Synthesis, Characterization and Pharmacological Screening of Some Novel 2- substituted and 1(H)-substituted Benzimidazole Derivatives as potent Anti-cancer agents

The most of drugs containing Benzimidazole ring is a prominent structural motif found in numerous therapeutically active compounds. Benzimidazole and its synthetic analogues have been found to exhibit industrial, agricultural and biological application such as antitubercular, anti-inflammatory, analgesic, anticancer, anticoagulant, as well as good antifungal and anti microbial activity. Recent advances in technology considers microwave irradiation energy as the most efficient means of heating reactions for chemical transformations that can be accomplished in a minutes. Microwave irradiation assists organic synthesis (MAOS) not only helps in implementing green chemistry but also led to progress in organic synthesis. We report pharmacological screening of some novel 2 substituted and 1(h)-substituted Benzimidazole derivatives.

Crystal structure, Hirshfeld and electronic transition analysis of 2-[(1H-benzimidazol-1-yl)methyl]benzoic acid

In the title compound, C15H12N2O2, the benzimidazole ring system is inclined to the benzene ring by 78.04 (10)°. The crystal structure features O—H...N and C—H...O hydrogen bonding and C—H...π and π–π interactions, which were investigated using Hirshfeld surface analysis.

Skin Damages—Structure Activity Relationship of Benzimidazole Derivatives Bearing a 5-Membered Ring System

In the search for scaffolds for multifunctional compounds we investigated the structure activity relationship of a class of benzimidazole derivatives bearing 5-membered ring. The newly synthesized and the already known compounds were divided into three classes that present different substituent at 5 position of the benzimidazole ring (-H, -COOH or –SO3H) and different heterocycle at position 2 (thiophene, furan or pyrrole). All the derivatives were synthesized and tested to determine their photoprotective profile against UV rays, in vitro antioxidant capacity against different radicals (DPPH and FRAP test), antifungal inhibitory activity (dermatophytes and Candida albicans), antiviral and antiproliferative activity. A Structure-Activity Relationship study indicated compound 10, bearing a pyrrole heterocycle on the benzimidazole ring, as the best multifunctional derivative of the series and as potential candidate for the development of drugs especially in case of melanoma.

Crystal structure of bis[2-(1H-benzimidazol-2-yl-κN 3)aniline-κN]bis(nitrato-κO)cadmium(II)

In the title compound, [Cd(NO3)2(C13H11N3)2], the CdII atom lies on a twofold rotation axis and is coordinated by four N atoms and two O atoms, provided by two bidentate 2-(1H-benzimidazol-2-yl)aniline ligands, and two nitrato O atoms, forming a distorted octahedral geometry [range of bond angles around the Cd atom = 73.82 (2)–106.95 (8)°]. In the ligand, the dihedral angle between the aniline ring and the benzimidazole ring system is 30.43 (7)°. The discrete complex molecule is stabilized by an intramolecular N—H...O hydrogen bond. In the crystal, intermolecular N—H...O hydrogen bonds link the molecules, forming a three-dimensional network.

Crystal structure and DFT study of 2-(pyren-1-yl)-1H-benzimidazole

In the title compound, C23H14N2, (I), the dihedral angle between the mean planes of the pyrene and benzimidazole ring systems is 42.08 (5)°, with a bridging C—C bond length of 1.463 (3) Å. In the crystal, molecules are linked by N—H...N hydrogen bonds, forming columns propagating along the b-axis direction. The columns are linked via C—H...π interactions, forming slabs parallel to the ab plane. There are no significant π–π interactions present in the crystal structure. The density functional theory (DFT) optimized structure, at the B3LYP/ 6-311G(d,p) level, is compared with the experimentally determined solid-state structure of the title compound.

Crystal structure and UV spectra of a 1,2-disubstituted benzimidazolium chloride

1-(2-Hydroxybenzyl)-2-(2-hydroxyphenyl)-1H-benzimidazol-3-ium chloride, C20H17N2O2 +·Cl−, was prepared by reaction of salicylaldehyde with o-phenylenediamine in the presence of trimethylsilyl chloride acting as a source of HCl. As a result of steric hindrance, the cation in the crystal is far from planar: the benzimidazole ring system makes dihedral angles of 55.49 (9) and 81.36 (8)° with the planes of the phenolic groups. The crystal packing is dominated by O—H...Cl and N—H...Cl hydrogen bonds, which link the cations and anions into four-membered rings and then into chains along [100]. The title compound exhibits two transitions in the UV region, which are revealed in the solid state and solution spectra as an absorption maximum at 280 nm and a shoulder at 320 nm. According to the results of TD–DFT calculation, both transitions have a π–π* nature and the molecular orbitals involved in these transitions are mostly localized on the benzimidazole ring system and on the phenyl ring attached to it at the 2-position.