Benzimidazoles have a wide spectrum of biological activity. The direction of their activity is closely associated with the individual elements of the structure. We have already described a significant tuberculostatic activity of some 2-phenalkyl- and 2-cyclohexylalkylbenzimidazoles [1]. We also reported synthesis and activity of 2-(2-cyclohexylethyl)-1H-benzo[d]imidazole analogues with benzimidazole type of structure. Their tuberculostatic activity in vitro was at the level appropriate for the administrated chemotherapeutics [2]. Here we disclosed the synthesis of novel 2-(2-phenalkyl)-1H-benzo[d]imidazoles substituted at the N-1 position. We synthesized structures with methylsulfonyl or phenylsulfonyl substituent at the N-1 position from benzimidazoles possessing different substituents at the benzene ring of benzimidazole system, styryl, phenethyl or 3,5-dichlorophenethyl moiety at the C-2 position.

Benzimidazoles in the presence of triethylamine were treated with methane- and benzenesulfonyl chloride in anhydrous dioxane, giving the corresponding sulfonamide derivatives. As a result of the synthesis twelve novel derivatives of 2-(2-phenylalkyl)-1H-benzo[d]imidazole have been obtained. All the newly synthesized compounds were characterized by IR, ¹H NMR, and ¹³C NMR spectra. They have been tested for tuberculostatic activity in vitro against M. tuberculosis sensitive and resistant “wild” strains and the standard strain H₃₇Rv. Their activity was lower than determined for benzimidazoles unsubstituted at the N-1 position.

This study is supported by the National Science Centre, Cracow (grant no. 2011/0 1/B/NZ4/01187).

References:

[1] H. Foks, D. Pancechowska-Ksepko, W. Kuźmierkiewicz, Z. Zwolska, E. Augustynowicz-Kopeć, M. Janowiec: Synthesis and Tuberculostatic Activity of New Benzimidazole Derivatives, Chem. Heterocycl. Compd., 42 (2006) 697–700.

[2]  K. Gobis, H. Foks, K. Bojanowski, E. Augustynowicz-Kopeć, A. Napiórkowska: Synthesis of novel 3-cyclohexylpropanoic acid-derived nitrogen heterocyclic compounds and their evaluation for tuberculostatic activity, Bioorg. Med. Chem. 20 (2012) 137-144.

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1. Novel 2-(2-phenalkyl)-1H-benzo[d]imidazoles: synthesis, characteristics, tuberculostatic and cytotoxic activities
2. Synthesis and tuberculostatic activity of novel 2-(2-cyclohexylethyl)-1H-benzo[d]imidazoles
3. Synthesis and antifungal activity of novel S-esters and S,S'-diesters of N'-(2-hydroxybenzoyl) hydrazinecarbo- dithioic acids
4. Synthesis and tuberculostatic activity of new N’-(6-methoxypyrazine-2-carbonyl)dithiocarbazic acid esters and their amidrazone analogs
5. Formation of 4-Pyridone-3-carboxamide-1-β-D-ribonucleoside triphosphate in the Erythrocytes, Endothelium and Cardiomyocytes and its Effect on ATP Concentration
6. THE IMPORTANCE OF THE TYPE OF ISONIAZID ACETYLATION IN MONITORING OF TUBERCULOSIS TREATMENT.
7. SYNTHESIS AND ANTITUBERCULOUS ACTIVITY OF NEW 3,5-DISUBSTITUTED- 1,2,4-OXADIAZOLES
8. NEW 3-ALKENYL DERIVATIVES OF RIFAMYCIN ANTIBIOTICS