Synthesis, Thermolysis, Photolysis and Antimicrobial Evaluation of some Novel Semicarbazones and Thiosemicarbazones Derived from 3-Methyl-2- benzothiazolinone Hydrazone | ||
| Egyptian Journal of Chemistry | ||
| Article 13, Volume 59, Issue 5, October 2016, Pages 867-885 PDF (843.68 K) | ||
| DOI: 10.21608/ejchem.2016.1483 | ||
| Abstract | ||
| REACTION of 3-methyl-2-benzothiazolinone hydrazone (1) with ...... some selected isocyanate and isothiocyanate reagents 2a−j gave the respective semicarbazones and thiosemicarbazones 3a−j. Thermolysis of compound 3a under reduced pressure gave N,N`−diethylurea (4) in addition to 1,2-bis(3-methylbenzo[d]thiazol- 2(3H)-ylidene)hydrazine (5). Compound 3a was almost quantitatively recovered upon its exposure to sunlight in methanol for 60 days. Elementary and spectroscopic measurements (IR, 1H NMR, 13C NMR, MS) are in good accord with the structures postulated for the new compounds. The single crystal X-ray crystallographic analysis of 3f was given and its data were discussed. The synthesized compounds 3aj as well as the hydrazone 1 were screened for their antibacterial properties against Bacillus subtilis (G+), Escherichia coli (G-), Pseudomonas aeruginosa (G-) and Staphylococcus aureus (G+) and for their antifungal properties against Aspergillus flavus and Candida albicans. Some of the tested compounds showed an activity against the four bacterial strains where their order of activity was found to be 1 > 3g > 3j > 3i > 3e > 3h > 3a. The MIC90 value of compound 1 against P. aeruginosa was 9 mg/ml. On the other hand only compound 1 showed a significant activity against A. flavus fungal species where it recorded an inhibition zone diameter value (16 mm/mg) which is very near to that of the standard drug, amphotericin B (17 mm/mg). However, the C. albicans was found to be insensitive to all of the investigated compounds. | ||
| Keywords | ||
| 3-Methyl-2-benzothiazolinone hydrazone; Semicarbazones; Thiosemicarbazones; Azines; X-ray crystallographic analysis; antimicrobial activity | ||
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