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A. Palmeira, M. H. Vasconcelos, A. Paiva, M. X. Fernandes, M. Pinto et al., Dual inhibitors of P-glycoprotein and tumor cell growth: (Re)discovering thioxanthones, Biochem. Pharmacol, vol.83, pp.57-68, 2012.

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M. Hedidi, J. Maillard, W. Erb, F. Lassagne, Y. S. Halauko et al., Bentabed-Ababsa, F. Mongin, Fused systems based on 2-aminopyrimidines: Synthesis combining deprotolithiation-in situ zincation with N-arylation reactions and biological properties, Eur. J. Org. Chem, pp.5903-5915, 2017.

Y. Shin, S. Han, U. De, J. Park, S. Sharma et al., Ru(II)-catalyzed selective C-H amination of xanthones and chromones with sulfonyl azides: Synthesis and anticancer evaluation, J. Org. Chem, vol.79, pp.9262-9271, 2014.

D. Wagner and S. Bräse, Ruthenium-catalyzed C-H activation of thioxanthones, Beilstein J. Org. Chem, vol.11, pp.431-436, 2015.

S. H. Han, S. Kim, U. De, N. K. Mishra, J. Park et al.,

. Kim, Synthesis of succinimide-containing chromones, naphthoquinones, and xanthones under Rh(III) catalysis: Evaluation of anticancer activity, J. Org. Chem, vol.81, pp.12416-12425, 2016.

G. Tan, Q. You, and J. You, Iridium-catalyzed oxidative heteroarylation of arenes and alkenes: Overcoming the restriction to specific substrates, ACS Catal, vol.8, pp.8709-8714, 2018.

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R. A. Altman, K. W. Anderson, and S. L. Buchwald, Pyrrole-2-carboxylic acid as a ligand for the Cucatalyzed reactions of primary anilines with aryl halides, J. Org. Chem, vol.73, pp.5167-5169, 2008.

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N. Brikci-nigassa, G. Bentabed-ababsa, W. Erb, F. Chevallier, L. Picot et al., Mongin, 2-Aminophenones, a common precursor to N-aryl isatins and acridines endowed with bioactivities, Tetrahedron, vol.74, pp.1785-1801, 2018.

J. Kim and S. Chang, Ammonium salts as an inexpensive and convenient nitrogen source in the Cucatalyzed amination of aryl halides at room temperature, Chem. Commun, pp.3052-3054, 2008.

P. Ji, J. H. Atherton, and M. I. Page, Copper(I)-catalyzed amination of aryl halides in liquid ammonia, J. Org. Chem, vol.77, pp.7471-7478, 2012.

H. S. Jung, T. Yun, Y. Cho, and H. B. Jeon, Simple and convenient copper-catalyzed amination of aryl halides to primary arylamines using NH 4 OH, Tetrahedron, vol.72, pp.5988-5993, 2016.

Y. Kitahara, T. Mizuno, and A. Kubo, Synthetic studies of benzo, Tetrahedron, vol.60, pp.4283-4288, 2004.

S. Klaeger, S. Heinzlmeir, M. Wilhelm, H. Polzer, B. Vick et al., The target landscape of clinical kinase drugs, Science, vol.358, p.1148, 2017.

R. Roskoski, Properties of FDA-approved small molecule protein kinase inhibitors, Pharmacol. Res, vol.144, pp.19-50, 2019.

H. L. Lightfoot, F. W. Goldberg, and J. Sedelmeier, Evolution of Small Molecule Kinase Drugs, ACS Medicinal Chemistry Letters, vol.10, pp.153-160, 2019.

L. S. Chen, S. Redkar, D. Bearss, W. G. Wierda, and V. Gandhi, Pim kinase inhibitor, SGI-1776, induces apoptosis in chronic lymphocytic leukemia cells, Blood, vol.114, issue.19, pp.4150-4157, 2009.

V. J. Cee, F. Chavez, B. Herberich, B. A. Lanman, L. H. Pettus et al., Discovery and Optimization of Macrocyclic Quinoxaline-pyrrolo-dihydropiperidinones as Potent Pim-1/2 Kinase Inhibitors, ACS Medicinal Chemistry Letters, vol.7, issue.4, pp.408-412, 2016.

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T. Katayama, S. Nakatsuka, H. Hirai, N. Yasuda, J. Kumar et al., Two-step synthesis of boron-fused double helicenes, J. Am. Chem. Soc, vol.138, pp.5210-5213, 2016.

R. Akué-gédu, E. Rossignol, S. Azzaro, S. Knapp, P. Filippakopoulos et al., Kinase Inhibitory Potencies, and in Vitro Antiproliferative Evaluation of New Pim Kinase Inhibitors, J. Med. Chem, vol.52, pp.6369-6381, 2009.

G. M. Morris, R. Huey, W. Lindstrom, M. F. Sanner, R. K. Belew et al., AutoDock and AutoDockTools: Automated docking with selective receptor flexibility, J. Comput. Chem, vol.30, pp.2785-2791, 2009.

O. Trott and A. J. Olson, AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading, J. Comput. Chem, vol.31, pp.455-461, 2010.

V. Pogacic, A. N. Bullock, O. Fedorov, P. Filippakopoulos, C. Gasser et al., Structural analysis identifies imidazo[1,2-b]pyridazines as PIM kinase inhibitors with in vitro antileukemic activity, Cancer Res, vol.67, pp.6916-6924, 2007.

X. Wang, W. Blackaby, V. Allen, G. K. Chan, J. H. Chang et al., Optimization of Pan-Pim Kinase Activity and Oral Bioavailability Leading to Diaminopyrazole (GDC-0339) for the Treatment of Multiple Myeloma, J. Med. Chem, vol.62, pp.2140-2153, 2019.

X. Wang, A. Kolesnikov, S. Tay, G. Chan, Q. Chao et al., Discovery of 5-azaindazole (GNE-955) as a potent pan-Pim inhibitor with optimized bioavailability, J. Med. Chem, vol.60, pp.4458-4473, 2017.

E. F. Pettersen, T. D. Goddard, C. C. Huang, G. S. Couch, D. M. Greenblatt et al., UCSF Chimera-A visualization system for exploratory research and analysis, J. Comput. Chem, vol.25, pp.1605-1612, 2004.

Y. Zhang, Z. Wang, X. Li, and N. S. Magnuson, Pim kinase-dependent inhibition of c-Myc degradation, Oncogene, vol.27, issue.35, pp.4809-4819, 2008.

N. M. Santio, S. K. Landor, L. Vahtera, J. Ylä-pelto, E. Paloniemi et al., Phosphorylation of Notch1 by Pim kinases promotes oncogenic signaling in breast and prostate cancer cells, Oncotarget, vol.7, issue.28, pp.43220-43238, 2016.

D. Horiuchi, R. Camarda, A. Y. Zhou, C. Yau, O. Momcilovic et al., PIM1 kinase inhibition as a targeted therapy against triple-negative breast tumors with elevated MYC expression, Nat. Med, vol.22, issue.11, pp.1321-1329, 2016.

N. M. Santio, R. L. Vahakoski, E. Rainio, J. A. Sandholm, S. S. Virtanen et al., Pim-selective inhibitor DHPCC-9 reveals Pim kinases as potent stimulators of cancer cell migration and invasion, Molecular cancer, vol.9, p.279, 2010.
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J. Wu, J. Du, X. Fu, B. Liu, H. Cao et al., Iciartin, a novel FASN inhibitor, exerts anti-melanoma activities through IGF-1R/STAT3 signaling, Oncotarget, vol.7, issue.32, pp.51251-51269, 2016.

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J. Barbosa, R. T. Lima, D. Sousa, A. S. Gomes, A. Palmeira et al., Screening a small library of xanthones for antitumor activity and identification of a hit compound which induces apoptosis, Molecules, vol.21, issue.1, 2016.

M. Hedidi, J. Maillard, W. Erb, F. Lassagne, Y. S. Halauko et al., Bentabed-Ababsa, F. Mongin, Fused Systems Based on 2-Aminopyrimidines: Synthesis Combining Deprotolithiation-in situ Zincation with N-Arylation Reactions and Biological Properties, Eur. J. Org. Chem, issue.39, pp.5903-5915, 2017.

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D. Wagner and S. Bräse, Ruthenium-catalyzed C-H activation of thioxanthones, Beilstein J. Org. Chem, vol.11, pp.431-436, 2015.

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N. Brikci-nigassa, G. Bentabed-ababsa, W. Erb, F. Mongin, and I. Situ, Trans-Metal Trapping': An Efficient Way to Extend the Scope of Aromatic Deprotometalation, Synthesis, vol.50, issue.18, pp.3615-3633, 2018.
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M. Hedidi, W. Erb, F. Lassagne, Y. S. Halauko, O. A. Ivashkevich et al., Bentabed-Ababsa, F. Mongin, Functionalization of Pyridyl Ketones using Deprotolithiation-in situ Zincation, RSC Adv, vol.6, issue.68, pp.63185-63189, 2016.

F. Lassagne, T. Langlais, E. Caytan, E. Limanton, L. Paquin et al., From quinoxaline, pyrido[2,3-b]pyrazine and pyrido[3,4-b]pyrazine to pyrazino-fused carbazoles and carbolines, Molecules, vol.23, issue.11, 2018.
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R. Amara, G. Bentabed-ababsa, M. Hedidi, J. Khoury, H. Awad et al., Synthesis of N-Aryl and N-Heteroaryl ?-, ?-, and ?-Lactams Using Deprotometalation-Iodination and N-Arylation, and Properties Thereof, vol.49, pp.4500-4516, 2017.
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N. Brikci-nigassa, G. Bentabed-ababsa, W. Erb, F. Chevallier, L. Picot et al., Mongin, 2-Aminophenones, a common precursor to N-aryl isatins and acridines endowed with bioactivities, Tetrahedron, vol.74, issue.15, pp.1785-1801, 2018.

J. Kim and S. Chang, Ammonium salts as an inexpensive and convenient nitrogen source in the Cucatalyzed amination of aryl halides at room temperature, Chem. Commun, issue.26, pp.3052-3054, 2008.

P. Ji, J. H. Atherton, and M. I. Page, Copper(I)-catalyzed amination of aryl halides in liquid ammonia, J. Org. Chem, vol.77, issue.17, pp.7471-7478, 2012.

H. S. Jung, T. Yun, Y. Cho, and H. B. Jeon, Simple and convenient copper-catalyzed amination of aryl halides to primary arylamines using NH4OH, Tetrahedron, vol.72, issue.40, pp.5988-5993, 2016.

Y. Kitahara, T. Mizuno, and A. Kubo, Synthetic studies of benzo, Tetrahedron, vol.60, issue.19, pp.4283-4288, 2004.

S. Klaeger, S. Heinzlmeir, M. Wilhelm, H. Polzer, B. Vick et al.,

S. Greif, E. R. Schneider, J. Felder, G. Ruland, I. Medard et al., The target landscape of clinical kinase drugs, Science, vol.358, issue.6367, p.1148, 2017.

R. Roskoski, Properties of FDA-approved small molecule protein kinase inhibitors, Pharmacol. Res, vol.144, pp.19-50, 2019.

H. L. Lightfoot, F. W. Goldberg, and J. Sedelmeier, Evolution of Small Molecule Kinase Drugs, ACS Medicinal Chemistry Letters, vol.10, issue.2, pp.153-160, 2019.

L. S. Chen, S. Redkar, D. Bearss, W. G. Wierda, and V. Gandhi, Pim kinase inhibitor, SGI-1776, induces apoptosis in chronic lymphocytic leukemia cells, Blood, vol.114, issue.19, pp.4150-4157, 2009.

V. J. Cee, F. Chavez, B. Herberich, B. A. Lanman, L. H. Pettus et al.,

J. Andrews, D. Chen, J. Hickman, M. R. Laszlo, N. Lee et al., Discovery and Optimization of Macrocyclic Quinoxaline-pyrrolo-dihydropiperidinones as Potent Pim-1/2 Kinase Inhibitors, ACS Medicinal Chemistry Letters, vol.7, issue.4, pp.408-412, 2016.

C. J. Bataille, M. B. Brennan, S. Byrne, S. G. Davies, M. Durbin et al., Thiazolidine derivatives as potent and selective inhibitors of the PIM kinase family, Bioorg. Med. Chem, vol.25, issue.9, pp.2657-2665, 2017.

Y. Shen and C. Chen, Helicenes: Synthesis and Applications, Chem. Rev, vol.112, issue.3, pp.1463-1535, 2012.

M. Gingras, One hundred years of helicene chemistry. Part 3: applications and properties of carbohelicenes, Chem. Soc. Rev, vol.42, issue.3, pp.1051-1095, 2013.

R. H. Janke, G. Haufe, E. Würthwein, and J. H. Borkent, Racemization barriers of helicenes: A computational study, J. Am. Chem. Soc, vol.118, issue.25, pp.6031-6035, 1996.

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R. Akué-gédu, E. Rossignol, S. Azzaro, S. Knapp, P. Filippakopoulos et al.,

M. Cohen, F. Prudhomme, P. Anizon, and . Moreau, Kinase Inhibitory Potencies, and in Vitro Antiproliferative Evaluation of New Pim Kinase Inhibitors, J. Med. Chem, vol.52, issue.20, pp.6369-6381, 2009.

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O. Trott and A. J. Olson, AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading, J. Comput. Chem, vol.31, issue.2, pp.455-461, 2010.

V. Pogacic, A. N. Bullock, O. Fedorov, P. Filippakopoulos, C. Gasser et al., Structural analysis identifies imidazo[1,2-b]pyridazines as PIM kinase inhibitors with in vitro antileukemic activity, Cancer Res, vol.67, issue.14, pp.6916-6924, 2007.

X. Wang, W. Blackaby, V. Allen, G. K. Chan, J. H. Chang et al.,

J. Lyssikatos, M. Ly, J. G. Matteucci, V. Moffat, J. Munugalavadla et al., Optimization of Pan-Pim Kinase Activity and Oral Bioavailability Leading to Diaminopyrazole (GDC-0339) for the Treatment of Multiple Myeloma, J. Med. Chem, vol.62, issue.4, pp.2140-2153, 2019.

X. Wang, A. Kolesnikov, S. Tay, G. Chan, Q. Chao et al., Discovery of 5-azaindazole (GNE-955) as a potent pan-Pim inhibitor with optimized bioavailability, J. Med. Chem, vol.60, issue.10, pp.4458-4473, 2017.

E. F. Pettersen, T. D. Goddard, C. C. Huang, G. S. Couch, D. M. Greenblatt et al., UCSF Chimera-A visualization system for exploratory research and analysis, J. Comput. Chem, vol.25, issue.13, pp.1605-1612, 2004.

Y. Zhang, Z. Wang, X. Li, and N. S. Magnuson, Pim kinase-dependent inhibition of c-Myc degradation, Oncogene, vol.27, issue.35, pp.4809-4819, 2008.

N. M. Santio, S. K. Landor, L. Vahtera, J. Ylä-pelto, E. Paloniemi et al., Phosphorylation of Notch1 by Pim kinases promotes oncogenic signaling in breast and prostate cancer cells, Oncotarget, vol.7, issue.28, pp.43220-43238, 2016.

D. Horiuchi, R. Camarda, A. Y. Zhou, C. Yau, O. Momcilovic et al., PIM1 kinase inhibition as a targeted therapy against triple-negative breast tumors with elevated MYC expression, Nat. Med, vol.22, issue.11, pp.1321-1329, 2016.

N. M. Santio, R. L. Vahakoski, E. Rainio, J. A. Sandholm, S. S. Virtanen et al.,

P. Anizon, P. Moreau, and J. Koskinen, Pim-selective inhibitor DHPCC-9 reveals Pim kinases as potent stimulators of cancer cell migration and invasion, Molecular cancer, vol.9, p.279, 2010.
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C. Locatelli, F. B. Filippin-monteiro, and T. B. Creczynski, Recent Advances in the Biology, Therapy and Management of Melanoma, 2013.

B. Shannan, A. Watters, Q. Chen, S. Mollin, M. Dörr et al., PIM kinases as therapeutic targets against advanced melanoma, vol.7, pp.54897-54912, 2016.

J. Wu, J. Du, X. Fu, B. Liu, H. Cao et al., Iciartin, a novel FASN inhibitor, exerts anti-melanoma activities through IGF-1R/STAT3 signaling, Oncotarget, vol.7, issue.32, pp.51251-51269, 2016.

H. E. Gottlieb, V. Kotlyar, and A. Nudelman, NMR chemical shifts of common laboratory solvents as trace impurities, J. Org. Chem, vol.62, issue.21, pp.7512-7515, 1997.

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A. I. Vogel, A. R. Tatchell, B. S. Furnis, A. J. Hannaford, and P. W. Smith, Vogel's textbook of practical organic chemistry, 1996.

J. M. , A. Seggio, F. Chevallier, M. Yonehara, E. Jeanneau et al., Deprotonative Metalation of Five-membered Aromatic Heterocycles using Mixed Lithiumzinc Species, J. Org. Chem, vol.73, issue.1, pp.177-183, 2008.
URL : https://hal.archives-ouvertes.fr/hal-00784514

M. Hedidi, G. Bentabed-ababsa, A. Derdour, T. Roisnel, V. Dorcet et al., Synthesis of C,N'-linked bis-heterocycles using a deprotometalation-iodination-Narylation sequence and evaluation of their antiproliferative activity in melanoma cells, Bioorg. Med. Chem, vol.22, issue.13, pp.3498-3507, 2014.

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