Synthesis and characterization of new N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)amide/sulfonamide derivatives as possible antimicrobial and antitubercular agents
| Autor: | Pakkath Karuvalam Ranjith, Suchetha Kumari, Rajeesh Pakkath, Karickal R. Haridas |
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| Rok vydání: | 2014 |
| Předmět: |
Klebsiella pneumoniae
Stereochemistry Antitubercular Agents Microbial Sensitivity Tests Structure-Activity Relationship chemistry.chemical_compound Anti-Infective Agents Amide Drug Discovery Humans Candida albicans Pharmacology chemistry.chemical_classification Sulfonamides Bacteria biology Mycobacterium smegmatis Organic Chemistry Fungi Imidazoles Bacterial Infections Mycobacterium tuberculosis General Medicine biology.organism_classification Antimicrobial Amides Sulfonamide Mycoses chemistry Mycobacterium fortuitum Antibacterial activity |
| Zdroj: | European Journal of Medicinal Chemistry. 71:354-365 |
| ISSN: | 0223-5234 |
| Popis: | In this paper we report the SAR studies of a series of N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)amide and N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)sulfonamide derivatives 6(a-o) and 7(a-o), were synthesized in good yields and characterized by (1)H NMR, (13)C NMR and mass spectral analyses. The preparation of the key intermediate highlights an optimized palladium catalyzed (Pd₂(dba)₃/RuPhos) Buchwald cross-coupling of intermediate 2 and 3. The newly synthesized compounds were evaluated for their in vitro antibacterial activity against Staphylococcus aureus, (Gram-positive), Escherichia coli and Klebsiella pneumoniae (Gram-negative), antifungal activity against Candida albicans, Aspergillus flavus and Rhizopus sp. and antitubercular activity against Mycobacterium tuberculosis H37Rv, Mycobacterium smegmatis, Mycobacterium fortuitum and MDR-TB strains. The synthesized compounds displayed interesting antimicrobial activity. The compounds 7d, 7f, 7h and 7n displayed significant activity against Mycobacterium tuberculosis H37Rv strain. |
| Databáze: | OpenAIRE |
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