STUDY ON SYNTHESIS AND ANTIMICROBIAL ACTIVITIES OF SOME MICHAEL-TYPE ADDITION COMPOUNDS
Küçük Resim Yok
Tarih
2022
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
University of Ankara
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
Objective: Multidrug-resistant pathogenic bacteria, fungi, and Mycobacterium tuberculosis infections continue to be increasingly widespread worldwide. In organic chemistry, the tiya-Michael type addition is also significant reaction in the synthesis of bioactive compounds. In this study, the aim is to synthesize the series of new Michael type addition products 2-amino-3-[(2-nitro-1-phenylpropyl)thio]propanoic acid (IIa-IIg) and to investigate their in vitro, antibacterial, antifungal and antitubercular activity. Material and Method: IIa-IIg derivatives were performed combining ?-methyl-?-nitrostyrenes (Ia-Ig) with L-cysteine using Michael addition reaction and characterized by 1HNMR, FTIR, ESI-LC/MS and elemental analysis. Microdilution method and resazurin microtiter assay were used to determine antimicrobial activities. Result and Discussion: Comparing the activities of the synthesized compounds, IIa, IId and IIe were found to have significant activity, with a MIC value of 1.95 ?g/ml, against Mycobacterium tuberculosis H37Rv strain. All synthesized novel compounds displayed moderate activity against tested bacterial and fungi strains. Among the synthesized compounds, IIb exhibited the best antibacterial and antifungal activity, with MIC values of 31.25, 31.25 and 15.6 ?g/ml, against B. subtilis, E. faecium and C. albicans, respectively. It was clear that some of the synthesized compounds exhibited antimycobacterial activity which could be a very good candidate for clinical uses. © 2022 University of Ankara. All rights reserved.
Açıklama
Anahtar Kelimeler
-methyl- -nitrostyrene, Antibacterial activity, antifungal activity, antimycobacterial activity, Michael type addition, 2 amino 3 [(2 nitro 1 phenylpropyl)sulfanyl]propanoic acid, 2 amino 3 [(2 nitro 1 phenylpropyl)thio]propanoic acid, 2 amino 3 [[1 (4 chlorophenyl) 2 nitropropyl]sulfanyl]propanoic acid, 2 amino 3 [[1 (4 hydroxy 3 methoxyphenyl) 2 nitropropyl]sulfanyl]propanoic acid, 2 amino 3 [[1 (4 methoxyphenyl) 2 nitropropyl]sulfanyl]propanoic acid, 2 amino 3 [[1 (4 methylphenyl) 2 nitropropyl]sulfanyl]propanoic acid, 2 amino 3 [[1 (4 nitrophenyl) 2 nitropropyl]sulfanyl]propanoic acid, 2 amino 3 [[1 [4 (dimethylamino)phenyl] 2 nitropropyl]sulfanyl]propanoic acid, ampicillin, antifungal agent, antiinfective agent, aromatic compound, benzaldehyde derivative, beta methyl beta nitrostyrene, cysteine, ethane, fluconazole, isoniazid, nitroethane, resazurin, rifampicin, tuberculostatic agent, unclassified drug, aldol reaction, antibacterial activity, antibiotic resistance, antifungal activity, antimicrobial activity, Article, Bacillus subtilis, bacterial strain, broth dilution, Candida albicans, chemical structure, diastereoisomer, drug design, drug synthesis, electrospray mass spectrometry, elemental analysis, Enterococcus faecium, Fourier transform infrared spectroscopy, fungal strain, in vitro study, liquid chromatography-mass spectrometry, Michael addition, minimum inhibitory concentration, Mycobacterium tuberculosis, nonhuman, pharmacophore, proton nuclear magnetic resonance, retention time, thin layer chromatography, turbidity
Kaynak
Ankara Universitesi Eczacilik Fakultesi Dergisi
WoS Q Değeri
Scopus Q Değeri
Q4
Cilt
46
Sayı
2
