was not adsorbed efficiently using either C4BS or plain silica gel. Thus, C4BS can be introduced as a promising binder for selective adsorption of the quoted antidiabetic drugs in pharmaceutical effluents, while being reusable by aqueous/acetonitrile (1 : 1) extraction., Competing Interests: There are no conflicts to declare., (This journal is © The Royal Society of Chemistry.)

A novel series of coumarin derivatives linked to the N -benzyl triazole group were synthesized and evaluated against 15-lipoxygenase (15-LOX), and acetyl- and butyrylcholinesterase (AChE and BuChE) to find the most potent derivative against Alzheimer's disease (AD). Most of the compounds showed weak to moderate activity against ChEs. Among the most active BuChE and 15-LOX inhibitors, 8l and 8n exhibited an excellent neuroprotective effect, higher than the standard drug (quercetin) on the PC12 cell model injured by H 2 O 2 and significantly reduced aggregation of amyloid Aβ 1-42 , with potencies of 1.44 and 1.79 times higher than donepezil, respectively. Compound 8l also showed more activity than butylated hydroxytoluene (BHT) as the reference antioxidant agent in reducing the levels of H 2 O 2 activated by amyloid β in BV2 microglial cells. Kinetic and ligand-enzyme docking studies were also performed for better understanding of the mode of interaction between the best BuChE inhibitor and the enzyme. Considering the acceptable BuChE and 15-LOX inhibition activities as well as significant neuroprotection, and anti-amyloid aggregation activities, 8l and 8n could be considered as potential MTDLs for further modification and studies against AD., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2022 Pourabdi, Küçükkılınç, Khoshtale, Ayazgök, Nadri, Farokhi Alashti, Forootanfar, Akbari, Shafiei, Foroumadi, Sharifzadeh, Shafiee Ardestani, Abaee, Firoozpour, Khoobi and Mojtahedi.)

Ultrasonic irradiation was efficiently used for high yield synthesis of monoarylidene derivatives of cyclic systems directly from the reaction of ketone with various aldehydes under solvent-free conditions. Reactions took place rapidly in the presence of catalytic amounts of pyrrolidine, while no significant formation of the undesired bis by-products was observed. Moreover, the procedure was applicable to both homo- and heterocyclic ketones., (Copyright © 2012 Elsevier B.V. All rights reserved.)

In the title compound, C(18)H(17)Cl(2)NOS, the thio-pyran-one ring adopts a chair conformation, with the substituent in the axial position. The dihedral angle between the two benzene rings is 89.43 (1)°. In the crystal, mol-ecules form inversion dimers through inter-molecular N-H⋯O hydrogen bonds [graph set R(2) (2)(8)].

In the title compound, C(22)H(21)NOS, the thio-pyran-one ring adopts a chair-like conformation with the substituent in the axial position. The relative configuration of the racemic compound is 3R,7S according to the numbering scheme used in this publication. In the crystal packing, centrosymmetric dimers are built up via N-H⋯O hydrogen bonds, with graph set R(2) (2)(8).

The title compound, C(22)H(20)O, shows an approximately planar cyclo-hexenone ring [maximum deviation = 0.069 (4) Å], with a disordered position of the C=C bond [ratio = 0.71 (2)/0.29 (2)]. The benzene rings of the 4-methyl-benzyl-idene units, attached in the 2- and 6-positions to the cyclo-hexenone ring, are rotated in the same direction by 28.6 (4) and 22.4 (4)°, with respect to the mean plane of the cyclo-hexenone ring [fraction 0.71 (2); maximum deviation = 0.06 (3) Å]. In the crystal, mol-ecules are packed in the manner of a distorted hexa-gonal rod packing with their long axes all aligned along [201]. A number of C-H⋯π inter-actions stablize the crystal structure.

The title compound, C(22)H(22)O(5), crystallizes with two independent mol-ecules in the asymmetric unit, both of which possess pseudo-C(s) symmetry. The central 1,3-dioxanone rings have envelope conformations, with the C atom bearing the two methyl groups at the flap. The benzene rings of the meth-oxy-benzyl-idene units, attached in the 4- and 6-positions on the central 1,3-dioxanone rings, are tilted in the same direction with dihedral angles varying between 8.2 (1) and 18.1 (1)°. The crystal packing is influenced by π-stacking inter-actions of the parallel displaced type [centroid-centroid distance of 3.723 (1) Å for mol-ecule 1 and 3.884 (1) Å for mol-ecule 2, with ring slippages of 1.432 and 1.613 Å, respectively] and the T-shaped type, with the long mol-ecular axes all aligned along [010].

An aqueous medium containing catalytic amounts of a tertiary amine was employed to direct the chemoselectivity of the reaction of aldehydes with 1a. With DBU, 2 was formed at room temperature as a rare exemplary of Baylis-Hillman reactions in heterocyclic enones. DABCO alternated the pathway toward an aldol reaction to form syn/anti mixtures of 3 with the syn isomers being the major products. With Et(3)N, aldol condensation dominated., (© 2011 American Chemical Society)

The Diels-Alder reaction of styrylcyclohex-2-enone derivatives 1 with N-phenylmaleimide was shown to be an efficient pathway for the synthesis of substituted dehydrodecaline derivatives. At elevated temperatures, mixtures of endo/exo adducts were formed, while in the presence of TiCl4 exclusive formation of the endo stereoisomer was observed. Spectroscopic analysis and X-ray crystallography confirmed the formation of the endo adducts.

Smooth condensation of hydrazine derivatives with various beta-keto esters was performed under solvent-free conditions by using ultrasound irradiation to facilitate the formation of pyrazolone derivatives in good to excellent amounts within very short time periods.

An efficient and environmentally friendly procedure promoted by ultrasound irradiation is developed for stereoselective ring opening of various epoxides with aromatic and aliphatic amines under aqueous conditions in the presence of no catalyst or additive. Chemoselectivity of the protocol is shown by competition of piperidine and aniline to react with different epoxides resulting in exclusive formation of the respective products of piperidine.

A room temperature convenient disproportionation or reduction of aldehydes prompted by lithium bromide and triethylamine is described in a solvent-free environment. Distribution of the products to selectively direct the process toward Cannizzaro or Tishchenko reactions is controlled by the type of workup selection. The presence of hydrogen donor alcohols in the mixture completely diverts the process toward the Meerwein-Ponndorf-Verley reaction.

[reaction: see text] A room-temperature convenient Cannizzaro reaction prompted by magnesium bromide ethyl etherate and triethylamine is described for smooth conversion of aromatic aldehydes into their respective alcohols and carboxylic acids. The methodology is applicable to both inter- and intramolecular reactions and could be directed to obtain the carboxylic moiety in the form of an acid, an amide, or an ester compound depending on the selected reaction conditions or workup procedure.

Diels-Alder reactions of 2,4-hexadienol or its O-methyl ether with acrylate derivatives at 120 degrees C give mixtures of the four possible adducts with low selectivity. At ambient temperature and in the presence of Mg(II) or Al(III) Lewis acids, reactions of the dienol (but not the ether) are highly selective. Control experiments suggest that the Lewis acid serves both to tether the diene and dienophile and to induce an "intramolecular" reaction of the resulting "self-assembled" intermediate.