- Molecular iodine enabled generation of iminyl radicals from oximes: A facile route to imidazo[1,2-a]pyridines and its regioselective C-3 sulfenylated products from simple pyridines
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An iodine promoted simple and environment friendly protocol has been developed to access imidazo[1,2-a]pyridines from unfunctionalized pyridines and oxime esters. This straightforward method efficiently converts the substrates into corresponding products affording moderate to good yields with large functional group tolerance. Additionally extensive investigation revealed that regioselective domino C-3 methyl sulfenylated imidazo[1,2-a]pyridines were also accessible first time from pyridines and oxime esters in DMSO solvent. The reaction operates through metal-free generation of iminyl radicals from easily accessible oxime esters, to build up the second heterocyclic ring on pyridines.
- Singh, Deepak,Chowdhury, Soumyadeep Roy,Pramanik, Shyamal,Maity, Soumitra
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- Fluorescent Imidazo[1,2-a]pyrimidine Compounds as Biocompatible Organic Photosensitizers that Generate Singlet Oxygen: A Potential Tool for Phototheranostics
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Photodynamic therapy has been used to treat a variety of diseases, however, there is continuing search for new biocompatible photosensitizers. Herein, we demonstrate for the first time that imidazo[1,2-a]pyrimidine compounds are able to generate singlet oxygen species and can act as photosensitizers in the intracellular environment. Our results show that this class of compounds absorb and emit in the 400–500 nm region, present low cytotoxicity in the dark, are efficiently uptaken by cells, are fluorescent in intracellular medium, and generate singlet oxygen upon irradiation, killing cancer cells within 2 h at low concentration (2.0 μm). The imidazo[1,2-a]pyrimidine compounds are a potential new tool for phototheranostics, because they can be simultaneously used for fluorescence imaging and photodynamic therapy.
- Lima, Maria L. S. O.,Braga, Carolyne B.,Becher, Tiago B.,Odriozola-Gimeno, Mikel,Torrent-Sucarrat, Miquel,Rivilla, Iván,Cossío, Fernando P.,Marsaioli, Anita J.,Ornelas, Catia
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p. 6213 - 6222
(2021/02/01)
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- Direct one-pot synthesis of zolimidine pharmaceutical drug and imidazo[1,2-a]pyridine derivatives via I2/CuO-promoted tandem strategy
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An efficient one-pot synthetic protocol was developed for the synthesis of imidazo[1,2-a]pyridines from easily available starting materials: Aromatic ketones, α,β-unsaturated ketones, β-keto esters and 2-aminopyridines. The present reaction proceeded well in MeOH under the media of I2/CuO. By using this method, the marketed drug zolimidine could be prepared easily with 95% yield. All these target products were characterized by NMR, HRMS and IR spectra. Furthermore, the target compound 3fa was determined by X-ray crystallographic analysis.
- Cai, Qun,Liu, Mei-Cai,Mao, Bi-Ming,Xie, Xuan,Jia, Feng-Cheng,Zhu, Yan-Ping,Wu, An-Xin
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p. 881 - 884
(2015/03/04)
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- NOVEL COMPOUND HAVING AFFINITY FOR AMYLOID
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A compound that has affinity with amyloid, exhibits sufficiently rapid clearance from normal tissues, and is suppressed in toxicity such as mutagenicity is provided, which is represented by the following formula (1): or a salt thereof, wherein R1 is a group selected from hydrogen, hydroxyl group, carboxyl group, sulfate group, amino group, nitro group, cyano group, an alkyl substituent with one to 4 carbon atoms or an alkoxy substituent with one to 4 carbon atoms; R2 is a radioactive halogen substituent; and m is an integer of 0 to 2, and a low-toxic diagnostic agent for Alzheimer's disease comprising a compound represented by the above formula or a salt thereof is also provided.
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Page/Page column 11; 25
(2009/04/23)
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- 4-[ω-[4-Arylpiperazin-1-yl]alkoxy]phenylimidazo[1,2-a]pyridine derivatives: Fluorescent high-affinity dopamine D3 receptor ligands as potential probes for receptor visualization
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Sixteen long-chain arylpiperazines bearing the fluorescent moiety 2-phenylimidazo[1,2-a]pyridine were synthesized as fluorescent dopamine D 3 receptors ligands (385 nM i 3 compounds 15a and
- Leopoldo, Marcello,Lacivita, Enza,Passafiume, Elena,Contino, Marialessandra,Colabufo, Nicola A.,Berardi, Francesco,Perrone, Roberto
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p. 5043 - 5047
(2008/03/12)
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- Potential inhibitors of plasmodial heme oxygenase; an innovative approach for combating chloroquine resistant malaria
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Syntheses of imidazo-pyridines and substituted prolines and their effect on heme oxygenase activity of Plasmodium yoelii and corresponding infected host have been studied. Six compounds in vitro and one in vivo showed selective inhibition of parasite enzy
- Srivastava, Pratima,Pandey, Vikash Chandra,Misra, Anju Prabha,Gupta, Preeti,Raj, Kanwal,Bhaduri, Amiya Prasad
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p. 181 - 187
(2007/10/03)
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