2169-98-4

Usage

Uses

Used in Organic Synthesis:
3,4-Dimethoxy-benzaldoxim is used as a building block in organic synthesis for the creation of various complex organic molecules. Its unique structure allows for multiple points of reactivity, facilitating the formation of a wide range of compounds.
Used in Pharmaceutical Research:
In Pharmaceutical Research, 3,4-Dimethoxy-benzaldoxim is used as a precursor in the development of new drugs. Its potential biological activities, such as antioxidant properties and cancer cell growth inhibition, make it a promising candidate for further investigation and application in medicinal chemistry.
Used in Antioxidant Applications:
3,4-Dimethoxy-benzaldoxim is utilized as an antioxidant, protecting cells from oxidative damage caused by reactive oxygen species. Its ability to neutralize these harmful molecules contributes to its potential use in health and wellness products.
Used in Cancer Research:
In Cancer Research, 3,4-Dimethoxy-benzaldoxim is employed as a compound with potential anti-cancer properties. Its capacity to inhibit the growth of certain cancer cells is being studied for possible therapeutic applications in oncology.
Used in Agrochemical Synthesis:
3,4-Dimethoxy-benzaldoxim is used as a key intermediate in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural products to improve crop yield and protect against pests.
Used in Chemical Intermediates:
As a Chemical Intermediate, 3,4-Dimethoxy-benzaldoxim plays a crucial role in the synthesis of various pharmaceuticals and agrochemicals, serving as a stepping stone in the production of these compounds.

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

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 5763-61-1 3,4-dimethoxybenzylamine 
• 63-64-9 N-methylveratrylamine 
• 314768-38-2 (Z)-C-(3,4-dimethoxyphenyl)-N-methyl-nitrone 

Downstream Products

• 5763-61-1 3,4-dimethoxybenzylamine 
• 109979-90-0 1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methyl-3,4-dihydro-isoquinoline 
• 2024-83-1 veratronitrile 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 93-07-2 Veratric acid 
• 105363-12-0 N-hydroxy-3,4-dimethoxybenzenecarboximidoyl chloride 
• 59550-82-2 Veratrumaldehyd-oximester d. N,N-Diphenylcarbaminsaeure 
• 227804-35-5 N-(3,4-dimethoxybenzyl)hydroxylamine 
• 153788-75-1 3,4-dimethoxybenzonitrile oxide 
• 202406-74-4 3-(3,4-dimethoxyphenyl)-5-(4-pyridyl)-4,5-dihydroisoxazole 
• 370865-86-4 4-[3-(3,4-dimethoxy-phenyl)-4,5-dihydro-isoxazol-5-ylmethoxy]-3-methoxy-benzaldehyde 

Relevant academic research and scientific papers

Design, Synthesis and Anticancer Evaluation of New Substituted Thiophene-Quinoline Derivatives

A series of new isoxazolyl, triazolyl and phenyl based 3-thiophen-2-yl-quinoline derivatives were synthesized adopting click chemistry approach. In addition, the synthesis of new useful synthon, (2-chloroquinolin-3-yl) (thiophen-2-yl) methanol, is reported. The obtained compounds were characterized by spectral data analysis and evaluated for their anticancer activity. All the derivatives were subjected to in vitro MTT cytotoxicity screening assay against a panel of four different human cancer cell lines, liver (HepG-2), colon (HCT-116), human cervical cancer (HeLa) and breast (MCF-7). Out of a library of 17 compounds, two compounds have been identified as potent and selective cytotoxic agents against HeLa and MCF-7 cell lines. SAR studies for such hybridized analogues were investigated and phenyl derivatives were proved to be more potent than isoxazole and triazole derivatives. Furthermore, the promising compounds were selected for in vitro inhibition of EGFR-TK and Topo II enzymes. Also, they were subjected to cell cycle arrest analysis and apoptosis assay on MCF-7 cells. Our recent finding highlights these thiophene-quinoline analogues as a promising class of compounds for further studies concerning new anticancer therapies.

Tetrahydroquinoline-isoxazole/isoxazoline hybrid compounds as potential cholinesterases inhibitors: Synthesis, enzyme inhibition assays, and molecular modeling studies

A series of 44 hybrid compounds that included in their structure tetrahydroquinoline (THQ) and isoxazole/isoxazoline moieties were synthesized through the 1,3-dipolar cycloaddition reaction (1,3-DC) from the corresponding N-allyl/propargyl THQs, previously obtained via cationic Povarov reaction. In vitro cholinergic enzymes inhibition potential of all compounds was tested. Enzyme inhibition assays showed that some hybrids exhibited significant potency to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Especially, the hybrid compound 5n presented the more effective inhibition against AChE (4.24 μM) with an acceptable selectivity index versus BChE (SI: 5.19), while compound 6aa exhibited the greatest inhibition activity on BChE (3.97 μM) and a significant selectivity index against AChE (SI: 0.04). Kinetic studies were carried out for compounds with greater inhibitory activity of cholinesterases. Structure–activity relationships of the molecular hybrids were analyzed, through computational models using a molecular cross-docking algorithm and Molecular Mechanics/Generalized Born Surface Area(MM/GBSA) binding free energy approach, which indicated a good correlation between the experimental inhibition values and the predicted free binding energy.

Synthesis of isoxazoles via 1,3-dipolar cycloaddition reactions: Pharmacological screening for their antioxidant and antimicrobial activities

In the present study, we report the synthesis of series of novel substituted isoxazoles via 1,3-dipolar cycloaddition reaction. Nitrile oxides generated by the catalytic dehydrogenation of aldoximes by chloramine-T, were trapped in situ by 4-(furan-2-yl)b

In silico design and synthesis of N-arylalkanyl 2-naphthamides as a new class of non-purine xanthine oxidase inhibitors

A series of N-arylalkanyl 2-naphthamides (Xa~e), which were predicted from virtual molecular docking on a built xanthine oxidase template as potential inhibitors, were synthesized. Their inhibitory activity against xanthine oxidase was assayed. Among these prepared, compounds Xb (IC50 13.6?μM), Xc (IC50 13.1?μM), and Xd (IC50 12.5?μM) showed comparable inhibitory activity to allopurinol (IC50 22.1?μM). The in vitro assay result correlated well with molecular docking scores, ΔG?=??16.99, ?17.66, and ?17.13 Kcal/mol, respectively. On the potassium oxonate-induced hyperuricemic mice model, oral administration of Xc-Ac (40 mg/ Kg), the per-O-acetylated Xc, could reduce the blood uric acid level by 60% in comparison to the normal control group and is statistically significant (p .01) while compared with the hyperuricemic mice group.

Design, synthesis and biological evaluation of novel indanone containing spiroisoxazoline derivatives with selective COX-2 inhibition as anticancer agents

Objective: A new family of 3′-(Mono, di or tri-substituted phenyl)-4′-(4-(methylsulfonyl) phenyl) spiroisoxazoline derivatives containing indanone spirobridge was designed, synthesized, and evaluated for their selective COX-2 inhibitory potency and cytotoxicity on different cell lines. Methods: A synthetic reaction based on 1,3-dipolar cycloaddition mechanism was applied for the regiospecific formation of various spiroisoxazolines. The activity of the newly synthesized compounds was determined using in vitro cyclooxygenase inhibition assay. The toxicity of the compounds was evaluated by MTT assay. In addition, induction of apoptosis, and expression levels of Bax, Bcl-2 and caspase-3 mRNA in MCF-7 cells were evaluated following exposure to compound 9f. The docking calculations and molecular dynamics simulation were performed to study the most probable modes of interactions of compound 9f upon binding to COX-2 enzyme. Results: The docking results showed that the synthesized compounds were able to form hydrogen bonds with COX-2 involving methyl sulfonyl, spiroisoxazoline, meta-methoxy and fluoro functional groups. Spiroisoxazoline derivatives containing methoxy group at the C-3′ phenyl ring meta position (9f and 9g) showed superior selectivity with higher potency of inhibiting COX-2 enzyme. Furthermore, compound 9f, which possesses 3,4-dimethoxyphenyl on C-3′ carbon atom of isoxazoline ring, exhibited the highest COX-2 inhibitory activity, and also displayed the most potent cytotoxicity on MCF-7 cells with an IC50 value of 0.03 ± 0.01 μM, comparable with that of doxorubicin (IC50 of 0.062 ± 0.012 μM). The results indicated that compound 9f could promote apoptosis. Also, compared to the control group, the mRNA expression of Bax and caspase-3 significantly increased, while that of Bcl-2 significantly decreased upon exposure to compound 9f which may propose the activation of mitochondrial-associated pathway as the mechanism of observed apoptosis. Conclusion: In vitro biological evaluations accompanied with in silico studies revealed that indanone tricyclic spiroisoxazoline derivatives are good candidates for the development of new anti-inflammatory and anticancer (colorectal and breast) agents.

HCl-mediated cascade cyclocondensation of oxygenated arylacetic acids with arylaldehydes: one-pot synthesis of 1-arylisoquinolines

In this paper, a concise, open-vessel synthesis of 1-arylisoquinolines is describedviaHCl-mediated intermolecular cyclocondensation of oxygenated arylacetic acids with arylaldehydes in the presence of NH2OH and alcoholic solvents under mild and one-pot reaction conditions. A plausible mechanism is proposed and discussed herein. In the overall reaction process, only water was generated as the byproduct. Various environmentally friendly reaction conditions are investigated for convenient transformationviathe (4C + 1C + 1N) annulation. This protocol provides a highly effective ring closureviathe formations of one carbon-carbon (C-C) bond, two carbon-nitrogen (C-N) bonds and one carbon-oxygen (C-O) bond.

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.

Chlorotropylium Promoted Conversions of Oximes to Amides and Nitriles

Chlorotropylium chloride as a catalyst for the transformations of oximes, ketones, and aldehydes to their corresponding amides and nitriles in excellent yields (up to 99 %) and in short reaction times (mostly 10–15 min). Oximes were electrophilically attacked on the hydroxyl oxygen by chlorotropylium. The produced tropylium oxime ethers were the key intermediates, of which the ketoxime ether led to amide through Beckmann rearrangement, and the aldoxime ether led to nitrile by nitrogen base DBU assisted formal dehydration. This chlorotropylium activation protocol offered general, mild, and efficient avenues bifurcately from oximes to both amides and nitriles by one organocatalyst.

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.].

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.