Mahfoudh, NawalMarin-Ramos, Nagore I.Gil, Ana M.Jimenez, Ana I.Choquesillo-Lazarte, DuaneKawano, Daniel F.Campos, Joaquin M.Cativiela, Carlos2023-02-122023-02-122017-01-21Nawal Mahfoudh, Nagore I. Marín-Ramos, Ana M. Gil, Ana I. Jiménez, Duane Choquesillo-Lazarte, Daniel F. Kawano, el al. Cysteine-based 3-substituted 1,5-benzoxathiepin derivatives: Two new classes of anti-proliferative agents, Arabian Journal of Chemistry, Volume 11, Issue 3, 2018, Pages 426-441, ISSN 1878-53521878-5352http://hdl.handle.net/10668/18710Two 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. (C) 2017 The Authors. Production and hosting by Elsevier B.V. on behalf of King Saud University.enAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/alpha-Amino acidBenzoxathiepinDensity functional theoryHarpoon's basePurineTributyltin/iodinationBreast-cancer cellsAnticancer activityIdentificationPurinesInhibitorsChemistryDrugsLinesCysteineBreast NeoplasmsMCF-7 CellsUniversitiesPurinesNeoplastic Stem CellsOvarian Neoplasmsresearch articleopen accessCisteínaCélulas MCF-7Células Madre neoplásicasNeoplasias ováricasNeoplasias de la mamaPurinas10.1016/j.arabjc.2017.01.0111878-5379https://doi.org/10.1016/j.arabjc.2017.01.011426089200012