- 3-(Hydroxyimino)imidazo[1,2-a]pyridin-2(3H)-ylidene)-1-arylethanones as new red heterocyclic dyes: Synthesis, spectral studies, quantum-chemical investigations, and antibacterial activities
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The synthesis, optical properties, theoretical calculations, and antibacterial activities of a series of new red heterocyclic dyes derived from imidazo[1,2-a]pyridine are presented. 3-(Hydroxyimino)imidazo[1,2-a]pyridin-2(3H)-ylidene)-1-arylethanones are obtained from the reaction of 3-nitroimidazo[1,2-a]pyridine with substituted acetophenone derivatives in good yields (65%–72%). The structures are confirmed by spectral and analytical data, and the optical properties of the dyes are characterized by spectrophotometry. Density functional theory calculations are performed to provide the optimized geometries and relevant frontier orbitals. Calculated electronic absorption spectra are also obtained by the time-dependent density functional theory method. Moreover, the antibacterial activities (minimum inhibitory concentration) of the new dyes against Gram-positive and Gram-negative bacterial species are determined (minimum inhibitory concentration: 5–200 μg mL?1).
- Poormirzaei, Nazanin,Pordel, Mehdi,Yaghoobi, Elnaz,Shojaee, Saeed,Aminiyanfar, Masoud,Gonabadi, Atoosa
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- Vertically π-expanded imidazo[1,2-a]pyridine: The missing link of the puzzle
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The dehydrogenative coupling of imidazo[1,2-a]pyridine derivative has been achieved for the first time. In cases in which the most-electron-rich position of the electron-excessive heterocycle was blocked by a naphthalen-1-yl substituent, neither oxidative aromatic coupling nor reaction under Scholl conditions enabled the fusion of the rings. The only method that converted the substrate into the corresponding imidazo[5,1,2-de]naphtho[1,8-ab]quinolizine was coupling in the presence of potassium in anhydrous toluene. Moreover, we discovered new, excellent conditions for this anion-radical coupling reaction, which employed dry O2 from the start in the reaction mixture. This method afforded vertically fused imidazo[1,2-a]pyridine in 63% yield. Interestingly, whereas the fluorescence quantum yield (Φfl) of compound 3, despite the freedom of rotation, was close to 50 the Φfl value of flat naphthalene-imidazo[1,2-a]pyridine was only 5 . Detailed analysis of this compound by using DFT calculations and a low-temperature Shpolskii matrix revealed phosphorescence emission, thus indicating that efficient intersystem-crossing from the lowest-excited S 1 level to the triplet manifold was the competing process with fluorescence.
- Firmansyah, Dikhi,Banasiewicz, Marzena,Deperasińska, Irena,Makarewicz, Artur,Kozankiewicz, Boleslaw,Gryko, Daniel T.
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- New fluorescent heterocyclic systems from imidazo[1,2-a]pyridine: Design, synthesis, spectral studies and quantum-chemical investigations
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Two new fluorescent heterocyclic systems dipyrido[1′,2′:1,2]imidazo[4,5-b:4,5-e]pyridine-13-carbonitrile and pyrido[1′,2′:1,2]imidazo[4,5-b]pyrido[2′,1′:2,3]imidazo[4,5-e]pyridine-13-carbonitrile were synthesized by one-pot reaction of imidazo[1,2-a]pyridine with 2-(imidazo[1,2-a]pyridin-3-yl)acetonitrile and 2-(imidazo[1,2-a]pyridin-2-yl)acetonitrile, respectively, in MeOH/KOH solution via the nucleophilic substitution of hydrogen in high yields. Spectral and analytical data have confirmed the structures of the synthesized dyes. The optical and solvatochromic properties of the compounds were investigated and the results showed that they exhibited interesting photophysical properties. Density functional theory (DFT) calculations of fluorescent dyes were performed to provide the optimized geometries and relevant frontier orbitals by using the B3LYP hybrid functional and the 6–311?++ G(d,p) basis set. Calculated electronic absorption spectra were also obtained by time-dependent density functional theory (TD-DFT) method. In addition, electron density iso-surface map, intra- and intermolecular interactions of these fluorescent heterocyclic systems were evaluated by AIM (Atoms in Molecules) analysis.
- Pordel, Mehdi,Chegini, Hamed,Ramezani, Shirin,Daee, Mohammadreza
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- A new fluorescent probe of hydrazine: 2-[4-(imidazo[1,2-a]pyridin-3-ylethynyl)benzylidene]malononitrile
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Hydrazine is widely used in a plenty of fields as a raw material and is closely related to our healthy. A new fluorescent probe of hydrazine was designed and synthesized, choosing imidazo[1,2-α]pyridine as the electron acceptor, based on the intramolecular charge-transfer (ICT) effect. The probe, 2-[4-(imidazo[1,2-α]pyridin-3-ylethynyl)benzylidene]malononitrile (5), responds rapidly to hydrazine and exhibits obvious color changes from yellow to colorless, indicating its use as a color indicator for hydrazine. Sensing mechanism of probe 5 toward hydrazine was deduced through HOMOLUMO energy levels and the interfacial plots of the molecular orbitals. Its physical and chemical properties were demonstrated by UV, fluorescence, and singlecrystal X-ray diffraction via computation and experiment. The calculated data are consistent with experimental results.
- Zhao, Chunshen,Huang, Chao,Yang, Shuo,Chai, Huifang,Le, Yi,Liu, Li
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- Synthesis, DFT calculations, cyclic voltammetry and antibacterial activities of a new blue-violet dye and a new blue-green fluorescent heterocyclic system
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The new blue-violet dye 2-(3-hydroxyimino-2,3-dihydroimidazo[1,2-a]pyridin-2-yliden)-2-(2-thienyl)acetonitrile was prepared in high yield from the reaction of 3-nitroimidazo[1,2-a]pyridine with 2-(2-thienyl)acetonitrile by nucleophilic substitution of hydrogen. Acylation of the hydroxyl group led to a new heterocyclic system, (pyrido[2′,1′:2,3] imidazo[4,5-b]thieno[2,3-e]pyridine-11-carbonitrile) with very strong blue-green fluorescent properties. Physical, spectral and analytical data have confirmed the structures of the synthesized dyes. The optical and solvatochromic properties of these compounds were investigated and showed interesting photophysical properties. Density functional theory calculations of blue-violet and fluorescent dyes were performed to provide the optimized geometries, Mulliken atomic charges, relevant frontier orbitals and the prediction of 1H NMR chemical shifts. The electrochemical properties of these dyes were investigated by cyclic voltammetry and an oxidation wave was observed at a half-wave potential of -0.143 V versus SCE for the blue-violet dye. Also, these new compounds exhibited potent antibacterial activity against Gram positive and negative bacterial species.
- Baf, Mozhgan Mazloum Farsi,Pordel, Mehdi,Daghigh, Leila Rezaei
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- Synthesis of new dyes from imidazo[1,2-a]pyridine: Tautomerism, spectroscopic characterisation, DFT/TD-DFT calculations, atoms in molecules analyses and antibacterial activities
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The synthesis, optical properties, theoretical calculations and antibacterial activity of a series of new heterocyclic dyes from imidazo[1,2-a] pyridine are described. The key intermediate 2-[3-(hydroxyimino)imidazo[1,2-a]pyridin-2(3H)-ylidene]malononitrile was obtained via the nucleophilic substitution of hydrogen in 3-nitroimidazo[1,2-a]pyridine with malononitrile in basic methanol solution. Tautomerism, oxidation and alkylation studies on the dye led to the synthesis of new heterocyclic indigo-coloured, purple, and orange dyes in good yields. The structures of all newly synthesised compounds were confirmed by spectral and analytical data. The optical properties of the dyes were spectrally characterised and shown to exhibit interesting photophysical properties including high extinction coefficients. Density functional theory calculations of the dyes were performed to provide the optimised geometries and relevant frontier orbitals. Calculated electronic absorption spectra were also obtained by the time-dependent density functional theory method. In addition, electrostatic potential maps and electron density maps of the dyes were evaluated by AIM (atoms in molecules) analysis. Moreover, the new dyes exhibited potent antibacterial activity and their antibacterial activities (MIC) against Gram-positive and Gram-negative bacterial species were determined.
- Mohammadi, Samaneh,Pordel, Mehdi,Allameh, Sadegh,Chegini, Hamed
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- From Synthetic Simplified Marine Metabolite Analogues to New Selective Allosteric Inhibitor of Aurora B Kinase
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Significant inhibition of Aurora B was achieved by the synthesis of simplified fragments of benzosceptrins and oroidin belonging to the marine pyrrole-2-aminoimidazoles metabolites isolated from sponges. Evaluation of kinase inhibition enabled the discovery of a synthetically accessible rigid acetylenic structural analogue EL-228 (1), whose structure could be optimized into the potent CJ2-150 (37). Here we present the synthesis of new inhibitors of Aurora B kinase, which is an important target for cancer therapy through mitosis regulation. The biologically oriented synthesis yielded several nanomolar inhibitors. The optimized compound CJ2-150 (37) showed a non-ATP competitive allosteric mode of action in a mixed-type inhibition for Aurora B kinase. Molecular docking identified a probable binding mode in the allosteric site "F"and highlighted the key interactions with the protein. We describe the improvement of the inhibitory potency and specificity of the novel scaffold as well as the characterization of the mechanism of action.
- Juillet, Charlotte,Ermolenko, Ludmila,Boyarskaya, Dina,Baratte, Blandine,Josselin, Béatrice,Nedev, Hristo,Bach, Stéphane,Iorga, Bogdan I.,Bignon, Jér?me,Ruchaud, Sandrine,Al-Mourabit, Ali
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p. 1197 - 1219
(2021/02/05)
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- Discovery of imidazo[1,2-a]pyridine-thiophene derivatives as FLT3 and FLT3 mutants inhibitors for acute myeloid leukemia through structure-based optimization of an NEK2 inhibitor
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FMS-like tyrosine kinase 3 (FLT3) with an internal tandem duplication (ITD) mutation has been validated as a driver lesion and a therapeutic target for acute myeloid leukemia (AML). Currently, several potent small-molecule FLT3 kinase inhibitors are being evaluated or have completed evaluation in clinical trials. However, many of these inhibitors are challenged by the secondary mutations on kinase domain, especially the point mutations at the activation loop (D835) and gatekeeper residue (F691). To overcome the resistance challenge, we identified a novel series of imidazo[1,2-a]pyridine-thiophene derivatives from a NIMA-related kinase 2 (NEK2) kinase inhibitor CMP3a, which retained inhibitory activities on FTL3-ITDD835V and FLT3-ITDF691L. Through this study, we identified the imidazo[1,2-a]pyridine-thiophene derivatives as type-I inhibitors of FLT3. Moreover, we observed compound 5o as an inhibitor displaying equal anti-proliferative activities against FLT3-ITD, FTL3-ITDD835Y and FLT3-ITDF691L driven acute myeloid leukemia (AML) cell lines. Meanwhile, the apoptotic effects of compound supported its mechanism of anti-proliferative action. These results indicate that the imidazo[1,2-a]pyridine-thiophene scaffold is promising for targeting acquired resistance caused by FLT3 secondary mutations and compound 5o is an interesting lead in this direction.
- Zhang, Lingtian,Lakkaniga, Naga Rajiv,Bharate, Jaideep B.,Mcconnell, Nicholas,Wang, Xiuqi,Kharbanda, Anupreet,Leung, Yuet-Kin,Frett, Brendan,Shah, Neil P.,Li, Hong-yu
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- Synthesis of a new heterocyclic dye compound as an indicator in acid and base reactions
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In the present research, the use of 2-(3-hydroxyamino-2,3-dihydroimidazo[1,2-a]pyridine-2-ylidene)-2-(2-tienyl)acetonitrile as a new acid and base indicator in aquatic environments has been investigated. This compound has been synthesized by the reaction of 3-nitroimidazo [1,2-a] pyridine and 2-(2-thienyl) acetonitrile in a methanol solution by the hydrogen nucleophilic substitution. The aqueous-ethanol solution of this compound shows a change in color by adding acid and an base. For the potential function of this reagent as an indicator, the spectral properties of UV-Vis and the equilibrium of acid and base source have been examined. The results show that the reagent is an amphoteric with two stable ionization factors Ka and Kb with poor acid and base properties. Indicator dissociation constants in aqueous solutions specified by spectrophotometric method are pKa = 9.73 and pKb = 11.57. The types of base that can be titrated with this index have been reported. This index has been compared with effective acid and base indexes with similar pH range.
- Chenarboo, Mahdi Khorsandi,Ebrahimi, Mahmoud,Pordel, Mehdi,Razmi, Mina
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p. 287 - 290
(2021/09/28)
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- Microwave-assisted synthesis of 3-formyl substituted imidazo[1,2-a]pyridines
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An efficient, metal-free method for the synthesis of 3-formyl imidazo[1,2-a]pyridines is reported. The method utilises commercially available substrates and features a broad substrate scope. The intermediate enamine was isolated and a plausible reaction mechanism proposed.
- Kusy, Damian,Maniukiewicz, Waldemar,B?a?ewska, Katarzyna M.
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supporting information
(2019/10/16)
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- Sodium Salts (NaI/NaBr/NaCl) for the Halogenation of Imidazo-Fused Heterocycles
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We report herein an effective method for the halogenation of imidazo-fused heterocycles using readily available sodium salts (NaCl/NaBr/NaI) as halogen source and K2S2O8 (or) oxone as promoter. A variety of C-3 halogenated imidazo[1,2-a]pyridines and benzo[d]imidazo[2,1-b]thiazoles were obtained in good to excellent yields. The present method of halogenation has been also extended to 2-aminopyridines, 2-aminopyrimidine, indole, and isoquinoline with moderate to excellent yields.
- Semwal, Rashmi,Ravi, Chitrakar,Kumar, Rahul,Meena, Ramavatar,Adimurthy, Subbarayappa
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p. 792 - 805
(2019/01/24)
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- Imidazo[1,2-a]pyridine compounds and preparation method and application thereof
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The invention relates to a class of imidazo[1,2-a]pyridine compounds and a preparation method and application thereof. The imidazo[1,2-a]pyridine compounds are shown in a figure. The compounds and derivatives of the compounds have inhibitory effects on multiple cancers and tumors.
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Paragraph 0059; 0061
(2019/05/15)
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- Minodronic acid intermediate synthesis system and synthesis process thereof
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The invention discloses a minodronic acid intermediate synthesis system and a synthesis process thereof. The synthesis system comprises an agitating tank and a reaction kettle, the agitating tank comprises a rack, a mixing tank, and agitating assemblies, each agitating assembly comprises an agitating motor, an agitating shaft, agitating blades, and impellers, and a heater is arranged on the external wall of the mixing tank; the reaction kettle comprises a barrel, a feed inlet, a discharge outlet, a support, and a reaction kettle agitator; and the agitating tank is located upon the reaction kettle. The invention further discloses a preparation method of minodronate intermediate 2-(imidazo[1,2-a]pyridine-3-yl)acetate, which comprises the following steps: imidazo[1,2-a]pyridine and oxalyl chloride as starting materials undergo Friedel-Crafts acylation and Huang Ming-long reduction, and thereby the intermediate 2-(imidazo[1,2-a]pyridine-3-yl)acetate is obtained. According to the invention,environmental pollution is reduced, the reaction step is shortened, the whole reaction process is simplified, the preparation of 2-(imidazo[1,2-a]pyridine-3-yl)acetate is easy to control, the reaction conditions are mild, post-treatment is simple, and industrial production is easy.
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Paragraph 0043-0045
(2018/11/03)
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- Synthesis, Spectral Studies, and Quantum Chemical Investigations of a New Violet Dye and a Fluorescent Heterocyclic System
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The new violet dye 3-(hydroxyimino)imidazo[1,2-a]pyridin-2(3H)-ylidene)-2-(naphthalen-1-yl) acetonitrile was synthesized by reaction of 3-nitro-imidazo[1,2-a]pyridine with 1-naphthylacetonitrile. Cyclization of the latter compound in pyridine led to the formation of new fluorescent heterocyclic system benzo[f]pyrido[2’,1’:2,3] imidazo[4,5-b]quinoline. The structural assignments of the new compounds were based on their spectral and microanalytical data. The optical and solvatochromic properties of the compounds were investigated, and the results showed that they display interesting photophysical properties such as high values of extinction coefficient and fluorescence quantum yield. Moreover, the density functional theory (DFT) calculations were employed to gain a deeper insight into the geometry and relevant frontier orbitals of the compounds. Calculated electronic absorption spectra were also obtained by the time-dependent DFT method.
- Alipoor, Hamideh,Pordel, Mehdi,Morsali, Ali
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p. 313 - 319
(2018/09/26)
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- Preparation method of novel fluorescent probe used for detecting diamine
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The invention discloses a preparation method of a novel fluorescent probe used for detecting diamine. According to the preparation method, 2-aminopyridine is taken as an initial raw material, and a novel fluorescent probe compound 3-(imidazo[1,2-a]pyridine-3-yl)-1-phenyl-2-alkynyl-1-one is obtained via four steps of reaction. It is confirmed by study that a reaction product of the novel fluorescent probe compound with diamine possesses fluorescence performance, and the fluorescent intensity is increased with the increasing of concentration of diamine; and the fluorescence intensification factor is linearly dependent to the concentration of diamine; so that the novel fluorescent probe compound can be taken as a high sensitivity fluorescent probe used for detecting diamine.
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Paragraph 0019; 0020; 0030; 0031; 0041; 0042; 0052; 0053
(2017/10/07)
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- QUINOLINONE PYRIMIDINES COMPOSITIONS AS MUTANT-ISOCITRATE DEHYDROGENASE INHIBITORS
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The invention relates to inhibitors of mutant isocitrate dehydrogenase (mt-IDH) proteins with neomorphic activity useful in the treatment of cell-proliferation disorders and cancers, having the Formula: where A, B, W1, W2, W3, and R1-R6 are described herein.
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Paragraph 0819; 0820
(2016/04/19)
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- Iridium, ruthenium, and palladium complexes containing a mesoionic fused imidazolylidene ligand
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Imidazo[1,2-a]pyridine consisting of a pyridine fused to an imidazolium salt at the imidazolium N1-C2 bond and hence protected from forming normal imidazole-2-ylidene complexes undergoes selective activation of the C5-H bond with Ag2O, i.e. at the imidazolium carbon that is proximal to the pyridine nitrogen. While the silver carbene complex is unstable, transmetallation with [IrCp?Cl2]2, [RuCl2(cym)]2, and [PdCl(allyl)]2 afforded stable mesoionic carbene complexes. Two iridium(III) complexes containing one fused carbene ligand and one palladium(II) complex containing two carbene ligands at the metal centre were structurally characterized. The absence of substituents adjacent to the carbene carbon prevents wingtip group activation, and it imparts a reduced stability of the complexes in particular under (mildly) acidic conditions.
- Petronilho, Ana,Mueller-Bunz, Helge,Albrecht, Martin
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p. 117 - 123
(2015/02/19)
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- Computer aided drug discovery of highly ligand efficient, low molecular weight imidazopyridine analogs as FLT3 inhibitors
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The FLT3 kinase represents an attractive target to effectively treat AML. Unfortunately, no FLT3 targeted therapeutic is currently approved. In line with our continued interests in treating kinase related disease for anti-FLT3 mutant activity, we utilized pioneering synthetic methodology in combination with computer aided drug discovery and identified low molecular weight, highly ligand efficient, FLT3 kinase inhibitors. Compounds were analyzed for biochemical inhibition, their ability to selectively inhibit cell proliferation, for FLT3 mutant activity, and preliminary aqueous solubility. Validated hits were discovered that can serve as starting platforms for lead candidates.
- Frett, Brendan,McConnell, Nick,Smith, Catherine C.,Wang, Yuanxiang,Shah, Neil P.,Li, Hong-Yu
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p. 123 - 131
(2015/04/14)
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- NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles
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The pair NaBH4-TMEDA as hydride source and a palladium catalyst in THF prove to be an efficient system for the hydrodehalogenation of halogenated heterocycles with one or more heteroatoms. In general, Pd(OAc) 2-PPh3 rapidly hydrodehalogenates reactive halo-heterocycles such as bromo-pyridines, -quinolines, -thiophenes, -indoles, -imidazoles, etc., at room temperature in very good yields, whereas in most cases PdCl2(dppf) reduces less reactive halides such as chloro-pyridines, -quinolines, -pyrimidines and bromo-indoles, -benzofurans, etc. Moreover, PdCl2(tbpf) shows to be even more active removing the 2- and 5-chlorine from both thiophene and thiazole rings. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene and nitrile substituents. Moreover, with a proper selection of the catalyst it is also possible to obtain a good control in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.
- Chelucci, Giorgio,Figus, Susanna
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p. 191 - 209
(2014/07/21)
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- Pd-catalyzed oxidative cross-coupling of imidazo[1,2-a]pyridine with arenes
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A facile method for direct Pd(OAc)2-catalyzed oxidative cross-coupling of unactivated imidazo[1,2-a]pyridine with simple arenes has been developed. The reaction shows good reaction efficiency, high regioselectivity, and good functional-group compatibility. This approach provides a useful protocol for the preparation of imidazo[1,2-a]pyridine-arene structure of interest in biological and pharmaceutical materials.
- Wang, Shaohua,Liu, Wenjie,Cen, Jinghe,Liao, Jinqiang,Huang, Jianping,Zhan, Haiying
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supporting information
p. 1589 - 1592
(2014/03/21)
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- Pd(0)-catalyzed decarboxylative coupling and tandem C-H arylation/decarboxylation for the synthesis of heteroaromatic biaryls
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An effective Pd(0) carbene complex was successfully employed in the decarboxylative coupling of the heteroaromatic carboxylic acids (imidazo[1,2-a]pyridine and isoxazole) with aryl halides. For carboxyindoles, either decarboxylative coupling or tandem C-H arylation and decarboxylation occurred, leading to the formation of C2-monoarylated indoles.
- Nandi, Debkumar,Jhou, Yang-Ming,Lee, Jhen-Yi,Kuo, Bing-Chiuan,Liu, Chien-Yu,Huang, Pei-Wen,Lee, Hon Man
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p. 9384 - 9390
(2013/01/15)
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- Imidazo[1,2-a]pyridine C-nucleosides as antiviral agents
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This invention pertains to nucleoside analogs that have antiviral activity and improved metabolic stability, compositions comprising them, and methods of antiviral treatment employing them. More particularly, this invention pertains to imidazo[1,2-a]pyridine C-nucleosides, as exemplified by compounds such as imidazo[l,2-a]pyridine C5-nucleosides and imidazo[1,2-a]pyridine C3-nucleosides, and may be represented by formula (I), wherein exactly one of Q3and Q5is a sugar-like moiety; exactly one of Q3and Q5is —H; and Q2, Q6, Q7and Q8are independently imidazo[1,2-a]pyridine substituents, such as —H, —F, —Cl, —Br and —I.
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- Substituent effects on fluorescent properties of imidazo[1,2- α]pyridine-based compounds
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In order to search for novel fluorescent organic compounds, 20 derivatives of imidazo[1,2-a]pyridine (1) were synthesized, and their fluorescent properties were studied. Though the parent compound I (λ(fl) = 370.5 nm, Φ = 0.57 in ethanol) was in the liquid state at ambient temperature, 2-phenylimidazo[1,2-a]pyridine (5), 2-(2-naphthyl)imidazo[1,2- a]pyridine (16), 7-methylimidazo[1,2-a]pyridine (3), 7-methyl-2- phenylimidazo[1,2-a]pyridine (12), and 7-methyl-2(2-naphthyl)imidazo[1,2- a]pyridine (17) were found to give thermally stable solid compounds (mp 55- 190 °C) without much affecting the fluorescent properties of the parent compound (λ(fl) = 374-381 nm, Φ = 0.50-0.78 in ethanol). Among the 4'- substituted 2-phenyl derivatives, it was found that the introduction of the strong electron-donating amino and dimethylamino groups (2-(4- aminophenyl)imidazo[1,2-a]pyridine (7) and 2-[4- (dimethylamino)phenyl]imidazo[1,2-a]pyridine (8), respectively) caused marked red shift of their fluorescence (λ(fl) = 445 and 446 nm, respectively, in ethanol), thus providing the way for tuning the fluorescence color of the IP derivatives. The observed red shift of the fluorescence of 7 and 8 was ascribed to the contribution of the excited intramolecular charge transfer state.
- Tomoda, Haruhiko,Hirano, Takafumi,Saito, Shojiro,Mutai, Toshiki,Araki, Koji
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p. 1327 - 1334
(2007/10/03)
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- Mono-- or diketone tetracyclic derivatives and therapeutical uses thereof
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Invention concerning the therapeutic use of tetracyclic derivatives and their pharmaceutically acceptable salts having the following general formula: STR1 in which, independently of the other: X is a carbon or nitrogen atom, T is a carbon or nitrogen atom, L is an oxygen atom or ketone functional protective group, R1 is an atom of hydrogen, an atom of halogen, or a C1 to C5 alkyl radical, R2 is a hydrogen atom, a halogen atom, a nitro radical, or a C1 to C5 alkyl radical, n and m are equal to 0 or to 1, but not independently of the other, so that if n is equal to 1, then m is equal to 0, and if n is equal to 0, then m is equal to 1.
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- Tricyclic nitrogen ring compounds, their production and use
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Tricyclic compound of the formula: STR1 wherein ring A is a nitrogen-containing heterocyclic ring, having two nitrogen atoms as the hetero-atoms, which is optionally substituted with oxo or thioxo; ring Q may optionally be substituted; Y is an optionally substituted hydrocarbon group, an optionally substituted hydroxyl group or an optionally substituted mecapto group, excluding for methyl group as Y; R1 is a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group or an acyl group, or a salt thereof, having excellent PDGF-inhibiting activities, antihypertensive activities, activities of ameliorating renal diseases and activities of lowering lipid level.
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- Azaindole Derivatives with High Affinity for the Dopamine D4 Receptor: Synthesis, Ligand Binding Studies and Comparison of Molecular Electrostatic Potential Maps
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Piperazinylmethyl substituted pyrazolopyridines and related heterocycles were synthesized and found to recognize selectivity the dopamine D4 receptor. For the most potent derivative 10d a Ki value of 2.0 nM was observed. SAR studies including the comparison of molecular isopotential surfaces were performed.
- Loeber, Stefan,Huebner, Harald,Gmeiner, Peter
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- Synthesis of acyclo-C-nucleosides in the imidazo[1,2-a]pyridine and pyrimidine series as antiviral agents
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The synthesis and the antiviral activities of C-3 acyclic nucleoside analogues of imidazo[1,2-a]pyridine and pyrimidine are reported. From these compounds, 20, 21, 22, 23, 28, and 34 showed a specific activity against cytomegalovirus and/or varicella-zoster virus.
- Gueiffier, Alain,Lhassani, Mohammed,Elhakmaoui, Ahmed,Snoeck, Robert,Andrei, Graciela,Chavignon, Olivier,Teulade, Jean-Claude,Kerbal, Abdelali,Essassi, El Mokhtar,Debouzy, Jean-Claude,Witvrouw, Myriam,Blache, Yves,Balzarini, Jan,De Clercq, Erik,Chapat, Jean-Pierre
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p. 2856 - 2859
(2007/10/03)
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- Synthesis and antimuscarinic properties of some N-substituted 5- (aminomethyl)-3,3-diphenyl-2(3H)-furanones
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In a study aimed toward developing new, selective antimuscarinic drugs with potential utility in the treatment of urinary incontinence associated with bladder muscle instability, a series of N-substituted 5-(aminomethyl)- 3,3-diphenyl-2(3H)-furanones, conformationally-constrained lactone relatives of benactyzine, was prepared. The compounds were examined in several paradigms that measure muscarinic (M1, M2, and M3) receptor antagonist activity. Selected members of the series that displayed potency and/or selectivity in these tests were studied for their effects on urinary bladder contraction, mydriasis, and salivation in guinea pigs. These studies revealed that incorporation of the amino functionality into an imidazole or pyrazole ring resulted in some novel, potent, and selective antimuscarinic agents. Appropriate alkyl substitution of position 2 of the imidazole strikingly affected muscarinic, particularly M3, receptor activity and may reflect a complementary site of interaction. Some of the compounds selectively reduced bladder pressure in a cystometrogram (CMG) model without producing concomitant mydriatic and salivary effects. The separate and distinct action of several compounds of this series in these in vivo protocols suggests the possibility of subtypes of muscarinic receptors that may correspond to previously characterized molecular cloned subpopulations. In this article, structure-activity relationships for the series of substituted lactones are discussed. These studies led to the identification of (R)-[(2-isopropyl-1H- imidazol-1-yl)methyl]-4,5-dihydro-3,3-diphenyl-2(3H)-furanone (23) as a clinical candidate for treating urinary bladder dysfunction.
- Kaiser,Spagnuolo,Adams Jr.,Audia,Dupont,Hatoum,Lowe,Prosser,Sturm,Noronha-Blob
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p. 4415 - 4424
(2007/10/02)
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- 2-[(imidazo[1,2-a]pyridin-3-ylmethyl)sulfinyl]-1H-benzimidazoles useful in the treatment and prevention of ulcers
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This invention relates to 2-[(imidazo[1,2-a]pyridin-3-ylmethyl)sulfinyl]-1H-benzimidazoles that are useful in the treatment and prevention of ulcers.
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- peri-Substituted Imidazopyridines. A New Reductive Elimination Reaction
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A new reductive elimination reaction of 3,5-disubstituted imidazopyridines (3) with hydrazine is reported.Thus on treatment of the 3,5-dibromo (7a), 5-bromo-3-nitro (7b), and 3,5-dinitro (4) derivatives with hydrazine hydrate in hot ethanol, the bromine and nitro groups are replaced by hydrogen.A mechanism based on the conjugated relationship of these peri-substituents is proposed and used to explain the reported conversion of 1,3,5-trichloro-2,4,6-trinitrobenzene (9) into 1,3-dichloro-4,6-dinitrobenzene (10).A variety of other 3-nitro-5-substituted imidazopyridines (15)-(18) is described, but these could not be cyclised to 1,2,4-triazacyclopentindenes.The 3-amino-5-methoxycarbonyl derivative (19a) cyclises to the triazacyclopentindenone (20) with sodium methoxide.
- Rees, Charles W.,Smith, David I.
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p. 1159 - 1164
(2007/10/02)
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- Diazaindenes (Azaindoles). Part 7. Formation of Imidazopyridinium-8-carboxylate in an Attempt to prepare Pyrrolopyridin-3-one
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Attempts to obtain N-(3-carboxy-2-pyridyl)glycine (5) from 2-chloro-3-cyanopyridine are described.The ring-chain tautomerism of certain N-(2-pyridyl)aminoacetaldehydes is discussed.Three preparations of N-3-(carboxy-2-pyridyl)aminoacetaldehyde (20) and its cyclisation to the zwitterionic imidazopyridinium-8-carboxylate (23) are given.
- Parrick, John,Wilcox, Russel,Kelly, Anthony H.
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p. 132 - 135
(2007/10/02)
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- Certain substituted imidazo [1,2-a] pyridines
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Certain novel substituted imidazo [1,2-a] pyridines with a substituted amino group at the 2- or 3-position are active anthelmintic agents. The novel compounds are prepared from the appropriate substituted 2-aminopyridine precursor. Compositions which utilize said novel imidazo [1,2-a] pyridines as the active ingredient thereof for the treatment of helminthiasis are also disclosed.
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- Quaternary salts as hypoglycemic agents
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The synthesis of imidazo?1,2-a!pyridinium, imidazo?1,5-a!pyridinium, pyrrolo?1,2-a!pyrazinium, pyrazolo?1,5-a!pyridinium, imidazo?2,1-a!isoquinolinium and imidazo?5,1-a!isoquinolinium quaternary salts and their use as hypoglycemic agents.
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- Imidazopyridinium compounds as hypoglycemic agents
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The synthesis of imidazo[1,2-a]pyridinium, imidazo[1,5-a]pyridinium, pyrrolo[1,2-a]pyrazinium, pyrazolo[1,5-a]pyridinium, imidazo[2,1-a]isoquinolinium and imidazo[5,1-a]isoquinolinium quaternary salts and their use as hypoglycemic agents.
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