153788-75-1

Upstream product

• 2169-98-4 3,4-Dimethoxy-benzaldehyde oxime 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 105363-12-0 N-hydroxy-3,4-dimethoxybenzenecarboximidoyl chloride 

Downstream Products

• 1262439-29-1 N-(3-(3,4-dimethoxyphenyl)isoxazol-5-yl)methyl-2-(diethylamino)ethanamide 
• 457627-12-2 4-[3-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-butyraldehyde 
• 1186630-13-6 C₂₄H₂₇NO₇ 

Relevant academic research and scientific papers

Discovery, synthesis, and biological evaluation of a novel group of selective inhibitors of filoviral entry

Herein, we report the development of an antifiloviral screening system, based on a pseudotyping strategy, and its application in the discovery of a novel group of small molecules that selectively inhibit the Ebola and Marburg glycoprotein (GP)-mediated infection of human cells. Using Ebola Zaire GP-pseudotyped HIV particles bearing a luciferase reporter gene and 293T cells, a library of 237 small molecules was screened for inhibition of GP-mediated viral entry. From this assay, lead compound 8a was identified as a selective inhibitor of filoviral entry with an IC50 of 30 μM. To analyze functional group requirements for efficacy, a structure-activity relationship analysis of this 3,5-disubstituted isoxazole was then conducted with 56 isoxazole and triazole derivatives prepared using "click" chemistry. This study revealed that while the isoxazole ring can be replaced by a triazole system, the 5-(diethylamino)acetamido substituent found in 8a is required for inhibition of viral-cell entry. Variation of the 3-aryl substituent provided a number of more potent antiviral agents with IC50 values ranging to 2.5 μM. Lead compound 8a and three of its derivatives were also found to block the Marburg glycoprotein (GP)-mediated infection of human cells.

Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents

Several novel spiro derivatives of parthenin (1) have been synthesized by the dipolar cycloaddition using various dipoles viz; benzonitrile oxides, nitrones and azides with exocyclic double bond of C ring (α-methylene- γ-butyrolactone). Majority of the compounds exhibited improved anti-cancer activity compared to the parthenin, when screened for their in vitro cytotoxicity against three human cancer cell lines viz., SW-620, DU-145 and PC-3. In vivo screening of select analog revealed improved anti-cancer activity with low mammalian toxicity as compared to parthenin. The results of the cytotoxicity pattern of these derivatives reveals the SAR of these sesquiterpinoid lactones and possible role of α,β-unsaturated ketone of parthenin in inhibiting NF-kB. A mechanistic correlation of anti-cancer activity along with in vivo and western blotting experiments has been described.

A novel synthesis of isoxazoles via 1,3-dipolar cycloaddition of nitrile oxides to acetyl acetone

Nitrile oxides (2) isolated from the oxidative dehydrogenation of aldoximes (1) by chloramines-T react with acetyl acetone (3) to afford 4-acetyl-3-aryl-5-methyl isoxazoles (5) in good yield. All new compounds were characterized by IR, 1H NMR,

Design and Synthesis of a Piperazinylalkylisoxazole Library for Subtype Selective Dopamine Receptor Ligands

A piperazinylbutylisoxazole library was designed, synthesized and screened for the binding affinities to dopamine D2, D3, and D4 receptors. Several ligands were identified to possess high binding affinity and selectivity for the D3 and D4 receptors over the D2 receptor. Compounds 6s and 6t showed Ki values of 2.6 nM and 3.9 nM for the D3 receptor with 46- and 50-fold selectivity over te D2 receptor, respectively.

Intermodular 1,3-dipolar cycloaddition of nitrite oxides with vinyl acetate and acrylonitrile

Reaction of several nitrile oxides 2, isolated from the oxidative dehydrogenation of aldoximes by chloramine-T, with vinyl acetate and acrylonitrile proceeds in better yield than if the nitrile oxides are generated in situ. Solvent effects are also consid

1,3-DIPOLAR CYCLOADDITION REACTIONS INVOLVING CAPTODATIVE OLEFINS

A series of arylnitrile oxides (6a-e) were reacted with captodative olefins (4) to yield 5-acetyl-3-arylisoxazoles.No intermediate isoxazolines were formed, the olefins thus behaved as acetylene equivalents.A plausible explanation for the observed regiose

Unusual Chemo- and Stereo-selectivities in the rEactions of 1,2-Dichlorocyclopenes with Nitrile Oxides

1,2-Dichloro-3,3-dimethylcyclopropene reacts with a number of nitrile oxides to produce oxazines in moderate to good yield in a reaction which apparently involves an unusual formal 3-centre plus 3-centre cycloaddition of the dipole to an intermediate viny