31874-34-7

Usage

Uses

Used in Analytical Chemistry:
2,4-DIMETHOXYBENZALDOXIME is used as a reagent in spectrophotometric methods for the detection and quantification of metal ions such as copper, nickel, and cobalt. It forms colored complexes with these metal ions, facilitating their identification and measurement.
Used in Chelating Processes:
In the field of chemistry, 2,4-DIMETHOXYBENZALDOXIME serves as a chelating agent, which is instrumental in the separation and extraction of metal ions. This application is crucial for purifying samples and isolating specific metal ions for further analysis or processing.
Used in Pharmaceutical Development:
2,4-DIMETHOXYBENZALDOXIME holds potential in the development of pharmaceuticals, where it may contribute to the creation of new drugs or improve the synthesis processes of existing ones.
Used as a Precursor in Organic Synthesis:
2,4-DIMETHOXYBENZALDOXIME also functions as a precursor in the synthesis of other organic compounds, indicating its versatility and importance in organic chemistry for creating a variety of chemical products.

InChI:InChI=1/C9H11NO3/c1-12-8-4-3-7(6-10-11)9(5-8)13-2/h3-6,11H,1-2H3/b10-6+

Upstream product

• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 151-10-0 1,3-Dimethoxybenzene 
• 7647-01-0 hydrogenchloride 
• 71-43-2 benzene 
• 91-52-1 2,4 dimethoxybenzoic acid 

Downstream Products

• 31874-50-7 Boc-Gln(Dmb)-OBzl 
• 31874-48-3 (S)-2-Benzyloxycarbonylamino-4-(2,4-dimethoxy-benzylcarbamoyl)-butyric acid methyl ester 
• 31874-64-3 (S)-2-Benzyloxycarbonylamino-N-(2,4-dimethoxy-benzyl)-succinamic acid methyl ester 
• 20781-20-8 2,4-Dimethoxybenzylamine 
• 138420-88-9 (5R,8R)-8-(2,4-Dimethoxy-phenyl)-7-oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-dioxide 
• 74467-06-4 5-Chloro-2,4-dimethoxybenzaldehyde oxime 
• 74467-07-5 2,4-Dimethoxybenzohydroximinoyl chloride 
• 139435-99-7 2,4-Dimethoxy-benzaldehyde O-[2-hydroxy-3-(2-methyl-4-nitro-imidazol-1-yl)-propyl]-oxime 
• 4107-65-7 2,4-dimethoxybenzonitrile 
• 188119-32-6 2,4-Dimethoxy-benzonitrile N-oxide 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 227804-34-4 N-(2,4-dimethoxybenzyl)-hydroxylamine 
• 457627-13-3 4-[3-(2,4-dimethoxy-phenyl)-isoxazol-5-yl]-butyraldehyde 

Relevant academic research and scientific papers

Synthesis of 3,5-disubstituted isoxazolines as protein tyrosine phosphatase 1B inhibitors

The protein tyrosine phosphatases (PTPase) are a group of regulatory enzymes that are critically important to a wide variety of cellular functions. PTPase 1B has recently been implicated in the pathogenesis of diabetes, neuronal disease, and autoimmune diseases. A number of these PTPase that act as negative regulators of the insulin signaling cascade have been identified as novel targets for the therapeutic enhancement of insulin action in insulin-resistant disease states like type II diabetes. Therefore, in the present work we describes a study of the synthesis and structure-activity relationship (SAR) of chromene and 2,4-dimethoxy benzaldehyde-based isoxazolines, which are structurally related to potent PTPase inhibitors. Compounds 5-7 and 10-19 were synthesized via 1,3-dipolar cycloaddition reaction and evaluated against PTPase enzyme in vitro. Compounds 10, 14, and 19 displayed significant inhibitory activity with IC50 values of 69, 88, and 62.7 μM, respectively. Active compounds 10, 11, 14-16, and 19 were also tested in the STZ-S in vivo assay model, and compounds 10, 14, and 19 were found to be active.

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.

Facile synthesis and docking studies of 7-hydroxyflavanone isoxazoles and acrylates as potential anti-microbial agents

The present study is aimed to synthesize the novel 7-hydroxyflavanone derived compounds and to assess their biological activity. Two series of compounds such as 2-phenyl-7-((3-phenylisoxazol-5-yl)methoxy)chroman-4-ones (6a–h) and 4-oxo-2-phenylchroman-7-yl acrylates (8a–k) were synthesized from 7-hydroxyflavanone. All the compounds were subjected to anti-microbial activity and molecular docking studies. The results showed that the compounds 6e, 6g–h, 8h–i and 8k were exhibited most potent anti-microbial activity when compared with the standard drugs. Further, the docking studies revealed that the compounds 6a and 8h have the highest binding affinity score of sterol 14-α demethylase and DNA gyrase B respectively. This is the first report assigning unique synthesis of 7-hydroxyflavanone derivatives and their anti-microbial activity proved with in silico studies. Furthermore, the present study is useful for constructive research to synthesize novel compounds along with their biological activity. [Figure not available: see fulltext.].

Efficient transformation of electron-rich arenes into diethyl 3-arylisoxazole-4,5-dicarboxylates

Treatment of electron-rich arenes with Tf2O and DMF, followed by the reaction with NH2OH·HCl and then with Oxone in the presence of diethyl acetylenedicarboxylate generated diethyl 3-arylisoxazole-4,5-dicarboxylates in good to modera

A Threonine-Forming Oxazetidine Amino Acid for the Chemical Synthesis of Proteins through KAHA Ligation

α-Ketoacid-hydroxylamine (KAHA) ligation allows the coupling of unprotected peptide segments through the chemoselective formation of an amide bond. Currently, the most widely used variant employs a 5-membered cyclic hydroxylamine that forms a homoserine ester as the primary ligation product. In order to directly form amide-linked threonine residues at the ligation site, we prepared a new 4-membered cyclic hydroxylamine building block. This monomer was applied to the synthesis of wild-type ubiquitin-conjugating enzyme UbcH5a (146 residues) and Titin protein domain TI I27 (89 residues). Both the resulting UbcH5a and the variant with two homoserine residues showed identical activity to a recombinant variant in a ubiquitination assay.

Catalyst control in positional-selective C-H alkenylation of isoxazoles and a ruthenium-mediated assembly of trisubstituted pyrroles

High levels of catalyst control are demonstrated in determining the positional selectivity in C-H alkenylation of isoxazoles. A cationic rhodium-mediated, strong-directing group promotes C(sp2)-H activation at the proximal aryl ring whereas, the palladium-mediated electrophilic metallation leads to the C(sp2)-H activation at the distal position of the directing group. Synthetic elaboration of this C-H alkenylation product via ruthenium and copper co-catalysis leads to an efficient method for the assembly of densely substituted pyrroles.

CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines

This report details a general and enantioselective means for the synthesis of alkyl-substituted aziridines. This protocol offers a direct route for the synthesis of alkyl-substituted chiral aziridines from achiral starting materials. Readily accessed ally

Design and synthesis of neolamellarin a derivatives targeting heat shock protein 90

In this study, we designed and synthesized a novel family of neolamellarin A derivatives that showed high inhibitory activity toward heat shock protein 90 (Hsp90), a kinase associated with cell proliferation. The 3,4-bis(catechol)pyrrole scaffold and the benzyl group with methoxy modification at N position of pyrrole are essential to the Hsp90 inhibitory activity and cytotoxicity of these compounds. Western blot analysis demonstrated that these compounds induced dramatic depletion of the examined client proteins of Hsp90, and accelerated cancer cell apoptosis. Docking simulations suggested that the binding mode of 9p was similar to that of the VER49009, a potent inhibitor of Hsp90. Further molecular dynamics simulation indicated that the hydrophobic interactions as well as the hydrogen bonds contributed to the high affinity of 9p to Hsp90.

Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship

In our earlier study, we have reported that a phenolic compound 2-hydroxy-4-methoxybenzaldehyde from Janakia arayalpatra root extract was active against Viper and Cobra envenomations. Based on the structure of this natural product, libraries of synthetic structurally variant phenolic compounds were studied through molecular docking on the venom protein. To validate the activity of eight selected compounds, we have tested them in in vivo and in vitro models. The compound 21 (2-hydroxy-3-methoxy benzaldehyde), 22 (2-hydroxy-4-methoxybenzaldehyde) and 35 (2-hydroxy-3-methoxybenzylalcohol) were found to be active against venom-induced pathophysiological changes. The compounds 20, 15 and 35 displayed maximum anti-hemorrhagic, anti-lethal and PLA2 inhibitory activity respectively. In terms of SAR, the presence of a formyl group in conjunction with a phenolic group was seen as a significant contributor towards increasing the antivenom activity. The above observations confirmed the anti-venom activity of the phenolic compounds which needs to be further investigated for the development of new anti-snake venom leads.

Synthesis and biological evaluation of salicylic acid conjugated isoxazoline analogues on immune cell proliferation and angiogenesis

Mitogenicity is the ability of the natural or synthetic compounds to induce cell division or proliferation. A series of salicylic acid derivatives containing isoxazoline moiety (8a-j) were synthesized and their immunopharmacological activities targeting lymphocyte proliferation and angiogenesis were evaluated. The compounds 8a-j mitogenicity were investigated on immunological cells that include human peripheral blood lymphocytes and murine splenocytes in-vitro. The results implicate that among the series of 8a-j, compound 8e showed a potent proliferative response on both human and murine lymphocytes. The proliferative index of the compound 8e was comparable to the reference mitogen Con A and mitogenecity is due to increased secretion IL-2. In-vivo CAM and rat corneal angiogenesis assays were performed to assess the compound's effect on endothelial cell migration and proliferation which inferred that 8e also induces the proliferation of endothelial cells. The study reports the synthetic immunostimulatory and pro-angiogenic activity of novel mitogen 8e which could be translated into new drug in future.