Synthesis of Novel Thiazole-Based Heterocycles as New Anti-bacterial and Anti-fungal Agents. | ||||
| Egyptian Journal of Chemistry | ||||
| Volume 66, Issue 13, December 2023, Page 733-743 PDF (618 K) | ||||
| Document Type: Original Article | ||||
| DOI: 10.21608/ejchem.2023.180589.7326 | ||||
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| Authors | ||||
Marwa M. Fouad   1; Ahmad M. Farag 2; Galal H. Elgemeie 3; N. O. Shaker4; N. A. Alian4
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| 1Basic Sciences Department, Modern Academy for Engineering & Technology, Cairo, Egypt | ||||
| 2Chemistry department, Faculty of Science, Cairo University, Giza, Egypt | ||||
| 3Chemistry department, Faculty of Science, Helwan University, Cairo, Egypt | ||||
| 4Chemistry department, Faculty of Science (Girls), Al-Azhar University, Cairo, Egypt | ||||
| Abstract | ||||
| Due to the potential biological and medicinal effects of heterocyclic moieties, they have attracted attention, so the objective of the current work is to create some newly generated heterocyclic compounds with anticipated biological activity. This can be accomplished by reacting 5-methylthiazol-2-amine (1) and ethyl cyanoacetate (2) to yield 2-cyano-N-(5-methylthiazol-2-yl)acetamide (3). Compouund 3 reacts with aromatic aldehydes, aromatic diazonium salts 5a-c, hydrozonoyl halide derivatives 7a-c, active methylene reagents 2,11,14 , hydrazines and ethyl 2-cyanoacrylate derivatives 19a,b to form the corresponding acrylamide derivatives 4a,b, hydrazones 6a-c, aminopyrazoles 9a-c, pyridine-3-carbonitrile derivatives 13a,b,16, aminopyrazoles 18a,b and oxopyridine-3-carboxylate derivatives 21a,b, respectively. The sensitivity of acrylamide 4a to several chemical substances was investigated through its reaction with ethyl cyanoacetate (2), hydrazines, 3-amino-(2H)-1,2,4-triazole (28) and 5-methylthiazol-2-amine (1) to form phenylpyridine-3-carboxylate derivative 24, aminopyrazole derivatives 27a,b, triazolo[1,5-a]pyrimidine derivative 30 and thiazolo[3,2-a]pyrimidine derivative 32, respectively. All synthesized compounds' structures were verified using infrared radiation, 1H-NMR, and 13C-NMR. In addition, mass spectroscopy and elemental assessment were done. The antibacterial and antifungal properties of some of the created substances were also examined. From all the investigated substances, only 3, 9a, 9c, 4a, and 6c demonstrated good antibacterial activity, while compounds 16, 21a, 21b, and 24 demonstrated effective antifungal and antibacterial activities towards bacterial strains that were either Gram-positive or Gram-negative. | ||||
| Keywords | ||||
| Acrylamide; Aminopyrazole; Carbonitrile; Cyanoa acetamide; Hydrazines; Hydrozonoyl halide | ||||
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