Synthesis and Antimicrobial Activity of Nitroalkenyl Arenes was written by Nicoletti, Gina;Cornell, Hugh James;Hugel, Helmut Martin;White, Kylie S.;Nguyen, Thu;Zalizniak, Liliana;Nugegoda, Dayanthi. And the article was included in Anti-Infective Agents in 2013.Reference of 58442-17-4 This article mentions the following:
We report here on the synthesis of substituted nitroalkenyl arenes and their evaluation for microbiol. activity and for development as anti-infective drugs. Twenty compounds, based on the nitropropenyl benzene structure (1), were synthesized, chem. characterized and investigated for their min. inhibitory concentration (MIC) to bacteria and fungi and for toxicity to zebrafish eggs and embryos for comparative evaluation of potential mammalian toxicity. The compounds were broadly antimicrobial, with greater activity overall against Gram-pos. bacteria and fungi and less against enteric Gram-neg. rods. The antimicrobial activity spectrum of the compounds varied greatly. Two compounds, 14 (5-[(E)-2-nitroprop-1-enyl]-1,3-benzodioxole) and 9 (4-[(E)-2-nitroprop-1-enyl]-1-fluorobenzene), were the most broadly antimicrobial. The chem. groups most closely associated with microbial toxicity were the β-nitropropenyl side chain, fluoro, methylenedioxy and thiazole substitutions on the benzene ring. Thirteen compounds inhibited hatching of zebrafish eggs at concentrations ≤6 μg/mL. Egg toxicity did not correlate with inhibition of microbial growth or with rodent toxicity where data were available. Four compounds were investigated for effect on zebrafish embryonic development. The major effect observed was reduction of heart rate at 24 h with minimal or no morphol. abnormalities at the highest doses. It is hypothesised that this series of compounds act as tyrosine mimetics, inhibiting protein tyrosine phosphatases (PTP) and interfering with cell signaling in microorganisms. The data confirms the diversity in function and distribution of bacterial PTPs and the potential for the design of further nitroalkenyl arenes active against specific pathogens. In the experiment, the researchers used many compounds, for example, 1H-Benzimidazole-5-carbaldehyde (cas: 58442-17-4Reference of 58442-17-4).
1H-Benzimidazole-5-carbaldehyde (cas: 58442-17-4) belongs to imidazole derivatives. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Reference of 58442-17-4
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem