title: Synthesis and characterization of new N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)amide/sulfonamide derivatives as possible antimicrobial and antitubercular agents.
abstract: 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.
authors.affiliation: School of Chemical Sciences, Kannur University, Payyanur Campus, Edat P.O., 670327 Kannur, Kerala, India. Electronic address: pkranjith@rediffmail.com.
authors.forename: Pakkath Karuvalam
authors.initials: PK
authors.lastname: Ranjith
authors.affiliation: School of Chemical Sciences, Kannur University, Payyanur Campus, Edat P.O., 670327 Kannur, Kerala, India.
authors.forename: Rajeesh
authors.initials: R
authors.lastname: Pakkath
authors.affiliation: School of Chemical Sciences, Kannur University, Payyanur Campus, Edat P.O., 670327 Kannur, Kerala, India. Electronic address: krharidas2001@yahoo.com.
authors.forename: Karickal R
authors.initials: KR
authors.lastname: Haridas
authors.affiliation: Department of Biochemistry, Justice K.S. Hegde Medical Academy, Deralakatte, India.
authors.forename: Suchetha N
authors.initials: SN
authors.lastname: Kumari
mesh_terms: D000577:Amides / Q000737:chemistry* / Q000494:pharmacology*; D000890:Anti-Infective Agents / Q000737:chemistry* / Q000494:pharmacology*; D000995:Antitubercular Agents / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001424:Bacterial Infections / Q000188:drug therapy; D005658:Fungi / Q000187:drug effects; D006801:Humans; D007093:Imidazoles / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D009181:Mycoses / Q000188:drug therapy; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000577:Amides; D000890:Anti-Infective Agents; D000995:Antitubercular Agents; D007093:Imidazoles; D013449:Sulfonamides; C029899:imidazole
keywords: Antimicrobial activity; Antimycobacterial activity; Imidazole; Pd(2)(dba)(3); RuPhos