BIOMAT Database Logo BIOMAT Database Logo

Synthesis of new substituted chromen[4,3-c]pyrazol-4-ones and their antioxidant activities. 2011

Abdullah Sulaiman Al-Ayed
College of Science and Arts at Ar-Rass, Qassim University, P.O. Box 53, Saudi Arabia. salayedabdualla1@yahoo.com

A series of new coumarin derivatives 4 containing a 4-arylbut-3-en-2-one moiety were synthesized by condensation of 3-acetylcoumarin 1 with aryl aldehydes 2 in chloroform in the presence of piperidine. The interactions of 3-formyl-4-chlorocoumarin (3) with nitrogen-containg nucleophiles leading to the corresponding substituted chromen-[4,3-c]pyrazol-4-ones 5 are described. The structures of the obtained compounds were established on the basis of 1D NMR, 2D NMR and IR and further the compounds were evaluated for possible antioxidant activities. The coumarinic chalcone 4a has been found to be the most active (IC₅₀ = 2.07 μM) in this study.

UI MeSH Term Description Entries
D011720 Pyrazoles Azoles of two nitrogens at the 1,2 positions, next to each other, in contrast with IMIDAZOLES in which they are at the 1,3 positions.
D003374 Coumarins Synthetic or naturally occurring substances related to coumarin, the delta-lactone of coumarinic acid. 1,2-Benzopyrone Derivatives,1,2-Benzopyrones,Coumarin Derivative,Coumarine,1,2-Benzo-Pyrones,Benzopyran-2-ones,Coumarin Derivatives,Coumarines,1,2 Benzo Pyrones,1,2 Benzopyrone Derivatives,1,2 Benzopyrones,Benzopyran 2 ones,Derivative, Coumarin,Derivatives, 1,2-Benzopyrone,Derivatives, Coumarin
D000975 Antioxidants Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. Anti-Oxidant,Antioxidant,Antioxidant Activity,Endogenous Antioxidant,Endogenous Antioxidants,Anti-Oxidant Effect,Anti-Oxidant Effects,Anti-Oxidants,Antioxidant Effect,Antioxidant Effects,Activity, Antioxidant,Anti Oxidant,Anti Oxidant Effect,Anti Oxidant Effects,Anti Oxidants,Antioxidant, Endogenous,Antioxidants, Endogenous
D001578 Benzopyrans Compounds with a core of fused benzo-pyran rings. Benzopyran,Chromene,Chromenes
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer

Related Publications

Abdullah Sulaiman Al-Ayed
Cu(II)-Mediated aerobic oxidative synthesis of sulfonated chromeno[4,3-c]pyrazol-4(2H)-ones.
July 2022, Organic & biomolecular chemistry,
Abdullah Sulaiman Al-Ayed
Synthesis and antiviral activities of new pyrazolo[4,3-c]quinolin-3-ones and their ribonucleoside derivatives.
May 2004, Nucleosides, nucleotides & nucleic acids,
Abdullah Sulaiman Al-Ayed
Structural investigations on coumarins leading to chromeno[4,3-c]pyrazol-4-ones and pyrano[4,3-c]pyrazol-4-ones: New scaffolds for the design of the tumor-associated carbonic anhydrase isoforms IX and XII.
February 2018, European journal of medicinal chemistry,
Abdullah Sulaiman Al-Ayed
Synthesis, antiplatelet and antithrombotic activities of new 2-substituted benzopyrano[4,3-d]pyrimidin-4-cycloamines and 4-amino/cycloamino-benzopyrano[4,3-d]pyrimidin-5-ones.
January 2006, Bioorganic & medicinal chemistry,
Abdullah Sulaiman Al-Ayed
New 2-bromomethyl-8-substituted-benzo[c]chromen-6-ones. Synthesis and biological properties.
January 2005, Bioorganic & medicinal chemistry letters,
Abdullah Sulaiman Al-Ayed
Synthesis of substituted 6-amino-4-(2,4-dimethoxyphenyl)-[1,2]dithiolo[4,3-b]pyrrol-5-ones and their raising leukocyte count activities.
January 2013, Chemical & pharmaceutical bulletin,
Abdullah Sulaiman Al-Ayed
X-ray supramolecular structure, NMR spectroscopy and synthesis of 3-methyl-1-phenyl-1H-chromeno[4,3-c]pyrazol-4-ones formed by the unexpected cyclization of 3-[1-(phenyl-hydrazono)ethyl]-chromen-2-ones.
January 2011, Molecules (Basel, Switzerland),
Abdullah Sulaiman Al-Ayed
Photoinduced synthesis of new diisochromenochromen-4-ones and their antimicrobial activities.
January 2012, TheScientificWorldJournal,
Abdullah Sulaiman Al-Ayed
Synthesis of substituted 2,3-dihydro-4H-1,3-benzoxazin-4-ones and their biological activities.
September 1968, Journal of medicinal chemistry,
Abdullah Sulaiman Al-Ayed
Pd/C-mediated synthesis of α-pyrone fused with a five-membered nitrogen heteroaryl ring: a new route to pyrano[4,3-c]pyrazol-4(1H)-ones.
November 2009, Beilstein journal of organic chemistry,
Copied contents to your clipboard!