4075-60-9Relevant academic research and scientific papers
Novel positive allosteric modulators of A2B adenosine receptor acting as bone mineralisation promoters
Barresi, Elisabetta,Giacomelli, Chiara,Marchetti, Laura,Baglini, Emma,Salerno, Silvia,Greco, Giovanni,Da Settimo, Federico,Martini, Claudia,Trincavelli, Maria Letizia,Taliani, Sabrina
, p. 286 - 294 (2020/12/22)
Small-molecules acting as positive allosteric modulators (PAMs) of the A2B adenosine receptor (A2B AR) could potentially represent a novel therapeutic strategy for pathological conditions characterised by altered bone homeostasis, including osteoporosis. We investigated a library of compounds (4-13) exhibiting different degrees of chemical similarity with three indole derivatives (1-3), which have been recently identified by us as PAMs of the A2B AR able to promote mesenchymal stem cell differentiation and bone formation. Evaluation of mineralisation activity of 4-13 in the presence and in the absence of the agonist BAY60-6583 allowed the identification of lead compounds with therapeutic potential as anti-osteoporosis agents. Further biological characterisation of one of the most performing compounds, the benzofurane derivative 9, confirmed that such a molecule behaves as PAM of the A2B AR.
Fluorogenic Enzyme-Triggered Domino Reactions Producing Quinoxalin-2(1 H)-one-based Heterocycles
Bonnin, Quentin,Chevalier, Arnaud,Dejouy, Garance,Michaudet, Cédric,Picquet, Michel,Renault, Kévin,Romieu, Anthony,Valverde, Ibai E.
supporting information, p. 6494 - 6499 (2020/09/02)
A simple and effective biocompatible domino reaction triggered by a model protease and leading to the formation of strongly fluorescent quinoxalin-2(1H)-one N-heterocycles is described. Some positive attributes including versatility and the ability to pro
Sequential Cu-Catalyzed Four- and Five-Component Syntheses of Luminescent 3-Triazolylquinoxalines
Merkt, Franziska K.,Pieper, Konstantin,Klopotowski, Maximilian,Janiak, Christoph,Müller, Thomas J. J.
supporting information, p. 9447 - 9455 (2019/04/17)
3-Triazolylquinoxalines can be readily synthesized by applying two complementary synthetic protocols starting from heterocyclic π nucleophiles or (hetero)aryl glyoxylic acids in a consecutive four- or five-component reaction. Conceptually, the sequential use of a single cuprous salt for alkynylation and Cu-catalyzed alkyne-azide cycloaddition (CuAAC) in a one-pot fashion sets the stage for activation-alkynylation-cyclocondensation-CuAAC or glyoxylation-alkynylation-cyclocondensation-CuAAC sequences in good yields. The diversity-oriented generation of differently substituted 3-triazolylquinoxalines is an excellent entry to tunable emission solvatorchromic fluorophores with triazole ligation. The electronic structure, corroborated by DFT and TD-DFT calculations, rationalizes the charge transfer character of relevant absorptions and large Stokes shifts as well as the electronic innocence of the triazole substituents.
One-pot activation-alkynylation-cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines in a consecutive three-component fashion
G?rgen, Christina,Boden, Katharina,Reiss, Guido J.,Frank, Walter,Müller, Thomas J.J.
supporting information, p. 1360 - 1370 (2019/07/10)
A consecutive three-component activation-alkynylation-cyclization reaction of (hetero)aryl glyoxylic acids, oxalyl chloride, arylacetylenes, and hydrazides efficiently forms 1,5-diacyl-5-hydroxypyrazolines in moderate to good yields. The structures were unambiguously corroborated by comprehensive NMR spectroscopy and X-ray structure analyses of selected derivatives.
Three-Component Activation/Alkynylation/Cyclocondensation (AACC) Synthesis of Enhanced Emission Solvatochromic 3-Ethynylquinoxalines
Merkt, Franziska K.,H?wedes, Simon P.,Gers-Panther, Charlotte F.,Gruber, Irina,Janiak, Christoph,Müller, Thomas J. J.
supporting information, p. 8114 - 8125 (2018/04/02)
2-Substituted 3-ethynylquinoxaline chromophores can be readily synthesized by a consecutive activation–alkynylation–cyclocondensation (AACC) one-pot sequence in a three-component manner. In comparison with the previously published four-component glyoxylation starting from electron-rich π-nucleophiles, the direct activation of (hetero)aryl glyoxylic acids allows the introduction of substituents that cannot be directly accessed by glyoxylation. By introducing N,N-dimethylaniline as a strong donor in the 2-position, the emission solvatochromicity of 3-ethynylquinoxalines can be considerably enhanced to cover the spectral range from blue–green to deep red–orange with a single chromophore in a relatively narrow polarity window. The diversity-oriented nature of the synthetic multicomponent reaction concept enables comprehensive investigations of structure–property relationships by Hammett correlations and Lippert–Mataga analysis, as well as the elucidation of the electronic structure of the emission solvatochromic π-conjugated donor–acceptor systems by DFT and time-dependent DFT calculations with the PBEh1PBE functional for a better reproduction of the dominant charge-transfer character of the longest wavelength absorption band.
Novel synthesis of tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones via decarboxylative cyclization reaction of α-amino acids and α-ketoamides
Wu, Jia-shou,Jiang, Hua-jiang,Yang, Jian-guo,Jin, Zheng-neng,Chen, Ding-ben
supporting information, p. 546 - 551 (2017/01/16)
An efficient and practical method was developed for the synthesis of tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones based on the decarboxylative cyclization reaction of α-ketoamides and proline. In most cases, tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones were obtained with perfect diastereoselectivity to give trans-isomer in excellent yield.
AMINOESTER DERIVATIVES
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Page/Page column 60, (2016/11/21)
The invention relates to novel compounds which are both phosphodiesterase 4 (PDE4) enzyme inhibitors and muscarinic M3 receptor antagonists, methods of preparing such compounds, compositions containing them and therapeutic use thereof.
Enantioselective Construction of 3-Hydroxypiperidine Scaffolds by Sequential Action of Light and Rhodium upon N-Allylglyoxylamides
Ishida, Naoki,Ne?as, David,Masuda, Yusuke,Murakami, Masahiro
supporting information, p. 7418 - 7421 (2015/06/30)
3-Hydroxypiperidine scaffolds were enantioselectively constructed in an atom-economical way by sequential action of light and rhodium upon N-allylglyoxylamides. In a formal sense, the allylic C-H bond was selectively cleaved and enantioselectively added a
Organocatalytic Enantioselective Michael Reaction of Malononitrile with β,β-Disubstituted Nitroalkenes
Chen, Shengwei,Lou, Qinxin,Ding, Yuyang,Zhang, Shasha,Hu, Wenhui,Zhao, Junling
supporting information, p. 2437 - 2441 (2015/08/18)
We have developed and optimized an enantioselective Michael reaction of malononitrile with β,β-disubstituted nitroalkenes. This reaction was catalyzed by a cinchona alkaloid derived thiourea catalyst, producing products of high yields (up to 98 %) and ste
Reductive cyclization of halo-ketones to form 3-hydroxy-2-oxindoles via palladium catalyzed hydrogenation: a hydrogen-mediated Grignard addition
Shin, Inji,Ramgren, Stephen D.,Krische, Michael J.
supporting information, p. 5776 - 5780 (2015/08/03)
Abstract The reductive cyclization of N-oxoacyl ortho-bromoanilides to form 3-hydroxy-2-oxindoles under the conditions of palladium catalyzed hydrogenation is described. This work may be viewed as a prelude to intermolecular hydrogen-mediated Grignard-typ
