22966-16-1Relevant articles and documents
C3 amino-substituted chalcone derivative with selective adenosine rA1 receptor affinity in the micromolar range
Janse van Rensburg, Helena D.,Legoabe, Lesetja J.,Terre’Blanche, Gisella
, p. 1581 - 1605 (2020/11/20)
Abstract: To identify novel adenosine receptor (AR) ligands based on the chalcone scaffold, herein the synthesis, characterization and in vitro and in silico evaluation of 33 chalcones (15–36 and 37–41) and structurally related compounds (42–47) are reported. These compounds were characterized by radioligand binding and GTP shift assays to determine the degree and type of binding affinity, respectively, against rat (r) A1 and A2A ARs. The chalcone derivatives 24, 29, 37 and 38 possessed selective A1 affinity below 10?μM, and thus, are the most active compounds of the present series; compound 38 was the most potent selective A1 AR antagonist (Ki (r) = 1.6?μM). The structure–affinity relationships (SAR) revealed that the NH2-group at position C3 of ring A of the chalcone scaffold played a key role in affinity, and also, the Br-atom at position C3′ on benzylidene ring B. Upon in vitro and in silico evaluation, the novel C3 amino-substituted chalcone derivative 38—that contains an α,?-unsaturated carbonyl system and easily allows structural modification—may possibly be a synthon in future drug discovery. Graphic abstract: C3 amino-substituted chalcone derivative (38) with C3′ Br substitution on benzylidene ring B possesses selective adenosine rA1 receptor affinity in micromolar range.[Figure not available: see fulltext.]
A general approach to the synthesis of substituted isoxazolo[4,3-c] quinolines via chalcones
Madapa, Sudharshan,Sridhar, Divya,Yadav, Gaya P.,Maulik, Prakas R.,Batra, Sanjay
, p. 4343 - 4351 (2008/04/13)
A general and practical approach to the synthesis of substituted isoxazolo[4,3-c]quinolines from the substituted isoxazolines obtained by 1,3-dipolar cycloadditions between 2-nitrobenzonitrile oxide and chalcones is described. SnCl2·2H2O-mediated reduction of the nitro group, followed by intramolecular cyclization involving the amino and the keto groups in these substrates, furnished mixtures of isoxazolo[4,3-c] quinolines and 3,5-dihydroisoxazolo[4,3-c]-quinolines. In contrast, the reduction of these substrates with Fe/AcOH unexpectedly yielded 3-benzoylquinolin-4-yl-amine derivatives. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
A new and efficient one-pot solid-supported synthesis of 1,2,4,6-tetraaryl-1,4-dihydropyridines
Verma, Anil K.,Koul, Summon,Razdan, Tej K.,Kapoor, Kamal K.
, p. 1064 - 1073 (2007/10/03)
1,2,4,6-Tetraaryl-1,4-dihydropyridines were obtained by the one-pot reaction of chalcones and substituted anilines on the surface of Bi(III)nitrate-Al2O3. The reaction seems to proceed via β-oxygenation of Bi(III) enolised chalcones followed by Michael addition and heteroannulation with simultaneous retro aldol disproportionation. The presence of the ring-activating groups at ortho and para positions in the aniline seems to be essential for the reaction.