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Journal articles on the topic 'Imidazo[1;5-A]quinoxaline'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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1

Joshi, Gaurav, Monika Chauhan, Rakesh Kumar, et al. "Cyclocondensation reactions of an electron deactivated 2-aminophenyl tethered imidazole with mono/1,2-biselectrophiles: synthesis and DFT studies on the rationalisation of imidazo[1,2-a]quinoxaline versus benzo[f]imidazo[1,5-a][1,3,5]triazepine selectivity switches." Organic Chemistry Frontiers 5, no. 24 (2018): 3526–33. http://dx.doi.org/10.1039/c8qo00706c.

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2

Zhang, Zeyuan, Caixia Xie, Xiaochen Tan, et al. "I2-catalyzed one-pot synthesis of pyrrolo[1,2-a]quinoxaline and imidazo[1,5-a]quinoxaline derivatives via sp3and sp2C–H cross-dehydrogenative coupling." Organic Chemistry Frontiers 2, no. 8 (2015): 942–46. http://dx.doi.org/10.1039/c5qo00124b.

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An efficient I<sub>2</sub>-catalyzed cascade coupling protocol was developed for the synthesis of pyrrolo[1,2-a]quinoxaline and imidazo[1,5-a]quinoxaline derivativesviasp<sup>3</sup>and sp<sup>2</sup>C–H cross-dehydrogenative coupling.

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3

Moarbess, Georges, Carine Deleuze-Masquefa, Vanessa Bonnard, et al. "In vitro and in vivo anti-tumoral activities of imidazo[1,2-a]quinoxaline, imidazo[1,5-a]quinoxaline, and pyrazolo[1,5-a]quinoxaline derivatives." Bioorganic & Medicinal Chemistry 16, no. 13 (2008): 6601–10. http://dx.doi.org/10.1016/j.bmc.2008.05.022.

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4

Patinote, Cindy, Nour Bou Karroum, Georges Moarbess, et al. "Imidazo[1,2- a ]pyrazine, Imidazo[1,5- a ]quinoxaline and Pyrazolo[1,5- a ]quinoxaline derivatives as IKK1 and IKK2 inhibitors." European Journal of Medicinal Chemistry 138 (September 2017): 909–19. http://dx.doi.org/10.1016/j.ejmech.2017.07.021.

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5

Cobb, J., and G. W. H. Cheeseman. "Carbon-13 NMR spectra of pyrrolo[1,2-a]quinoxaline, pyrrolo[1,2-a]pyrazine and imidazo [1,2-a ] quinoxaline." Magnetic Resonance in Chemistry 24, no. 3 (1986): 231–37. http://dx.doi.org/10.1002/mrc.1260240309.

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6

Kalinin, Alexey A., Alexandra D. Voloshina, Nataliya V. Kulik, Vladimir V. Zobov, and Vakhid A. Mamedov. "Antimicrobial activity of imidazo[1,5-a]quinoxaline derivatives with pyridinium moiety." European Journal of Medicinal Chemistry 66 (August 2013): 345–54. http://dx.doi.org/10.1016/j.ejmech.2013.05.038.

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7

Parra, Stéphanie, Olivier Vitse, Véronique Bénézech, et al. "Metalation and halogen-metal exchange in the imidazo[1,2-a]quinoxaline series." Journal of Heterocyclic Chemistry 38, no. 1 (2001): 41–44. http://dx.doi.org/10.1002/jhet.5570380106.

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8

Jacobsen, E. Jon, Lindsay S. Stelzer, Ruth E. TenBrink, et al. "Piperazine Imidazo[1,5-a]quinoxaline Ureas as High-Affinity GABAALigands of Dual Functionality†." Journal of Medicinal Chemistry 42, no. 7 (1999): 1123–44. http://dx.doi.org/10.1021/jm9801307.

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9

Deleuze-Masquefa, Carine, Georges Moarbess, Sonia Khier, et al. "New imidazo[1,2-a]quinoxaline derivatives: Synthesis and in vitro activity against human melanoma." European Journal of Medicinal Chemistry 44, no. 9 (2009): 3406–11. http://dx.doi.org/10.1016/j.ejmech.2009.02.007.

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10

Parra, Stephanie, Olivier Vitse, Veronique Benezech, et al. "ChemInform Abstract: Metalation and Halogen-Metal Exchange in the Imidazo[1,2-a]quinoxaline Series." ChemInform 32, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.200126157.

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11

Khier, Sonia, Carine Deleuze-Masquéfa, Georges Moarbess, et al. "Pharmacology of EAPB0203, a novel imidazo[1,2-a]quinoxaline derivative with anti-tumoral activity on melanoma." European Journal of Pharmaceutical Sciences 39, no. 1-3 (2010): 23–29. http://dx.doi.org/10.1016/j.ejps.2009.10.006.

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12

Abdelhamid, Abdou O., Eman K. A. Abdelall, and Yasser H. Zaki. "ChemInform Abstract: Reactions with Hydrazonoyl Halides. Part 62. Synthesis and Antimicrobial Evaluation of Some New Imidazo[1,2-a]pyrimidine, Imidazo[1,2-a]pyridine, Imidazo[1,2-b]pyrazole, and Quinoxaline Derivatives." ChemInform 41, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.201035040.

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13

Zhang, Zeyuan, Caixia Xie, Xiaochen Tan, et al. "ChemInform Abstract: I2-Catalyzed One-Pot Synthesis of Pyrrolo[1,2-a]quinoxaline and Imidazo[1,5-a]quinoxaline Derivatives via sp3and sp2C-H Cross-Dehydrogenative Coupling." ChemInform 46, no. 48 (2015): no. http://dx.doi.org/10.1002/chin.201548170.

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14

Jacobsen, E. Jon, Lindsay S. Stelzer, Kenneth L. Belonga, et al. "3-Phenyl-Substituted Imidazo[1,5-a]quinoxalin-4-ones and Imidazo[1,5-a]quinoxaline Ureas That Have High Affinity at the GABAA/Benzodiazepine Receptor Complex†." Journal of Medicinal Chemistry 39, no. 19 (1996): 3820–36. http://dx.doi.org/10.1021/jm960070+.

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15

MURRAY, BERNARD P., NIGEL J. GOODERHAM, ALAN R. BOOBIS, and DONALD S. DAVIES. "3,8-Dimethyl-2-nitro-imidazo[4,5-f]quinoxaline(Nitro-MeIQx) is a potent direct-acting mutagen." Biochemical Society Transactions 17, no. 3 (1989): 540–41. http://dx.doi.org/10.1042/bst0170540.

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16

Khier, Sonia, Georges Moarbess, Carine Deleuze-Masquefa, et al. "Quantitation of imidazo[1,2-a]quinoxaline derivatives in human and rat plasma using LC/ESI-MS." Journal of Separation Science 32, no. 9 (2009): 1363–73. http://dx.doi.org/10.1002/jssc.200800668.

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17

Singh, Rahul, Ravinder Kumar, Mallesh Pandrala, et al. "Facile synthesis of C6‐substituted benz[4,5]imidazo[1,2‐ a ]quinoxaline derivatives and their anticancer evaluation." Archiv der Pharmazie 354, no. 7 (2021): 2000393. http://dx.doi.org/10.1002/ardp.202000393.

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18

Kumar, Manvendra, Gaurav Joshi, Sahil Arora, et al. "Design and Synthesis of Non-Covalent Imidazo[1,2-a]quinoxaline-Based Inhibitors of EGFR and Their Anti-Cancer Assessment." Molecules 26, no. 5 (2021): 1490. http://dx.doi.org/10.3390/molecules26051490.

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A series of 30 non-covalent imidazo[1,2-a]quinoxaline-based inhibitors of epidermal growth factor receptor (EGFR) were designed and synthesized. EGFR inhibitory assessment (against wild type) data of compounds revealed 6b, 7h, 7j, 9a and 9c as potent EGFRWT inhibitors with IC50 values of 211.22, 222.21, 193.18, 223.32 and 221.53 nM, respectively, which were comparable to erlotinib (221.03 nM), a positive control. Furthermore, compounds exhibited excellent antiproliferative activity when tested against cancer cell lines harboring EGFRWT; A549, a non-small cell lung cancer (NSCLC), HCT-116 (colo

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19

Huang, Liye, Ruina Yu, Xinhai Zhu, and Yiqian Wan. "A recyclable Cu-catalyzed C–N coupling reaction in water and its application to synthesis of imidazo[1,2-a]quinoxaline." Tetrahedron 69, no. 42 (2013): 8974–77. http://dx.doi.org/10.1016/j.tet.2013.07.036.

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20

TenBrink, Ruth E., Wha B. Im, Vimala H. Sethy, Andrew H. Tang, and Don B. Carter. "Antagonist, Partial Agonist, and Full Agonist Imidazo[1,5-a]quinoxaline Amides and Carbamates Acting through the GABAA/Benzodiazepine Receptor." Journal of Medicinal Chemistry 37, no. 6 (1994): 758–68. http://dx.doi.org/10.1021/jm00032a008.

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21

Zohdi, Hussein F., Tabia A. Osman, and Abdou O. Abdelhamid. "Heterocycles from Pyrazoloylhydroximoyl Chloride: Synthesis of Certain Quinoxaline, Benzothiadiazine, Benzoxadiazine, Quinazolinone, Imidazo[1,2-a]pyridine, Imidazo[1,2-a]pyrimidine, Isoxazole, Pyrazolo[3,4-d]pyridazine and Pyrrolidino[3,4-d]isoxazolin-4,." Journal of the Chinese Chemical Society 44, no. 6 (1997): 617–23. http://dx.doi.org/10.1002/jccs.199700095.

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22

Jacobsen, E. Jon, Ruth E. TenBrink, Lindsay S. Stelzer та ін. "High-Affinity Partial Agonist Imidazo[1,5-a]quinoxaline Amides, Carbamates, and Ureas at the γ-Aminobutyric Acid A/Benzodiazepine Receptor Complex†". Journal of Medicinal Chemistry 39, № 1 (1996): 158–75. http://dx.doi.org/10.1021/jm940765f.

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23

Srinivas, B., B. Prasanna, and M. Ravinder. "ChemInform Abstract: Synthesis of Some New Tetrazolo[1,5-a]quinazolino[2,3-c]imidazo[4,5-b]quinoxaline Derivatives as Antimicrobial Agents." ChemInform 45, no. 27 (2014): no. http://dx.doi.org/10.1002/chin.201427181.

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24

Moarbess, Georges, Jean-François Guichou, Stéphanie Paniagua-Gayraud, et al. "New IKK inhibitors: Synthesis of new imidazo[1,2-a]quinoxaline derivatives using microwave assistance and biological evaluation as IKK inhibitors." European Journal of Medicinal Chemistry 115 (June 2016): 268–74. http://dx.doi.org/10.1016/j.ejmech.2016.03.006.

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25

Abdel-Aziz, Hatem A., Nehal A. Hamdy, Amira M. Gamal-Eldeen, and Issa M. I. Fakhr. "Synthesis of New 2-Substituted 6-Bromo-3-methylthiazolo[3,2-a]- benzimidazole Derivatives and their Biological Activities." Zeitschrift für Naturforschung C 66, no. 1-2 (2011): 7–16. http://dx.doi.org/10.1515/znc-2011-1-202.

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1-(6-Bromo-3-methyl-1,3-thiazolo[3,2-a]benzimidazol-2-yl)ethanone (2) was prepared by bromination at ambient temperature of 1-(3-methylthiazolo[3,2-a]benzimidazol-2-yl)ethanone (1). The structure of 2 was determined by single-crystal X-ray diffraction. The precursor 5 was synthesized by heating a mixture of acetyl 2 and bromine. Various 2-substituted 6-bromo-3-methylthiazolo[3,2-a]benzimidazoles containing 1,3-thiazole, 1,4-benzothiazine, quinoxaline or imidazo[1,2-a]pyridine moieties were prepared starting from bromoacetyl 5. Taken together from the biological investigations, 2, 5, and 7a wer

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26

Huang, Liye, Ruina Yu, Xinhai Zhu, and Yiqian Wan. "ChemInform Abstract: A Recyclable Cu-Catalyzed C-N Coupling Reaction in Water and Its Application to Synthesis of Imidazo[1,2-a]quinoxaline." ChemInform 45, no. 9 (2014): no. http://dx.doi.org/10.1002/chin.201409067.

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27

TENBRINK, R. E., W. B. IM, V. H. SETHY, A. H. TANG, and D. B. CARTER. "ChemInform Abstract: Antagonist, Partial Agonist, and Full Agonist Imidazo(1,5-a) quinoxaline Amides and Carbamates Acting Through the GABAA/ Benzodiazepine Receptor." ChemInform 25, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.199431175.

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28

Lovelette, Charles, William S. Barnes, John H. Weisburger, and Gary M. Williams. "Improved synthesis of the food mutagen 2-amino-3,7,8-trimethyl-3H-imidazo[4,5-f]quinoxaline and activity in a mammalian DNA repair system." Journal of Agricultural and Food Chemistry 35, no. 6 (1987): 912–15. http://dx.doi.org/10.1021/jf00078a015.

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29

Sundaram, G. S. M., B. Singh, C. Venkatesh, H. Ila, and H. Junjappa. "Dipolar Cycloaddition of Ethyl Isocyanoacetate to 3-Chloro-2-(methylthio)/2-(methylsulfonyl)quinoxalines: Highly Regio- and Chemoselective Synthesis of Substituted Imidazo[1,5-a]quinoxaline-3-carboxylates†." Journal of Organic Chemistry 72, no. 13 (2007): 5020–23. http://dx.doi.org/10.1021/jo070590k.

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30

Varano, Flavia, Daniela Catarzi, Vittoria Colotta, et al. "Synthesis of a set of ethyl 1-carbamoyl-3-oxoquinoxaline-2-carboxylates and of their constrained analogue imidazo[1,5-a]quinoxaline-1,3,4-triones as glycine/NMDA receptor antagonists." European Journal of Medicinal Chemistry 36, no. 2 (2001): 203–9. http://dx.doi.org/10.1016/s0223-5234(00)01203-4.

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31

ZAHRAN, M. A., A. A. HASSANIEN, H. A. EMAM, M. Z. EL-SAID, and Y. A. AMMAR. "ChemInform Abstract: Synthesis of New Pyrazolo[1,5-a]-s-triazine, Pyrazolo[5,1-c]-as-triazines, Pyrazolo[1′,5′:1,2]imidazo[4,5-b]quinoxaline, and Pyrazolo[1,5-a]pyrimidines." ChemInform 29, no. 10 (2010): no. http://dx.doi.org/10.1002/chin.199810139.

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32

Varano, Flavia, Daniela Catarzi, Vittoria Colotta, et al. "ChemInform Abstract: Synthesis of a Set of Ethyl 1-Carbamoyl-3-oxoquinoxaline-2-carboxylates and of Their Constrained Analogue Imidazo[1,5-a]quinoxaline-1,3,4-triones as Glycine/NMDA Receptor Antagonists." ChemInform 32, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.200135162.

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33

Frandsen, Henrik, Spiros Grivas, Robert J. Turesky, Rolf Andersson, Lars O. Dragsted, and John C. Larsen. "Formation of DNA adducts by the food mutagen 2-amino-3,4,8-trimethyl-3H-imidazo [4,8-f]quinoxaline (4,8-DiMeIQx) in vitro and in vivo. Identification of a N-(2′-deoxyguanosin-8-yl)-4,8-DiMeIQx adduct." Carcinogenesis 15, no. 11 (1994): 2553–58. http://dx.doi.org/10.1093/carcin/15.11.2553.

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34

Deleuze-Masquefa, Carine, Georges Moarbess, Sonia Khier, et al. "ChemInform Abstract: New Imidazo[1,2-a]quinoxaline Derivatives: Synthesis and in vitro Activity Against Human Melanoma." ChemInform 40, no. 48 (2009). http://dx.doi.org/10.1002/chin.200948169.

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35

Dobeneck, Michaela, Ramandeep Kaur, Benedikt Platzer, Dirk M. Guldi та Andreas Hirsch. "A Small Dye Puzzle: π‐Conjugation of Perylenes with External Aromatic Compounds via Imidazo‐Quinoxaline Bridges". ChemPhotoChem, 19 листопада 2020. http://dx.doi.org/10.1002/cptc.202000243.

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36

Dobeneck, Michaela, Ramandeep Kaur, Benedikt Platzer, Dirk M. Guldi та Andreas Hirsch. "A Small Dye Puzzle: π‐Conjugation of Perylenes with External Aromatic Compounds via Imidazo‐Quinoxaline Bridges". ChemPhotoChem, 10 грудня 2020. http://dx.doi.org/10.1002/cptc.202000277.

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37

Dobeneck, Michaela, Ramandeep Kaur, Benedikt Platzer, Dirk M. Guldi та Andreas Hirsch. "A Small Dye Puzzle: π‐Conjugation of Perylenes with External Aromatic Compounds via Imidazo‐Quinoxaline Bridges". ChemPhotoChem, 7 грудня 2020. http://dx.doi.org/10.1002/cptc.202000278.

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38

Abdelhamid, Abdou O., Eman K. A. Abdelall, and Yasser H. Zaki. "Reactions with hydrazonoyl halides 62: Synthesis and antimicrobial evaluation of some new imidazo[1,2-a]pyrimidine, imidazo [1,2-a]pyridine, imdazo[1,2-b]pyrazole, and quinoxaline derivatives." Journal of Heterocyclic Chemistry, 2010, NA. http://dx.doi.org/10.1002/jhet.307.

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39

Alamdari, M. H. "The synthesis of imidazo[4',5':5,6]cycloocta[1,2-B]quinoxaline-2-ones and a – thione." Bulletin of the Chemical Society of Ethiopia 27, no. 3 (2013). http://dx.doi.org/10.4314/bcse.v27i3.17.

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40

MOHAN, J., G. S. R. ANJANEYULU, and KIRAN KIRAN. "ChemInform Abstract: Heterocyclic Systems Containing a Bridgehead Nitrogen Atom. Synthesis of Thiadiazolo(2′,3′:2,1)imidazo(4,5-b)quinoxaline, Imidazo(2,1-b)-1,3,4-thiadiazoles, and Their Brominated Products." ChemInform 21, no. 4 (1990). http://dx.doi.org/10.1002/chin.199004190.

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41

Sundaram, G. S. M., B. Singh, C. Venkatesh, H. Ila, and H. Junjappa. "Dipolar Cycloaddition of Ethyl Isocyanoacetate to 3-Chloro-2-(methylthio)/2-(methylsulfonyl)quinoxalines: Highly Regio- and Chemoselective Synthesis of Substituted Imidazo[1,5-a]quinoxaline-3-carboxylates." ChemInform 38, no. 50 (2007). http://dx.doi.org/10.1002/chin.200750174.

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42

Karuppiah, Nagaraj, Pakkirisamy Pakkirisamy, and Gunasekaran Gladwin. "Kinetic study of surfactant cobalt (III) complexes by [Fe(CN)6 4-]: Outer-Sphere Electron-Transfer in Ionic liquids and Liposome Vesicle." International Journal of Agricultural and Life Sciences, December 31, 2020, 300–317. http://dx.doi.org/10.22573/spg.ijals.020.s122000101.

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UV-Vis., absorption spectroscopy are used to monitor the electron transfer reaction between the surfactant cobalt(III) complexes, cis-[Co(ip)2(C14H29NH2)2]3+, cis-[Co(dpq)2(C14H29NH2)2]3+ and cis-[Co(dpqc)2(C14H29NH2)2]3+ (ip = imidazo[4,5-f][1,10]phenanthroline, dpq = dipyrido[3,2-d:2’-3’-f]quinoxaline, dpqc = dipyrido[3,2-a:2’,4’-c](6,7,8,9-tetrahydro)phenazine, C14H29NH2=Tetradecylamine) and [Fe(CN)6]4- ion in liposome vesicles (DPPC) and ionic liquids ((BMIM)Br) were investigated at different temperatures under pseudo first order conditions using an excess of the reductant. The reactions w

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