Synthesis and Antimicrobial Studies of Some Novel Bis-[1,3,4]thiadiazole and Bis-thiazole Pendant to Thieno[2,3-b]thiophene Moiety
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
Reactions of Compound 1 with Hydrazonoyl Halides 3a or 3b-d or 3e-g or 3-(2-bromoacetyl)-2Hchromen- 2-one (7)
General Procedure
3,3′-(3,4-Dimethylthieno[2,3-b]thiophene-2,5-diyl)bis(2-(3,5-diphenyl-1,3,4-thiadiazol-2(3H)- ylidene)-3-oxopropanenitrile) (6a)
Diethyl 5,5′-(2,2′-(3,4-dimethylthieno[2,3-b]thiophene-2,5-diyl)bis(1-cyano-2-oxoethan-2-yl-1- ylidene))bis(4-phenyl-4,5-dihydro-1,3,4-thiadiazole-2-carboxylate)(6b)
Diethyl 5,5′-(2,2′-(3,4-dimethylthieno[2,3-b]thiophene-2,5-diyl)bis(1-cyano-2-oxoethan-2-yl-1- ylidene))bis(4-p-tolyl-4,5-dihydro-1,3,4-thiadiazole-2-carboxylate) (6c)
Diethyl 5,5′-(2,2′-(3,4-dimethylthieno[2,3-b]thiophene-2,5-diyl)bis(1-cyano-2-oxoethan-2-yl-1- ylidene))bis(4-(4-chlorophenyl)-4,5-dihydro-1,3,4-thiadiazole-2-carboxylate)(6d)
3,3′-(3,4-Dimethylthieno[2,3-b]thiophene-2,5-diyl)bis(2-(5-acetyl-3-p-tolyl-1,3,4-thiadiazol-2(3H)- ylidene)-3-oxopropanenitrile)(6e)
3,3′-(3,4-Dimethylthieno[2,3-b]thiophene-2,5-diyl)bis(2-(5-acetyl-3-(4-chlorophenyl)-1,3,4- thiadiazol-2(3H)-ylidene)-3-oxopropanenitrile)(6f)
3,3′-(3,4-Dimethylthieno[2,3-b]thiophene-2,5-diyl)bis(2-(5-acetyl-3-(3-chlorophenyl)-1,3,4- thiadiazol-2(3H)-ylidene)-3-oxopropanenitrile)(6g)
3,3′-(3,4-Dimethylthieno[2,3-b]thiophene-2,5-diyl)bis(3-oxo-2-(4-(2-oxo-2H-chromen-3-yl)-3- phenylthiazol-2(3H)-ylidene)propanenitrile) (10)
Diethyl 2,2′-(2,2′-(3,4-dimethylthieno[2,3-b]thiophene-2,5-diyl)bis(1-cyano-2-oxoethan-2-yl-1- ylidene))bis(4-methyl-3-phenyl-2,3-dihydrothiazole-5-carboxylate) (13)
3.1. Antimicrobial Evaluation
4. Conclusions
Acknowledgments
References
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Sample/Tested Organism | 6a | 6b | 6c | 6d | 6e | 6f | 6g | 10 | Standard | |
---|---|---|---|---|---|---|---|---|---|---|
Fungi | Itraconazole | Clotrimazole | ||||||||
Aspergillus fumigatus (AF) | 11.7 ± 0.2 | 15.4 ± 0.09 | 13.3 ± 0.2 | 16.4 ± 0.3 | 9.3 ± 0.2 | 17.4 ± 0.08 | 12.2 ± 0.09 | 14.3 ± 0.2 | 28.5 ± 0.05 | 26 ± 0.1 |
Geotrichum candidum (GC) | 13.5 ± 0.1 | 14.9 ± 0.05 | 14.4 ± 0.1 | 18.1 ± 0.08 | 11.4 ± 0.1 | 18.3 ± 0.3 | 14.4 ± 0.03 | 16.7 ± 0.08 | 27.1 ± 0.06 | 23.1 ± 0.03 |
Candida albicans (CA) | 10.4 ± 0.08 | NA | 10.2 ± 0.09 | 13.7 ± 0.05 | NA | NA | NA | 11.9 ± 0.1 | 26.1 ± 0.02 | 18.3 ± 0.01 |
Syncephalastrum racemosum (SR) | NA | 12.1 ± 0.08 | NA | NA | 8.2 ± 0.09 | 14.2 ± 0.08 | 9.2 ± 0.08 | NA | 22.3 ± 0.09 | 20.5 ± 0.02 |
Gram Positive Bacteria | Penicillin G | Streptomycin | ||||||||
Staphylococcus aureus (SA) | 11.2 ± 0.1 | 17.9 ± 0.05 | 11.3 ± 0.05 | 15.4 ± 0.5 | 9.4 ± 0.05 | 18.9 ± 0.01 | 13.8 ± 0.1 | 13.4 ± 0.3 | 29.4 ± 0.08 | 25.1 ± 0.08 |
Bacillis subtilis (BS) | 13.7 ± 0.07 | 16.1 ± 0.01 | 9.0 ± 0.08 | 18.4 ± 0.1 | 10.6 ± 0.08 | 20.9 ± 0.03 | 16.6 ± 0.03 | 14.7 ± 0.09 | 32.5 ± 0.06 | 29.1 ± 0.04 |
Gram Negative Bacteria | Penicillin G | Streptomycin | ||||||||
Pseudomonas aeruginosa (PA) | NA | 10.1 ± 0.01 | NA | NA | NA | 12.1 ± 0.01 | NA | NA | 28.3 ± 0.05 | 24.3 ± 0.08 |
Escherichia coli (EC) | 8.3 ± 0.09 | 14.5 ± 0.2 | 10.1 ± 0.07 | 13.7 ± 0.05 | 7.4 ± 0.07 | 15.2 ± 0.5 | 9.5 ± 0.2 | 10.9 ± 0.2 | 33.5 ± 0.7 | 25.6 ± 0.04 |
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Kheder, N.A.; Mabkhot, Y.N. Synthesis and Antimicrobial Studies of Some Novel Bis-[1,3,4]thiadiazole and Bis-thiazole Pendant to Thieno[2,3-b]thiophene Moiety. Int. J. Mol. Sci. 2012, 13, 3661-3670. https://doi.org/10.3390/ijms13033661
Kheder NA, Mabkhot YN. Synthesis and Antimicrobial Studies of Some Novel Bis-[1,3,4]thiadiazole and Bis-thiazole Pendant to Thieno[2,3-b]thiophene Moiety. International Journal of Molecular Sciences. 2012; 13(3):3661-3670. https://doi.org/10.3390/ijms13033661
Chicago/Turabian StyleKheder, Nabila Abdelshafy, and Yahia Nasser Mabkhot. 2012. "Synthesis and Antimicrobial Studies of Some Novel Bis-[1,3,4]thiadiazole and Bis-thiazole Pendant to Thieno[2,3-b]thiophene Moiety" International Journal of Molecular Sciences 13, no. 3: 3661-3670. https://doi.org/10.3390/ijms13033661