Using of calixnarenes in water provided a hydrophobic cavity that successfully carried out the synthesis reactions at short times with high yields. By utilizing mcr chemistry, we developed a protocol to functionalize the c3 position of imidazo1,2 apyridine through a three component, decarboxylation r. The paper deals with the recent progress realised in the comprehension of. Some of the newly synthesized compounds were screened for theirantimycobacterial activities. Imidazo 1, 2 a pyridine 2 carboxylic acid ethyl ester cas number 38922779. The molecular structures of the target compounds were characterized by single crystal xray diffraction analysis. Use of the information, documents and data from the echa website is subject to the terms and conditions of this legal notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the echa website may be reproduced, distributed andor used, totally or in part, for noncommercial purposes provided that echa is. An efficient, catalyst and solventfree synthesis of imidazo1,2a. Environmentally friendly and fast synthesis of imidazo1,2apyridine.
Department of chemistry, dr b r ambedkar national institute of technology, jalandhar 144011, india. A new approach to the synthesis of 2 aminoimidazo1,2apyridine. The reaction also enables the formation of alkenylsubstituted imidazoheterocycles by using unsaturated ketones as substrates. While both types are able to show fluorescence, the imidazo 1, 2 apyridines are mostly known for their pharmaceutical activity as nonsteroidal antiinflammatory drugs nsaids, gaba receptor agonists, and other drugs 2011saunders483.
Design, synthesis, and biological evaluation of novel imidazo. Medicinal attributes of imidazo1,2apyridine derivatives. Here, ligandbased drug design approach yielded a series of 23 novel 64nitrophenoxy1himidazo4,5bpyridine derivatives. Media in category imidazo1,2apyridines the following 16 files are in this category, out of 16 total. This catalyst system is recoverable with a simple extraction using an organic. Crystal correlation of heterocyclic imidazo1,2 a pyridine. Synthesis of novel imidazo1,2apyridines with potent activity. Imidazo 1, 2 apyridine derivatives with different hydroxyaryl units 1 3, which could potentially form an intramolecular hydrogenbonded sevenmembered ring in either a planar or a twisted conformation, were newly developed, and the effect of conformation and steric repulsion on the excitedstate intramolecular proton transfer esipt luminescence was evaluated. Chemoselective iodination of 6substituted imidazo1,2 a. Imidazo1,2 apyridine based compounds are clinically important to the treatments of heart and circulatory failures, while many are under. Wo 2001014375 a1 imidazo1,2apyridine and pyrazolo2.
Compound 4a was obtained in four steps starting with two succesive brominations of 2acetylfuran first. Ring b is phenyl or phenyl fused to a c57cycloalkyl ring. Medicinal attributes of imidazo1,2 apyridine derivatives. The molecular electrostatic potential calculations were performed to investigate the chemoselectivity of the substitution reaction. Pdf a convenient and efficient synthesis, without any organic solvent or catalyst is described for the preparation of imidazo 1,2a pyridine. The structure of n2phenylimidazo1,2apyridin3ylacetamidei consists of isolated molecules which packing is shown in fig. Further studies were conducted on the fluorescence behaviour of imidazo1,2 apyridine derivatives. Microwaveassisted synthesis of 3formyl substituted imidazo1,2a. The combination of cs 2 co 3 and pdoac 2 enables the coupling of imidazo1, 2. Synthesis of novel imidazo1,2apyridines with potent activity against. May 14, 2015 a series of imidazo1,2 apyridine derivatives against cmet was designed by means of bioisosteric replacement. Herein, we reported a straightforward and general route for the synthesis of 3 nitrosoimidazo1,2apyridines. A novel activation mode of ethyl tertiary amines in which simultaneous selective cleavage of cc bond and cn bond of ethyl group with molecular oxygen as terminal oxidant. The present study aimed to investigate the anticancer activity of imidazo1,2a pyridine 57 in the a375 and wm115 melanoma and hela cervical cancer cell lines.
This series demonstrates potent in vitro inhibition of hcv replication ec 50 apr 17, 2020 a collection of 2. Imidazo1,2apyridines and pyrimidines are important organic fluorophores which have been investigated as biomarkers and photochemical sensors. The required building block of imidazopyridine was synthesized from commercially available 5,5diaminopyridine3ol. Crystal correlation of heterocyclic imidazo1,2apyridine.
Novel potent imidazo1,2apyridinenglycinylhydrazone. Imidazo1,2pyridines 1ab are potent inhibitors of hcv in the in vitro replicon 10 system, with measured ec50s for wild type wt genotype 1a and 1b replicons of apyridine derivatives against cmet was designed by means of bioisosteric replacement. The effect on the luminescent property by substituents in the heterocycle and phenyl rings, have been studied as well. In this investigation, series of 3hydroxymethyl imidazo 1, 2 a pyridines and pyrimidines were synthesized and evaluated in relation. Pdf synthesis of novel imidazo1,5apyridine derivates. Typical procedure for synthesis of the imidazo 1, 2 apyridine 4a using calix6arene in water. A copperiicatalyzed tandem reaction between pyridine ketone and benzylamine proceeded via an efficient condensationaminationoxidative dehydrogenation process, affording 1,3diarylated imidazo1,5apyridines in excellent yields using clean o 2 as an oxidant. Many compounds possess very promising biological activity as anticancer agents 7, antimicrobial 8, antitubercular 9, antisepsis 10, antiviral 11, antimalarial 12, antiinflammatory, anticonvulsant 14.
Development of imidazo1,2apyridine derivatives with an. The present invention relates to derivatives of imidazo 1, 2 a pyridines of the formula i, in which r, r1 to r4 and n have the meanings indicated in the claims, which modulate the transcription of endothelial nitric oxide no synthase and are valuable pharmacologically active compounds. Jul 12, 2012 a series of imidazo 1, 2 a pyridines which directly bind to hcv nonstructural protein 4b ns4b is described. Imidazo4,5bpyridine has been proved to be a useful scaffold for medicinal agents 6,7. Rawal, jitender bariwal and virender singh affiliation.
Specifically, the compounds of the formula i upregulate the expression of the enzyme. Ethyl imidazo1,2apyridine2carboxylate 97% sigmaaldrich. Novel imidazo1,2 apyridine derivatives with potent autotaxinenpp2 inhibitor activity. Fluorescent property of 3hydroxymethyl imidazo1,2a. An imidazopyridine is a nitrogen containing heterocycle that is also a class of drugs that contain this same chemical substructure. Nitrosylation of imidazo1,2apyridines in metal free system. Wo 2008104278 a1 imidazo1,2a pyridines and their use as.
The molecular structures of the target compounds were characterized by single crystal xray diffraction. A highly efficient synthesis of 3formyl imidazo1,2 apyridine and imidazo1,2apyrimidine, under cucatalyzed aerobic oxidative conditions and by utilizing ethyl tertiary amines as carbon sources, is disclosed. Xray crystallography this is an open access article distributed under the creative commons attribution license which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Imidazo1,2apyridines and pyrimidines are important organic fluorophores which. Zsuynqzacjixsquhfffaoysan 2 2,5dimethylthiophen3yl imidazo 1, 2 apyridine chemical compound. In this investigation, series of 3hydroxymethyl imidazo1,2apyridines and pyrimidines were. Cucatalyzed synthesis of 3formyl imidazo1,2apyridines.
Pdf synthesis and characterization of imidazo1,2apyridines. Dec 19, 2018 tuberculosis is an airborne disease, mostly affecting young adults in their productive years. Green synthesis of imidazo1,2apyridines in aqueous medium. An efficient synthesis of imidazo1,2apyridines and 2,4disubstituted thiazoles. A novel activation mode of ethyl tertiary amines in which simultaneous selective cleavage of cc bond and cn bond of ethyl. Here, ligandbased drug design approach yielded a series of 23 novel 64nitrophenoxy1h imidazo 4,5b pyridine derivatives. Imidazo1,5apyridine synthesis organic chemistry portal. Wo 2001014375 a1 imidazo1,2apyridine and pyrazolo2,3a. Abstractin this work, we describe the design, synthesis and pharmacological evaluation of novel.
Typical procedure for synthesis of the imidazo1,2 apyridine 4a using calix6arene in water. The structure of n 2phenylimidazo1,2 a pyridin3ylacetamidei consists of isolated molecules which packing is shown in fig. A novel fluorescent sensor based on imidazo1,2apyridine. Catalyst free, c3 functionalization of imidazo1,2a. Design, synthesis, and biological evaluation of novel 3. Predicted data is generated using the us environmental protection agencys episuite. Buy imidazo1,2 apyridine 5carboxylic acid cas 479028723, a biochemical for proteomics research, from santa cruz. Medicinal chemistry research, volume 21, issue 4 springer. Tuberculosis is an airborne disease, mostly affecting young adults in their productive years. Several imidazo1,2 apyridine derivatives were reported to be fluorescent in nature17.
A compound of formula i wherein ring a is imidazol1,2apyrid3yl or pyrazolo2,3apyrid3yl. The required building block of imidazopyridine was synthesized from commercially available 5,5diaminopyridine3ol followed by four step sequence. Imidazo 1,2 apyridine an example of imidazopyridine and a core structure of zolpidem and some compounds described below. From this reaction, two classes of fused nheterocycle, naphtho1. In general, they are gaba a receptor agonists, however recently proton pump inhibitors.
The aminomethylation morpholino and piperidinomethylation of 2 2 furylimidazo1,2 a pyridine proceeds primarily at the 3 position of the imidazopyridine system at equimolecular ratios of the reagents, but also proceeds at the 5 position of the furan ring when there is a slight excess of formaldehyde and amine. Specifically, the compounds of the formula i upregulate the expression of the enzyme endothelial no. Pdf recent progress in the pharmacology of imidazo1,2a. Synthesis of imidazo1,2 apyridine, pyrido1,2 apyrimidine, and 3cyanocoumarin article pdf available in monatshefte fuer chemiechemical monthly 14812 october 2017 with 86 reads. Imidazo1,2apyridines that directly interact with hepatitis. Compound 4a was obtained in four steps starting with two succesive brominations of 2. Use of the information, documents and data from the echa website is subject to the terms and conditions of this legal notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the echa website may be reproduced, distributed andor used, totally or in part, for noncommercial purposes provided. Their antiproliferative activities against cancer cell lines were evaluated. Imidazo 1, 2 a pyridines and pyrimidines are important organic fluorophores which have been investigated as biomarkers and photochemical sensors. Synthesis, biological evaluation and molecular docking. This article is from chemistry central journal, volume 6. Imidazo1,2apyridine2carboxaldehyde 97% sigmaaldrich.
Discuss1 2substituted imidazo1,2 apyridine chemical class 0 title claims description 37. In this paper, palladiumcatalyzed oxidative cycloaromatization of 2phenylimidazo1,2 apyridine pip with internal alkyne is studied. Imidazo1,2apyridine synthesis organic chemistry portal. Imidazo1,2 a pyridine2carbaldehyde cas number 118000434. Introduction the imidazo4,5bpyridine ring system 5, 8 represent a core skeleton of a class of heterocyclic compound analogues of purine with their diversity of biological activity 15, depending on the substituents on the pyridine ring. Tandem approach for the synthesis of imidazo1,2apyridines. Imidazo1,2 apyridine and quinazolin43hone derivatives were synthesized. Some new thiazolidines and spirothiazolidines derived from hydrazones of2methylimidazo1,2 apyridine 3carboxylic acid hydrazide, a bioisosteric derivative ofisoniazid, were synthesized and characterized by analytical, ir, 1h and cnmr andmass spectral data. Multicomponent reactions mcrs are robust tools for the rapid synthesis of complex, small molecule libraries for use in drug discovery and development. Imidazo1,2 apyridine is a bicyclic system with a bridgehead nitrogen atom, of growing interest in medicinal chemistry. Most examples have acetamido, bromo, cyano, or formyl substituents at the 4position. Media in category imidazo 1, 2 a pyridines the following 16 files are in this category, out of 16 total.
In the heterocyclic literature, two types of imidazopyridines are commonly distinguished. Imidazo1,2apyridines and pyrido1,2apyrimidines are. Green synthesis of imidazo1,2apyridines using calix6. Jan 30, 2019 imidazo1,2 apyridine based compounds are clinically important to the treatments of heart and circulatory failures, while many are under development for pharmaceutical uses. A compound of formula i wherein ring a is imidazol 1,2apyrid3yl or pyrazolo 2,3apyrid3yl. The compounds 1b, 1i and 10b were evaluated for their pi3k inhibitory activity and selectivity. Imidazo1, 2 apyridine, sar, groebkeblackburnbienayme reaction. In general, these spiro compounds have been prepared from the reactions of 23himidazo 1,2apyridinones, readily obtainable from the alkaline treatment of the corresponding 2amino1 ethoxycarbonylmethylpyridinium halides, with 1,4dihalides such as. The present invention relates to derivatives of imidazo1,2apyridines of the formula i, in which r, r1 to r4 and n have the meanings indicated in the claims, which modulate the transcription of endothelial nitric oxide no synthase and are valuable pharmacologically active compounds. An new, efficient synthesis of imidazo1,5 apyridine derivatives starting from 3chloro5trifluoromethylpyridine2 ylmethanamine1 has been developed. Functionalized imidazo1,2 apyridine and imidazo1,2apyrimidine systems are of great interest due to their biological activities anaflous et al. Jun 29, 2018 3 and 8iodoimidazo1,2apyridines were synthesized from imidazo1,2 apyridine under different substitution conditions.
A cuicatalyzed aerobic oxidative synthesis of imidazo1,2 apyridines from 2aminopyridines and acetophenones is compatible with a broad range of functional groups. Article information, pdf download for an efficient, catalyst and solventfree. It has long been known that imidazo1,2 apyridine derivatives exhibit diverse biological activities 1 and were used as antiviral, 2 antiulcer, 3 antibacterial, 4 antifungal, 5 antiprotozoal, 6 antiherpes, 7 antiinflammatory. Wo 2008104278 a1 imidazo1,2a pyridines and their use. In this study, a selective, potent cmet inhibitor, 22e was identified, with ic 50 values of 3.
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