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Polymorphism of four biologically active 3-(4,5-diaryl-4H-1,2,4-triazole-3-yl)propenoic acid derivatives has been investigated. Traditional solution-based solid-state forms screening revealed three anhydrous forms of 3-[4-phenyl-5-(2-pyridyl)-4H-1,2,4-triazole-3-yl]propenoic acid. Noteworthy, two pairs of concomitant polymorphs were detected for this system. Two other compounds were found to be dimorphic. The molecular and crystal structures of all obtained crystal forms were established by single-crystal X-ray diffraction. The resulting crystal structures were analyzed in terms of molecular conformation, intermolecular interaction patterns, and crystal packing motifs. The experimental studies were supported by extended lattice and interaction energy calculations. It was found that the carboxylic group adopts the anti conformation in all studied forms and is involved in the intramolecular O–H···Ntriazole hydrogen bonding. In consequence, the association modes are dominated by the weak C–H···O, C–H···N hyd...

The series of new 1,2,4-triazole derivatives with methacrylic acid moiety were synthesized and characterized by NMR and IR spectroscopy as well as X-ray crystallography. The influence of newly synthesized compounds on the inflammation on the level of cytokine production and the proliferation of human peripheral blood mononuclear cells (PBMC) were experimentally evaluated. Obtained triazoles showed antiproliferative activity and diverse effects on cytokine production. Two compounds demonstrated potentially anti-inflammatory activity and comparable effects with ibuprofen.

Two new 1,2,4-triazole-containing alkenoic acid derivatives were obtained from the reaction of N -phenyl-(pyridin-2-yl)carbohydrazonamide with itaconic anhydride, depending on the reaction conditions. The structures of 2-((4-phenyl-5-(pyridin-2-yl)-4 H -1,2,4-triazol-3-yl)methyl)acrylic acid or ( E )-2-methyl-3(4-phenyl-5-(pyridine-2-yl)-4 H -1,2,4-triazol-3-yl)acrylic acid were confirmed by means of 1D and 2D NMR spectroscopic data as well as by single-crystal X-ray diffraction analysis. The experiential 1 H and 13 C chemical shifts were compared with those calculated with B3LYP, EDF1, and EDF2 density functional theories. The theoretical study of the observed terminal-to-internal alkene isomerization was performed with density functional (DFT) B3LYP/6-31+G ∗ method using SM8 water and DMF solvation models. Antimicrobial activities of the newly prepared alkenoic acid derivatives were verified experimentally by a broth microdilution method.

A new 1,2,4-triazole derivative, 2-(4-phenyl-5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)cyclohexanecarboxylic acid, C20H20N4O2 (I), and its dimethyl sulfoxide solvate 1:1 (II) have been synthesized and their crystal structure was established. Compound (I) was screened for its antiproliferative and antiinflammatory activity. Structural analysis indicated the substantial difference between two symmetry independent molecules in (I) and this in (II), it manifests in the relative orientation of pyridine/phenyl and triazole rings, as well as in the orientation of carboxyl group with respect to cyclohexane ring. The molecules A and B in the crystal (I) form two hydrogen-bonded chains through O–Hcarboxyl and Ntriazole atoms, giving separate catemers of symmetry independent molecules. The catemer of (IA) running along the 21 axis is homochiral, while the catemer (IB) is racemic—formed about the c glide plane. In the crystalline solvate (II) complexation of (I) with DMSO induced enantiomeric self-resolution. Obtained crystals are racemic twins, in which each part is built of one enantiomer of (I) having the relative configuration 11S,12R or 11R,12S. A pair of host–guest molecules is linked by the O–Hcarboxyl⋯ODMSO hydrogen bond.

(Z)-3-(3,4-diaryl-1,2,4-triazole-5-yl)prop-2-enoic acid derivatives were obtained in the course of the reaction of N 3-substituted amidrazones with maleic anhydride, and isomerized into the (E) isomers by heating under reflux in acetic acid solution. The molecular structure of the compounds obtained was confirmed by IR and 1H NMR spectroscopy, and by X-ray crystallography for (2E)-3-(4,5-diphenyl-4H-1,2,4-triazol-3-yl)prop-2-enoic acid. The antiviral and immunomodulating activity of several of the compounds was examined.

Process of thermal decomposition and stability of the methyl esters of 3-(2-pyridyl)-4-phenyl-1,2,4-triazol-5-carboxylic acid (I), 3-(2-pyridyl)-4-(4-methyl-phenyl)-1,2,4-triazol-5-carboxylic acid (II), 3-(2-pyridyl)-4-(4-methyl-phenyl)-5-oxo-1,2,4-triazine-6-acetic acid (III) and 3-(2-pyridyl)-4-phenyl-5-oxo-1,2,4-triazine-6-acetic acid (IV) were studied. The compounds are stable up to fusion point. Next they decompose in several overlapping stages. Among the decomposition products CO2, H2O, NH3 and CH3OH molecules are presented. When kept in air under atmospheric pressure at temperature over the range of 20-80°C and relative humidity over the range of 50-90% the esters do not change their structure and composition.

The title compound, C13H10N4, is a disubstituted 1,2,4-triazole derivative. The pyridyl and phenyl rings form dihedral angles of 46.7 (3) and 55.9 (4)°, respectively, with the central triazole ring. The mol­ecules in the crystal structure form two types of centrosymmetrically related dimers through hydro­phobic C—H⋯N and π–π intermolecular interactions.

The title compound, C14H12N4, is a disubstituted 1,2,4-triazole derivative. The triazole ring is planar and its dihedral angles with the attached pyridyl and methyl­phenyl rings are 25.2 (3) and 66.9 (3)°, respectively. The crystal structure is stabilized by a number of C—H⋯N hydrogen bonds and C—H⋯π intermolecular interactions.

New 3-(3,4-diaryl-1,2,4-triazole-5-yl)propenoic acid derivatives (8–14) were synthesized by condensation of N3-substituted amidrazones (1–7) with maleic anhydride. Molecular structure of obtained compounds was confirmed by an elemental analysis, IR and 1H NMR spectra, and the X-ray crystallography for compound 11. The influence of the compound 9 on the central nervous system (CNS) of mice in some behavioural test was examined. The investigated compound showed anticonvulsive activity and potent antinociceptive action.

The crystal structure of the title compound, C14H12N4, is built from two symmetry-independent mol­ecules which are nearly related by translation by the vector a/2. The two mol­ecules exhibit almost identical bond distances and angles but they show significantly different conformations. The relative orientations of the pyridyl and benzene rings about the triazole ring are different in the two mol­ecules, and they pack differently in the crystal structure. Weak inter­molecular C—H⋯N, C—H⋯π and π⋯π inter­actions stabilize the crystal structure [the distance between the triazole ring centroids is 3.687 (4) A].