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Journal articles on the topic 'Imidazopyridine'

Author: Grafiati

Published: 4 June 2021

Last updated: 14 June 2025

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1

Sonawane, Ravindra S., Kiran D. Patil, and Avinash V. Patil. "Design, Synthesis and Pharmacological Evaluation of Novel Imidazopyridine Analogues as Proton Pump Antagonist." Asian Journal of Chemistry 32, no. 4 (2020): 776–82. http://dx.doi.org/10.14233/ajchem.2020.22433.

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A series of novel imidazopyridine derivatives as proton pump inhibitors was designed with compounds of CID data base and explored considering AZD0865 as standard. Many compounds were identified and docked in proton pump ATPase pocket (PDB ID: 4ux2). Molecular docking studies revealed that many compounds showed good proton pump ATPase inhibitory activity. The docking poses revealed the interaction of ligands with amino acid. The standard drug AZD0865 had docking score of -7.112302 and displayed interactions with Asn138 and Asp137. A series of novel imidazopyridine derivatives as proton pump inhibitors were docked, synthesized and characterized by IR, NMR, CHN and MS spectral analysis. The target imidazopyridines were prepared from substituted 2-aminonicotinic acid and 2-bromo-1-substituted ethanone. in vitro Studies explained that few compounds exhibited moderate to good proton pump ATPase inhibitory activity in comparison with the reference drugs i.e. AZD0865. Compounds 11 and 12 shown higher activities with the IC50 4.3. Compounds 1, 4, 6, 7, 8, 10 and 13 showed weak anti-ulcer activity with its IC50 5.2, 5.8, 5.5, 5.1, 4.9, 4.6 and 5.9 and positive control AZD0865 shown IC50 2.0.

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2

Sonawane, R. S., Mrunal Shirsat, S. R. Patil, J. C. Hundiwale, and A. V. P. atil. "Design and Synthesis of Novel Imidazopyridine Analogues and Evaluation as H+/K+-ATPase Antagonist." Asian Journal of Chemistry 32, no. 11 (2020): 2685–92. http://dx.doi.org/10.14233/ajchem.2020.22697.

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CID data base were explored considering AZD0865 as standard and docked in proton pump ATPase pocket (PDB ID: 4ux2) to find out novel imidazopyridine derivatives as proton pump inhibitors. A number of compounds showed good proton pump ATPase inhibitory activity as per the molecular docking study as compared to standard compound AZD0865. The compound AZD0865showed a docking score of -7.11 and revealed the interactions with amino acids Asn 138 and Asp 137. A series of novel imidazopyridine derivatives as proton pump inhibitors were docked, synthesized and characterized by IR, NMR, CHN and MS spectral analysis. The target imidazopyridines were prepared from the intermediate substituted 2-aminonicotinic acid and 2-bromo-1-substituted ethanone. in vitro pharmacological studies explained that some compounds exhibited moderate to good proton pump ATPase inhibitory activity in comparison with the reference drugs i.e. AZD0865. Compound N-(3-(aminomethyl)benzyl)-3-(benzylamino)-2-(o-tolyl)imidazo[1,2-a]pyridine-8-carboxamide and N-(3-(aminomethyl)benzyl)-3-(benzylamino)-2-(4-ethylphenyl)imidazo[1,2-a]pyridine-8-carboxamide showed higher activities with the IC50 6.2 and 6.0 μg. Many compounds showed IC50 as weak antiulcer activity as compared to positive control AZD0865.

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3

Peterson, Emily A., Alessandro A. Boezio, Paul S. Andrews, et al. "Discovery and optimization of potent and selective imidazopyridine and imidazopyridazine mTOR inhibitors." Bioorganic & Medicinal Chemistry Letters 22, no. 15 (2012): 4967–74. http://dx.doi.org/10.1016/j.bmcl.2012.06.033.

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4

Carreño, Alexander, Manuel Gacitúa, Juan A. Fuentes, et al. "Theoretical and experimental characterization of a novel pyridine benzimidazole: suitability for fluorescence staining in cells and antimicrobial properties." New Journal of Chemistry 40, no. 3 (2016): 2362–75. http://dx.doi.org/10.1039/c5nj02772a.

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5

Kamal, Ahmed, G. Bharath Kumar, V. Lakshma Nayak, et al. "Design, synthesis and biological evaluation of imidazopyridine/imidazopyrimidine-benzimidazole conjugates as potential anticancer agents." MedChemComm 6, no. 4 (2015): 606–12. http://dx.doi.org/10.1039/c4md00400k.

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6

Priyanga, Selvarasu, Themmila Khamrang, Marappan Velusamy, Sellamuthu Karthi, Balasubramaniem Ashokkumar, and Ramasamy Mayilmurugan. "Coordination geometry-induced optical imaging of l-cysteine in cancer cells using imidazopyridine-based copper(ii) complexes." Dalton Transactions 48, no. 4 (2019): 1489–503. http://dx.doi.org/10.1039/c8dt04634d.

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7

Sayeed, Ibrahim Bin, V. Lakshma Nayak, Mohd Adil Shareef, Neeraj Kumar Chouhan, and Ahmed Kamal. "Design, synthesis and biological evaluation of imidazopyridine–propenone conjugates as potent tubulin inhibitors." MedChemComm 8, no. 5 (2017): 1000–1006. http://dx.doi.org/10.1039/c7md00043j.

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8

Parenty, Alexis, and Leroy Cronin. "One-Pot Synthesis of Imidazopyridine Derivatives." Synthesis 2008, no. 9 (2008): 1479–85. http://dx.doi.org/10.1055/s-2007-1000936.

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9

Shinde, Vikki N., Shiv Dhiman, Rangan Krishnan, Dalip Kumar, and Anil Kumar. "Synthesis of imidazopyridine-fused indoles via one-pot sequential Knoevenagel condensation and cross dehydrogenative coupling." Organic & Biomolecular Chemistry 16, no. 33 (2018): 6123–32. http://dx.doi.org/10.1039/c8ob01449c.

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10

Swami, Suman, Debasis Behera, Arunava Agarwala, Ved Prakash Verma та Rahul Shrivastava. "β-Carboline–imidazopyridine hybrids: selective and sensitive optical sensors for copper and fluoride ions". New Journal of Chemistry 42, № 12 (2018): 10317–26. http://dx.doi.org/10.1039/c8nj01851k.

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11

Li, Yibiao, Shuo Huang, Jiaming Li, et al. "Access to 2-pyridinylamide and imidazopyridine from 2-fluoropyridine and amidine hydrochloride." Organic & Biomolecular Chemistry 18, no. 45 (2020): 9292–99. http://dx.doi.org/10.1039/d0ob01904f.

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An efficient method to synthesize 2-pyridinylamides and imidazopyridine has been developed, and the protocol uses inexpensive and readily available 2-fluoropyridine and amidine derivatives as the starting materials.

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12

Samanta, Sadhanendu, and Alakananda Hajra. "Ruthenium-catalyzed tandem annulation/arylation for the synthesis of unsymmetrical bis(heteroaryl)methanes." Organic & Biomolecular Chemistry 16, no. 37 (2018): 8390–94. http://dx.doi.org/10.1039/c8ob01892h.

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A new Ru-catalyzed tandem annulation/arylation strategy has been developed to afford unsymmetrical bis(heteroaryl)methanes containing furan and indole as well as indole and imidazopyridine moieties in high yields.

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13

Roy, Mithun, Balabhadrapatruni V. S. K. Chakravarthi, Chelliah Jayabaskaran, Anjali A. Karande, and Akhil R. Chakravarty. "Correction: Impact of metal binding on the antitumor activity and cellular imaging of a metal chelator cationic imidazopyridine derivative." Dalton Transactions 48, no. 42 (2019): 16126. http://dx.doi.org/10.1039/c9dt90223f.

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Correction for ‘Impact of metal binding on the antitumor activity and cellular imaging of a metal chelator cationic imidazopyridine derivative’ by Mithun Roy et al., Dalton Trans., 2011, 40, 4855–4864.

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14

Yan, Hong, Zhong-Yi Mao, Zhong-Wei Hou, Jinshuai Song, and Hai-Chao Xu. "A diastereoselective approach to axially chiral biaryls via electrochemically enabled cyclization cascade." Beilstein Journal of Organic Chemistry 15 (March 28, 2019): 795–800. http://dx.doi.org/10.3762/bjoc.15.76.

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A diastereoselective approach to axially chiral imidazopyridine-containing biaryls has been developed. The reactions proceed through a radical cyclization cascade to construct the biaryls with good to excellent central-to-axial chirality transfer.

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15

Saha, Moumita, and Asish R. Das. "Hypervalent iodine promoted ortho diversification: 2-aryl benzimidazole, quinazoline and imidazopyridine as directing templates." Organic & Biomolecular Chemistry 18, no. 5 (2020): 941–55. http://dx.doi.org/10.1039/c9ob02533b.

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(Diacetoxyiodo)benzene (PIDA) promoted Pd-catalyzed efficient ortho C(sp²)–H acetoxylation, arylation, iodination and nitration are achieved using (NH)-free 2-substituted benzimidazole, quinazoline and imidazopyridine as chelating substrates.

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16

Gao, Yongyuan, Yang Wang, Jie Zhou, Haibo Mei, and Jianlin Han. "An electrochemical oxidative homo-coupling reaction of imidazopyridine heterocycles to biheteroaryls." Green Chemistry 20, no. 3 (2018): 583–87. http://dx.doi.org/10.1039/c7gc03563b.

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An electrochemical homo-coupling reaction of imidazopyridine heterocycles has been developed for the synthesis of biheteroaryls. This reaction features good compatibility, high yields and excellent regioselectivities, which provides an efficient access to biheteroaryl compounds.

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17

Costa, Marta, and M. Fernanda Proença. "Selective synthesis of some imidazopyridine-fused chromones." Tetrahedron 67, no. 45 (2011): 8622–27. http://dx.doi.org/10.1016/j.tet.2011.09.054.

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18

Roy, Mithun, Balabhadrapatruni V. S. K. Chakravarthi, Chelliah Jayabaskaran, Anjali A. Karande, and Akhil R. Chakravarty. "Impact of metal binding on the antitumor activity and cellular imaging of a metal chelator cationic imidazopyridine derivative." Dalton Transactions 40, no. 18 (2011): 4855–64. http://dx.doi.org/10.1039/c0dt01717e.

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Water soluble cationic imidazopyridine species (1) having metal binding sites induces metal-assisted caspase dependent apoptosis in cancer cells and enhanced photodynamic effect in the presence of Fe²⁺or Zn²⁺ions.

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19

Sanaeishoar, Haleh, Roya Nazarpour, and Fouad Mohave. "Novel one-pot pseudo four component reaction: expeditious synthesis of functionalized imidazo[1,2-a]pyridines." RSC Advances 5, no. 84 (2015): 68571–78. http://dx.doi.org/10.1039/c5ra10891h.

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A new and efficient one-pot synthesis of imidazo[1,2-a] pyridines is described. A C-3 imine substituent was installed on the imidazopyridine framework under mild conditions to form the corresponding products in good to excellent yields.

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20

Srivastava, Suman, Neha Thakur, Ashutosh Singh, et al. "Development of a fused imidazo[1,2-a]pyridine based fluorescent probe for Fe3+ and Hg2+ in aqueous media and HeLa cells." RSC Advances 9, no. 51 (2019): 29856–63. http://dx.doi.org/10.1039/c9ra04743c.

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A new fluorescent sensor 5 having fused imidazopyridine scaffold has been synthesized via cascade cyclization. It exhibits highly sensitive and selective detection of Fe³⁺ (‘turn-on’) and Hg²⁺ (‘turn-off’) in vitro and in HeLa cells.

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21

Wang, Jingcai, Yuting Leng, Zongqiang Hu, Yuping Pan, Shiwei Wang, and Yangjie Wu. "TEMPO-mediated cross dehydrogenative coupling aminomethylation of imidazopyridine." Tetrahedron Letters 61, no. 10 (2020): 151590. http://dx.doi.org/10.1016/j.tetlet.2019.151590.

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22

Bottaï, T., F. Cartault, R. Pouget, J. P. Blayac, and P. Petit. "An Imidazopyridine Anxiolytic Alters Glucose Tolerance in Patients." Clinical Neuropharmacology 18, no. 1 (1995): 79–82. http://dx.doi.org/10.1097/00002826-199502000-00011.

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23

Cartwright, Matthew W., Graham Sandford, Jamaal Bousbaa, et al. "Imidazopyridine and pyrimidinopyridine systems from perfluorinated pyridine derivatives." Tetrahedron 63, no. 30 (2007): 7027–35. http://dx.doi.org/10.1016/j.tet.2007.05.016.

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24

Pinter, Piermaria, Rebecca Pittkowski, Johannes Soellner, and Thomas Strassner. "The Chameleonic Nature of Platinum(II) Imidazopyridine Complexes." Chemistry - A European Journal 23, no. 57 (2017): 14173–76. http://dx.doi.org/10.1002/chem.201703908.

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25

Kaplancikli, Zafer Asim, Gülhan Turan-Zitouni, Ahmet Özdemr, and Gilbert Revial. "Synthesis and anticandidal activity of some imidazopyridine derivatives." Journal of Enzyme Inhibition and Medicinal Chemistry 23, no. 6 (2008): 866–70. http://dx.doi.org/10.1080/14756360701811114.

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26

Gallud, Audrey, Ophélie Vaillant, Ludovic T. Maillard, et al. "Imidazopyridine-fused [1,3]-diazepinones: Synthesis and antiproliferative activity." European Journal of Medicinal Chemistry 75 (March 2014): 382–90. http://dx.doi.org/10.1016/j.ejmech.2014.01.044.

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27

Blass, Benjamin. "Substituted Benzimidazole and Imidazopyridine Compounds Useful as Cyp17 Modulators." ACS Medicinal Chemistry Letters 3, no. 8 (2012): 614–15. http://dx.doi.org/10.1021/ml300157r.

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28

Costa, Marta, and M. Fernanda Proenca. "ChemInform Abstract: Selective Synthesis of Some Imidazopyridine-Fused Chromones." ChemInform 43, no. 10 (2012): no. http://dx.doi.org/10.1002/chin.201210169.

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29

Su, Jung-Chen, Chuan-Hsun Chang, Szu-Hsien Wu, and Chung-Wai Shiau. "Novel imidazopyridine suppresses STAT3 activation by targeting SHP-1." Journal of Enzyme Inhibition and Medicinal Chemistry 33, no. 1 (2018): 1248–55. http://dx.doi.org/10.1080/14756366.2018.1497019.

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30

Sanger, D. J., and B. Zivkovic. "Discriminative stimulus effects of alpidem, a new imidazopyridine anxiolytic." Psychopharmacology 113, no. 3-4 (1994): 395–403. http://dx.doi.org/10.1007/bf02245215.

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31

Liang, Gui-Bai, Xiaoxia Qian, Dennis Feng, et al. "Synthesis and SAR studies of potent imidazopyridine anticoccidial agents." Bioorganic & Medicinal Chemistry Letters 17, no. 13 (2007): 3558–61. http://dx.doi.org/10.1016/j.bmcl.2007.04.041.

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32

Zivkovic, B., P. George, Gh Perrault, et al. "Pharmacological profile of SL 85.0274, a novel imidazopyridine anxiotytic." European Journal of Pharmacology 183, no. 4 (1990): 1462–63. http://dx.doi.org/10.1016/0014-2999(90)94605-w.

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33

Wang, Wei, Yuzhi Lu, Enhui Chen, Kang Shen, and Jun Li. "Anti-tumor compounds identification from gossypol Groebke imidazopyridine product." Bioorganic Chemistry 114 (September 2021): 105146. http://dx.doi.org/10.1016/j.bioorg.2021.105146.

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34

Durand, A., J. P. Thénot, G. Bianchetti, and P. L. Morselli. "Comparative Pharmacokinetic Profile of Two Imidazopyridine Drugs: Zolpidem and Alpidem." Drug Metabolism Reviews 24, no. 2 (1992): 239–66. http://dx.doi.org/10.3109/03602539208996294.

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35

Papadakis, Georgios, Maria Gerasi, Robert Snoeck, et al. "Synthesis of New Imidazopyridine Nucleoside Derivatives Designed as Maribavir Analogues." Molecules 25, no. 19 (2020): 4531. http://dx.doi.org/10.3390/molecules25194531.

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The strong inhibition of Human Cytomegalovirus (HCMV) replication by benzimidazole nucleosides, like Triciribine and Maribavir, has prompted us to expand the structure–activity relationships of the benzimidazole series, using as a central core the imidazo[4,5-b]pyridine scaffold. We have thus synthesized a number of novel amino substituted imidazopyridine nucleoside derivatives, which can be considered as 4-(or 7)-aza-d-isosters of Maribavir and have evaluated their potential antiviral activity. The target compounds were synthesized upon glycosylation of suitably substituted 2-aminoimidazopyridines, which were prepared in six steps starting from 2-amino-6-chloropyridine. Even if the new compounds possessed only a slight structural modification when compared to the original drug, they were not endowed with interesting antiviral activity. Even so, three derivatives showed promising cytotoxic potential.

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36

W.K.R, Werner, and Klaus G. R. Pacher. "Synthesis and structural assignment of some N-substituted imidazopyridine derivatives." Tetrahedron 48, no. 48 (1992): 10549–58. http://dx.doi.org/10.1016/s0040-4020(01)88351-4.

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37

Marchenko, Irina, Tatiana Borodina, Daria Trushina, et al. "Mesoporous particle-based microcontainers for intranasal delivery of imidazopyridine drugs." Journal of Microencapsulation 35, no. 7-8 (2018): 657–66. http://dx.doi.org/10.1080/02652048.2019.1571642.

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38

Özden, Seçkin, Hamide Ertepinar, and Ömer Geban. "QSAR Study on Antibacterial Effects of Benzimidazole and Imidazopyridine Derivatives." Collection of Czechoslovak Chemical Communications 60, no. 12 (1995): 2178–88. http://dx.doi.org/10.1135/cccc19952178.

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A set of benzimidazole (I) and imidazopyridine (II) derivatives previously tested for their antibacterial activities against Staphylococcus aureus (S. aureus), Pseudomonas aeruginosa (P. aeruginosa), Escherichia coli (E. coli), and Bacillus subtilis (B. subtilis) were analyzed by quantitative structure-activity relationship (QSAR) and the activity contributions for structural and substituent effects were determined using multiple regression procedure. The resulting QSAR revealed that for the activity contribution against S. aureus and P. aeruginosa the substituents of p-position on the phenyl moiety play important role, and besides the p-substituents the substituents in other positions improve the activity. For the potency against E. coli, the character of six membered ring of the fused ring system becomes important besides the substituents effects at the p-position of the phenyl group. It was also found that both the benzimidazole ring system and p-substituted benzyl moiety have significant structural effects besides the lipophilicity of the substituents at R3 for the activity against B. subtilis.

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39

Patat, Alain, Marcus M. Naef, Elisabeth Van Gessel, Alain Forster, Catherine Dubruc, and Pierre Rosenzweig. "Flumazenil antagonizes the central effects of zolpidem, an imidazopyridine hypnotic." Clinical Pharmacology and Therapeutics 56, no. 4 (1994): 430–36. http://dx.doi.org/10.1038/clpt.1994.157.

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40

YUTILOV, YU M., and L. I. SHCHERBINA. "ChemInform Abstract: Willgerodt-Reaction of a Number of Imidazopyridine Derivatives." ChemInform 28, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199701186.

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41

Scribner, Andrew, Richard Dennis, Jean Hong, et al. "Synthesis and biological activity of imidazopyridine anticoccidial agents: Part I." European Journal of Medicinal Chemistry 42, no. 11-12 (2007): 1334–57. http://dx.doi.org/10.1016/j.ejmech.2007.02.006.

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42

Scribner, Andrew, Richard Dennis, Shuliang Lee, et al. "Synthesis and biological activity of imidazopyridine anticoccidial agents: Part II." European Journal of Medicinal Chemistry 43, no. 6 (2008): 1123–51. http://dx.doi.org/10.1016/j.ejmech.2007.09.013.

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43

Biftu, Tesfaye, Dennis Feng, Michael Fisher, et al. "Synthesis and SAR studies of very potent imidazopyridine antiprotozoal agents." Bioorganic & Medicinal Chemistry Letters 16, no. 9 (2006): 2479–83. http://dx.doi.org/10.1016/j.bmcl.2006.01.092.

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44

Buonfiglio, Rosa, Federica Prati, Martina Bischetti, Claudia Cavarischia, Guido Furlotti та Rosella Ombrato. "Discovery of Novel Imidazopyridine GSK-3β Inhibitors Supported by Computational Approaches". Molecules 25, № 9 (2020): 2163. http://dx.doi.org/10.3390/molecules25092163.

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The interest of research groups and pharmaceutical companies to discover novel GSK-3β inhibitors has increased over the years considering the involvement of this enzyme in many pathophysiological processes and diseases. Along this line, we recently reported on 1H-indazole-3-carboxamide (INDZ) derivatives 1–6, showing good GSK-3β inhibition activity. However, they suffered from generally poor central nervous system (CNS) permeability. Here, we describe the design, synthesis, and in vitro characterization of novel imidazo[1,5-a]pyridine-1-carboxamide (IMID 1) and imidazo[1,5-a]pyridine-3-carboxamide (IMID 2) compounds (7–18) to overcome such liability. In detail, structure-based approaches and fine-tuning of physicochemical properties guided the design of derivatives 7–18 resulting in ameliorated absorption, distribution, metabolism, and excretion (ADME) properties. A crystal structure of 16 in complex with GSK-3β enzyme (PDB entry 6Y9S) confirmed the in silico models. Despite the nanomolar inhibition activity, the new core compounds showed a reduction in potency with respect to INDZ derivatives 1–6. In this context, Molecular Dynamics (MD) and Quantum Mechanics (QM) based approaches along with NMR investigation helped to rationalize the observed structure activity relationship (SAR). With these findings, the key role of the acidic hydrogen of the central core for a tight interaction within the ATP pocket of the enzyme reflecting in good GSK-3β affinity was demonstrated.

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45

Genin, Michael J., Isabel C. Gonzalez Valcarcel, William G. Holloway, et al. "Imidazopyridine and Pyrazolopiperidine Derivatives as Novel Inhibitors of Serine Palmitoyl Transferase." Journal of Medicinal Chemistry 59, no. 12 (2016): 5904–10. http://dx.doi.org/10.1021/acs.jmedchem.5b01851.

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46

Chen, Gaozhi, Zhiguo Liu, Yali Zhang, et al. "Synthesis and Anti-inflammatory Evaluation of Novel Benzimidazole and Imidazopyridine Derivatives." ACS Medicinal Chemistry Letters 4, no. 1 (2012): 69–74. http://dx.doi.org/10.1021/ml300282t.

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47

Renneberg, Dorte, and Peter B. Dervan. "Imidazopyridine/Pyrrole and Hydroxybenzimidazole/Pyrrole Pairs for DNA Minor Groove Recognition." Journal of the American Chemical Society 125, no. 19 (2003): 5707–16. http://dx.doi.org/10.1021/ja0300158.

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48

Sato, Yoshiyuki, Yu Onozaki, Tetsuya Sugimoto, et al. "Imidazopyridine derivatives as potent and selective Polo-like kinase (PLK) inhibitors." Bioorganic & Medicinal Chemistry Letters 19, no. 16 (2009): 4673–78. http://dx.doi.org/10.1016/j.bmcl.2009.06.084.

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49

Kibriya, Golam, Sadhanendu Samanta, Sourav Jana, Susmita Mondal, and Alakananda Hajra. "Visible Light Organic Photoredox-Catalyzed C–H Alkoxylation of Imidazopyridine with Alcohol." Journal of Organic Chemistry 82, no. 24 (2017): 13722–27. http://dx.doi.org/10.1021/acs.joc.7b02582.

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50

Futatsugi, Kentaro, Daniel W. Kung, Suvi T. M. Orr, et al. "Discovery and Optimization of Imidazopyridine-Based Inhibitors of Diacylglycerol Acyltransferase 2 (DGAT2)." Journal of Medicinal Chemistry 58, no. 18 (2015): 7173–85. http://dx.doi.org/10.1021/acs.jmedchem.5b01006.

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