Theoretical Studies on Hydroxamic Acids

Kakkar, Rita

doi:10.1007/978-3-642-38111-9_2

Cited by 14 publications

(12 citation statements)

References 133 publications

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“… 5 They can be found in two different tautomeric forms, as depicted in Figure 2 a: the keto form 1a is the most stable tautomer observed in acidic medium, while the iminol form 1b prevails in basic conditions. 6 Hydroxamic acids are weak acids ( Figure 2 b). 7 They can be considered diprotic acids: in water solvent, the hydroxyl group of HAs loses the first proton with a p K a ranging between 8.5 and 9.5, while deprotonation in DMSO mainly involves the loss of the hydrogen from the −NH group.…”

Section: Physical and Chemical Propertiesmentioning

confidence: 99%

Hydroxamic Acid Derivatives: From Synthetic Strategies to Medicinal Chemistry Applications

et al. 2021

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Since the approval of three hydroxamic acid-based HDAC inhibitors as anticancer drugs, such functional groups acquired even more notoriety in synthetic medicinal chemistry. The ability of hydroxamic acids (HAs) to chelate metal ions makes this moiety an attractive metal binding group—in particular, Fe(III) and Zn(II)—so that HA derivatives find wide applications as metalloenzymes inhibitors. In this minireview, we will discuss the most relevant features concerning hydroxamic acid derivatives. In a first instance, the physicochemical characteristics of HAs will be summarized; then, an exhaustive description of the most relevant methods for the introduction of such moiety into organic substrates and an overview of their uses in medicinal chemistry will be presented.

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Section: Physical and Chemical Propertiesmentioning

confidence: 99%

Hydroxamic Acid Derivatives: From Synthetic Strategies to Medicinal Chemistry Applications

et al. 2021

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“…Hydroxamates features the general formula-R(C�O)NHOH, where R could be an alkyl or aryl group. e -(C�O)NHOH moiety is the key functional group binding to iron and hence has been developed and applied in medicine in treating cardiovascular diseases, metal poisoning, and overload of iron and anticancer and antitumor agents [15][16][17][18]. Other applications are extended to corrosion inhibition, mineral floatation, and extraction of toxic metals [19,20].…”

Section: Introductionmentioning

confidence: 99%

“…Also, it has been used to design novel chemicals never before synthesized as it saves the cost of trial and error compared to wet labs concerning time and chemicals [23,24]. However, despite the applications of hydroxamates, there is a dearth of literature on theoretical studies of hydroxamates, and this is due to the challenge in modeling transition metal complexes [15,19]. Nevertheless, DFT has been used in studying transition metal complexes [25,26].…”

Section: Introductionmentioning

confidence: 99%

Molecular Design of Novel Chemicals for Iron Sulfide Scale Removal

Onawole

Hussein

Nimir

et al. 2021

Journal of Chemistry

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Scale deposition is a pertinent challenge in the oil and gas industry. Scales formed from iron sulfide are one of the troublous scales, particularly pyrite. Moreover, the use of biodegradable environmentally friendly chemicals reduces the cost compared to the conventional removal process. In this work, the chelating abilities of four novel chemicals, designed using the in silico technique of density functional theory (DFT), are studied as potential iron sulfide scale removers. Only one of the chemicals containing a hydroxamate functional group had a good chelating ability with Fe2+. The chelating strength and ecotoxicological properties of this chemical were compared to diethylenetriaminepentaacetic acid (DTPA), an already established iron sulfide scale remover. The new promising chemical surpassed DTPA in being a safer chemical and having a greater binding affinity to Fe2+ upon optimization, hence, a better choice. The presence of oxime (-NHOH) and carbonyl (C=O) moieties in the new chemical showed that the bidentate form of chelation is favored. Moreover, the presence of an intramolecular hydrogen bond enhanced its chelating ability.

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“…According to [1], hydroxamic acid (HA), represented by the general formula, R-CO-NHOH, is a compound derived from oxoacid by replacing the –OH in it by –NHOH, and its hydrocarbyl derivatives. The HAs are much weaker acids as compared with the corresponding carboxylic acids despite having identical carbon chains, however, they possess stronger abilities for selectively chelating metal ions [2].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of N-Methyl Fatty Hydroxamic Acids from Ketapang Seed Oil Catalyzed by Lipase

Suhendra¹,

Gunawan²,

Hajidi³

2019

Molecules

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N-methyl fatty hydroxamic acid (N-MFHA), which is a derivative of hydroxamic acid (HA), was synthesized from ketapang seed oil (Terminalia catappa L.). In general, HAs have wide applications due to their chelating properties and biological activities. N-MFHAs were synthesized using immobilized lipase (Lipozyme TL IM) in biphasic medium which was the ketapang seed oil dissolved in hexane and N-methylhydroxylamine dissolved in water. The products were characterized through color testing and FT-IR spectroscopy after purification. Various factors affecting the enzyme activity investigated in the study included the effect of incubation time, the amount of lipase used, and the temperature. On the basis of the results, the optimum conditions for the synthesis of N-MFHA obtained are 25 h of incubation time, a temperature of 40 °C, and a ratio of 1:100 for the amount of enzyme (g)/oil (g). At the optimum conditions of the reaction, 59.7% of the oils were converted to N-MFHA.

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Theoretical Studies on Hydroxamic Acids

Cited by 14 publications

References 133 publications

Hydroxamic Acid Derivatives: From Synthetic Strategies to Medicinal Chemistry Applications

Hydroxamic Acid Derivatives: From Synthetic Strategies to Medicinal Chemistry Applications

Molecular Design of Novel Chemicals for Iron Sulfide Scale Removal

Synthesis and Characterization of N-Methyl Fatty Hydroxamic Acids from Ketapang Seed Oil Catalyzed by Lipase

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