25185-95-9

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Dichlorobenzaldoxime is used as a reagent for the synthesis of various pharmaceuticals, contributing to the development of new medications and therapeutic agents. Its role in this industry is crucial for creating the building blocks of life-saving drugs.
Used in Agrochemical Industry:
In the agrochemical sector, 2,6-Dichlorobenzaldoxime is employed as a precursor in the production of agrochemicals, which are essential for enhancing crop protection and agricultural productivity.
Used in Dye Production:
2,6-Dichlorobenzaldoxime is used as an intermediate in the manufacturing process of dyes, playing a significant role in the coloration and enhancement of various materials and products.
Used in Organic Compounds Synthesis:
As a versatile reagent, 2,6-Dichlorobenzaldoxime is utilized in the synthesis of a range of organic compounds, broadening its applications across different industries that rely on organic chemistry for their products and processes.

InChI:InChI=1/C7H5Cl2NO/c8-6-2-1-3-7(9)5(6)4-10-11/h1-4,11H/b10-4-

Upstream product

• 83-38-5 2,6-dichlorobenzaldehyde 
• 50-30-6 2,6-dichlorobenzoic acid 

Downstream Products

• 1194-65-6 2,6-dichloro-benzonitrile 
• 13180-88-6 2-[1-(2,6-Dichloro-phenyl)-meth-(Z)-ylideneaminooxy]-3,5-dinitro-benzoic acid methyl ester 
• 278597-28-7 methyl 3-(2,6-dichlorophenyl)-5-(propan-2-yl)-1,2-oxazole-4-carboxylate 
• 2008-58-4 2,6-dichlorobenzamide 
• 54268-07-4 Methyl-2,6-dichlorophenylcarbamat 
• 6590-95-0 2,6-dichlorophenylisothiocyanate 
• 52909-99-6 C₁₄H₁₀Cl₂NO₃S 
• 958948-34-0 2-(4-chlorophenyl)-5-(3-(2,6-dichlorophenyl)-5-methyl-4,5-dihydroisoxazol-5-yl)-1,3,4-oxadiazole 

Relevant academic research and scientific papers

Design, synthesis and antimycobacterial activity of various 3-(4-(substitutedsulfonyl)piperazin-1-yl)benzo[ d[isoxazole derivatives

In this communication, we synthesized a series of twenty four novel 3-(4-(substitutedsulfonyl)piperazin-1-yl)benzo[d]isoxazole analogues, characterized using various spectroscopic techniques and evaluated for their in vitro anti-tubercular activity against Mycobacterium tuberculosis (MTB) H37Rv strain. The titled compounds exhibited Minimum inhibitory concentration (MIC) between 3.125 and >50 μg/mL. Among the tested compounds, 5c, 6a, 6j and 6p exhibited moderate activity (MIC Combining double low line 12.5 μg/mL), while 5a and 6i exhibited good activity (MIC Combining double low line 6.25 μg/mL) and 6b (MIC Combining double low line 3.125 μg/mL) exhibited very good anti-tubercular activity. In addition, the analogues 5a, 5c, 6a, 6b, 6i, 6j and 6p were subjected to toxicity studies against mouse macrophage (RAW 264.7) cell lines to analyse the selectivity profile of the newly synthesized compounds and selectivity index of the most active compound was found to be >130 indicating suitability of the compound for further drug development. Structure of 6b was further substantiated through single crystal XRD.

AN IMPROVED PROCESS FOR PREPARATION OF PURE ALDOXIME

The present invention relates to an improved process for preparing aldoximes of formula (I) with high purity and high yield. The improved process for preparing aldoxime is fast, simple, highly efficient, and reproducible. The improved process for the preparation of aldoxime, which is synthesized in the higher yield under oximation reaction of aldehyde with hydroxylamine hydrochloride merely in aqueous medium using of in situ heat generation.

Palladium-Catalyzed (3+3) Annulation of Allenylethylene Carbonates with Nitrile Oxides

In this paper, we designed and synthesized a new type of cyclic carbonates, allenylethylene carbonates (AECs). With AECs as reactive precursors, we developed palladium-catalyzed (3+3) annulation of AECs with nitrile oxides. Various AECs worked well in this reaction under mild reaction conditions. A variety of 5,6-dihydro-1,4,2-dioxazine derivatives with allenyl quaternary stereocenters can be accessed in a facile manner in high yields (≤98%).

Discovery of BMS-986318, a Potent Nonbile Acid FXR Agonist for the Treatment of Nonalcoholic Steatohepatitis

Herein we report the discovery and preclinical biological evaluation of 6-(2-(5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)isoxazol-4-yl)-7-azaspiro[3.5]non-1-en-7-yl)-4-(trifluoromethyl)quinoline-2-carboxylic acid, compound 1 (BMS-986318), a nonbile acid farnesoid X receptor (FXR) agonist. Compound 1 exhibits potent in vitro and in vivo activation of FXR, has a suitable ADME profile, and demonstrates efficacy in the mouse bile duct ligation model of liver cholestasis and fibrosis. The overall profile of compound 1 supports its continued evaluation.

Discovery of a novel and orally active Farnesoid X receptor agonist for the protection of acetaminophen-induced hepatotoxicity

Acetaminophen (APAP) overdose is a leading cause of acute hepatic failure and liver transplantation, while the existing treatments are poorly effective. Therefore, it is necessary to develop effective therapeutic drugs for APAP-induced hepatotoxicity. Farnesoid X receptor (FXR) is a potential target for the treatment of liver disease, and the activation of FXR protects mice against APAP-induced hepatotoxicity. Compound 5, a glycine-conjugated derivative of FXR agonist 4, was designed to extend the chemical space of existing FXR agonists. Molecular modeling study indicated that compound 5 formed hydrogen bond network with key residues of FXR. Moreover, compound 5 (10?mg/kg) revealed better protective effects against APAP-induced hepatotoxicity than parent compound 4 (30?mg/kg). Further mechanical research indicated that compound 5 regulated the expressions of genes related to FXR and oxidative stress. These findings suggest that compound 5 is a promising FXR agonist suitable for further research, and it is the first time to verify that the glycine-conjugated derivative five exerted better protective effects than its parent compound.

A Strategy for Accessing Aldehydes via Palladium-Catalyzed C?O/C?N Bond Cleavage in the Presence of Hydrosilanes

We report the catalytic reduction of both active esters and amides by selective C(acyl)?X (X=O, N) cleavage to access aldehyde functionality via a palladium-catalyzed strategy. Reactions are promoted by hydrosilanes as reducing reagents with good to excellent yields and with excellent chemoselectivity for C(acyl)?N and C(acyl)?O bond cleavage. Carboxylic acid C(acyl)?O bonds are activated by 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) to form triazine ester intermediates, which further react with hydrosilanes to yield aldehydes in one-pot two-step procedures. We demonstrate that C(acyl)?O cleavage/formylation offers higher yields and broader substrate scopes compared with C(acyl)?N cleavage under the same reaction conditions.

Discovery and Optimization of Non-bile Acid FXR Agonists as Preclinical Candidates for the Treatment of Nonalcoholic Steatohepatitis

Farnesoid X receptor (FXR) plays a key role in bile acid homeostasis, inflammation, fibrosis, and metabolism of lipid and glucose and becomes a promising therapeutic target for nonalcoholic steatohepatitis (NASH) or other FXR-dependent diseases. The phase III trial results of obeticholic acid demonstrate that the FXR agonists emerge as a promising intervention in patients with NASH and fibrosis, but this bile acid-derived FXR agonist brings severe pruritus and an elevated risk of cardiovascular disease for patients. Herein, we reported our efforts in the discovery of a series of non-bile acid FXR agonists, and 36 compounds were designed and synthesized based on the structure-based drug design and structural optimization strategies. Particularly, compound 42 is a highly potent and selective FXR agonist, along with good pharmacokinetic profiles, high liver distribution, and preferable in vivo efficacy, indicating that it is a potential candidate for the treatment of NASH or other FXR-dependent diseases.

Synthesis and SAR study of simple aryl oximes and nitrofuranyl derivatives with potent activity against Mycobacterium tuberculosis

Background: Oximes and nitrofuranyl derivatives are particularly important compounds in medicinal chemistry. Thus, many researchers have been reported to possess antibacterial, antiparasitic, insecticidal and fungicidal activities. Methods: In this work, we report the synthesis and the biological activity against Mycobacterium tuberculosis H37RV of a series of fifty aryl oximes, ArCH=N-OH, I, and eight nitrofuranyl compounds, 2-nitrofuranyl-X, II. Results: Among the oximes, I: Ar = 2-OH-4-OH, 42, and I: Ar = 5-nitrofuranyl, 46, possessed the best activity at 3.74 and 32.0 μM, respectively. Also, 46, the nitrofuran compounds, II; X = MeO, 55, and II: X = NHCH2Ph, 58, (14.6 and 12.6 μM, respectively), exhibited excellent biological activities and were non-cytotoxic. Conclusion: The compound 55 showed a selectivity index of 9.85. Further antibacterial tests were performed with compound 55 which was inactive against Enterococcus faecalis, Klebisiella pneumonae, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhymurium and Shigel-la flexneri. This study adds important information to the rational design of new lead anti-TB drugs. Structure-activity Relationship (SAR) is reported.

Design and Structural Optimization of Dual FXR/PPARδActivators

Nonalcoholic steatohepatitis (NASH) is considered as severe hepatic manifestation of the metabolic syndrome and has alarming global prevalence. The ligand-activated transcription factors farnesoid X receptor (FXR) and peroxisome proliferator-activated receptor (PPAR) δhave been validated as molecular targets to counter NASH. To achieve robust therapeutic efficacy in this multifactorial pathology, combined peripheral PPAR?-mediated activity and hepatic effects of FXR activation appear as a promising multitarget approach. We have designed a minimal dual FXR/PPARδactivator scaffold by rational fusion of pharmacophores derived from selective agonists. Our dual agonist lead compound exhibited weak agonism on FXR and PPARδand was structurally refined to a potent and balanced FXR/PPARδactivator in a computer-aided fashion. The resulting dual FXR/PPARδmodulator comprises high selectivity over related nuclear receptors and activates the two target transcription factors in native cellular settings.

COMPOUNDS USEFUL IN MODULATING THE FARNESOID X RECEPTOR AND METHODS OF MAKING AND USING THE SAME

Provided are compounds that can act as a modulator of a farnesoid X receptor (FXR) and that can be useful in the treatment of diseases and/or disorders associated with the FXR. Compositions including such compounds are also provided along with methods for preparing compounds of the present invention and their use.