Pyridine Derivatives—A New Class of Compounds That Are Toxic to E. coli K12, R2–R4 Strains

A preliminary study of 2-amino-4-aryl-3,5-dicarbonitrile-6-thiopyridines as new potential antimicrobial drugs was performed. Special emphasis was placed on the selection of the structure of target pyridine derivatives with the highest biological activity against different types of Gram-stained bacteria by lipopolysaccharide (LPS). Herein, Escherichia coli model strains K12 (without LPS in its structure) and R2–R4 (with different lengths of LPS in its structure) were used. Studied target compounds were provided with yields ranging from 53% to 91% by the lipase-catalyzed one pot multicomponent reaction of various aromatic aldehydes with malononitrile, and thiols. The presented work showed that the antibacterial activity of the studied pyridines depends on their structure and affects the LPS of bacteria. Moreover, the influence of the pyridines on bacteria possessing smooth and rough LPS and oxidative damage to plasmid DNA caused by investigated compounds was indicated. Additionally, the modification of the bacterial DNA with the tested compounds was performed to detect new potential oxidative damages, which are recognized by the Fpg protein. The obtained damage modification values of the analyzed compounds were compared with the modifications after antibiotics were used in this type of research. The presented studies demonstrate that 2-amino-4-aryl-3,5-dicarbonitrile-6-thiopyridines can be used as substitutes for known antibiotics. The observed results are especially important in the case of the increasing resistance of bacteria to various drugs and antibiotics.

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α-Amidoamids as New Replacements of Antibiotics—Research on the Chosen K12, R2–R4 E. coli Strains

Materials ◽

10.3390/ma13225169 ◽

2020 ◽

Vol 13 (22) ◽

pp. 5169

Author(s):

Paweł Kowalczyk ◽

Arleta Madej ◽

Mateusz Szymczak ◽

Ryszard Ostaszewski

Keyword(s):

Escherichia Coli ◽

Antibacterial Activity ◽

Biological Activity ◽

Plasmid Dna ◽

Alkyl Chain ◽

Antimicrobial Drugs ◽

E Coli ◽

Different Types ◽

Preliminary Study ◽

Selection Of

A preliminary study of α-amidoamids as new potential antimicrobial drugs was performed. Special emphasis was placed on selection of structure of α-amidoamids with the highest biological activity against different types of Gram-stained bacteria by lipopolysaccharide (LPS). Herein, Escherichia coli model strains K12 (without LPS in its structure) and R1–R4 (with different length LPS in its structure) were used. The presented work showed that the antibacterial activity of α-amidoamids depends on their structure and affects the LPS of bacteria. Moreover, the influence of various newly synthesized α-amidoamids on bacteria possessing smooth and rought LPS and oxidative damage of plasmid DNA caused by all newly obtained compounds was indicated. The presented studies clearly explain that α-amidoamids can be used as substitutes for antibiotics. The chemical and biological activity of the analysed α-amidoamids was associated with short alkyl chain and different isocyanides molecules in their structure such as: tetr-butyl isocyanide or 2,5-dimethoxybenzyl isocyanide. The observed results are especially important in the case of the increasing resistance of bacteria to various drugs and antibiotics.

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1,2-Diarylethanols—A New Class of Compounds That Are Toxic to E. coli K12, R2–R4 Strains

Materials ◽

10.3390/ma14041025 ◽

2021 ◽

Vol 14 (4) ◽

pp. 1025

Author(s):

Paweł Kowalczyk ◽

Damian Trzepizur ◽

Mateusz Szymczak ◽

Grzegorz Skiba ◽

Karol Kramkowski ◽

...

Keyword(s):

Biological Activity ◽

Bacterial Resistance ◽

Inhibitory Concentration ◽

Initial Study ◽

New Drugs ◽

Bacterial Dna ◽

E Coli ◽

New Class ◽

Chemical Groups ◽

Selection Of

An initial study of 1,2-diarylethanols derivatives as new potential antibacterial drugs candidates was conducted. Particular emphasis was placed on the selection of the structure of 1,2-diarylethanols with the highest biological activity of lipopolysaccharides (LPS) in the model strains of Escherichia coli K12 (without LPS in its structure) and R2–R4 (with different lengths of LPS in its structure). In the presented studies, based on the conducted minimum inhibitory concentration (MIC) and MBC tests, it was demonstrated that the antibacterial (toxic) effect of 1,2-diarylethanols depends on their structure and the length of LPS bacteria in the membrane of specific strains. Moreover, the oxidative damage of bacterial DNA isolated from bacteria after modification with newly synthesized compounds after application of the repair enzyme Fpg glycosylases was analysed. The analysed damage values were compared with modification with appropriate antibiotics; bacterial DNA after the use of kanamycin, streptomycin, ciprofloxacin, bleomycin and cloxicillin. The presented research clearly shows that 1,2-diarylethanol derivatives can be used as potential candidates for substitutes for new drugs, e.g., the analysed antibiotics. Their chemical and biological activity is related to two aromatic groups and the corresponding chemical groups in the structure of the substituent. The observed results are particularly important in the case of increasing bacterial resistance to various drugs and antibiotics, especially in nosocomial infections and neoplasms, and in the era of pandemics caused by microorganisms.

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Facile and efficient synthesis of a new class of bis(3′-indolyl)pyridine derivatives via one-pot multicomponent reactions

Tetrahedron Letters ◽

10.1016/j.tetlet.2008.01.054 ◽

2008 ◽

Vol 49 (11) ◽

pp. 1777-1781 ◽

Cited By ~ 83

Author(s):

Song-Lei Zhu ◽

Shun-Jun Ji ◽

Xiao-Ming Su ◽

Chang Sun ◽

Yu Liu

Keyword(s):

Multicomponent Reactions ◽

Pyridine Derivatives ◽

Efficient Synthesis ◽

One Pot ◽

New Class

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Selective synthesis of tetrahydroimidazo[1,2-a]pyridine and pyrrolidine derivatives via a one-pot two-step reaction

Organic & Biomolecular Chemistry ◽

10.1039/c7ob01860f ◽

2017 ◽

Vol 15 (38) ◽

pp. 8072-8077 ◽

Cited By ~ 8

Author(s):

Yu Zhang ◽

Jing Sun ◽

Guo-Liang Shen ◽

Chao-Guo Yan

Keyword(s):

Amino Acid ◽

Addition Reaction ◽

Aromatic Aldehydes ◽

Selective Synthesis ◽

Pyridine Derivatives ◽

Alkyl Esters ◽

One Pot

In the presence of triethylamine, the addition reaction of substituted α-amino acid alkyl esters with dialkyl but-2-ynedioate afforded active β-enamino esters, which in turn reacted with aromatic aldehydes and malononitrile to give tetrahydroimidazo[1,2-a]pyridine derivatives in moderate yields.

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Cu(OAc)2 as a green promoter for one-pot synthesis of 2-amino-4,6-diarylpyridine- 3-carbonitrile as antibacterial agents

Bulletin of the Chemical Society of Ethiopia ◽

10.4314/bcse.v34i1.14 ◽

2020 ◽

Vol 34 (1) ◽

pp. 149-156

Author(s):

Bi Bi Fatemeh Mirjalili ◽

Soghra Khabnadideh ◽

Ahmad Gholami ◽

Leila Zamani ◽

...

Keyword(s):

Bacterial Infections ◽

Acid Catalyst ◽

Aromatic Aldehydes ◽

Antimicrobial Activities ◽

Antimicrobial Drugs ◽

One Pot ◽

One Pot Synthesis ◽

Microdilution Method ◽

Acetophenone Derivatives ◽

Broth Microdilution Method

The extensive use of antimicrobial drugs and their resistance against bacterial infections have led to discover new antimicrobial compounds. In this study, we wish to report, one-pot synthesis of 2-amino-3-cyanopyridine derivatives (1a-14a). These compounds were synthesized in the presence of Cu(OAc)2 as a highly effective heterogeneous acid catalyst. Here we evaluated the antimicrobial activities of these compounds against different species of microorganisms including gram positive and gram negative bacteria as well as fungi. Standard antimicrobial methods include disc diffusion and Broth microdilution method according to the protocol of the Clinical and Laboratory Standards Institute (CLSI). Synthesis of 2-amino-3-cyanopyridine derivatives were done via reaction of aromatic aldehydes, acetophenone derivatives, malononitrile and ammonium acetate in the presence of Cu(OAc)2 under reflux condition. The results show compound 2-amino-6-(4-chlorophenyl)-4-phenylnicotinonitrile (10a) had the best antimicrobial efficacy toward C. albicans, E. faecalis, P. aeroginosa and E. coli. In conclusion, comparing the structure and activity of the compounds (10a), this compound with the presence of Cl residue at para-position of phenyl ring improves the antibacterial and antifungal activity. Bull. Chem. Soc. Ethiop. 2020, 34(1), 149-156. DOI: https://dx.doi.org/10.4314/bcse.v34i1.14

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ChemInform Abstract: Facile and Efficient Synthesis of a New Class of Bis(3′-indolyl)pyridine Derivatives via One-Pot Multicomponent Reactions.

ChemInform ◽

10.1002/chin.200826120 ◽

2008 ◽

Vol 39 (26) ◽

Author(s):

Song-Lei Zhu ◽

Shun-Jun Ji ◽

Xiao-Ming Su ◽

Chang Sun ◽

Yu Liu

Keyword(s):

Multicomponent Reactions ◽

Pyridine Derivatives ◽

Efficient Synthesis ◽

One Pot ◽

New Class

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Facile and Efficient Synthesis of a New Class of Indole-Substituted Pyridine Derivatives via One-Pot Multicomponent Reactions

Synthesis ◽

10.1055/s-0029-1216873 ◽

2009 ◽

Vol 2009 (16) ◽

pp. 2697-2708

Author(s):

Shun-Jun Ji ◽

Kai Zhao ◽

Xiao-Ping Xu ◽

Song-Lei Zhu ◽

Da-Qing Shi ◽

...

Keyword(s):

Multicomponent Reactions ◽

Pyridine Derivatives ◽

Efficient Synthesis ◽

One Pot ◽

New Class

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δ-Lactones—A New Class of Compounds That Are Toxic to E. coli K12 and R2–R4 Strains

Materials ◽

10.3390/ma14112956 ◽

2021 ◽

Vol 14 (11) ◽

pp. 2956

Author(s):

Paweł Kowalczyk ◽

Barbara Gawdzik ◽

Damian Trzepizur ◽

Mateusz Szymczak ◽

Grzegorz Skiba ◽

...

Keyword(s):

Biological Activity ◽

Pathogenic Bacteria ◽

Bacterial Resistance ◽

Biologically Active ◽

Toxic Activity ◽

Bacterial Dna ◽

E Coli ◽

New Class ◽

Anti Cancer ◽

Taste And Smell

Lactones are among the well-known organic substances with a specific taste and smell. They are characterized by antibacterial, antiviral, anti-inflammatory, and anti-cancer properties. In recent years, among this group of compounds, new biologically active substances have been searched by modifying the main (leading) structure with new analogs with stronger or different responses that may have a toxic effect on the cells of pathogenic bacteria and constitute an alternative to commonly used antibiotics. A preliminary study of δ-lactone derivatives as new potential candidates for antibacterial drugs was conducted. Particular emphasis was placed on the selection of the structure of lactones with the highest biological activity, especially those with fluorine in their structure as a substituent in terms of action on bacterial lipopolysaccharide (LPS) in the model strains of Escherichia coli K12 (without LPS in its structure) and R2–R4 (LPS of different lengths in its structure). In the presented studies, on the basis of the conducted MIC and MBC tests, it was shown that the antibacterial (toxic) activity of lactones depends on their structure and the length of the bacterial LPS in the membrane of specific strains. Moreover, oxidative damage of bacterial DNA isolated from bacteria after modification with newly synthesized compounds after application of the repair enzyme Fpg glycosylase was analyzed. The analyzed damage values were compared with the modification with appropriate antibiotics: ciprofloxacin, bleomycin, and cloxacillin. The presented research clearly shows that lactone derivatives can be potential candidates as substitutes for drugs, e.g., the analyzed antibiotics. Their chemical and biological activity is related to coumarin derivatives and the corresponding δ-lactone groups in the structure of the substituent. The observed results are of particular importance in the case of increasing bacterial resistance to various drugs and antibiotics, especially in nosocomial infections and neoplasms, and in the era of a microbial pandemic.

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Convenient Synthesis of 2,4-Disubstituted Chromeno[4,3-b]Pyridine by Microwave Assisted One Pot Three Component Protocol

Letters in Organic Chemistry ◽

10.2174/1570178617999200630125810 ◽

2020 ◽

Vol 17 ◽

Author(s):

Ghanshyam Jadhav ◽

Vijay Medhane ◽

Dattatray Deshmukh

Keyword(s):

Reaction Time ◽

Microwave Irradiation ◽

Aromatic Aldehydes ◽

Pyridine Derivatives ◽

Substituted Anilines ◽

One Pot ◽

Microwave Assisted ◽

Synthetic Strategy ◽

Convenient Synthesis ◽

Scalable Synthesis

: We herein, describe efficient and scalable synthesis of 2,4-diaryl substituted chromene [43-b] pyridine derivatives using multicomponent reaction strategy by microwave irradiation of 4-amino 2-oxo-2H-chromene, aromatic aldehydes and substituted anilines. This synthetic strategy was found to be very useful as it follows environment benign protocol, also it gives good outcome in terms of yield and requires shorter reaction time.

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