Synthesis and biological investigations of 2-(tetrahydropyran-2'-yl) and 2-(tetrahydrofuran-2'-yl)benzimidazoles.
A set of benzimidazole derivatives bearing on position 2 a tetrahydropyranyl or tetrahydrofuranyl residue was prepared and tested for antitumoral, anti HIV-1 and other pharmacological activities. While the anti-HIV activity was completely lacking, moderate antitumoral activity was found in a few compounds; particularly the 5,6-dichloro-2-(tetrahydropyran-2-yl)-benzimidazole (8) was able to inhibit the growth of 19 cell lines of humane tumors at near micromolar concentration. On the other hand compounds 4, 6-8 and 10 exhibited significant tracheal relaxant activity in vitro at concentration 3-10 micrograms/ml, thus resulting superior to theophylline and comparable to amrinone.
Novelli
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Dipartimento di Scienze Farmaceutiche, Università di Genova, Italy.
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D000818:Animals; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology; D006168:Guinea Pigs; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D009130:Muscle, Smooth / Q000187:drug effects; D011714:Pyrans / Q000138:chemical synthesis* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013601:T-Lymphocytes / Q000187:drug effects / Q000821:virology
D019380:Anti-HIV Agents; D000970:Antineoplastic Agents; D001562:Benzimidazoles; D005663:Furans; D011714:Pyrans