274-76-0Relevant academic research and scientific papers
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
Poormirzaei, Nazanin,Pordel, Mehdi,Yaghoobi, Elnaz,Shojaee, Saeed,Aminiyanfar, Masoud,Gonabadi, Atoosa
, p. 167 - 173 (2020)
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).
Vertically π-expanded imidazo[1,2-a]pyridine: The missing link of the puzzle
Firmansyah, Dikhi,Banasiewicz, Marzena,Deperasińska, Irena,Makarewicz, Artur,Kozankiewicz, Boleslaw,Gryko, Daniel T.
, p. 2483 - 2493 (2014)
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.
New fluorescent heterocyclic systems from imidazo[1,2-a]pyridine: Design, synthesis, spectral studies and quantum-chemical investigations
Pordel, Mehdi,Chegini, Hamed,Ramezani, Shirin,Daee, Mohammadreza
, p. 105 - 112 (2017)
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.
A new fluorescent probe of hydrazine: 2-[4-(imidazo[1,2-a]pyridin-3-ylethynyl)benzylidene]malononitrile
Zhao, Chunshen,Huang, Chao,Yang, Shuo,Chai, Huifang,Le, Yi,Liu, Li
, p. 848 - 850 (2017)
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.
Synthesis, DFT calculations, cyclic voltammetry and antibacterial activities of a new blue-violet dye and a new blue-green fluorescent heterocyclic system
Baf, Mozhgan Mazloum Farsi,Pordel, Mehdi,Daghigh, Leila Rezaei
, p. 6925 - 6930 (2014)
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.
Synthesis of new dyes from imidazo[1,2-a]pyridine: Tautomerism, spectroscopic characterisation, DFT/TD-DFT calculations, atoms in molecules analyses and antibacterial activities
Mohammadi, Samaneh,Pordel, Mehdi,Allameh, Sadegh,Chegini, Hamed
, p. 143 - 148 (2017)
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.
From Synthetic Simplified Marine Metabolite Analogues to New Selective Allosteric Inhibitor of Aurora B Kinase
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
, p. 1197 - 1219 (2021/02/05)
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.
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
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
, (2021/09/04)
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.
Synthesis of a new heterocyclic dye compound as an indicator in acid and base reactions
Chenarboo, Mahdi Khorsandi,Ebrahimi, Mahmoud,Pordel, Mehdi,Razmi, Mina
, p. 287 - 290 (2021/09/28)
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.
Imidazo[1,2-a]pyridine compounds and preparation method and application thereof
-
Paragraph 0059; 0061, (2019/05/15)
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.
