56935-60-5

Usage

Uses

Used in Pharmaceutical Industry:
2-CHLORO-N-HYDROXY-BENZAMIDINE is used as a chemical intermediate for the synthesis of various organic compounds, contributing to the development of new pharmaceutical products.
Used in Enzyme Kinetics Research:
2-CHLORO-N-HYDROXY-BENZAMIDINE is used as a potent inhibitor of trypsin and related serine proteases, serving as a valuable tool in the study of enzyme kinetics.
Used as an Antithrombotic Agent:
2-CHLORO-N-HYDROXY-BENZAMIDINE is used in the medical field as an antithrombotic agent, leveraging its ability to inhibit serine proteases that play a role in blood clotting.
Used in Organic Synthesis:
2-CHLORO-N-HYDROXY-BENZAMIDINE is used as a reagent in organic synthesis, facilitating the creation of a range of chemical products.
Used in Drug Preparation:
2-CHLORO-N-HYDROXY-BENZAMIDINE is used as a substrate for the preparation of benzamidine-based drugs, highlighting its importance in the synthesis of specific medicinal compounds.

Upstream product

• 873-32-5 2-Chlorobenzonitrile 
• 3717-26-8 2-chlorobenzaldoxime 
• 29568-74-9 2-chloro-N-hydroxybenzimidoyl chloride 
• 7664-41-7 ammonia 

Downstream Products

• 69792-82-1 3,5-bis(2-chlorophenyl)-1,2,4-oxadiazole 
• 69792-83-2 3-(o-chlorophenyl)-5-(p-chlorophenyl)-1,2,4-oxadiazole 
• 388575-78-8 3-(o-chlorophenyl)-5-(m-nitrophenyl)-1,2,4-oxadiazole 
• 873-32-5 2-Chlorobenzonitrile 
• 609-66-5 2-chlorobenzamide 
• 1271705-73-7 C₁₁H₉ClN₂O₃ 
• 45765-25-1 (2-chlorophenyl)cyanamide 
• 1608090-93-2 3-(2-chlorophenyl)-5-ferrocenyl-1,2,4-oxadiazole 
• 330460-47-4 3-(2-chloro)phenyl-5-(4-methyl)phenyl-[1,2,4]oxadiazole 
• 261704-60-3 3-(2-chlorophenyl)-5-(phenyl)-1,2,4-oxadiazole 
• 69792-84-3 5-(2-chlorophenyl)-3-(2,4-dichlorophenyl)-1,2,4-oxadiazole 
• 1001467-30-6 C₁₈H₂₂ClN₃O₃ 
• 1352079-06-1 1-{4-[3-(2-chlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}-4,4,4-trifluorobutan-1-one 
• 1242965-58-7 4-[3-(2-chlorophenyl)[1,2,4]oxadiazol-5-yl]piperidine hydrochloride 

Relevant academic research and scientific papers

Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine

Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.

Design, synthesis, and biological evaluation of 1,2,4-oxadiazole-containing pyrazolo[3,4-b]pyridinones as a new series of AMPKɑ1β1γ1 activators

Adenosine monophosphate-activated protein kinase (AMPK) plays a key role in maintaining whole-body homeostasis and has been regarded as a therapeutic target for the treatment of diabetic nephropathy (DN). Herein, a series of 1,2,4-oxadiazole-containing py

Efficient synthesis of novel 1-hydroxy-2,4,5-trisubstituted imidazole derivatives via a one-pot, four-component reaction between hydroxylamine, benzonitriles, arylglyoxals and cyclic 1,3-dicarbonyl compounds

A simple, and efficient procedure for the synthesis of novel 2,5-diaryl-1-hydroxy-1H-imidazol-4-yl derivatives via a one-pot, four-component reaction between hydroxylamine, benzonitriles, arylglyoxals and cyclic 1,3-dicarbonyl compounds (Melrum’s acid or dimedone) in ethanol under reflux conditions without using bases and catalysts is reported. All the products were obtained in good yields and their structures were established from their spectroscopic data.

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.).

Oxadiazole Derivatives as Dual Orexin Receptor Antagonists: Synthesis, Structure–Activity Relationships, and Sleep-Promoting Properties in Rats

The orexin system plays an important role in the regulation of wakefulness. Suvorexant, a dual orexin receptor antagonist (DORA) is approved for the treatment of primary insomnia. Herein, we outline our optimization efforts toward a novel DORA. We started our investigation with rac-[3-(5-chloro-benzooxazol-2-ylamino)piperidin-1-yl]-(5-methyl-2-[1,2,3]triazol-2-ylphenyl)methanone (3), a structural hybrid of suvorexant and a piperidine-containing DORA. During the optimization, we resolved liabilities such as chemical instability, CYP3A4 inhibition, and low brain penetration potential. Furthermore, structural modification of the piperidine scaffold was essential to improve potency at the orexin 2 receptor. This work led to the identification of (5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-{(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl}methanone (51), a potent, brain-penetrating DORA with in vivo efficacy similar to that of suvorexant in rats.

Synthesis and antibacterial evaluation of 3,5-Diaryl-1,2,4-oxadiazole derivatives

This manuscript reports the synthesis of twenty 3,5-diaryl-1,2,4-oxadiazole derivatives, nine of which are novel compounds. The amidoxime reaction with acyl chlorides obtained from substituted benzoic acids was used. All compounds were tested against five standard (American Type Culture Collection (ATCC)) bacteria: Escherichia coli, Pseudomonas aeruginosa, Enterococcus faecalis, Proteus mirabilis and Staphylococcus aureus. Screening assays were carried out using agar-diffusion technique, in which 100 μM heterocyclic compounds solutions (20percent dimethylsulfoxide/water) were employed. The minimum inhibitory concentrations (MIC) of the active compounds were determined by serial dilutions at decreasing concentrations in microtiter plates. The nitrated derivatives gave the best test results, where MIC = 60 μM (E. coli) was the lowest value found for an ortho-nitrated derivative. The activity of these compounds possibly involves a mechanism via free radicals. S. aureus and P. aeruginosa were resistant to all compounds.

Synthesis, characterisation and photophysical studies of oxadiazolyl coumarin: A new class of blue light emitting fluorescent dyes

A library of novel 1, 2, 4-oxadiazole linked coumarin dyes have been synthesised via condensation of corresponding acid 6 and N’-hydroxybenzimidamide 8. This new class of organic compounds were examined for their fluorescent properties and found to emit blue light in the visible region of the spectrum with very high Stoke's shift values. Most of these compounds demonstrated high quantum yields and fluorescence life time in nano-second range which makes them quite lucrative to be used as new fluorescent probes. The highest quantum yield of 0.68 was shown by compound 9j which also shows high Stoke's shift value. The electronic structure of these coumarin-based donor–π–acceptor (D–π–A)-type organic dyes have been examined by Density Functional Theory (DFT). TGA analysis of few of the compounds show that they are stable up to temperature range of 0–245?°C. The synthesised compounds were characterised by NMR and mass spectrometry and the structure of two of these compounds have been confirmed by X-ray crystallography.

Indazole-oxadiazole derivative, medicinal composition containing derivative, and application of derivative in tumor prevention

The invention discloses an indazole-oxadiazole derivative with the structure represented by general formula a shown in the description, or a pharmaceutically acceptable salt or solvate thereof. In the formula, X is O or N, Y is N, Z is N or O, and all groups are as defined in the description. The invention also discloses a medicinal composition adopting the derivative as an active component, and a use of the derivative. Compounds synthesized in the invention have an HIF-1 inhibition effect, and most of the compounds have a substantial HIF-1 inhibition effect, have strong in-vivo and in-vitro anti-HIF-1 effect on human colorectal carcinoma cell strains (HCT116) and other tumor cell strains, and can be used for treating tumor diseases.

Nitrobenzofurazan derivatives of N′-hydroxyamidines as potent inhibitors of indoleamine-2,3-dioxygenase 1

Tryptophan metabolism through the kynurenine pathway is considered as a crucial mechanism in immune tolerance. Indoleamine 2,3-dioxygenase 1 (IDO1) plays a key role in tryptophan catabolism in the immune system and it is also considered as an important therapeutic target for the treatment of cancer and other diseases that are linked with kynurenine pathway. In this study, a series of nitrobenzofurazan derivatives of N′-hydroxybenzimidamides (1) and N′-hydroxy-2-phenylacetimidamides (2) were synthesized and their inhibitory activities against human IDO1 enzyme were tested using in-vitro and cellular enzyme activity assay. The optimization leads to the identification of potent compounds, 1d, 2i and 2k (IC50 = 39-80 nM), which are either competitive or uncompetitive inhibitors of IDO1 enzyme. These compounds also showed IDO1 inhibition potencies in the nanomolar range (IC50 = 50-71 nM) in MDA-MB-231 cells with no/negligible amount of cytotoxicity. The stronger selectivity of the potent compounds for IDO1 enzyme over tryptophan 2,3-dioxygenase (TDO) enzyme (312-1593-fold) also makes them very attractive for further immunotherapeutic applications.

Novel benzimidazole-oxadiazole hybrid molecules as promising antimicrobial agents

In the present study, we describe the design and expeditious synthesis of novel 2-aryl-5-(3-aryl-[1,2,4]-oxadiazol-5-yl)-1-methyl-1H-benzo[d]imidazole hybrid molecules as promising antimicrobial agents. The core moiety 2-aryl-ethyl-1H-benzo[d]imidazole-5-