Synthesis and biological evaluation of new coumarins bearing 2,4-diaminothiazole-5-carbonyl moiety

A series of new coumarin-containing compounds 3a-l and 4a-c was designed and synthesized based on the chalcone-type 4-amino-5-cinnamoylthiazole scaffold 2, and screened for their in vitro anticancer and antioxidant activities. Representatively, the 2-thiomorpholinothiazole derivative 3k with IC50 va...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2018-07, Vol.155, p.483-491
Main Authors: Ayati, Adileh, Oghabi Bakhshaiesh, Tayebeh, Moghimi, Setareh, Esmaeili, Rezvan, Majidzadeh-A, Keivan, Safavi, Maliheh, Firoozpour, Loghman, Emami, Saeed, Foroumadi, Alireza
Format: Article
Language:English
Subjects:
Anticancer
Antioxidant
Coumarin
Cytotoxic activity
Thiazole
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Summary:A series of new coumarin-containing compounds 3a-l and 4a-c was designed and synthesized based on the chalcone-type 4-amino-5-cinnamoylthiazole scaffold 2, and screened for their in vitro anticancer and antioxidant activities. Representatively, the 2-thiomorpholinothiazole derivative 3k with IC50 values of 7.5–16.9 μg/ml demonstrated good cytotoxic effects against tested cell lines MCF-7, HepG2 and SW480. Further investigation by flow cytometric analysis confirmed that this compound induces apoptotic cell death in MCF-7 cells and cause G1-phase arrest in the cell cycle. Moreover, most of compounds had intrinsic potential for radical scavenging activity and ferric-reducing power as investigated by DPPH and FRAP assays. [Display omitted] •New coumarin-containing compounds 3a-l and 4a-c was synthesized.•All compounds were screened for their anticancer and antioxidant activities.•Compound 3k can induce apoptotic and causes G1-phase arrest in the cell cycle.•DPPH and FRAP assays confirmed the antioxidant potential of synthesized compounds.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2018.06.015