[Synthesis and biological activity of isomeric 5- and 6-nitro-1-alkylbenzimidazoles].
Either the alkylation of 5(6)-nitro-benzimidazoles (R = H, CH3) or the nitration of 1-alkyl-benzimidazoles afforded corresponding mixtures of 1-alkyl-5-nitro- and 1-alkyl-6-nitro-benzimidazoles (III, IV, VII, VIII, XI). Fractional crystallization from water was employed for isolation of 6-nitro isomers V, VI and IX from mixtures III, IV and VII. On the other hand, application of this isolation method to mixtures VIII and XI proved unsuccessful. 6-Nitro-compound X and 5-nitro derivatives XIII and XV were obtained by direct syntheses. From calibration curves depicting dependence of absorbance of the mixtures upon their composition, percentage ratios of 5-nitro to 6-nitro isomers in the mixtures were estimated. Usefulness of thin-layer chromatography, and UV and IR spectrometry for identification of 5-nitro and 6-nitro isomers was stated; e. g. 5-nitro isomers have higher epsilon values, while 6-nitro isomers exhibit two vmax values of the benzene ring. Compounds IV, IX and X proved to exert antihelminthic, antibacterial and antiphlogistic activities.
Domagalina
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Zawisza
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D000818:Animals; D000890:Anti-Infective Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000969:Antinematodal Agents; D001424:Bacterial Infections / Q000188:drug therapy*; D001562:Benzimidazoles / Q000138:chemical synthesis / Q000627:therapeutic use*; D055598:Chemical Phenomena; D002621:Chemistry; D004353:Drug Evaluation, Preclinical; D007249:Inflammation / Q000188:drug therapy; D051379:Mice; D009349:Nematode Infections / Q000188:drug therapy*; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000627:therapeutic use*
D000890:Anti-Infective Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000969:Antinematodal Agents; D001562:Benzimidazoles; D009574:Nitro Compounds
Synteza i działanie biologiczne izomerycznych 5- i 6-nitro-1-alkilobenzimidazoli.