Synthesis and antibacterial activity of N-amino-derivatives of condensed pyridines

Background & Objective:New diaryl-substituted pyrimidinedione compounds, their thioxo derivatives as well as their bicyclic thiazole compounds were synthesized and characterized.Methods:The glycosylamino derivatives of the synthesized disubstituted derivatives of the pyrimidine scaffold were also prepared via reaction of the N3-amino derivatives with a number of monosaccharides followed by acetylation.Results:The anticancer activity of the synthesized compounds was studied against human liver cancer (HepG2) and RPE-1cell lines. Compounds 2a, 2b, 3a and 12 showed potent activities with IC50 results comparable to that of doxorubicin.Conclusion:Docking investigations into Cyclin-dependent kinase 2 (CDK-2) enzyme, a potential target for cancer medication, were also reported showing the possible binding interaction into the enzyme active site to support their activity behavior.

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Synthesis and Evaluation of Aromatic Surfactants as Potential Antibacterial and Cytotoxic Agents

Letters in Organic Chemistry ◽

10.2174/1570178615666181023151308 ◽

2019 ◽

Vol 16 (6) ◽

pp. 478-484

Author(s):

Kenia Barrantes ◽

Mary Fuentes ◽

Luz Chacón ◽

Rosario Achí ◽

Jorge Granados-Zuñiga ◽

...

Keyword(s):

Antibacterial Activity ◽

Hela Cells ◽

Cytotoxic Agents ◽

Cytotoxic Activities ◽

Hydroxybenzoic Acid ◽

Derivatives Of

Two ether and one ester derivatives of the 4-nitro-3-hydroxybenzoic acid were synthesized and characterized. The in vitro antimicrobial and cytotoxic activities of the three novel compounds were also evaluated. The aromatic derivatives showed antibacterial activity against one of the four microorganisms tested and two compounds (C8 and NOBA) had a lower IC50 in HeLa cells.

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The Effect of N-4 Substituent on Antibacterial Activity of Novel Hydroxymethyl/Aminomethyl Derivatives of 1,2,4-Triazole-3-thione

Letters in Drug Design & Discovery ◽

10.2174/157018012800673056 ◽

2012 ◽

Vol 9 (6) ◽

pp. 633-637 ◽

Cited By ~ 1

Author(s):

Tomasz Plech ◽

Monika Wujec ◽

Urszula Kosikowska ◽

Anna Malm ◽

Magdalena Barylka ◽

...

Keyword(s):

Antibacterial Activity ◽

Aminomethyl Derivatives ◽

Derivatives Of

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Structure-Activity Relationship and Antimicrobial Evaluation of N-Phenylpyrazole Curcumin Derivatives

Current Bioactive Compounds ◽

10.2174/1573407215666190124115010 ◽

2020 ◽

Vol 16 (4) ◽

pp. 481-488

Author(s):

Heli Sanghvi ◽

Satyendra Mishra

Keyword(s):

Antibacterial Activity ◽

Gram Negative Bacteria ◽

Pyrazole Derivatives ◽

Gram Positive ◽

Gram Negative ◽

E Coli ◽

Curcumin Derivatives ◽

Structure Activity ◽

Electron Donating Groups ◽

Derivatives Of

Background: Curcumin, one of the most important pharmacologically significant natural products, has gained significant consideration among scientists for decades since its multipharmacological activities. 1, 3-Dicarbonyl moiety of curcumin was found to be accountable for the rapid degradation of curcumin molecule. The aim of present work is to replace 1, 3-dicarbonyl moiety of curcumin by pyrazole and phenylpyrazole derivatives with a view to improving its stability and to investigate the role of substitution in N-phenylpyrazole curcumin on its antibacterial activity against both Gram-positive as well as Gram-negative bacteria. Methods: Pyrazole derivatives of curcumin were prepared by heating curcumin with phenyhydrazine/ substituted phenyhydrazine derivatives in AcOH. The residue was purified by silica gel column chromatography. Structures of purified compounds were confirmed by 1H NMR and Mass spectroscopy. The synthesized compounds were evaluated for their antibacterial activity by the microdilution broth susceptibility test method against gram positive (S. aureus) and gram negative (E. coli). Results: Effects of substitution in N-phenylpyrazole curcumin derivatives against S. aureus and E. coli were studied. The most active N-(3-Nitrophenylpyrazole) curcumin (12) exhibits twenty-fold more potency against S. aureus (MIC: 10μg/mL)) and N-(2-Fluoroophenylpyrazole) curcumin (5) fivefold more potency against E. coli (MIC; 50 μg/mL) than N-phenylpyrazole curcumin (4). Whereas, a remarkable decline in anti-bacterial activity against S. aureus and E. coli was observed when electron donating groups were incorporated in N-phenylpyrazole curcumin (4). Comparative studies of synthesized compounds suggest the effects of electron withdrawing and electron donating groups on unsubstituted phenylpyrazole curcumin (4). Conclusion: The structure-activity relationship (SAR) results indicated that the electron withdrawing and electron donating at N-phenylpyrazole curcumin played key roles for their bacterial inhibitory effects. The results of the antibacterial evaluation showed that the synthesized pyrazole derivatives of curcumin displayed moderate to very high activity in S. aureus. In conclusion, the series of novel curcumin derivatives were designed, synthesized and tested for their antibacterial activities against S. aureus and E. coli. Among them, N-(3-Nitrophenylpyrazole curcumin; 12) was most active against S. aureus (Gram-positive) and N-(2-Fluoroophenylpyrazole) curcumin (5) against E. coli (Gram-negative) bacteria.

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Thermal cyclocondensations of 3-N(4- and 5-benzimidazolyl and benztriazolyl)amino derivatives of 2-propenoic acid

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19872918 ◽

1987 ◽

Vol 52 (12) ◽

pp. 2918-2925 ◽

Cited By ~ 10

Author(s):

Viktor Milata ◽

Dušan Ilavský

Keyword(s):

Uv Spectra ◽

Propenoic Acid ◽

Amino Derivatives ◽

Derivatives Of ◽

C Nmr ◽

Ir And Uv Spectra

The cyclization of 3-N(4- and 5-benzimidazolyl and benztriazolyl)amino-2-cyano- and 2-ethoxycarbonyl-2-propenoate esters Ia, b-IVa, b under the conditions of the Gould-Jacobs reaction leads to angularly ring-fused substituted imidazo or triazolo[4,5-f] (V, VI) and [4,5-h] (VII, VIII) quinolines, respectively. The esters Vb-VIIIb have been transformed into the corresponding chloroderivatives Vc-VIIIc. 3-N(5-Benzimidazolyl and 5-benztriazolyl)amino-2-cyano-2-propenenitriles are cyclized in the presence of aluminium(III) chloride to give the aminoquinolines Vd, VId. The structure of the products has been characterized by their 1H, 13C NMR, IR, and UV spectra.

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