65567-36-4

Upstream product

• 39201-89-3 (E)-3,4,5-trimethoxybenzaldehyde oxime 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 18638-99-8 3,4,5-trimethoxybenzylamine 

Downstream Products

• 392336-41-3 3,4,5-trimethoxybenzaldehyde O-[(2E,4E,8RS)-8-(tert-butyldiphenylsilanyloxy)-5-methyl-8-thiophen-2-ylocta-2,4-dienyl]oxime 
• 120802-91-7 5-Phenyl-3-(3,4,5-trimethoxy-phenyl)-4,5-dihydro-isoxazole 
• 120802-93-9 3-(3',4',5'-trimethoxyphenyl)-5-(3'',4''-dimethoxybenzyl)-4,5-dihydroisoxazole 
• 18638-99-8 3,4,5-trimethoxybenzylamine 
• 1038358-13-2 3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazole-5-carboxylic acid 
• 1394002-08-4 N-(4-chloro-2-(isopropylcarbamoyl)-6-methylphenyl)-3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazole-5-carboxamide 
• 1394002-05-1 N-(4-chloro-2-methyl-6-(propylcarbamoyl)phenyl)-3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazole-5-carboxamide 
• 1407515-91-6 C₂₀H₁₈N₂O₆ 
• 1394002-27-7 C₂₁H₁₉ClN₂O₆ 
• 1394002-24-4 N-(2-(methylcarbamoyl)phenyl)-3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazole-5-carboxamide 
• 1394002-21-1 N-(2-(isopropylcarbamoyl)phenyl)-3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazole-5-carboxamide 
• 1394002-17-5 N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazole-5-carboxamide 
• 1394002-14-2 N-(4-chloro-2-(diethylcarbamoyl)-6-methylphenyl)-3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazole-5-carboxamide 
• 1394002-11-9 N-(4-chloro-2-(cyclohexylcarbamoyl)-6-methylphenyl)-3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazole-5-carboxamide 

Relevant academic research and scientific papers

1,3-dipolar cycloaddition reactions of the compound obtaining from cyclopentadiene-PTAD and biological activities of adducts formed selectively

After known adduct (4) was synthesized by cycloaddition reaction of cyclopentadiene with 4-phenyl-1,2,4-triazoline-3,5-dione, seven new isoxazoline derivatives were synthesized from reactions of 4 with corresponding oximes prepared from benzaldehyde derivatives in the existence of the aqueous NaOCl in CH2Cl2 at 0°C—RT via nitrile oxides. Four new pyrazoline derivatives were also synthesized from reactions of 4 with corresponding prepared reagents via nitrile imines. Selectively, each of all isoxazole and pyrazoline derivatives was synthesized by 1,3-dipolar cycloaddition reactions of compound 4 with the corresponding reagents. Based on the results of their biological activity analyses, Ki values for acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and alpha-glucosidase (α-Gly) enzymes were obtained in this range 32.15 ± 5.73–107.44 ± 19.52 22.57 ± 4.30–186.07 ± 23.51, and 69.08 ± 8.54–528.07 ± 38.46 nM, respectively. Besides that, these compounds were subjected to molecular docking to describe the interaction against AChE, BChE, and α-Gly enzymes in which important interactions were visualized and evaluated with residues of the binding region in each target enzyme.

3-methyl-4-oxa-5-azahomoadamantane as an organocatalyst for the aerobic oxidation of primary amines to oximes in water

A simple and efficient catalytic system for the aerobic oxidation of primary amines into corresponding oximes has been developed, with 3-methyl-4-oxa-5-azahomoadamantane as catalyst, acetaldoxime as co-catalyst and water as solvent. This process, which uses oxygen (O2) as an economic and green oxidant and water as a green solvent, tolerates a wide range of substrates, affording the target oximes in moderate to excellent yields. It was found that high selectivity was achieved when 3-methyl-4-oxa-5-azahomoadamantane was used, and E-type oximes were the only detected products. A possible mechanism for this catalytic process is proposed.

Design, synthesis and in vitro cytotoxicity evaluation of new 3',4'-bis (3,4,5-trisubstituted)-4'H-spiro[indene-2,5'-isoxazol]-1(3H)-one derivatives as promising anticancer agents

A new series of 3',4'-bis(3,4,5-trimethoxyphenyl)-4'H-spiro[indene-2,5'-isoxazol]-1(3H)-one derivatives was designed and synthesized. The cytotoxic effects of the synthesized compounds were evaluated on several different human cancer cells. Among them, compound 9e displayed the most potent in vitro antiproliferative activity with IC50 values of 0.07±0.01 μM on T47D cells. Another potent derivative 9h displayed an IC50 value of 0.12±0.07 μM against T47D cells, comparable to that of the positive controls (Colchicine' Cisplatin' Vincristine' Vinblastine' Doxorubicin' Celecoxib). The structure-activity relationships were discussed and both anti-tubulin and COX-2 inhibitory effects were proposed for the developed compounds

A novel and efficient catalytic system including TEMPO/acetaldoxime/InCl3 for aerobic oxidation of primary amines to oximes

A simple and efficient catalytic system including TEMPO/acetaldoxime/InCl3 for aerobic oxidation of primary amines to corresponding oximes by using toluene as the solvent is described. This practical method can use O2 as the economic and green oxidant, tolerate a wide range of substrates, which can afford the target oximes in moderate to excellent yields.

Anthranilic acid-based diamides derivatives incorporating aryl-isoxazoline pharmacophore as potential anticancer agents: Design, synthesis and biological evaluation

A series of novel anthranilic diamides derivatives containing aryl-isoxazoline moiety were designed and synthesized as a part of our ongoing search for potential anticancer agents. Their structures were confirmed by 1H NMR, 13C NMR and ESI-MS analyses. The preliminary assays showed that some of the compounds displayed moderate to good antitumor activities against human lung cancer (NCI-H460), hepatocellular liver carcinoma (HepG2), gastric cancer (SGC-7901 and BGC-823) and breast epithelial adenocarcinoma (MCF-7) cell lines at μM level, which might be developed as novel lead scaffold for potential anticancer agents.

Synthesis and Antitubercular Activity of 4-(5-Nitro-2-furyl/2-pyrazinyl/1-adamantyl)-2-(alkyl/aryl/arylamino)thiazoles

The reaction of haloketones, obtained from Arndt-Eistert reaction on the acid chlorides of 1-adamantane, 5-nitrofuroic acid and pyrazine-2-carboxylic acid, with different thioamides and thioureas affords the title thiazoles (I-III).Some of them exhibit interesting antitubercular activity at 6.25 to 0.38 μg/ml concentration against H37Rv strain of M. tubercolosis in vitro testing.The structure activity relationship (SAR) has also been discussed.

Synthesis and structure activity relationships of selected isomeric oxime O ethers as anticholinergic agents

A series of isomeric (Z)- and (E)-oxime O-β-dimethylaminoethyl ether methylhalide derivatives was synthesized, and their (Z)- and (E)-assignments were made on the basis of chemical and spectral data. The respective (Z)- and (E)-isomers were evaluated as anticholinergic agents on the rat ileum. The antimuscarinic potencies of the respective (Z)- and (E)-isomers were compared to determine the effect upon potency of this type of geometric isomerism. Three general structure-activity relationships are discernible among the synthesized compounds: (a) among oxime O-ethers derived from aromatic aldehydes, the higher potency consistently resides in the isomer where the aryl substituent is (E) to the ammonium ether substituent; (b) among oxime O-ethers derived from diaryl ketones, the (Z)- and (E)-isomers are approximately equipotent; and (c) oxime O-ethers derived from diaryl ketones are the most potent of the synthesized compounds.