209973-90-0Relevant articles and documents
Studying the cytotoxicity of coumarin–chalcone hybrids by a prooxidant strategy in A549 cells
Shang, Ya-jing,Wei, Qiang,Sun, Zhi-bin
, p. 2287 - 2292 (2018/10/31)
Abstract: Curcumin, bearing two electrophilic α,β-unsaturated ketones, is a promising anticancer agent by an electrophilicity-based prooxidant strategy (ROS-generating) due to the Michael acceptors. Considering that ROS generation depends on Michael acceptor unit, we have designed and synthesized two series coumarin–chalcone hybrids containing one or two Michael acceptor units through Claisen–Schmidt condensation, and evaluated the cytotoxicity against A549 cells as well as ROS accumulation. (E)-3-[3-(2-Hydroxyphenyl)acryloyl]-2H-chromen-2-one was identified as the strongest ROS inducer and cytotoxic agent. The structure–activity relationships (SAR) indicated that the Michael acceptor unit was more important than the position of hydroxyl to the cytotoxicity mediated by increasing the cellular lever of ROS. In addition, (E)-3-[3-(2-hydroxyphenyl)acryloyl]-2H-chromen-2-one caused S-phase cell cycle arrest in A549 cells. Therefore, this work provides an example of coumarin–chalcone scaffold as cytotoxic agent by a prooxidant (ROS-generating agent) strategy. Graphical abstract: [Figure not available: see fulltext.].
A rapid access to new coumarinyl chalcone and substituted chromeno[4,3-c]pyrazol-4(1H)-ones and their antibacterial and DPPH radical scavenging activities
Hamdi, Naceur,Fischmeister, Cedric,Puerta, M. Carmen,Valerga, Pedro
experimental part, p. 522 - 530 (2012/05/04)
A series of new coumarin derivatives 4 containing a chalcone moiety were synthesized by condensation of 3-acetyl-4-hydroxycoumarin 1 with aryl or heteroaryl aldehydes 2 in the presence of piperidine in chloroform. The interaction of 3-formyl-4-chloro-coumarin 3 with nitrogen compound nucleophiles are described and lead to the corresponding substituted chromen[4,3-c] pyrazol-4-ones 5. The structures of the obtained compounds were established on the basis of IR|1D|2D NMR, while crystal structure of 3-acetyl-4-hydroxy coumarin 1 was determined using X-ray diffraction and further were evaluated for possible antibacterial and antioxidant activities. The coumarinic chalcone 4d has been found to be the most active (IC50 = 2.07 μM) in this study.
Expedious synthesis for α, β-unsaturated coumarin derivatives using boran chelates: A novel class of potential antibacterial and antioxidant agents
Hamdi, Naceur,Bouabdallah, Feten,Romerosa, Antonio,Benhassen, Rached
experimental part, p. 1261 - 1268 (2011/11/29)
A new family of coumarin derivatives (4a-i) containing a chalcone moiety was synthesized by condensation of 3-acetyl-4-difluoro boryloxycoumarin (2) with aryl and heteroaryl aldehydes with piperidine in chloroform. Resulting compounds were characterized by IR, 13C, 1H NMR and UV visible spectroscopy. Compound 3-((2E)-3-(3,4,5-Trimethoxy-phenyl)prop-2-enoyl)- 2(H)-chromen-2-one (4g) was characterized by single crystal X-ray diffraction. The antioxidant and antibacterial activities of the obtained compounds 4a-i was evaluated. The biological activity found for these compounds is discussed against their structural features, physical and chemical properties.
Design and synthesis of a novel series of nonpeptidic HIV-1 protease inhibitors
Hariprasad,Talele,Kulkarni, Vithal M.
, p. 365 - 372 (2007/10/03)
Using molecular modelling and the X-ray crystal structures of peptide, (1-(naphthoxy-acetyl)-L-histidyl-5(S)-amino-6-cyclohexyl-3 (R),4(R)-dihydroxy-2(R)-isopropylhexanoyl-L-isoleucine N-(2-pyridylmethyl)amide (U-75875) and nonpeptide-derived inhibitors,
