ChemInform Abstract: Synthesis of Hydroxamic Acids by Activation of Carboxylic Acids with N,N′‐Carbonyldiimidazole: Exploring the Efficiency of the Method.

Usachova, Natalija; Leitis, Gundars; Jirgensons, Aigars; Kalvinsh, Ivars

doi:10.1002/chin.201031081

Cited by 5 publications

(6 citation statements)

References 1 publication

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“…In contrast, the desired hydroxamic acid derivative was accessed via a two-step procedure. Initial conversion of N -Boc-protected α-aminocarboxylic acid 5 to the corresponding N -Boc-protected α-aminohydroxamic acid 7 was achieved in good yield by CDI-mediated activation followed by condensation with NH 2 OH·HCl under the reported conditions . Finally, the desired α-aminohydroxamic acid 8 was obtained in the HCl salt form through N -Boc deprotection of 7 .…”

Section: Resultsmentioning

confidence: 99%

Two-Pronged Attack: Dual Inhibition of Plasmodium falciparum M1 and M17 Metalloaminopeptidases by a Novel Series of Hydroxamic Acid-Based Inhibitors

et al. 2014

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Plasmodium parasites, the causative agents of malaria, have developed resistance to most of our current antimalarial therapies, including artemisinin combination therapies which are widely described as our last line of defense. Antimalarial agents with a novel mode of action are urgently required. Two Plasmodium falciparum aminopeptidases, PfA-M1 and PfA-M17, play crucial roles in the erythrocytic stage of infection and have been validated as potential antimalarial targets. Using compound-bound crystal structures of both enzymes, we have used a structure-guided approach to develop a novel series of inhibitors capable of potent inhibition of both PfA-M1 and PfA-M17 activity and parasite growth in culture. Herein we describe the design, synthesis, and evaluation of a series of hydroxamic acid-based inhibitors and demonstrate the compounds to be exciting new leads for the development of novel antimalarial therapeutics.

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Section: Resultsmentioning

confidence: 99%

Two-Pronged Attack: Dual Inhibition of Plasmodium falciparum M1 and M17 Metalloaminopeptidases by a Novel Series of Hydroxamic Acid-Based Inhibitors

et al. 2014

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“…We used several synthetic methods to prepare hydroxamic acids. For the syntheses of cinnamic hydroxamic acids 13 – 15 , 19 , and 22 , the corresponding carboxylic acids 59a – e were activated with either oxalyl chloride/DMF or 1,1′-carbonyldiimidazole (CDI) followed by treatment with a hydroxylamine solution (Scheme ). Carboxylic acids 59b and 59c , which are not commercially available, were readily obtained from ethyl esters 58b and 58c , respectively.…”

Section: Resultsmentioning

confidence: 99%

“…N-Hydroxycinnamamide (13). 27 A mixture of cinnamic acid (59a, 148 mg, 1.0 mmol) and CDI (243 mg, 1.5 mmol) in THF (2 mL) was stirred at rt for 80 min. NH 2 OH•HCl (138 mg, 2.0 mmol) was then added, and the reaction mixture was allowed to stir overnight.…”

Section: ■ Conclusionmentioning

confidence: 99%

Hydroxamic Acids Block Replication of Hepatitis C Virus

Xü

Qiu

et al. 2014

J. Med. Chem.

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Intrigued by the role of protein acetylation in hepatitis C virus (HCV) replication, we tested known histone deacetylase (HDAC) inhibitors and a focused library of structurally simple hydroxamic acids for inhibition of a HCV subgenomic replicon. While known HDAC inhibitors with varied inhibitory profiles proved to be either relatively toxic or ineffective, structure-activity relationship (SAR) studies on cinnamic hydroxamic acid and benzo[b]thiophen-2-hydroxamic acid gave rise to compounds 22 and 53, which showed potent and selective anti-HCV activity and therefore are promising starting points for further structural optimization and mechanistic studies.

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“…The starting hydroxamic acid (N-hydroxy-4-phenylbutanamide) was prepared according to a literature procedure for a related compound. 17 To a flame-dried 100 mL round-bottom flask was added 4-phenylbutanoic acid (4.43 g, 27.0 mmol, 1.00 equiv) and THF (45.0 mL). After adding carbonyldiimidazole (CDI) (6.57 g, 40.5 mmol, 1.50 equiv), the reaction mixture was stirred under nitrogen at rt for 1 h, and then, hydroxylamine chloride (3.75 g, 54.0 mmol, 2.00 equiv) was added.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis of Azolo[1,3,5]triazines via Rhodium(III)-Catalyzed Annulation of N-Azolo Imines and Dioxazolones

2018

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A wide range of azolo[1,3,5]triazines were obtained by Rh(III)-catalyzed annulation of N-azolo imines and dioxazolones. The reaction proceeds by the first catalytic C-H amidation of an imidoyl C-H bond followed by cyclodehydration. Good yields were obtained for N-azolo imines derived from aminoazoles and aromatic and heteroaromatic aldehydes. A range of dioxazolone amidating reagents were employed to introduce aryl, heteroaryl, and alkyl substituents. The reaction was also performed with a benchtop setup at 1 mmol scale using microwave heating.

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ChemInform Abstract: Synthesis of Hydroxamic Acids by Activation of Carboxylic Acids with N,N′‐Carbonyldiimidazole: Exploring the Efficiency of the Method.

Cited by 5 publications

References 1 publication

Two-Pronged Attack: Dual Inhibition of Plasmodium falciparum M1 and M17 Metalloaminopeptidases by a Novel Series of Hydroxamic Acid-Based Inhibitors

Two-Pronged Attack: Dual Inhibition of Plasmodium falciparum M1 and M17 Metalloaminopeptidases by a Novel Series of Hydroxamic Acid-Based Inhibitors

Hydroxamic Acids Block Replication of Hepatitis C Virus

Synthesis of Azolo[1,3,5]triazines via Rhodium(III)-Catalyzed Annulation of N-Azolo Imines and Dioxazolones

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