22755-95-9

Upstream product

• 67-56-1 methanol 
• 22252-15-9 trans-4-methoxychalcone 
• 149-73-5 trimethyl orthoformate 
• 959-33-1 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 
• 956215-94-4 3-(4-methoxyphenyl)-1-phenyl-2,3-ditosyloxypropanone 

Downstream Products

• 66558-45-0 3.3-Diaethoxy-2-(4-methoxyphenyl)-1-phenylpropan-1-on 
• 116485-59-7 4-(4-methoxyphenyl)-5-phenylisoxazole 

Relevant academic research and scientific papers

A comparative evaluation of monomethoxy substituted o-diarylazoles as antiproliferative microtubule destabilizing agents

Monomethoxy substituted o-diarylazoles with isoxazole, triazole, pyrazole, or pyrrole linkers were synthesized and evaluated for antimitotic antitubulin activity in a sea urchin embryo model. Structure–activity relationship study revealed that only isoxazole heterocycle together with the unsubstituted phenyl ring next to the heteroatom endowed the molecule with appropriate configuration to exhibit antiproliferative effect by microtubule destabilizing mode of action.

Computational modeling and target synthesis of monomethoxy-substituted o-diphenylisoxazoles with unexpectedly high antimitotic microtubule destabilizing activity

The ability of monomethoxy-substituted o-diphenylisoxazoles 2a-d to interact with the colchicine site of tubulin was predicted using computational modeling, docking studies, and calculation of binding affinity. The respective molecules were synthesized in high yields by three steps reaction using easily available benzaldehydes, acetophenones, and arylnitromethanes as starting material. The calculated antitubulin effect was confirmed in vivo in a sea urchin embryo model. Compounds 2a and 2c showed high antimitotic microtubule destabilizing activity compared to that of CA4. Isoxazole 2a also exhibited significant cytotoxicity against human cancer cells in NCI60 screen. For the first time, isoxazole-linked CA4 derivatives 2a and 2c with only one methoxy substituent were identified as potent antimitotic microtubule destabilizing agents. These molecules could be considered as promising structures for further optimization.

The chemistry of α,β-ditosyloxyketones: Novel routes for the synthesis of desoxybenzoins and α-aryl-β-ketoaldehyde dimethylacetals from α,β-chalcone ditosylates

The reaction of α,β-chalcone ditosylates 3 with potassium hydroxide in suitable conditions leads to 1,2-aryl shift and carbon-carbon bond cleavage, thereby providing a novel route for the synthesis of 1,2-diarylethan-1-ones 4 and 1,2-diaryl-3,3-dimethoxy propan-1-ones 5. Georg Thieme Verlag Stuttgart.

Synthesis of isoflavones from 2′-hydroxychalcones using poly[4-(diacetoxy)iodo]styrene or related hypervalent iodine reagent

Isoflavones are synthesized in an one-pot reaction by treating the hypervalent iodine(III) reagent, [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser's reagent) with 2′-benzoyloxychalcones in MeOH. A combined use of (diacetoxyiodo)benzene (DIB)/p-toluenesulfoni

SOLVOHYPERIODINATION. A COMPARISON WITH SOLVOTHALLATION

C6H5IO/CH3OH and a catalyst such as FSO3H, CF3SO3H or BF3-Et2O as well as C6H5(OH)OTs-CH3OH, react with chalcones, acetophenones and styrenes to yield rearranged products.The overall course of these reactions is analogous to that of Tl(NO3)3-CH3OH in reaction with the same compounds.

Thallium in Organic Synthesis. 57. Reaction of Chalcones and Chalcone Ketals with Thallium(III) Trinitrate

Treatment of chalcones (ArCH=CHCOAr') with thallium(III) trinitrate (TTN) in acidic methanol or in trimethyl orthoformate (TMOF) gives 3,3-dimethoxy-1,2-diarylpropan-1-ones (oxythallation, Ar rearrangement) and/or methyl 2,3-diaryl-3-methoxypropanoates (in situ ketal formation, oxythallation, Ar' rearrangement).The effect of substituents on Ar and Ar' on the ratio of the above rearrangement products has been examined.