119841-74-6

Basic information

• Product Name: Benzenecarboximidoyl chloride, N,2-dihydroxy-
• Synonyms: N,2-dihydroxybenzenecarboximidoyl chloride;Benzenecarboximidoyl chloride,N,2-dihydroxy;N,2-dihydroxybenzimidoyl chloride
• CAS NO: 119841-74-6
• Molecular Formula: C7H6ClNO2
• Molecular Weight: 171.583
• Mol File: 119841-74-6.mol

Chemical Properties

• CAS DataBase Reference: Benzenecarboximidoyl chloride, N,2-dihydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenecarboximidoyl chloride, N,2-dihydroxy-(119841-74-6)
• EPA Substance Registry System: Benzenecarboximidoyl chloride, N,2-dihydroxy-(119841-74-6)

Safety Data

• Hazardous Substances Data: 119841-74-6(Hazardous Substances Data)

Upstream product

• 90-02-8 salicylaldehyde 
• 94-67-7 salicylaldehyde-oxime 

Downstream Products

• 59564-29-3 3-(2-hydroxyphenyl)-4-phenylisoxazole 
• 574-12-9 isoflavone 
• 97904-75-1 isoflavanone 
• 120559-26-4 Acetic acid 2-(4-phenyl-isoxazol-3-yl)-phenyl ester 
• 16263-52-8 3-chlorobenzisoxazole 
• 165532-43-4 ethyl 4,5-dihydro-3-(2-hydroxyphenyl)isoxazole-5-carboxylate 
• 712347-85-8 4,5-dihydro-3-(2-hydroxyphenyl)isoxazole-5-carboxylic acid 
• 1235471-24-5 4,5-dihydro-3-(2-hydroxyphenyl)isoxazole-5-carboxylic acid 4-(sec-butyl)phenylamide 
• 1246465-41-7 5-(3-(2-hydroxyphenyl)isoxazol-5-yl)-N-phenylpentanamide 
• 597553-45-2 ethyl 3-(2-hydroxyphenyl)-6-methyl-4-oxo-4,5,6,7-tetrahydrobenzo[d]isoxazole-5-carboxylate 

Relevant articles and documents

Synthesis and molecular modeling studies of N-Hydroxyindazolecarboximidamides as novel indoleamine 2,3-Dioxygenase 1 (IDO1) inhibitors

Indoleamine 2,3-dioxygenase 1 (IDO1) is an immunosuppressive enzyme that is highly overexpressed in various cancer cells and antigen-presenting cells. It has emerged as an attractive therapeutic target for cancer immunotherapy, which has prompted high interest in the development of small-molecule inhibitors. To discover novel IDO1 inhibitors, we designed and synthesized a series of N-hydroxyindazolecarboximidamides. Among the compounds synthesized, compound 8a inhibited both tryptophan depletion and kynurenine production through the IDO1 enzyme. Molecular docking studies revealed that 8a binds to IDO1 with the same binding mode as the analog, epacadostat (INCB24360). Here, we report the synthesis and biological evaluation of these hydroxyindazolecarboximidamides and present the molecular docking study of 8a with IDO1.

Simple one-pot synthesis of 5-(chloromethyl)isoxazoles from aldoximes and 2,3-dichloro-1-propene

[Figure not available: see fulltext.] A one-pot synthesis of 3-substituted 5-chloromethylisoxazoles from available starting aldoximes and 2,3-dichloro-1-propene, serving both as a solvent and reagent, is proposed. Excess 2,3-dichloro-1-propene is recovered after the reaction. The synthesis is effective for oximes of both aromatic and aliphatic aldehydes.

Five-membered azole heterocyclic compound and its preparation method, pharmaceutical composition and use thereof

The present invention relates to a five-membered azole heterocycle compound represented by the following general formula (I), a preparation method of the five-membered azole heterocycle compound, a drug composition of the five-membered azole heterocycle compound, and a use of the five-membered azole heterocycle compound in preparation of drugs for prevention or treatment of TGR5-mediated diseases. The formula (I) is represented by the instruction.

Design, synthesis, and structure-activity relationships of 3,4,5-trisubstituted 4,5-dihydro-1,2,4-oxadiazoles as TGR5 agonists

Given its role in the mediation of energy and glucose homeostasis, the G-protein-coupled bile acid receptor1 (TGR5) is considered a potential target for the treatment of type2 diabetes mellitus and other metabolic disorders. By thorough analysis of diverse structures of published TGR5 agonists, a hypothetical ligand-based pharmacophore model was built, and a new class of potent TGR5 agonists, based on the novel 3,4,5-trisubstituted 4,5-dihydro-1,2,4-oxadiazole core, was discovered by rational design. Three distinct synthetic methods for constructing 4,5-dihydro-1,2,4-oxadiazoles and extensive structure-activity relationship studies are reported herein. Compound (R)-54n, the structure of which was determined by single-crystal X-ray diffraction and quantum chemical solid-state TDDFT-ECD calculations, showed the best potency, with an EC50 value of 1.4nM toward hTGR5. Its favorable properties invitro warrant further investigation.

Design and synthesis of novel isoxazole-based HDAC inhibitors

A series of isoxazole-based histone deacetylase (HDAC) inhibitors structurally related to SAHA were designed and synthesized. The isoxazole moiety was inserted in the vicinity of the Zn2+-binding group in order to check its participation in the coordinating process. New isoxazole-based histone deacetylase inhibitors structurally related to SAHA were designed and synthesized to check the participation of the isoxazole moiety in the Zn 2+coordination.

Synthesis and biological activity of 3-substituted isoxazolecarboxamides

A series of novel 3-substituted isoxazolecarboxamides have been prepared. A key step was 1,3-dipolar cycloaddition of nitrile oxides to α,β-unsaturated esters. Some of these compounds exhibited high fungicidal activities against Alternaria alternata, Botrytis cinerea, Rhizoctonia solani, Fusarium culmorum, and Phytophthora cactorum.

The synthesis of benzhydroximoyl chloride and nitrile oxides under solvent free conditions

Benzhydroximoyl chlorides were prepared as nitrile oxide precursors with acidic (HCl) silica gel/Oxone in solvent less media in excellent yields with the selective chlorination of aldoximes vs. aromatic substitution. Nitrile oxides were generated by Huisg

A novel one-pot synthesis of hydroximoyl chlorides and 2-isoxazolines using N-tert-butyl-N-chlorocyanamide

Treatment of aldoximes with N-tert-butyl-N-chlorocyanamide gave hydroximoyl chlorides in quantitative yields in less than a minute, which on dehydrohalogenation in the presence of triethylamine gave the corresponding nitrile oxides. The nitrile oxides underwent 1,3-dipolar addition to dipolarophiles and gave 2-isoxazolines in excellent yields under mild conditions.

Facile construction and divergent transformation of polycyclic isoxazoles: Direct access to polyketide architectures

(Matrix presented) Base-promoted cyclocondensation of C-chloro oximes with cyclic 1,3-diketones affords functionalized isoxazoles in good yield and under convenient reaction conditions. This process enables the synthesis of highly substituted products wit

Use of Nitrile Oxides in Synthesis. A Novel Synthesis of Chalcones, Flavanones, Flavones and Isoflavones

Novel methodology is developed for a three-step synthesis of chalcones, flavanones, flavones and isoflavones. 1.Salicylaldoxime is chlorinated to the corresponding hydroxamoyl chloride in the presence of pyridine, and cycloadded to styrene and phenylacetylene. 2.The isoxazole derivatives formed are reductively cleaved over Raney-Ni to β-hydroxyketones or 1,3 diketones. 3.Acid-catalyzed cyclization gives the flavonoids.Use of ω-methoxy- or ω-dialkylamino-substituted styrenes (enamines) leads regioselectively to 4-aryl-substituted isoxazoles and derived isoflavones.