64893-54-5

Usage

Uses

Used in Organic Synthesis:
N'-HYDROXY-2-NAPHTHALENECARBOXIMIDAMIDE is utilized as a reagent in organic synthesis for its ability to facilitate the creation of various compounds. Its mild oxidizing properties make it a valuable component in chemical reactions, contributing to the formation of desired products.
Used in Pharmaceutical Research:
In the pharmaceutical industry, N'-HYDROXY-2-NAPHTHALENECARBOXIMIDAMIDE is employed as a key reagent in the synthesis of pharmaceutical drugs. Its role in the development of new medications is crucial, as it can be involved in the creation of molecules with potential therapeutic applications.
Used in the Synthesis of Heterocyclic Compounds:
N'-HYDROXY-2-NAPHTHALENECARBOXIMIDAMIDE is also used in the synthesis of heterocyclic compounds, which are an important class of organic compounds with at least one ring composed of both carbon and non-carbon atoms. N'-HYDROXY-2-NAPHTHALENECARBOXIMIDAMIDE's properties make it suitable for the formation of these complex structures, which are prevalent in many biologically active molecules.
Used in Chemical Research Applications:
Beyond its applications in synthesis and pharmaceuticals, N'-HYDROXY-2-NAPHTHALENECARBOXIMIDAMIDE is also utilized in broader chemical research. Its versatility as a reagent and mild oxidizing agent allows it to be employed in a wide range of studies, contributing to the advancement of chemical knowledge and innovation.

Upstream product

• 613-46-7 2-naphthalenecarbonitrile 
• 20893-80-5 naphthalene-2-diazonium chloride 
• 66-99-9 β-naphthaldehyde 
• 51873-98-4 2-naphthaldoxime 
• 91-58-7 2-chloronaphthalene 
• 580-13-2 2-bromonaphthalene 

Downstream Products

• 1161923-80-3 5-anilino-3-(2-naphthyl)-1,2,4-thiadiazole 
• 613-46-7 2-naphthalenecarbonitrile 
• 65004-21-9 3-(naphthalen-2-yl)-5-phenyl-1,2,4-oxadiazole 
• 1161923-88-1 5-cyclohexylamino-3-(2-naphthyl)-1,2,4-oxadiazole 

Relevant academic research and scientific papers

Development of Potent 3-Br-isoxazoline-Based Antimalarial and Antileishmanial Compounds

Starting from the structure of previously reported 3-Br-isoxazoline-based covalent inhibitors of P. falciparum glyceraldehyde 3-phosphate dehydrogenase, and with the intent to improve their metabolic stability and antimalarial activity, we designed and synthesized a series of simplified analogues that are characterized by the insertion of the oxadiazole ring as a bioisosteric replacement for the metabolically labile ester/amide function. We then further replaced the oxadiazole ring with a series of five-membered heterocycles and finally combined the most promising structural features. All the new derivatives were tested in vitro for antimalarial as well as antileishmanial activity. We identified two very promising new lead compounds, endowed with submicromolar antileishmanial activity and nanomolar antiplasmodial activity, respectively, and a very high selectivity index with respect to mammalian cells.

Novel 1,2,4-oxadiazole-chalcone/oxime hybrids as potential antibacterial DNA gyrase inhibitors: Design, synthesis, ADMET prediction and molecular docking study

New antibacterial drugs are urgently needed to tackle the rapid rise in multi-drug resistant bacteria. DNA gyrase is a validated target for the development of new antibacterial drugs. Thus, in the present investigation, a novel series of 1,2,4-oxadiazole-

Novel chalcone/aryl carboximidamide hybrids as potent anti-inflammatory via inhibition of prostaglandin E2 and inducible NO synthase activities: design, synthesis, molecular docking studies and ADMET prediction

Two series of chalcone/aryl carboximidamide hybrids 4a–f and 6a–f were synthesised and evaluated for their inhibitory activity against iNOS and PGE2. The most potent derivatives were further checked for their in?vivo anti-inflammatory activity utilising carrageenan-induced rat paw oedema model. Compounds 4c, 4d, 6c and 6d were proved to be the most effective inhibitors of PGE2, LPS-induced NO production, iNOS activity. Moreover, 4c, 4d, 6c and 6d showed significant oedema inhibition ranging from 62.21% to 78.51%, compared to indomethacin (56.27 ± 2.14%) and celecoxib (12.32%). Additionally, 4c, 6a and 6e displayed good COX2 inhibitory activity while 4c, 6a and 6c exhibited the highest 5LOX inhibitory activity. Compounds 4c, 4d, 6c and 6d fit nicely into the pocket of iNOS protein (PDB ID: 1r35) via the important amino acid residues. Prediction of physicochemical parameters exhibited that 4c, 4d, 6c and 6d had acceptable physicochemical parameters and drug-likeness. The results indicated that chalcone/aryl carboximidamides 4c, 4d, 6c and 6d, in particular 4d and 6d, could be used as promising lead candidates as potent anti-inflammatory agents.

Imidazole hydrochloride promoted synthesis of 3,5-disubstituted-1,2,4-oxadiazoles

Imidazole hydrochloride as an additive promotes the reaction of amidoximes and DMA derivatives to generated 3,5-disubstituted-1,2,4-oxadiazoles in low to excellent yields without the use of coupling reagents, oxidants, strong acids or bases and other additives.

Optimization of the synthesis of het/aryl-amidoximes using an efficient green chemistry

This work focuses on optimizing an efficient green synthesis of arylamidoximes from appropriate nitrile and hydroxylamine hydrochloride in water and triethylamine (1.6 mol equivalent) as a base at room temperature for 6 h. This new green synthetic methodology is compared with previously known methods. The main advantages of this new process reported are good yield, easier work-up and short reaction times. Moreover, some of the synthesized arylamidoximes converted to 1,2,4-oxadiazole derivatives 13a,b and 14via the reaction with (4-acetylphenoxy)acetic acid 12.

SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)

A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.

Design, synthesis and biological evaluation of triaryl compounds as novel 20S proteasome inhibitors

Thirty novel triaryl compounds were designed and synthesized based on the known proteasome inhibitor PI-1840. Most of them showed significant inhibition against the β5c subunit of human 20S proteasome, and five of them exhibited IC50 values at the sub-micromolar level, which were comparable to or even more potent than PI-1840. The most active two (1c and 1d) showed IC50 values of 0.12 and 0.18 μM against the β5c subunit, respectively, while they displayed no obvious inhibition against the β2c, β1c and β5i subunits. Molecular docking provided informative clues for the subunit selectivity. The potent and subunit selective proteasome inhibitors identified herein represent new chemical templates for further molecular optimization.

Synthesis and Biological Evaluation of Sigma-1 (σ1) Receptor Ligands Based on Phenyl-1,2,4-oxadiazole Derivatives

In this study, a series of phenyl-1,2,4-oxadiazole derivatives were synthesized and evaluated for anti-allodynic activity. Structure–activity relationship studies identified 1-{4-[3-(2,4-dichlorophenyl)-1,2,4-oxadiazol-5-yl]butyl}piperidine (39) with excellent affinity for the σ1 receptor and selectivity for the σ2 receptor, with poor activity to other central nervous system neurotransmitter receptors and transporters associated with pain. Compound 39 exhibited dose-dependent efficacy in suppressing the formalin-induced flinching and attenuating mechanical allodynia in chronic constriction injury-induced neuropathic rats. These results suggest that compound 39 exerts potent antihyperalgesic activity and could be considered as a promising candidate for treating neuropathic pain.

Investigation around the Oxadiazole Core in the Discovery of a New Chemotype of Potent and Selective FXR Antagonists

Recent findings have shown that Farnesoid X Receptor (FXR) antagonists might be useful in the treatment of cholestasis and related metabolic disorders. In this paper, we report the discovery of a new chemotype of FXR antagonists featured by a 3,5-disubsti

Efficient Synthesis of Functionalized Indene Derivatives via Rh(III)-Catalyzed Cascade Reaction between Oxadiazoles and Allylic Alcohols

A highly efficient rhodium(III)-catalyzed synthesis of novel functionalized indene derivatives has been achieved via C?H activation/intramolecular aldol condensation. This cascade reaction is an atom economical protocol which could be further applied to build more complex compounds. (Figure presented.).