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

Abstract

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 IC 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.

Coumarins: A Unique Scaffold With Versatile Biological Behavior

“…The combined studies of molecular docking, pharmacophore hypothesis, and MD studies exposed remarkably information on the structural features of the molecules, which are essential to explore drug interactions and designing of the novel drug molecule. Emami et al [48] synthesized a new series of 3-(4-aminothiazole-5-carbonyl)-2Hchromen-2-ones,(3a-l) and (4a-c) with a cyclic amine, substituted cyclic amine, aniline or substituted aniline moieties, and investigated for cytotoxic potential employing MTT assay against MCF-7, HepG2, and SW400 cell lines. The thiomorpholine derivative (3k) was potent with (IC 50 values: 7.5-16.9 μg/ml).…”

Green Decarboxylative Aminoalkylation of Coumarin‐3‐Carboxylic Acids

“…Prompted by the abovementioned factors along with our experience in coumarin chemistry and biological properties, herein, we wish to report a green protocol for the carbon‐carbon bond formation reaction between coumarin‐3‐carboxylic acid, formaldehyde and without any catalyst or additive.…”

An efficient synthesis of novel heterocyclic systems incorporating coumarin moiety

“…Coumarins are a group of heterocyclic compounds naturally present in a large variety of plant families especially in fruits, seeds, roots, and leaves . Coumarins as oxygen‐containing heterocycles are obtained from both natural and synthetic sources, and they possess a variety of biological activities including antioxidant, anti‐inflammatory, anticancer, anti‐HIV, antitumor, anticoagulant, antibiotic, antiproliferative, antidepressant, antiasthmatic, antiplasmodial, antiplatelet, antimalarial, antiviral, anti‐influenza, antifungal, antibacterial, antimicrobial, and α‐glucosidase inhibitors . Photochemical, photophysical, fluorescence, optical, and photoluminescence properties of coumarin derivatives were investigated and discussed .…”