《Revision of the Regioselectivity of the Beirut Reaction of Monosubstituted Benzofuroxans with Benzoylacetonitrile. 6-Substituted quinoxaline-2-carbonitrile 1,4- dioxides: Structural Characterization and Estimation of Anticancer Activity and Hypoxia Selectivity》 was written by Buravchenko, Galina I.; Scherbakov, Alexander M.; Korlukov, Alexander A.; Dorovatovskii, Pavel V.; Shchekotikhin, Andrey E.. Name: 3-Oxo-3-phenylpropanenitrileThis research focused ontirapazamine benzofuroxan anticancer agent hypoxia normoxia adenocarcinoma; 6(7)-substituted-3-phenylquinoxaline-2-carbonitrile 1,4-dioxides; Beirut reaction; CIGAR-HMBC method; X-ray structural analysis; antiproliferative activity; hypoxia-selective cytotoxins; structural isomers.. The article conveys some information:
Objective: The preparation, isolation, structure characterization, and screening for anticancer activity of the first representatives of 6-substituted quinoxaline-2-carbonitrile 1,4-dioxides have been described. Materials and Methods: A series of 7- and 6-halogeno-3-phenylquinoxaline-2-carbonitrile 1,4-dioxides was synthesized by the Beirut reaction. The cytotoxicity was assessed by MTT test (72 h incubation) in normoxia (21% O2) and hypoxia (1% O2) conditions. Results: We found that during the Beirut reaction between a benzofuroxan bearing an electron withdrawing group and benzoylacetonitrile in the presence of triethylamine, in addition to well-known 7-substituted quinoxaline-2-carbonitrile 1,4-dioxides 7-11a, the 6-isomers 7-11b are formed. Moreover, the yield of the 6- isomers increased with the increase in the electron-withdrawing character of the substituent. For benzofuroxans with CO2Me and CF3 groups, 6-substituted quinoxaline-2-carbonitrile 1,4-dioxides 10-11b were the major products. Despite similarities in physicochem. and spectroscopic properties, the obtained isomers exhibit considerable differences in their anticancer activity and hypoxia selectivity. Conclusion: Substituents and their electronic effects play a key role in the formation of 7- and 6-substituted quinoxaline-2-carbonitrile 1,4-dioxides in the Beirut reaction and in the cytotoxicity properties of the obtained isomers. The experimental process involved the reaction of 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Name: 3-Oxo-3-phenylpropanenitrile)
3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used in the synthesis of substituted naphtho[1,8-bc]pyrans. It was also used as building block in the preparation of 4H-pyrans, 2-pyridones, furans and carbocyclics.Name: 3-Oxo-3-phenylpropanenitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts