000069781 001__ 69781
000069781 005__ 20191212100704.0
000069781 0247_ $$2doi$$a10.1016/j.arabjc.2017.01.011
000069781 0248_ $$2sideral$$a104927
000069781 037__ $$aART-2018-104927
000069781 041__ $$aeng
000069781 100__ $$aMahfoudh, N.
000069781 245__ $$aCysteine-based 3-substituted 1, 5-benzoxathiepin derivatives: Two new classes of anti-proliferative agents
000069781 260__ $$c2018
000069781 5060_ $$aAccess copy available to the general public$$fUnrestricted
000069781 5203_ $$aTwo distinct series of the 3-amino-1, 5-benzoxathiepin scaffold, derived from L-cysteine, were synthesized and evaluated for their anti-proliferative activity in the breast cancer MDA-MB-231 and MCF-7 cells, and in the ovarian carcinoma SKOV-3 cell line. (3R)-Amino-3, 4-dihydro-2H-1, 5-benzoxathiepin [(R)-10] was diversified into two forms: (a) by incorporating different amino acids at its position 3, through an amide bond; and (b) by construction of the purine ring to give 6-chloro-9-[2-(3, 4-dihydro-2H-1, 5-benzoxathiepin-(3R)-yl)]-9H-purine [(R)-28]. Nevertheless, when the introduction of iodine was tried at position 2 of the purine ring of (R)-28, 2-{[2-(6-chloro-2-iodo-9H-purin-9-yl) prop-2-en-1-yl] thio} phenol (34) was obtained. Compound 34 shows activity against cancer cells. Interestingly, 34 inhibits mammosphere formation at the micromolar range, demonstrating activity against cancer stem cells. Although further studies of its targets and mechanism of action are needed, these findings support the therapeutic potential of this compound in cancer.
000069781 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E40$$9info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2013-40855-R
000069781 540__ $$9info:eu-repo/semantics/openAccess$$aby-nc-nd$$uhttp://creativecommons.org/licenses/by-nc-nd/3.0/es/
000069781 590__ $$a3.298$$b2018
000069781 591__ $$aCHEMISTRY, MULTIDISCIPLINARY$$b59 / 172 = 0.343$$c2018$$dQ2$$eT2
000069781 592__ $$a0.605$$b2018
000069781 593__ $$aChemistry (miscellaneous)$$c2018$$dQ2
000069781 593__ $$aChemical Engineering (miscellaneous)$$c2018$$dQ2
000069781 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000069781 700__ $$aMarin-Ramos, N.I.
000069781 700__ $$0(orcid)0000-0002-5114-080X$$aGil, A.M.
000069781 700__ $$0(orcid)0000-0001-8057-4861$$aJimenez, A.I.$$uUniversidad de Zaragoza
000069781 700__ $$aChoquesillo-Lazarte, D.
000069781 700__ $$aKawano, D.F.
000069781 700__ $$aCampos, J.M.
000069781 700__ $$0(orcid)0000-0003-3222-0828$$aCativiela, C.$$uUniversidad de Zaragoza
000069781 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000069781 773__ $$g11, 3 (2018), 426-441$$pARABIAN JOURNAL OF CHEMISTRY$$tARABIAN JOURNAL OF CHEMISTRY$$x1878-5352
000069781 8564_ $$s1780747$$uhttps://zaguan.unizar.es/record/69781/files/texto_completo.pdf$$yVersión publicada
000069781 8564_ $$s84102$$uhttps://zaguan.unizar.es/record/69781/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000069781 909CO $$ooai:zaguan.unizar.es:69781$$particulos$$pdriver
000069781 951__ $$a2019-12-12-10:05:42
000069781 980__ $$aARTICLE