Conversion of lignin pyrolysis oil to cyclohexyl methyl ethers as a promising biomass-derived solvent

A mixture of cyclohexyl methyl ethers was prepared from Kraft lignin pyrolysis oil for use as a biomass-derived aliphatic solvent.

4-Amino-5-{[cyclohexyl(methyl)amino]methyl}isophthalonitrile

The title compound, C16H20N4, was synthesized by cyanation of bromhexine. The compound crystallizes with two unique molecules in the asymmetric unit. The substituted aniline and cyclohexane rings are inclined to one another by 37.26 (6)° in one molecule and by 22.84 (7)° in the other. In the crystal packing, intra- and intermolecular N—H...N hydrogen bonds and an intermolecular C—H...N contact were observed.

Design, synthesis and evaluation of benzofuran-acetamide scaffold as potential anticonvulsant agent

A series of N-(2-(benzoyl/4-chlorobenzoyl)-benzofuran- 3-yl)-2-(substituted)-acetamide derivatives (4a-l, 5a-l) was synthesized in good yield. All synthesized compounds were in agreement with elemental and spectral data. The anticonvulsant activity of all synthesized compounds was assessed against the maximal electroshock induced seizures (MES) model in mice. Neurotoxicity was evaluated using the rotarod method. The majority of compounds exhibited anticonvulsant activity at a dose of 30 mg kg-1 body mass during 0.5-4 h, indicating their ability to prevent seizure spread at low doses. Relative to phenytoin, [N-(2-(4-chlorobenzoyl)benzofuran-3-yl)-2-(cyclohexyl( methyl) amino)-acetamide] (5i) and [N-(2-(4-chlorobenzoyl)benzofuran-3-yl)-2-(4-methylpiperidin-1- yl)-acetamide] (5c) demonstrated comparable relative anticonvulsant potency of 0.74 and 0.72, respectively, whereas [(N-(2-(4-chlorobenzoyl)benzofuran-3-yl)-2-(4-(furan-2-carbonyl)-piperazin-1-yl)-acetamide] (5f) exhibited the lowest relative potency of 0.16. The ALD50 of tested compounds ranged from 1.604 to 1.675 mmol kg-1 body mass. The ED50 of synthesized compounds ranged from 0.055 to 0.259 mmol kg-1 (~23.4 to 127.6 mg kg-1) body mass. The pharmacophore mapping of the examined compounds on standard drugs (phenobarbital, phenytoin, ralitolin and carbamazepine) strongly suggests that these compounds may exert their anticonvulsant activity via the same established mechanism as that of known drugs.

Syntheses and structures of four new mixed-amide phosphoric triamides

Phosphoric triamides have extensive applications in biochemistry and are also used asO-donor ligands. Four new mixed-amide phosphoric triamide structures, namelyrac-N-tert-butyl-N′,N′′-dicyclohexyl-N′′-methylphosphoric triamide, C17H36N3OP, (I),rac-N,N′-dicyclohexyl-N′-methyl-N′′-(p-tolyl)phosphoric triamide, C20H34N3OP, (II),N,N′,N′′-tricyclohexyl-N′′-methylphosphoric triamide, C19H38N3OP, (III), and 2-[cyclohexyl(methyl)amino]-5,5-dimethyl-1,3,2λ5-diazaphosphinan-2-one, C12H26N3OP, (IV), have been synthesized and studied by X-ray diffraction and spectroscopic methods. Structures (I) and (II) are the first diffraction studies of acyclic racemic mixed-amide phosphoric triamides. The P—N bonds resulting from the different substituent –N(CH3)(C6H11), (C6H11)NH–, 4-CH3-C6H4NH–, (tert-C4H9)NH– and –NHCH2C(CH3)2CH2NH– groups are compared, along with the different molecular volumes and electron-donor strengths. In all four structures, the molecules form extended chains through N—H...O hydrogen bonds.

Crystal structure of {[2-hydroxy-2-(3-methoxyphenyl)cyclohexyl]methyl}dimethylammonium benzoate

The title compound, C16H26NO2+·C7H5O2−, is a benzoate salt of the painkiller Tramadol. The six-membered cyclohexane ring of the cation adopts a slightly distorted chair conformation and carries OH and 3-methoxyphenyl substituents at the 2-position and a protonated methylazaniumylmethyl group at the 3-position. In addition, a weak intramolecular C—H...O hydrogen bond is observed in the cation. In the crystal, weak O—H...O, N—H...O and C—H...O hydrogen bonds link the components into chains along [010]. A C—H...π contact is also observed.