116485-64-4Relevant academic research and scientific papers
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.
, (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.
The chemistry of α,β-ditosyloxy ketones: A new and convenient route to 4,5-diarylisoxazoles from α,β-chalcone ditosylates
Kamal, Raj,Sharma, Deepak,Wadhwa, Deepak,Prakash, Om
experimental part, p. 93 - 96 (2012/02/03)
The reaction of α,β-chalcone ditosylates with hydroxyl-amine hydrochloride under suitable conditions leads to a 1,2-aryl shift, thereby providing a new route to 4,5-disubstituted isoxazoles. Georg Thieme Verlag Stuttgart. New York.
