RT Journal Article
T1 Cysteine-based 3-substituted 1,5-benzoxathiepin derivatives: Two new classes of anti-proliferative agents
A1 Mahfoudh, Nawal
A1 Marin-Ramos, Nagore I.
A1 Gil, Ana M.
A1 Jimenez, Ana I.
A1 Choquesillo-Lazarte, Duane
A1 Kawano, Daniel F.
A1 Campos, Joaquin M.
A1 Cativiela, Carlos
K1 alpha-Amino acid
K1 Benzoxathiepin
K1 Density functional theory
K1 Harpoon's base
K1 Purine
K1 Tributyltin/iodination
K1 Breast-cancer cells
K1 Anticancer activity
K1 Identification
K1 Purines
K1 Inhibitors
K1 Chemistry
K1 Drugs
K1 Lines
AB Two 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.
PB Elsevier science bv
PB Elsevier BV
SN 1878-5352
YR 2017
FD 2017-01-21
LK http://hdl.handle.net/10668/18710
UL http://hdl.handle.net/10668/18710
LA en
NO Nawal 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 1878-5352
NO We thank the Ministerio de Economı´a y Competitividad(grant CTQ2013-40855-R), Gobierno de Arago´ n–FondoSocial Europeo (research group E40), and the IntramuralCSIC (201530E011) for providing X-ray structural facilitiesfor this work.
DS RISalud
RD Apr 4, 2025