The substituted 2 phenylimidazo 1, 2 a pyridine derivatives have been synthesized by a one pot two component reaction of 2. Synthesis of imidazo1,2apyridines via multicomponent. Synthesis and anticancer activity of bis2arylimidazo1,2. We enable science by offering product choice, services, process excellence and our people make it happen. Imidazo1,2apyridine6carboxaldehyde 97% sigmaaldrich. Imidazo1,2apyridine synthesis organic chemistry portal. Green synthesis of imidazo1,2apyridines in aqueous medium. Imidazo1,2apyridines that directly interact with hepatitis. Onepot synthesis of benzo4,5 imidazo 1,2 a pyridine derivatives in aqueous conditions. Jun 29, 2018 3 and 8iodoimidazo1,2apyridines were synthesized from imidazo1,2 apyridine under different substitution conditions. Imidazo 1,2a pyridine an example of imidazopyridine and a core structure of zolpidem and some compounds described below. Fecl3catalyzed c3 functionalization of imidazo1,2a. Compound 4a was obtained in four steps starting with two succesive brominations of 2acetylfuran first.
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. Chromones and imidazo1,2apyridines are a privileged core of high interest in medicinal chemistry. The coiicl 2 6h 2 o catalyzed ch activationdirect arylation of imidazo 1, 2. Although lots of synthetic methods of imidazo 1, 2. A straightforward synthesis of 2 phenylimidazo1,2 apyridine is described. Several imidazo 1, 2 a pyridine derivatives were reported to be fluorescent in nature17. Selenoamides as powerful scaffold to build imidazo1,5a.
It has long been known that imidazo1,2apyridine derivatives exhibit diverse biological activities 1 and were used as antiviral, 2 antiulcer, 3 antibacterial, 4 antifungal, 5 antiprotozoal, 6 antiherpes, 7 antiinflammatory. We have previously shown that intracerebroventricular i. Key words imidazo 1,2a pyridine, 2aminopyridine, tandem reaction, multicomponent reaction, ch activation 1 introduction among nitrogenfused azoles, imidazo 1,2apyridines have a lead role in the literature because of their wide variety of applications in various disciplines like medicinal chemistry, organometallics, and material. A convenient synthesis of c3aryloxymethyl imidazo1,2. An imidazo 1, 2 a pyridine series of atx inhibitors was identified out of a highthroughput screening hts. A practical and efficient approach to imidazo1,2apyridinefused. Novel imidazo1,2apyridine inhibits aktmtor pathway and. Synthesis and evaluation of tricarbonyl 99mtclabeled 24. Based on the predicted binding modes of compounds 5 and 14 in docking studies, a new series of cmet inhibitorharboring 31hpyrrolo3,2cpyridin 1 ylsulfonyl imidazo 1,2a pyridine. Catalyst free, c3 functionalization of imidazo1,2a. Pdf 2phenylimidazo1,2apyridine derivatives as ligands.
The combination of cs 2 co 3 and pdoac 2 enables the coupling of imidazo 1, 2. Imidazo 1, 2 a pyridine is a bicyclic system with a bridgehead nitrogen atom, of growing interest in medicinal chemistry. Pdf the imidazo1,2apyridine scaffold is recognized as a privileged structure and it represents a promising area for identification of lead. This invention relates generally to imidazo 1,2a pyridine based modulators of liver x receptors lxrs having formula i and related methods. Other copperi salts such as cucl, cui, and cuotf in similar quantities could not a. The cyclization reaction could be realized with the aid of. Synthesis and evaluation of tricarbonyl 99m tc labeled 24chlorophenyl imidazo 1,2a pyridine analogs as novel spect imaging radiotracer for tsporich cancer by ji young choi 1,2, rosa maria iacobazzi 3,4, mara perrone 3, nicola margiotta 5, annalisa cutrignelli 3, jae ho jung 1, do dam park 1, byung seok moon 1, nunzio denora 3. Imidazo1,2apyridine scaffold as prospective therapeutic. Multicomponent reactions mcrs are robust tools for the rapid synthesis of complex, small molecule libraries for use in drug discovery and development.
Synthesis of imidazo1,2apyridines via multicomponent gbbr. This transformation provides a rapid and concise access to multifunctional imidazo1,5apyridines. Imidazo 1,2a pyridine is a bicyclic system with a bridgehead nitrogen atom, of growing interest in medicinal chemistry. Tandem approach for the synthesis of imidazo1,2apyridines. The molecular structures of the target compounds were characterized by single crystal xray diffraction analysis.
Further studies were conducted on the fluorescence behaviour of imidazo 1,2a pyridine derivatives. Screening conditions for synthesis of imidazo 1,2a pyridine 3amine 6a. A cuicatalyzed aerobic oxidative synthesis of imidazo1,2 apyridines from 2aminopyridines and acetophenones is compatible with a broad range of functional groups. A general method for the exclusive formation of imidazo 1,5apyridines. A similar family of compounds, the imidazo 1, 2 a pyridine 3hydrazones, have been synthesized but are all inactive against m. General experimental procedure for synthesis of imidazo 1,2a pyridine derivatives 1a1s. The qsar study shows a significant correlation of activity with global. Imidazo1,2pyridinebased tosylhydrazone was prepared and treated with k 2 co 3 in dioxane at 110c to generate the corresponding carbene in situ. Nov 20, 2008 reproducible switching of the polymorph. In the present study, effects of a newly synthesized azaindolizinone derivative, spiro imidazo 1,2 a pyridine 3,2indan23 h one zset1446, were assessed in rats with learning deficits. An imidazopyridine is a nitrogen containing heterocycle that is also a class of drugs that contain this same chemical substructure.
Learn more about 2 chloromethylimidazo1,2a pyridine. Imidazo1,2apyridines have been reported to display a wide range of biological activities. Pdf synthesis of imidazo1,2apyridinechromones by a mw. Imidazo 1, 2 a pyridine 3amines were synthesised using the groebke reaction and tested for antihiv activity. Supporting information access new chemical space for drug. By utilizing mcr chemistry, we developed a protocol to functionalize the c3 position of imidazo 1,2a pyridine through a three component, decarboxylation r. Compound nd10885 2, showed significant activity in the lung, 36 spleen and liver in a mouse m. Subsequently, some imidazo 1,2a pyridine compounds were developed and tested for their pi3kakt pathway inhibiting ability 2325. The so obtained gbb product imidazo 1,2a pyridine 4a bearing an amino group and an acetylene unit may then undergo a sequential 6exodig cyclizationretroene reaction to form the desired imidazo 1,2a pyridine fused isoquinoline 6a.
Recent developments in the synthesis of imidazo1,2apyridines. Prepared from 6methyl2ptolyl imidazo1,2a pyridine 3ylacetaldehyde 6b and 4bromo 1,3,5trimethyl1hpyrazole using the. Several imidazo 1,2a pyridine derivatives were reported to be fluorescent in nature17. The imidazo 1,2apyridines bearing different substituents showed excellent migratory aptitude and resulted corresponding nacetoxymethyl, nalkoxymethyl and n. Jul 12, 2012 a series of imidazo 1, 2 a pyridines which directly bind to hcv nonstructural protein 4b ns4b is described. The current study, aimed to investigate the exact anticancer effect of these compounds in melanoma and cervical. The reaction is designed to demonstrate to students the preparation of a bridged nheterocycle, in which the heteroatom occupies a bridgehead position. A pidamediated 1,2ipsomigration of imidazo 1,2a pyridine ring via the formation of aziridine intermediate in the mannich bases derived from imidazo 1,2apyridines, 2pyridylamines or arylamines and formaldehyde is reported. Discovery, structureactivity relationship, and binding mode. This series demonstrates potent in vitro inhibition of hcv replication ec 50 2 substituted nprop 2 yn 1 ylaminopyridines is an efficient, mild, new and practical method for the stereospecific synthesis of eexohalomethylene bicyclic pyridones bearing the imidazo 1, 2 a pyridine heterocyclic ring system. Green synthesis of imidazo1,2apyridines using calix6. We aimed to evaluate the use of ionic liquid in the synthesis of substituted imidazo 1, 2 a pyridine derivatives and their antibacterial activity against grampositive and gramnegative bacteria.
Selenoamides as potent scaffold to give imidazo 1,5apyridines in excellent yields. A series of nine novel imidazo1,2apyridinchromones and nine novel imidazo1,2apyridin 6fluorochromones were synthesized in good to excellent yields by a mw assisted groebke blackburnbienayme reaction gbb under mild thermal and acidic. Chemoselective iodination of 6substituted imidazo1,2 a. Compounds prepared from 2 chlorobenzaldehyde, and a combination of cyclohexyl isocyanide and a 6substituted 2 aminopyridine showed good inhibitory activity in a reverse transcriptase assay and whole cell antihiv infectivity assays.
It has long been known that imidazo 1,2a pyridine derivatives exhibit diverse biological activities 1 and were used as antiviral, 2 antiulcer, 3 antibacterial, 4 antifungal, 5 antiprotozoal, 6 antiherpes, 7 antiinflammatory. For examples, numerous functionalized imidazo 1,2apyridines, especially the c3 substituted ones, are found to possess pharmaceutical and biological activities such as antitumor, antiviral, antiprotozoal, antiapoptotic, antipyretic. Copperpromoted regioselective intermolecular diamination of. 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. Imidazo 1, 2 a pyridine is one of the most potential bicyclic 56 heterocyclic rings that is recognized as a drug prejudice scaffold due to its broad range of applications in medicinal chemistry. Consequently, they have attracted much attention, and methods for their syntheses have been actively pursued. Pdf imidazo1,2apyridine is a bicyclic system with a bridgehead nitrogen atom, of growing interest in medicinal chemistry. General experimental procedure and data for the synthesis of imidazo 1,2a pyridine starting material iia. Wo2001014375a1 imidazo1,2apyridine and pyrazolo2,3a. Imidazo 1,2apyridinean example of imidazopyridine and a core structure of zolpidem and some compounds described below. Carboline imidazo 1,2 apyridine and imidazo1,2 apyrazine conjugates nisha devi,a dharmender singh,a honey,a satbir mor,b sandeep chaudharyc, ravindra kumar rawald, vipin kumar,a asim kumar chowdhurya and virender singha adepartment of chemistry, dr b r ambedkar national institute of technology, jalandhar. Caroline casteraducros et al synthesized series of imidazo 1, 2a pyridine derivatives 20 and evaluated them for antileishmanial activity 33. Crystal correlation of heterocyclic imidazo1,2 a pyridine. In modern synthetic chemistry, there is an urgent need to design and develop new green and.
The compound can be purified either by direct recrystallization or silica gel column. Synthesis and characterization of 2phenylimidazo1,2a. Selected imidazo 1, 2 a pyridines with pharmacological activity and our synthetic targets. Further studies were conducted on the fluorescence behaviour of imidazo 1, 2 a pyridine derivatives. Recent developments in the synthesis of imidazo1,2a.
Ionic liquid promoted synthesis of 2phenylimidazo 1,2a. The paper deals with the recent progress realised in the comprehension of. Molbase encyclopedia provides imidazo 1,2apyridin3ylmethanol 3048943 1 basic information, physical and chemical properties, safety information, toxicity, customs data, synthetic routes, maps, msds, generation methods and uses, and its upstream and downstream products, find imidazo 1,2apyridin3ylmethanol introduction, on the molbase encyclopedia. In the present study, effects of a newly synthesized azaindolizinone derivative, spiroimidazo1,2 a pyridine3,2indan23 h one zset1446, were assessed in rats with learning deficits.
The molecular electrostatic potential calculations were performed to investigate the chemoselectivity of the substitution reaction. Jan 30, 2019 imidazo 1, 2 a pyridine based compounds are clinically important to the treatments of heart and circulatory failures, while many are under development for pharmaceutical uses. Imidazo1,2 apyridine c7h6n2 cid 78960 structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities. Synthesis of novel imidazo1,2apyridines with potent activity against herpesviruses. Imidazo1,2 apyridine 274760 buy and find out price and availability, msds, properties of tcis high quality specialty chemicals. Imidazo1,5apyridine synthesis organic chemistry portal. Scheme 1 synthesis of imidazopyridine derivatives from. In general, they are gaba a receptor agonists, however recently proton pump inhibitors. Another inhibitor series found to have antitb activity are the imidazo 1, 2 a pyridine 3nitroso compounds, but they exhibit undesirable toxicity in a vero cell line.
The reaction also enables the formation of alkenylsubstituted imidazoheterocycles by using unsaturated ketones as substrates. It was coupled with a variety of aryl alcohols in one pot to obtain a series of imidazo1,2pyridine derivatives possessing aryl ether moiety at c3 position. The method is comparable with direct arylation of imidazo 1. A cocrystal structure with one of these compounds and atx revealed a novel binding mode with occupancy of the hydrophobic pocket and channel of atx but no interaction with zinc ions of the catalytic site.
Effects of a novel cognitive enhancer, spiroimidazo1,2. Here, we found that chronic oral administration of spiro imidazo 1,2 a pyridine 3,2indan23 h one zset1446st101 0. The product is obtained in moderate to high yield and is highly crystalline. Pdf recent progress in the pharmacology of imidazo1,2a. Olfactory bulbectomy obx in mice elicits impaired memory and cognitive functions. In the present study, we investigated the availability of radiolabeled drm106. 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.
Key words imidazo1,2apyridine, 2aminopyridine, tandem reaction, multicomponent reaction, ch activation 1 introduction among nitrogenfused azoles, imidazo1,2apyridines have a lead role in the literature because of their wide variety of applications in various disciplines like medicinal chemistry, organometallics, and material. A practical and efficient approach to imidazo1,2apyridine. Chapter 5 synthesis of imidazo pyridine derivatives. Identification of novel imidazo1,2apyridine inhibitors. Our group has therefore designed and synthesized novel imidazo 1,2apyridines compounds 57. Effects of a novel cognitive enhancer, spiroimidazo1,2a. Imidazo 1,2a pyridine and its derivatives have attracted considerable attention due to their wide applications in medicinal chemistry and material sciences.
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