62921-44-2Relevant 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.
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.
An Efficient One–pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides
Slagbrand, Tove,Kervefors, Gabriella,Tinnis, Fredrik,Adolfsson, Hans
, p. 1990 - 1995 (2017/06/09)
A Mo(CO)6 (molybdenumhexacarbonyl) catalyzed reductive functionalization of amides to afford 5-amino substituted 4,5-dihydroisoxazoles is presented. The reduction of amides generates reactive enamines, which upon the addition of hydroximinoyl chlorides and base undergoes a 1,3-dipolar cycloaddition reaction that gives access to the desired heterocyclic compounds. The transformation of amides is highly chemoselective and tolerates functional groups such as nitro, nitriles, esters, and ketones. Furthermore, a versatile scope of 4,5-dihydroisoxazoles derived from a variety of hydroximinoyl chlorides and amides is demonstrated. (Figure presented.).
SYNTHESIS AND PROPERTIES OF AZOLES AND THEIR DERIVATIVES. PART XX. STUDIES ON THE THERMOLYSIS OF REGIO AND STEREOISOMERIC DIARYLNITRO-Δ2-ISOXAZOLINES
Baranski, Andrzej,Cholewka, Elzbieta
, p. 483 - 494 (2007/10/02)
Thermolysis of stereoisomeric 3,5-diaryl-4-nitro-Δ2-isoxazolines 1, 3, depending on the applied solvent, leads to 3,5-diarylisoxazoles 4 or mixtures of 3,5-diarylisoxazoles 4 and 3,5-diaryl-4-nitroisoxazoles 6.Under similar conditions, 3,4-diar
