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Ursane-type triterpenoids containing functionalized heterocyclic substituents were chemically modified. Aminomethylation of ursane hybrids with 1,3,4-oxadiazole- and 1,2,4-triazolethiones occurred smoothly to form new potentially biologically active derivatives of pentacyclic triterpenoids containing 4-morphlinomethyl-5-thioxo-1,3,4-oxadiazole or 4-morpholinomethyl-5-thioxo-1,2,4-triazole substituents. Nucleophilic substitution of a methanesulfonyl group in a 1,3,4-oxadiazole substituent of a pentacyclic triterpenoid synthesized ursane-type hybrids with 2-hydroxyoxadiazoles and 2-dialkylaminooxadiazoles. [ABSTRACT FROM AUTHOR]

In this research, the new hydrazine‐1‐carbothioamides (IC32 and IC34) having unsubstituted benzimidazole skeleton were converted to 1, 2, 4‐triazole derivatives (IC42 and IC44) by N‐cyclization reaction using the microwave‐assisted synthesis method in the basic medium with high efficiency in a short time. 2‐Amino‐1,3,4‐thiadiazole derivatives (IC52 and IC54) were obtained from the carbothioamides in the acidic medium by S‐cyclization using the conventional method. The structure of all compounds was confirmed by FT‐IR, 1H NMR, and 13C NMR spectroscopic techniques. The optimized structures, theoretical NMR shielding values in DMSO‐d6 solvent, the frontier molecular orbital, molecular electrostatic potential, and non‐linear optical properties of these molecules were calculated in the Gaussian 09 W package program by using DFT method/B3LYP function and 6‐311++G (d, p) basis set. All calculations except NMR calculations were performed in the gas phase and the obtained results were interpreted within the related sections. The discovery of new drugs is of great importance in combating health problems and improving the quality of human life. In the light of this information, molecular docking with Autodock Vina and physicochemical calculations with the SwissADME server were performed at the end of the article. Therefore, the inhibiting potential of the ligands containing different groups in their structure was investigated for the first time in this study. [ABSTRACT FROM AUTHOR]

The title compound, C23H22FN5S, exists in a trans conformation with respect to the methene C=C and the acyclic N=C bonds. The 1,2,4-triazole-5(4H)-thione ring makes dihedral angles of 88.66 (9) and 84.51 (10)°, respectively, with the indole and benzene rings. In the crystal, molecules are linked by pairs of N—H...S hydrogen bonds, forming inversion dimers with an R22(8) ring motif. The dimers are linked via C—H...π interactions, forming chains along [1-10]. The chains are linked via π—π interactions involving inversion-related triazole rings [centroid–centroid distance = 3.4340 (13) Å], forming layers parallel to the ab plane.

The title compound, C10H9FN4S, crystallizes with two molecules (A and B) in the asymmetric unit. The dihedral angle between the planes of the trizole and fluorobenzene rings is 7.3 (3)° in molecule A and 41.1 (3)° in molecule B. Molecule A features an intramolecular C—H...S hydrogen bond, which closes an S(6) ring. In the crystal, A+B dimers linked by pairs of N—H...S hydrogen bonds occur, generating R22(8) loops. Weak π–π stacking contacts [centroid–centroid separation = 3.739 (6) Å] are also observed.