13C NMR spectra and biological activity of N-(1H-benzimidazol-2-yl)benzamides

Pilyugin, V. S.; Sapozhnikov, Yu. E.; Davydov, A. M.; Chikisheva, G. E.; Vorob’eva, T. P.; Klimakova, E. V.; Kiseleva, G. V.; Kuznetsova, S. L.; Давлетов, Р. Д.; Сапожникова, Н. А.; Yumadilov, R. Kh.

doi:10.1134/s1070363206100264

Cited by 11 publications

(7 citation statements)

References 7 publications

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“…calcd for C 14 H 10 ClN 3 O: C, 61.89; H, 3.71;N,15.47;found: C,61.55;H,3.77;N,imidazol-2(3H)-ylidene)-2,4-dichlorobenzamide (3c). 33 Colorless powder; m.p. : 240−243 °C; yield: 70% (428 mg); 1 H NMR (400 MHz, DMSO−d 6 ): δ 7.14 (dd, J = 5.9, 3.2 Hz, 2H, Ar−H), 7.46 (dd, J = 5.9, 3.2 Hz, 2H, Ar−H), 7.54 (dd, J = 8.3, 1.9 Hz, 1H, Ar−H), 7.73−7.75 (m, 2H, Ar−H), 12.31 (br s, 2H, NH).…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

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Synthesis, Fungicidal Activity, and Molecular Docking of 2-Acylamino and 2-Thioacylamino Derivatives of 1H-benzo[d]imidazoles as Anti-Tubulin Agents

Обыденнов

Калинина

Galieva

et al. 2021

J. Agric. Food Chem.

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This work deals with the synthesis and evaluation of fungicidal activity of benzimidazole derivatives, which are structural analogues of commercial anti-tubulin fungicides. A number of N-acyl and N-thioacyl derivatives of 2-amino-1H-benzo[d]imidazole were prepared, and their fungicidal activity against 13 strains of phytopathogenic fungi was studied. The most active compounds against the majority of the studied strains were 3a, 4l, and 4o, and the EC50 values of these compounds were in the range 2.5–20 μg/mL. Compound 3a showed the highest activity against the P. infestans strain, the growth of which is not suppressed by carbendazim. The formation of ligand–receptor complexes of various tautomeric forms of the studied benzimidazoles with homologous models of β-tubulins of B. cinerea, F. oxysporum, and P. infestans was modeled. Induced fit docking has been used for the simulation. The obtained data suggest the possibility of binding of benzimidazole fungicides to β-tubulin in the ″nocodazole cavity″ in the tautomeric form bearing a double exocyclic CN bond. The importance of the formation of hydrogen bonds of benzimidazoles with the amino acid residue Val236 along with the Glu198 residue is also revealed in the present study.

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Section: ■ Materials and Methodsmentioning

confidence: 99%

“…1,122.8,122.9,128.3,128.5,132.5,133.1,149.5,166.3,167.1. MS (EI,70 eV): m/z 309 [M + ] ( 23), 281 (18), 105 (100), 77 (33). IR (ATR, ZnSe, cm −1 ): v 674, 772, 1017772, , 1246772, , 1275772, , 1568772, , 1696 H, 4.89; N, 13.58; found: C, 66.37; H, 4.50; N, 13.39.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Synthesis, Fungicidal Activity, and Molecular Docking of 2-Acylamino and 2-Thioacylamino Derivatives of 1H-benzo[d]imidazoles as Anti-Tubulin Agents

Обыденнов

Калинина

Galieva

et al. 2021

J. Agric. Food Chem.

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“…1-Methyl-3-pyridin-2-ylurea 2d , finally, was prepared in decent yield by reacting 2-aminopyridine with methyl isocyanate again in DMF at ambient temperature. N -(1-Methyl-1 H -benzoimidazol-2-yl)acetamide 3a was produced by acetylation of commercially available 1-methyl-1 H -benzoimidazol-2-ylamine with acetyl chloride/pyridine in CH 2 Cl 2 . Extensive NMR spectroscopy was necessary to prove that the acetyl group is attached to the endocyclic nitrogen; reaction with acetic anhydride (neat) led to the identical product.…”

Section: Methodsmentioning

confidence: 99%

Intramolecular Hydrogen Bonding in Medicinal Chemistry

2010

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The formation of intramolecular hydrogen bonds has a very pronounced effect on molecular structure and properties. We study both aspects in detail with the aim of enabling a more rational use of this class of interactions in medicinal chemistry. On the basis of exhaustive searches in crystal structure databases, we derive propensities for intramolecular hydrogen bond formation of five- to eight-membered ring systems of relevance in drug discovery. A number of motifs, several of which are clearly underutilized in drug discovery, are analyzed in more detail by comparing small molecule and protein-ligand X-ray structures. To investigate effects on physicochemical properties, sets of closely related structures with and without the ability to form intramolecular hydrogen bonds were designed, synthesized, and characterized with respect to membrane permeability, water solubility, and lipophilicity. We find that changes in these properties depend on a subtle balance between the strength of the hydrogen bond interaction, geometry of the newly formed ring system, and the relative energies of the open and closed conformations in polar and unpolar environments. A number of general guidelines for medicinal chemists emerge from this study.

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“…Potential applications of macrocyclic Schiff base as supramolecular devices are contrast agents in magnetic resonance imaging (MRI), radiopharmaceuticals and as models for biological systems [9][10][11][12]. Over recent years the increasing microbial resistances to antibiotics initiated considerable interest in synthesis of new compounds with potential effects against pathogenic bacteria and fungi [13,14]. Biological activities of Schiff bases are attributed to formation of stable chelating complexes with the transition metals present in the cells.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and antibacterial activities of Cr(III), Co(III), Ni(II), and Mn(III) complexes of heptadentate Schiff base ligand derived from tris(2-aminoethyl)amine

Matin

Khojasteh

2015

Russ J Gen Chem

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This is the first study of the antibacterial activity of heptadentate Schiff base ligand (trensal) and its Cr(III), Co(III), Ni(II), and Mn(III) complexes that have been synthesized from the heptadentate Schiff base ligand derived from salicylaldehyde and tris(2-aminoethyl)amine. Heptadentate Schiff base ligand and its complexes were characterized by elemental analysis, 1 H and 13 C NMR, IR, and UV-Vis spectroscopy. The products were tested in vitro against the bacterial species, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and Bacillus cereus by disc diffusion and micro-broth dilution methods. All compounds demonstrated potent antibacterial activity higher than the Schiff base ligand. Staphylococcus aureus was the most susceptible bacterial species to Co(III) complex while Escherichia coli and Pseudomonas aeruginosa required a relatively higher minimum inhibition concentrations of Cr(III) and Ni(II) complexes. Co(III) complex was the most potent inhibitor against Pseudomonas aeruginosa. Mn(III) complex was active against Pseudomonas aeruginosa.

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13C NMR spectra and biological activity of N-(1H-benzimidazol-2-yl)benzamides

Cited by 11 publications

References 7 publications

Synthesis, Fungicidal Activity, and Molecular Docking of 2-Acylamino and 2-Thioacylamino Derivatives of 1H-benzo[d]imidazoles as Anti-Tubulin Agents

Synthesis, Fungicidal Activity, and Molecular Docking of 2-Acylamino and 2-Thioacylamino Derivatives of 1H-benzo[d]imidazoles as Anti-Tubulin Agents

Intramolecular Hydrogen Bonding in Medicinal Chemistry

Synthesis, characterization, and antibacterial activities of Cr(III), Co(III), Ni(II), and Mn(III) complexes of heptadentate Schiff base ligand derived from tris(2-aminoethyl)amine

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