74007-53-7Relevant academic research and scientific papers
A comparative evaluation of monomethoxy substituted o-diarylazoles as antiproliferative microtubule destabilizing agents
Kislyi, Victor P.,Koblov, Ivan A.,Maksimenko, Anna S.,Samet, Alexander V.,Semenov, Victor V.,Semenova, Marina N.,Silyanova, Eugenia A.,Ushkarov, Vladimir I.
, p. 120 - 122 (2022/03/08)
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
Stroylov, Victor S.,Svitanko, Igor V.,Maksimenko, Anna S.,Kislyi, Victor P.,Semenova, Marina N.,Semenov, Victor V.
supporting information, (2020/10/21)
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.
SOLVOHYPERIODINATION. A COMPARISON WITH SOLVOTHALLATION
Moriarty, Robert M.,Khosrowshahi, Jaffar S.,Prakash, Om
, p. 2961 - 2964 (2007/10/02)
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
Taylor, Edward C.,Conley, Richard A.,Johnson, David K.,McKillop, Alexander,Ford, Michael E.
, p. 3433 - 3436 (2007/10/02)
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.
