Synthesis and biological activity of 1,3,4-oxa(thia)diazole, 1,2,4-triazole-5-(thio)one and S-substituted derivatives of 3-((2-carboxyethyl)phenylamino)propanoic acid
| Autor: | Zigmuntas Jonas Beresnevičius, V. Mickevičius, Ilona Jonuškienė, Kristina Kantminienė, Ingrida Tumosienė, Jūratė Šiugždaitė |
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| Rok vydání: | 2015 |
| Předmět: |
Antioxidant
010405 organic chemistry Stereochemistry Chemistry medicine.medical_treatment Thio 1 2 4-Triazole Biological activity General Chemistry 010402 general chemistry Antimicrobial 01 natural sciences Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound Propanoic acid medicine Diazole Antibacterial activity |
| Zdroj: | Research on Chemical Intermediates. 42:4459-4477 |
| ISSN: | 1568-5675 0922-6168 |
| DOI: | 10.1007/s11164-015-2290-0 |
| Popis: | A series of novel derivatives of 3-((2-carboxyethyl)phenylamino)propanoic acid bearing two identical substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole, or 1,2,4-triazole moieties were synthesized and their molecular structures were confirmed by IR, 1H, 13C NMR spectroscopy, and elemental analysis data. The synthesized compounds were screened for their reducing power, free radical scavenging, plant growth regulating, and antimicrobial properties. 5,5′-((Phenylazanediyl)bis(ethane-2,1-diyl))bis(4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione) showed excellent antioxidant activity, three times higher than that of the antibiotic control (cefazolin). 2,2′-((((Phenylazanediyl)bis(ethane-2,1-diyl))bis(4-phenyl-4H-1,2,4-triazole-5,3-diyl))bis(sulfanediyl))diacetate exhibited notable bactericidal activity against Pseudomonas aeruginosa with MBC and MIC values 7.3 µg/ml, whereas 12 compounds displayed significant fungicidal activity against Candida albicans with MIC value 3.9 µg/ml. Synthesis of compounds 2–27. R: 2, 5, 7, 10, 13, 15-27 C6H5–; 3, 8, 11 4-Cl-C6H4–; 4, 9, 12 CH3–; 6, 14 2.6-(CH3)2-C6H3–; R′: 15 CH3CH2–; 16 (CH3)2CH–; 17 (CH3)2CHCH2–; 18 CH3CH2CH2CH2–; 19 (CH3)2CHCH2CH2–; 20 CH3CH2CH2CH2CH2–; 21 NH2COCH2–; 22 C6H5CH2–; 23 C6H5COCH2–; 24 4-ClC6H4COCH2–; 25 4-NO2C6H4COCH2–; 26 C2H5OCOCH2–. |
| Databáze: | OpenAIRE |
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