The role of hydrazide compounds in asymmetric synthesis

Ziarani, Ghodsi Mohammadi; Vavsari, Vaezeh Fathi

doi:10.1016/j.tetasy.2016.12.001

Cited by 10 publications

(8 citation statements)

References 40 publications

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“…The importance of chiral hydrazides is not purely esoteric: they have previously been employed as chiral catalysts in their own right. 40 Whilst this reaction technically falls outside of the scope of this review, it paves the way for future developments in catalytic N-X axial atropisomer synthesis.…”

Section: Scheme 32 Enantioselective Synthesis Of Axial N-n Biaryls 4dmentioning

confidence: 99%

Catalytic Enantioselective Synthesis of C–N Atropisomeric Heterobiaryls

Knipe¹,

Sweet²

2022

Synthesis

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Molecules containing an atropisomeric C–N biaryl axis are gaining increasing attention in catalytic and medicinal chemistry. Despite this rising interest, relatively few approaches towards their catalytic enantioselective synthesis have been reported. Here we review these approaches, with a focus on the mechanism of asymmetric induction. Some common themes emerge: Brønsted acid catalysed cyclo-condensation and palladium-catalysed ring-closure are the most common and successful approaches. Meanwhile, the more direct but challenging axial C–N bond formation strategy remains in its infancy, with just two reports to-date. We hope this review will inform and inspire other researchers to develop new creative approaches to this important chemical motif.1 Introduction2 Cyclo-Condensation3 Proximal C–N Bond Formation4 Desymmetrisation of Intact Axes5 ortho-C–H Functionalisation6 Cycloaddition7 Axial C–N Bond Formation8 Atropisomeric N–N Axes: An Emerging Class of Heterobiaryls9 Conclusion and Outlook

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Section: Scheme 32 Enantioselective Synthesis Of Axial N-n Biaryls 4dmentioning

confidence: 99%

Catalytic Enantioselective Synthesis of C–N Atropisomeric Heterobiaryls

Knipe¹,

Sweet²

2022

Synthesis

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“…7 Because of their biological action, hydrazide molecules are useful in medicinal chemistry. 8,9 The hydrazide moiety is used as an active functional group in several chemical processes in organic synthesis, not just because its derivatives have good pharmacological effects. 9 A spectrum of transition metals can easily coordinate with the hydrazide ligand.…”

Section: Introductionmentioning

confidence: 99%

“…8,9 The hydrazide moiety is used as an active functional group in several chemical processes in organic synthesis, not just because its derivatives have good pharmacological effects. 9 A spectrum of transition metals can easily coordinate with the hydrazide ligand. 10 Furthermore, it is well recognized that complexing organic molecules with transition metals is one strategy to increase their biological activity.…”

Section: Introductionmentioning

confidence: 99%

UV protective textile: Experimental and DFT computational studies on the function of some metal complexes of hydrazide derivatives on cellulose fabrics

Saeed,

Aldubayyan,

Al‐Hakimi

et al. 2023

Applied Organom Chemis

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Ultraviolet (UV) radiation is harmful to the skin. Therefore, it capitalized on the properties of thiophene and pyridine derivatives to prepare new textileprotective agents with improved UV protection factor (UPF) factor. This embodies the preparation and characterization of "2-((3-cyano-4-(4-methoxyphenyl)-6-(thiophene-2-yl)pyridine-2-yl)oxy)acetohydrazide" (HZ) in complex with Ni(II), Cu(II), Zn(II), or Cd(II), using proton nuclear magnetic resonance ( 1 H NMR), carbon-13 nuclear magnetic resonance ( 13 C NMR), X-ray diffraction analysis (XRD), Fourier transform infrared spectroscopy (FTIR), and thermal analysis techniques. Characterization of cotton fabric-based cellulose (CELL) in complex with the synthesized agents using FTIR spectroscopy, X-ray spectroscopy, and scanning electron microscopy-energy dispersive X-ray analysis (SEM-EDX) revealed deposition of the hydrazide and its metal complexes on the cellulosic fiber. Interestingly, cellulose complexation with Cu(II) was observed to have the highest value of the UPF. Computation of the reactivity indices using density functional theory (DFT) supports this finding, where the electrophilicity parameter of the modified fabric was found to correlate with the UPF wherein Cu(II) shows the highest value. The synthesized complexes could, therefore, provide lead structures for developing new UVprotective agents with enhanced coating characteristics.

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“…For example, oxadiazoles, triazoles amine, Schiff bases, and pyrazoles are some known derivatives of hydrazides with significant biological activities [8]. Owing to their chemical reactivity and biological activities [9], hydrazide-based compounds are useful substrates in both realms of chemical reactions and medicinal chemistry (Figure 3). They impart potent pharmacological activities due to the presence of toxophoric N-C=O linkage, thus displaying antiviral, antimicrobial, local anesthetic, anticonvulsant, antioxidant, anti-inflammatory, anticancer, and possible antimycotic properties [8,10].…”

Section: Introductionmentioning

confidence: 99%

“…While its reactivity through the N2 has largely been restricted to the production of hydrazones, it has also been studied in Michael addition reactions and cross-coupling reactions. A brief review of the literature reveals that in the asymmetric synthesis of organic compounds of medicinal importance, hydrazides serve the role of reagents as well as the role of chiral catalysts [9]. The fascination with hydrazides is not simply a consequence of their derivatives with good pharmacological activity; the hydrazide moiety is used as an active functional group in numerous chemical reactions, including the synthesis of tetrazoles [11], the preparation of spiroquinazolinones [12,13], Ugi-azide reactions [12], Ugi-multicomponent reactions [14], and many more organic reactions.…”

Section: Introductionmentioning

confidence: 99%

Designing Functionally Substituted Pyridine-Carbohydrazides for Potent Antibacterial and Devouring Antifungal Effect on Multidrug Resistant (MDR) Strains

et al. 2022

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The emergence of multidrug-resistant (MDR) pathogens and the gradual depletion of available antibiotics have exacerbated the need for novel antimicrobial agents with minimal toxicity. Herein, we report functionally substituted pyridine carbohydrazide with remarkable antimicrobial effect on multi-drug resistant strains. In the series, compound 6 had potent activity against four MDR strains of Candida spp., with minimum inhibitory concentration (MIC) values being in the range of 16–24 µg/mL and percentage inhibition up to 92.57%, which was exceptional when compared to broad-spectrum antifungal drug fluconazole (MIC = 20 µg/mL, 81.88% inhibition). Substitution of the octyl chain in 6 with a shorter butyl chain resulted in a significant anti-bacterial effect of 4 against Pseudomonas aeruginosa (ATCC 27853), the MIC value being 2-fold superior to the standard combination of ampicillin/cloxacillin. Time-kill kinetics assays were used to discern the efficacy and pharmacodynamics of the potent compounds. Further, hemolysis tests confirmed that both compounds had better safety profiles than the standard drugs. Besides, molecular docking simulations were used to further explore their mode of interaction with target proteins. Overall results suggest that these compounds have the potential to become promising antimicrobial drugs against MDR strains.

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The role of hydrazide compounds in asymmetric synthesis

Cited by 10 publications

References 40 publications

Catalytic Enantioselective Synthesis of C–N Atropisomeric Heterobiaryls

Catalytic Enantioselective Synthesis of C–N Atropisomeric Heterobiaryls

UV protective textile: Experimental and DFT computational studies on the function of some metal complexes of hydrazide derivatives on cellulose fabrics

Designing Functionally Substituted Pyridine-Carbohydrazides for Potent Antibacterial and Devouring Antifungal Effect on Multidrug Resistant (MDR) Strains

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