Structure Determination and Quantum Chemical Analysis of 1,3-Dipolar Cycloaddition of Nitrile Imines and New Dipolarophiles and POM Analyses of the Products as Potential Breast Cancer Inhibitors

Autor:	Thoraya A. Farghaly, Ikhlass M. Abbas, Walid Hassan, Nadia T. Al-Qurashi, M. S. Lotfy, T. Ben Hadda
Rok vydání:	2020
Předmět:	Quantum chemical Reaction mechanism Nitrile 010405 organic chemistry Organic Chemistry Imine 01 natural sciences Medicinal chemistry Cycloaddition 0104 chemical sciences chemistry.chemical_compound chemistry 1 3-Dipolar cycloaddition Stereoselectivity Molecular orbital
Zdroj:	Russian Journal of Organic Chemistry. 56:1258-1271
ISSN:	1608-3393 1070-4280
DOI:	10.1134/s1070428020070210
Popis:	The 1,3-dipolar cycloaddition of nitrile imines to 11-aryl-4-(arylmethylidene)-1,2,3,4,11,11a-hexahydrodibenzo[b,e][1,4]thiazepines possessing exocyclic C=C and endocyclic C=N bonds as dipolarophilic sites showed site selectivity, depending on the type of C-substituent in the nitrile imine. 1,3-Dipolar cycloaddition of C-aryl nitrile imines occurred selectively to the exocyclic C=C bond, whereas the endocyclic C=N bond was involved in the cycloaddition with C-ethoxycarbonyl nitrile imines. A combination of total energy and molecular orbital plots for the highest occupied and lowest unoccupied molecular orbitals was used to verify the proposed reaction mechanisms and stereoselectivity. Some of the isolated products exhibited moderate to good antitumor activity. The results of POM analysis of the relative cytotoxicity of these new derivatives in comparison to Doxorubicin are also reported.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::eaa3498ce9135ba61e6e087c96ab5490 https://doi.org/10.1134/s1070428020070210 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
Nepřihlášeným uživatelům se plný text nezobrazuje	K zobrazení výsledku je třeba se přihlásit.