2199-89-5Relevant academic research and scientific papers
Coumarin derivatives act as novel inhibitors of human dipeptidyl peptidase III: Combined in vitro and in silico study
?ubari?, Domagoj,Agi?, Dejan,Be?lo, Drago,Kara?i?, Zrinka,Karna?, Maja,Lisjak, Miroslav,Lon?ari?, Melita,Molnar, Maja,Popovi?, Boris M.,Rastija, Vesna,Tomi?, Sanja
, (2021/06/22)
Dipeptidyl peptidase III (DPP III), a zinc-dependent exopeptidase, is a member of the metalloproteinase family M49 with distribution detected in almost all forms of life. Although the physiological role of human DPP III (hDPP III) is not yet fully elucida
Construction of 3,4-Dihydrocoumarin Derivatives with Adjacent Quaternary and Tertiary Stereocenters: Organocatalytic Asymmetric Michael Addition of 2-Oxochroman-3-carboxylate Esters to trans-β-Nitroolefins
Jin, Hui,Cho, Soo Min,Hwang, Geum-Sook,Ryu, Do Hyun
supporting information, p. 163 - 167 (2017/01/14)
An asymmetric Michael addition of 2-oxochroman-3-carboxylate esters to trans-β-nitroolefins is described. This strategy can give direct access to dihydrocoumarin derivatives bearing adjacent quaternary and tertiary stereocenters with up to >99% yield, >20:1 dr, and >99% ee. The adduct was further transformed to a spiro-dihydrocoumarin compound in three steps with good yield. (Figure presented.).
Condensation of salicylaldehydes with ethyl 4,4,4-trichloro-3-oxobutanoate: A facile approach for the synthesis of substituted 2H-chromene-3-carboxylates
Sairam, Mudulkar,Saidachary, Gannerla,Raju, Bhimapaka China
supporting information, p. 1338 - 1343 (2015/03/04)
A highly efficient and simple protocol has been developed for the preparation of ethyl 2-oxo-2H-chromene-3-carboxylates 3a-v by the condensation of salicylaldehydes 1a-v with ethyl 4,4,4-trichloro-3-oxobutanoate 2 for the first time. The reaction is proceeding via Knoevenagel pathway followed by a selective addition of the phenolic hydroxyl group to the carbonyl group adjacent to the CCl3 group rather than ester carbonyl due to a strong electron withdrawing effect and produced coumarin derivative 3a with the elimination of CHCl3.
Copper(I)-promoted cycloalkylation-peroxidation of unactivated alkenes via sp3 C-H functionalisation
Banerjee, Arghya,Santra, Sourav Kumar,Mishra, Aniket,Khatun, Nilufa,Patel, Bhisma K.
supporting information, p. 1307 - 1312 (2015/01/30)
A copper(i)-promoted cycloalkylation-peroxidation strategy has been developed via a three-component reaction involving cycloalkanes, tert-butyl hydroperoxide (TBHP) and internal conjugated alkenes possessing electron-withdrawing groups (EWGs). This process installs C-O and C-C bonds via sp3 C-H functionalisation with concomitant generation of two stereocentres. This regioselective radical addition of coumarin system is opposite to that of styrene.
New coumarin derivatives: Design, synthesis and use as inhibitors of hMAO
He, Xu,Chen, Yan-Yan,Shi, Jing-Bo,Tang, Wen-Jiang,Pan, Zhi-Xiang,Dong, Zhi-Qiang,Song, Bao-An,Li, Jun,Liu, Xin-Hua
, p. 3732 - 3738 (2014/07/07)
A series new 2H-chromene-3-carboxamides (4a-4i) and S-2H-chromene-3- carbothioates (5j-5t) were synthesized and evaluated as monoamine oxidase A and B inhibitors. Among them, compound 5k (IC50 = 0.21 μM, IC 50 iproniazid = 7.65 μM) showed the most activity and higher MAO-B selectivity (189.2-fold vs 1-fold) with respect to the MAO-A isoform. The need to clarify at a 3D level some important molecular aspects of discussed SAR, we undertaked a number of docking simulations to better assess. The steric effect was analyzed interms of both posing and scoring by investigating the nature of the binding interactions. The docking results of active compound 5k with hMAO-B complex indicated that conserved residue ILE 199 was important for ligand binding via Sigma-Pi interaction.
New 2H-chromene-3-carboxamide derivatives: Design, synthesis and use as inhibitors of hMAO
Pan, Zhi-Xiang,He, Xu,Chen, Yan-Yan,Tang, Wen-Jian,Shi, Jing-Bo,Tang, Yu-Lan,Song, Bao-An,Li, Jun,Liu, Xin-Hua
, p. 278 - 284 (2014/05/20)
A series new 2H-chromene-3-carboxamide derivatives 4a-4t were synthesized and evaluated as monoamine oxidase A and B (MAO-A and MAO-B) inhibitors. Among them, compound 4d (IC50 = 0.93 μM, IC50 iproniazid = 7.80 μM) showed the most ac
Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives
Secci, Daniela,Carradori, Simone,Bolasco, Adriana,Chimenti, Paola,Yá?ez, Matilde,Ortuso, Francesco,Alcaro, Stefano
experimental part, p. 4846 - 4852 (2011/11/13)
Several 3-carbonyl (1-26), 3-acyl (27-52), and 3-carboxyhydrazido (53-58) coumarins have been synthesized in high yields (72-99%) and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Different substituents on the coumarin nucleus were evaluated for their effect on biological activity and isoform selectivity. Substitution at position C7 of the 3-ethyl ester coumarin ring, or the introduction of a hydrazido substituent at C3, were important to obtain highly potent and selective hMAO-B inhibitors with IC50 values in the nanomolar range. Some derivatives were also submitted to a stability test and showed no chemical cleavage in vitro.
Synthesis, selective anti-Helicobacter pylori activity, and cytotoxicity of novel N-substituted-2-oxo-2H-1-benzopyran-3-carboxamides
Chimenti, Franco,Bizzarri, Bruna,Bolasco, Adriana,Secci, Daniela,Chimenti, Paola,Granese, Arianna,Carradori, Simone,Rivanera, Daniela,Zicari, Alessandra,Scaltrito, M. Maddalena,Sisto, Francesca
experimental part, p. 4922 - 4926 (2010/10/02)
N-substituted-3-carboxamido-coumarin derivatives were prepared and evaluated for selective antibacterial activity against 20 isolates of Helicobacter pylori clinical strains, including five metronidazole resistant ones. Some of them possessed the best activity against H. pylori metronidazole resistant strains with MIC values lower than the drug reference (metronidazole). Furthermore, anti-inflammatory activity through the inhibition of the IL-8 production was investigated.
Synthesis of Coumarin-3-O-acylisoureas by Dicyclohexylcarbodiimide
Bonsignore, Leonardo,Cottiglia, Filippo,Maccioni, Anna M.,Secci, Daniela,Lavagna, Silvio M.
, p. 573 - 578 (2007/10/02)
The synthesis and isolation of some O-acylisoureas are described.The reaction between dicyclohexylcarbodiimide and coumarin-3-carboxylic acids leads to coumarin-dicyclohexylisourea derivatives, isolated as the main products, and to coumarin-dicyclohexylur
