Bayram G.Nzeyimana A.Utku S.Ülger M.Aslan G.Berçin E.2023-01-122023-01-122022101539181015-3918https://doi.org/10.33483/jfpau.867768qhttps://hdl.handle.net/11454/79912Objective: 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.en10.33483/jfpau.867768qinfo:eu-repo/semantics/closedAccess-methyl- -nitrostyreneAntibacterial activityantifungal activityantimycobacterial activityMichael type addition2 amino 3 [(2 nitro 1 phenylpropyl)sulfanyl]propanoic acid2 amino 3 [(2 nitro 1 phenylpropyl)thio]propanoic acid2 amino 3 [[1 (4 chlorophenyl) 2 nitropropyl]sulfanyl]propanoic acid2 amino 3 [[1 (4 hydroxy 3 methoxyphenyl) 2 nitropropyl]sulfanyl]propanoic acid2 amino 3 [[1 (4 methoxyphenyl) 2 nitropropyl]sulfanyl]propanoic acid2 amino 3 [[1 (4 methylphenyl) 2 nitropropyl]sulfanyl]propanoic acid2 amino 3 [[1 (4 nitrophenyl) 2 nitropropyl]sulfanyl]propanoic acid2 amino 3 [[1 [4 (dimethylamino)phenyl] 2 nitropropyl]sulfanyl]propanoic acidampicillinantifungal agentantiinfective agentaromatic compoundbenzaldehyde derivativebeta methyl beta nitrostyrenecysteineethanefluconazoleisoniazidnitroethaneresazurinrifampicintuberculostatic agentunclassified drugaldol reactionantibacterial activityantibiotic resistanceantifungal activityantimicrobial activityArticleBacillus subtilisbacterial strainbroth dilutionCandida albicanschemical structurediastereoisomerdrug designdrug synthesiselectrospray mass spectrometryelemental analysisEnterococcus faeciumFourier transform infrared spectroscopyfungal strainin vitro studyliquid chromatography-mass spectrometryMichael additionminimum inhibitory concentrationMycobacterium tuberculosisnonhumanpharmacophoreproton nuclear magnetic resonanceretention timethin layer chromatographyturbidityArticle4621821932-s2.0-85131886725Q4