Chiral lactic hydrazone derivatives as potential bioactive antibacterial agents: Synthesis, spectroscopic, structural and molecular docking studies

Noshiranzadeh, Nader; Heidari, Azam; Haghi, Fakhri; Bikas, Rahman; Lis, Tadeusz

doi:10.1016/j.molstruc.2016.09.006

Cited by 54 publications

(12 citation statements)

References 53 publications

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“…These bands are related to the O–H groups of ligand and the ν (NH) of the oxazolidine ring, respectively. [ 27 ] Another important feature of the FT‐IR spectrum of compound 1 is the appearance of two very strong bands at 2080 and 2056 cm −1 . Since these bands are absent in the FT‐IR spectrum of the free ligand, they can be considered as the new bands.…”

Section: Resultsmentioning

confidence: 99%

1D Azido bridged Cu(II) coordination polymer with 1,3‐oxazolidine ligand as an effective catalyst for green click synthesis of 1,2,3‐triazoles

Bikas

Ajormal

Noshiranzadeh

et al. 2020

Applied Organom Chemis

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A new 1D azido bridged Cu(II) coordination polymer with 1,3‐oxazolidine based ligand, [Cu(H3L)(μ1,3‐N3)(N3)]n (1), was synthesized and characterized by elemental analysis and spectroscopic methods. The structure of 1 was also determined by single crystal X‐ray analysis which indicated the 1D polymeric chain is generated by end‐to‐end (EE) azide bridge. The obtained compound was employed as catalyst in green click synthesis of β‐hydroxy‐1,2,3‐triazoles from one‐pot three‐component cycloaddition reaction of epoxide‐azide‐alkyne. The catalytic reactions were carried out in water as a safe, cheap and green solvent. The catalytic studies indicated that the obtained 1D azido bridged Cu(II) coordination polymer is an active catalyst for preparing β‐hydroxy‐1,2,3‐triazoles. The effect of temperature on the selectivity of the catalytic system was studied and the results indicated this catalytic system has high selectivity at low temperatures. The structure the product obtained from the reaction of 2,3‐epoxypropylphenylether, azide and 1‐ethynyl‐1‐cyclohexanol (T4) was determined by single crystal X‐ray analysis. The results indicate Cu(II) coordination polymers can be a new class of catalytic systems for green click synthesis of 1,2,3‐triazoles.

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Section: Resultsmentioning

confidence: 99%

1D Azido bridged Cu(II) coordination polymer with 1,3‐oxazolidine ligand as an effective catalyst for green click synthesis of 1,2,3‐triazoles

Bikas

Ajormal

Noshiranzadeh

et al. 2020

Applied Organom Chemis

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“…A very interesting biological activity of the hydrazide–hydrazone of lactic acid was described by Noshiranzadeh et al [ 140 ]. They synthesized a number of this type of lactic acid derivatives, two of which ( Figure 33 ) showed particular activity against the selected bacterial strains (Minimum Inhibitory Concentration MIC = 64–128 µg/mL), which turned out to be lower than the reference gentamicin.…”

Section: Hydrazide–hydrazonesmentioning

confidence: 99%

Different Schiff Bases—Structure, Importance and Classification

et al. 2022

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Schiff bases are a vast group of compounds characterized by the presence of a double bond linking carbon and nitrogen atoms, the versatility of which is generated in the many ways to combine a variety of alkyl or aryl substituents. Compounds of this type are both found in nature and synthesized in the laboratory. For years, Schiff bases have been greatly inspiring to many chemists and biochemists. In this article, we attempt to present a new take on this group of compounds, underlining of the importance of various types of Schiff bases. Among the different types of compounds that can be classified as Schiff bases, we chose hydrazides, dihydrazides, hydrazones and mixed derivatives such as hydrazide–hydrazones. For these compounds, we presented the elements of their structure that allow them to be classified as Schiff bases. While hydrazones are typical examples of Schiff bases, including hydrazides among them may be surprising for some. In their case, this is possible due to the amide-iminol tautomerism. The carbon–nitrogen double bond present in the iminol tautomer is a typical element found in Schiff bases. In addition to the characteristics of the structure of these selected derivatives, and sometimes their classification, we presented selected literature items which, in our opinion, represent their importance in various fields well.

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“…The high antibacterial activity of compound 1 is possibly attributed to the presence of an electronegative NO 2 substituent. The authors concluded that the compounds with electron-withdrawing groups like I, Br, or NO 2 generally showed better antibacterial activity in comparison with the compounds containing electron-donating OCH 3 or OH groups [11]. Heidari et al published the study which aimed to investigate the effects of subminimum inhibitory concentrations of compound 1 against Pseudomonas aeruginosa PAO1 quorum sensing related virulence factors (Figure 1).…”

Section: Antimicrobial Activity 21 Antibacterial Activitymentioning

confidence: 99%

Updated Information on Antimicrobial Activity of Hydrazide–Hydrazones

Popiołek

2021

IJMS

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Hydrazide–hydrazones possess a wide spectrum of bioactivity, including antibacterial, antitubercular, antifungal, anticancer, anti-inflammatory, anticonvulsant, antidepressant, antiviral, and antiprotozoal properties. This review is focused on the latest scientific reports regarding antibacterial, antimycobacterial, and antifungal activities of hydrazide–hydrazones published between 2017 and 2021. The molecules and their chemical structures presented in this article are the most active derivatives, with discussed activities having a hydrazide–hydrazone moiety as the main scaffold or as a side chain. Presented information constitute a concise summary, which may be used as a practical guide for further design of new molecules with antimicrobial activity.

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Chiral lactic hydrazone derivatives as potential bioactive antibacterial agents: Synthesis, spectroscopic, structural and molecular docking studies

Cited by 54 publications

References 53 publications

1D Azido bridged Cu(II) coordination polymer with 1,3‐oxazolidine ligand as an effective catalyst for green click synthesis of 1,2,3‐triazoles

1D Azido bridged Cu(II) coordination polymer with 1,3‐oxazolidine ligand as an effective catalyst for green click synthesis of 1,2,3‐triazoles

Different Schiff Bases—Structure, Importance and Classification

Updated Information on Antimicrobial Activity of Hydrazide–Hydrazones

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