Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro-salicylaldehyde.
A series of Schiff bases (compounds 1-26) were synthesized by reacting 5-chloro-salicylaldehyde and primary amines, 15 (compounds 2-4, 6, 7, 10, 12-17, 23, 25 and 26) of which were first reported. The chemical structures of these compounds were confirmed by means of (1)H NMR, (13)C NMR, ESI-MS and elemental analyses. The compounds were assayed for antibacterial (Bacillus subtilis, Escherichia coli, Pseudomonas fluorescence and Staphylococcus aureus) and antifungal (Aspergillus niger, Candida albicans and Trichophyton rubrum) activities by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl trtrazolium bromide) method. Among the compounds tested, (E)-4-chloro-2-((4-fluorobenzylimino)methyl)phenol (2) showed the most favorable antimicrobial activity with MICs of 45.2, 1.6, 2.8, 3.4, and 47.5 microg/mL against B. subtilis, E. coli, P. fluorescence, S. aureus and A. niger, respectively.
Shi
Lei
L
Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, Jiangsu 210093, People's Republic of China.
Ge
Hui-Ming
HM
Tan
Shu-Hua
SH
Li
Huan-Qiu
HQ
Song
Yong-Chun
YC
Zhu
Hai-Liang
HL
Tan
Ren-Xiang
RX
D000447:Aldehydes / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects*; D005658:Fungi / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D012545:Schiff Bases / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
C527448:5-chloro-salicylaldehyde; D000447:Aldehydes; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D012545:Schiff Bases