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Synthesis of novel 1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)-uracil and -thymine, and their corresponding S-oxidized derivatives
Authors:M del Carmen Núñez  Fernando Rodríguez-Serrano  Antonia Aránega  Antonio Espinosa
Institution:a Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, c/ Campus de Cartuja s/n, 18071 Granada, Spain
b Departamento de Biología Celular, Facultad de Ciencias, Avda. Severo Ochoa s/n, 18071 Granada, Spain
c Departamento de Ciencias de la Salud, Facultad de Ciencias Experimentales y de la Salud, Paraje de las Lagunillas s/n, 23071 Jaén, Spain
d Departamento de Ciencias Morfológicas, Facultad de Medicina, Avenida de Madrid s/n, 18071 Granada, Spain
Abstract:On the basis of molecular variations on isosteric replacements from the prototype 1-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-5-fluorouracil a series of 3-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)-uracil or -thymine O,N-acetals was prepared. The nature of the cis- and trans-sulfoxide isomers was established by means of their conformational analyses carried out with Sybyl and after comparing the theoretical results with the 1H NMR responses of the target molecules. (RS)-3-(1,1-Dioxo-2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)thymine and (1S*,3S*)-1-(1-oxo-3,5-dihydro-2H-4,1-benzoxathiepin-3-yl)thymine were found to be inhibitors of the MCF-7 cell growth.
Keywords:Antitumour compounds  Benzoxathiepins  Computer-assisted methods  Uracils
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