Research on Chemical Intermediates p. 4459 - 4477 (2016)
Update date:2022-08-06
Topics:
Tumosien?
Jonu?kien?
Kantminien?
?iug?dait?
Mickevi?ius
Beresnevi?ius
Abstract: 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. Graphical Abstract: 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–.[Figure not available: see fulltext.]
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