New piperidine-hydrazone derivatives: Synthesis, biological evaluations and molecular docking studies as AChE and BChE inhibitors

Karaman, Nurcan; Sıcak, Yusuf; Taşkın‐Tok, Tuğba; Karaküçük‐İyidoğan, Ayşegül; Dikmen, Miriş; Koçyığıt‐Kaymakcioğlu, Bedia; Oruç‐Emre, Emine Elçin

doi:10.1016/j.ejmech.2016.08.037

Cited by 48 publications

(10 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Hydrazide–hydrazones are of great interest due to their antibacterial, antifungal, antitubercular, antiviral, analgesic, anticonvulsant, and larvicidal activities . Hydrazide–hydrazones are also potent inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and poly(ADP‐ribose) glycohydrolase . Besides this, due to azomethine linkage in their structure, hydrazide–hydrazones play a significant role as organic intermediates for the development of new compounds …”

Section: Introductionmentioning

confidence: 99%

New hydrazide–hydrazones of isonicotinic acid: synthesis, lipophilicity and in vitro antimicrobial screening

et al. 2018

View full text Add to dashboard Cite

This study describes the synthesis, lipophilicity and in vitro antimicrobial assays of 15 new hydrazide-hydrazones of isonicotinic acid. New derivatives were obtained on the basis of the condensation reaction of isonicotinic acid hydrazide with different aromatic aldehydes. The chemical structure of synthesized compounds was confirmed by spectral methods. Experimental lipophilicity of new isonicotinic acid derivatives was determined using reversed-phase thin-layer chromatography. All synthesized compounds were subjected to in vitro antimicrobial assays against reference strains of Gram-positive bacteria, Gram-negative bacteria and fungi belonging to Candida spp. Some of the synthesized hydrazide-hydrazones proved to be significant antibacterial compounds and more potent than commonly used chemotherapeutic agents.

show abstract

Section: Introductionmentioning

confidence: 99%

New hydrazide–hydrazones of isonicotinic acid: synthesis, lipophilicity and in vitro antimicrobial screening

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Similarly, interactions of aromatic protons H h with C h carbon at 129.8 ppm, H i with C i carbon at 115 ppm, H e with C e carbon at 130.5 ppm, H f proton with C f carbon at 120.4 ppm were found. In the literature, it was reported that carbonyl peaks were observed at 160–180 ppm, so the peak at 160.79 ppm was accepted as carbonyl peak of oxazolidinone . As a result, the peaks at 131.72, 132.57, 136.81, 159.00 ppm belonged to the ipso carbons.…”

Section: Resultsmentioning

confidence: 99%

Design and evaluation of biological activities of 1,3‐oxazolidinone derivatives bearing amide, sulfonamide, and thiourea moieties

Karaman

Zainel

Kapkac

et al. 2018

Archiv der Pharmazie

Self Cite

View full text Add to dashboard Cite

1,3-Oxazolidine-2-one is an important heterocyclic ring participating in the chemical structure of many drugs. In this research, 22 new amide/sulfonamide/thiourea derivatives (1-22) were obtained by the reaction of (S)-4-(4-aminobenzyl)-2(1H)-1,3-oxazolidinone with 4-substituted benzoyl chlorides, 4-substituted benzene sulfonyl chlorides, and 4-substituted phenyl isothiocyanates. The structures of all synthesized compounds were clarified by FT-IR, NMR, and mass spectroscopic and elemental analysis techniques. The synthesized compounds were screened for their antimicrobial activity. Antimicrobial susceptibility and cellular physiology were evaluated using the microbroth dilution assay and the flow cytometry method. As a result, it was determined that compound 16 displayed better antimicrobial activity than chloramphenicol against Gram-positive bacteria, especially Staphylococcus aureus. In order to understand the mechanism of effect of the compounds on the cell membrane, fluorescence microscopy was used. Cell membrane damage of the Gram positive bacteria treated with compound 16 was observed as a result of intense staining with propidium iodide. In addition, genotoxicity, cytotoxicity, and absorption, distribution, metabolism, and excretion (ADME) parameters of compound 16 were examined and it was found as non-mutagenic and non-cytotoxic at the concentration at which it showed antimicrobial activity. According to the calculated ADME parameters and drug likeness scores, the compounds can be good drug candidates, especially compound 16.

show abstract

“…The docking method was also used to determine the BChE inhibitory mechanism of analog 202. A molecular docking investigation revealed that analog 202 connected to the BChE enzyme more efficiently than AChE owing to its orientations and various sorts of interactions with the enzyme 249 ( Table 8 ).…”

Section: Synthetic Cholinesterase Inhibitorsmentioning

confidence: 99%

Inhibitory potential of nitrogen, oxygen and sulfur containing heterocyclic scaffolds against acetylcholinesterase and butyrylcholinesterase

et al. 2022

View full text Add to dashboard Cite

show abstract

New piperidine-hydrazone derivatives: Synthesis, biological evaluations and molecular docking studies as AChE and BChE inhibitors

Cited by 48 publications

References 38 publications

New hydrazide–hydrazones of isonicotinic acid: synthesis, lipophilicity and in vitro antimicrobial screening

New hydrazide–hydrazones of isonicotinic acid: synthesis, lipophilicity and in vitro antimicrobial screening

Design and evaluation of biological activities of 1,3‐oxazolidinone derivatives bearing amide, sulfonamide, and thiourea moieties

Inhibitory potential of nitrogen, oxygen and sulfur containing heterocyclic scaffolds against acetylcholinesterase and butyrylcholinesterase

Contact Info

Product

Resources

About