STUDY ON SYNTHESIS AND ANTIMICROBIAL ACTIVITIES OF SOME MICHAEL-TYPE ADDITION COMPOUNDS

Year 2021, Volume: 45 Issue: 2, 182 - 193, 31.05.2021

Gül Bayram , Abdoul Nzeyımana Semra Utku , Mahmut Ülger , Gönül Aslan , Erdoğan Berçın

https://doi.org/10.33483/jfpau.867768

Abstract

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 β-methyl-β-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 µg/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 µg/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.

Keywords

Antibacterial activity, antifungal activity, antimycobacterial activity, β-methyl-β-nitrostyrene, Michael type addition

Supporting Institution

Mersin University

Project Number

2018-1-AP2-2782.

Thanks

This work was supported by the Mersin University Scientific Research Funds (Grant number 2018-1-AP2-2782).

BAZI MICHAEL TİPİ KATIM ÜRÜNLERİNİN SENTEZ ÇALIŞMASI VE ANTİMİKROBİYAL AKTİVİTELERİ

Abstract

Amaç: Çoklu ilaca dirençli patojenik bakteri, mantar ve Mycobacterium tuberculosis enfeksiyonları dünya çapında giderek yaygınlaşmaya devam etmektedir. Organik kimyada, tiya-Michael tipi katım ayrıca biyoaktif bileşiklerin sentezinde önemli bir reaksiyondur. Bu çalışmada, 2-amino-3-[(2-nitro-1-fenilpropil)tiyo]propanoik asit Michael tip yeni katım ürünlerinin (IIa-IIg) sentezi ve antibakteriyel, antifungal ve antitüberküler aktivitelerinin araştırılması amaçlanmıştır.

Gereç ve Yöntem: L-sistein ile β-metil-β-nitrostirenlerdenin (Ia-Ig) Michael katım reaksiyonu kullanılarak IIa-IIg türevleri sentezlenmiş ve yapıları ¹HNMR, FTIR, ESI-LC/MS ve elemental analiz ile karakterize edilmiştir. Mikrodilüsyon yöntemi ve resazurin mikrotitre deneyi antimikrobiyal aktivitelerinin belirlenmesinde kullanılmıştır.

Sonuç ve Tartışma: Sentezlenen bileşiklerin aktiviteleri karşılaştırıldığında, IIa, IId ve IIe Mycobacterium tuberculosis H37Rv suşuna karşı, 1.95 µg/ml’lik MIC değeri ile dikkat çekici aktiviteye sahip olarak bulunmuştur. Yeni sentezlenen bileşiklerin hepsi test edilen bakteri ve mantar suşlarına karşı orta derecede aktivite göstermişlerdir. Sentezlenen bileşikler arasında, IIb, B. subtilis, E. faecium ve C. albicans'a karşı sırasıyla 31.25, 31.25 ve 15.6 µg/ml MIC değerleri ile en iyi antibakteryel ve antifungal aktivite sergilemiştir Sentezlenen bazı bileşikler gösterdikleri antimikobakteriyel aktiviteden dolayı klinik kullanım için iyi bir aday olacakları açıktır.

Keywords

Antibakteriyel aktivite, antifungal aktivite, antimikobakteriyel etki, β-metil-β-nitrostiren, Michael tip katılım

Project Number

2018-1-AP2-2782.

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