3470-53-9Relevant academic research and scientific papers
Quinoxaline compound, preparation method and application of quinoxaline compound in medicine
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Paragraph 0337-0340, (2021/07/24)
The invention provides a quinoxaline compound, a preparation method and application of the quinoxaline compound in medicine, and particularly relates to a quinoxaline compound with PAR4 antagonistic activity, a preparation method of the quinoxaline compound, a pharmaceutical composition containing the quinoxaline compound and application of the quinoxaline compound. Specifically, the invention provides a compound shown as a general formula I and/or II or a tautomer or pharmaceutically acceptable salt thereof, a preparation method of the compound, and application of the compound or the tautomer or the pharmaceutically acceptable salt in medicines for preventing and/or treating thromboembolic diseases.
A Conformationally Restricted Aza-BODIPY Platform for Stimulus-Responsive Probes with Enhanced Photoacoustic Properties
Zhou, Effie Y.,Knox, Hailey J.,Liu, Chang,Zhao, Weili,Chan, Jefferson
supporting information, p. 17601 - 17609 (2019/11/11)
Photoacoustic (PA) dyes, which absorb near-infrared (NIR) light to generate an ultrasonic signal, can be detected at centimeter depths in tissues with significantly higher resolution than dyes imaged with fluorescence-based methods. As such, PA agents show great promise as research tools for the study of live-animal disease models. However, the development of activatable PA probes has been hampered by the relative scarcity of appropriate PA-active molecular platforms with properties that can be manipulated in a rational manner. Herein we synthesized and evaluated six modifications to the aza-BODIPY dye platform with respect to their absorbance, fluorescence, and PA properties. We identified a promising conformationally restricted aza-BODIPY (CRaB) scaffold that prioritizes three criteria necessary for the design of stimulus-responsive dyes with optimal ratiometric PA response: absorbance at NIR wavelengths, strong PA intensity, and large Δλ upon interaction with the desired stimulus. Using this scaffold, we synthesized three chemically diverse stimulus-responsive PA probes and demonstrated between 2- and 8-fold improvements in theoretical ratiometric response in vitro. This suggests that improvements in PA parameters are generalizable. Finally, we validated the in vitro turnover of each CRaB PA probe and demonstrated the in vivo potential of the CRaB scaffold by direct comparison to an established hypoxia-responsive probe for the detection of tumor hypoxia.
Keto-benzo[h]-Coumarin-Based Near-Infrared Dyes with Large Stokes Shifts for Bioimaging Applications
Niu, Guangle,Liu, Weimin,Xiao, Hongyan,Zhang, Hongyan,Chen, Jianhong,Dai, Qing,Ge, Jiechao,Wu, Jiasheng,Wang, Pengfei
, p. 498 - 504 (2016/03/12)
Fluorescence imaging is a promising tool for the visualization of biomolecules in living systems and there is great demand for new fluorescent dyes that absorb and emit in the near-infrared (NIR) region. Herein, we constructed three new fluorescent dyes (NBC dyes) based on keto-benzo[h]coumarin (k-BC) and benzopyrilium salts. These dyes showed large Stokes shifts (>100nm) and NIR emission (>800nm). The relationship between the structures and optical properties of these dyes was further investigated by using density functional theory calculations at the B3LYP/6-3G level of theory. Fluorescence images indicated that the fabricated dyes exhibited good photostability and low cytotoxicity and, thus, have potential applications as imaging agents in living cells and animals.
Discovery of Potent and Selective Agonists of δ Opioid Receptor by Revisiting the "message-Address" Concept
Shen, Qing,Qian, Yuanyuan,Huang, Xiaoqin,Xu, Xuejun,Li, Wei,Liu, Jinggen,Fu, Wei
supporting information, p. 391 - 396 (2016/05/19)
The classic "message-address" concept was proposed to address the binding of endogenous peptides to the opioid receptors and was later successfully applied in the discovery of the first nonpeptide δ opioid receptor (DOR) antagonist naltrindole. By revisiting this concept, and based on the structure of tramadol, we designed a series of novel compounds that act as highly potent and selective agonists of DOR among which (-)-6j showed the highest affinity (Ki = 2.7 nM), best agonistic activity (EC50 = 2.6 nM), and DOR selectivity (more than 1000-fold over the other two subtype opioid receptors). Molecular docking studies suggest that the "message" part of (-)-6j interacts with residue Asp1283.32 and a neighboring water molecule, and the "address" part of (-)-6j packs with hydrophobic residues Leu3007.35, Val2816.55, and Trp2846.58, rendering DOR selectivity. The discovery of novel compound (-)-6j, and the obtained insights into DOR-agonist binding will help us design more potent and selective DOR agonists.
Nitrogen-doped graphene-activated iron-oxide-based nanocatalysts for selective transfer hydrogenation of nitroarenes
Jagadeesh, Rajenahally V.,Natte, Kishore,Junge, Henrik,Beller, Matthias
, p. 1526 - 1529 (2015/03/14)
Nanoscaled iron oxides on carbon were modified with nitrogen-doped graphene (NGr) and found to be excellent catalysts for the chemoselective transfer hydrogenation of nitroarenes to anilines. Under standard reaction conditions, a variety of functionalized and structurally diverse anilines, which serve as key building blocks and central intermediates for fine and bulk chemicals, were synthesized in good to excellent yields.
Highly selective transfer hydrogenation of functionalised nitroarenes using cobalt-based nanocatalysts
Jagadeesh, Rajenahally V.,Banerjee, Debasis,Arockiam, Percia Beatrice,Junge, Henrik,Junge, Kathrin,Pohl, Marga-Martina,Radnik, J?rg,Brückner, Angelika,Beller, Matthias
supporting information, p. 898 - 902 (2015/03/04)
Anilines are important feedstock for the synthesis of a variety of chemicals such as dyes, pigments, pharmaceuticals and agrochemicals. The chemoselective catalytic reduction of nitro compounds represents the most important and prevalent process for the manufacture of functionalized anilines. Consequently, the development of selective catalysts for the reduction of nitro compounds in the presence of other reducible groups is a major challenge and is crucial. In this regard, herein we show that the cobalt oxide (Co3O4-NGr@C) based nano-materials, prepared by the pyrolysis of cobalt-phenanthroline complexes on carbon constitute highly selective catalysts for the transfer hydrogenation of nitroarenes to anilines using formic acid as a hydrogen source. Applying these catalysts, a series of structurally diverse and functionalized nitroarenes have been reduced to anilines with unprecedented chemo-selectivity tolerating halides, olefins, aldehyde, ketone, ester, amide and nitrile functionalities.
Design, synthesis, structure, and dehydrogenation reactivity of a water soluble o-iodoxybenzoic acid derivative bearing a trimethylammonium group
Cui, Li-Qian,Dong, Zhi-Lei,Liu, Kai,Zhang, Chi
supporting information; experimental part, p. 6488 - 6491 (2012/02/02)
5-Trimethylammonio-1, 3-dioxo-1, 3-dihydro-1λ5-benzo[d][1, 2]iodoxol-1-ol anion (AIBX 1a), an o-iodoxybenzoic acid (IBX) derivative having the trimethylammonium moiety on its phenyl ring, possesses very good solubility in water and distinct oxidative properties from IBX, which is demonstrated in the oxidation of various β-keto esters to the corresponding dehydrogenated products using water as cosolvent. The regeneration of AIBX 1a can be easily realized from the reaction mixture due to its good water solubility.2011 American Chemical Society.
The application of the schmidt reaction and beckmann rearrangement to the synthesis of bicyclic lactams: Some mechanistic considerations
Crosby, Ian T.,Shin, James K.,Capuano, Ben
, p. 211 - 226 (2011/06/21)
The syntheses of some methoxy-substituted bicyclic lactams, of the types 3 and 4, are reported employing two different conditions for the Schmidt reaction of appropriate ketones and employing two different conditions for the Beckmann rearrangement of the corresponding ketoximes. The alkyl to aryl migration ratios of the reactions were determined by high-performance liquid chromatography analysis of the reactions. The mechanisms of the reactions reported are discussed, some limitations of the reported mechanisms identified, and an alternative mechanism proposed in light of the outcomes of the various reactions. Application of the Schmidt reaction and Beckmann rearrangement was used for the synthesis of some chloro bicyclic lactams, of the types 3 and 4. CSIRO 2010.
Highly potent, non-basic 5-HT6 ligands. Site mutagenesis evidence for a second binding mode at 5-HT6 for antagonism
Harris III, Ralph N.,Stabler, Russel S.,Repke, David B.,Kress, James M.,Walker, Keith A.,Martin, Renee S.,Brothers, Julie M.,Ilnicka, Mariola,Lee, Simon W.,Mirzadegan, Tara
scheme or table, p. 3436 - 3440 (2010/07/16)
A series of 5-HT6 ligands derived from (R)-1-(amino)methyl-6-(phenyl)sulfonyltetralin was prepared that yielded several non-basic analogs having sub-nanomolar affinity. Ligand structure-activity relationships, receptor point mutation studies, and molecular modeling of these novel ligands all combined to reveal a new alternative binding mode to 5-HT6 for antagonism.
Conformationally constrained analogues of N′-(4-tert-butylbenzyl)-N-(4-methylsulfonylaminobenzyl)thiourea as TRPV1 antagonists
Lim, Ju-Ok,Jin, Mi-Kyoung,Ryu, HyungChul,Kang, Dong Wook,Lee, Jeewoo,Pearce, Larry V.,Tran, Richard,Toth, Attila,Blumberg, Peter M.
experimental part, p. 322 - 331 (2009/04/07)
A series of bicyclic analogues having indan and tetrahydronaphthalene templates in the A-region were designed as conformationally constrained analogues of our previously reported potent TRPV1 antagonists (1, 3). The activities for rat TRPV1 of the conformationally restricted analogues were moderately or markedly diminished, particularly in the case of the tetrahydronaphthalene analogues. The analysis indicated that steric constraints at the benzylic position in the bicyclic analogues may be an important factor for their unfavorable interaction with the receptor.
