Novel Arcyriaflavin-A Derivatives as PIM Kinase Inhibitors for Treating Cancer


Cite item

Full Text

Abstract

The present application reports a series of novel Arcyriaflavin-A derivatives as PIM kinase inhibitors for the effective treatment of cancer. The application also describes the synthesis of compounds in detail, use, pharmaceutical composition, pharmaceutically acceptable salts, and treatment.

About the authors

Surya De

Department of Chemistry, Conju-Prob

Author for correspondence.
Email: info@benthamscience.net

References

  1. Walhekar, V.; Bagul, C.; Kumar, D.; Muthal, A.; Achaiah, G.; Kulkarni, R. Topical advances in PIM kinases and their inhibitors: Medicinal chemistry perspectives. Biochim. Biophys. Acta Rev. Cancer, 2022, 1877(3), 188725. doi: 10.1016/j.bbcan.2022.188725 PMID: 35367531
  2. Rathi, A.; Kumar, D.; Hasan, G.M.; Haque, M.M.; Hassan, M.I. Therapeutic targeting of PIM KINASE signaling in cancer therapy: Structural and clinical prospects. Biochim. Biophys. Acta, Gen. Subj., 2021, 1865(11), 129995. doi: 10.1016/j.bbagen.2021.129995 PMID: 34455019
  3. Panchal, N.K.; Sabina, E.P. A serine/threonine protein PIM kinase as a biomarker of cancer and a target for anti-tumor therapy. Life Sci., 2020, 255, 117866. doi: 10.1016/j.lfs.2020.117866 PMID: 32479955
  4. Asati, V.; Mahapatra, D.K.; Bharti, S.K. PIM kinase inhibitors: Structural and pharmacological perspectives. Eur. J. Med. Chem., 2019, 172, 95-108. doi: 10.1016/j.ejmech.2019.03.050 PMID: 30954777
  5. Le, B.T.; Kumarasiri, M.; Adams, J.R.J.; Yu, M.; Milne, R.; Sykes, M.J.; Wang, S. Targeting Pim kinases for cancer treatment: Opportunities and challenges. Future Med. Chem., 2015, 7(1), 35-53. doi: 10.4155/fmc.14.145 PMID: 25582332
  6. Swords, R.; Kelly, K.; Carew, J.; Nawrocki, S.; Mahalingam, D.; Sarantopoulos, J.; Bearss, D.; Giles, F. The Pim kinases: New targets for drug development. Curr. Drug Targets, 2011, 12(14), 2059-2066. doi: 10.2174/138945011798829447 PMID: 21777193
  7. Nawijn, M.C.; Alendar, A.; Berns, A. For better or for worse: The role of Pim oncogenes in tumorigenesis. Nat. Rev. Cancer, 2011, 11(1), 23-34. doi: 10.1038/nrc2986 PMID: 21150935
  8. Anizon, F.; Shtil, A.A.; Danilenko, V.N.; Moreau, P. Fighting tumor cell survival: Advances in the design and evaluation of Pim inhibitors. Curr. Med. Chem., 2010, 17(34), 4114-4133. doi: 10.2174/092986710793348554 PMID: 20939820
  9. Qin, R.; You, F.M.; Zhao, Q.; Xie, X.; Peng, C.; Zhan, G.; Han, B. Naturally derived indole alkaloids targeting regulated cell death (RCD) for cancer therapy: From molecular mechanisms to potential therapeutic targets. J. Hematol. Oncol., 2022, 15(1), 133. doi: 10.1186/s13045-022-01350-z PMID: 36104717
  10. Gotlib, J.; Kluin-Nelemans, H.C.; George, T.I.; Akin, C.; Sotlar, K.; Hermine, O.; Awan, F.T.; Hexner, E.; Mauro, M.J.; Sternberg, D.W.; Villeneuve, M.; Huntsman Labed, A.; Stanek, E.J.; Hartmann, K.; Horny, H.P.; Valent, P.; Reiter, A. Efficacy and safety of midostaurin in advanced systemic mastocytosis. N. Engl. J. Med., 2016, 374(26), 2530-2541. doi: 10.1056/NEJMoa1513098 PMID: 27355533
  11. Stone, R.M.; Mandrekar, S.J.; Sanford, B.L.; Laumann, K.; Geyer, S.; Bloomfield, C.D.; Thiede, C.; Prior, T.W.; Döhner, K.; Marcucci, G.; Lo-Coco, F.; Klisovic, R.B.; Wei, A.; Sierra, J.; Sanz, M.A.; Brandwein, J.M.; de Witte, T.; Niederwieser, D.; Appelbaum, F.R.; Medeiros, B.C.; Tallman, M.S.; Krauter, J.; Schlenk, R.F.; Ganser, A.; Serve, H.; Ehninger, G.; Amadori, S.; Larson, R.A.; Döhner, H. Midostaurin plus chemotherapy for acute myeloid leukemia with a FLT3 mutation. N. Engl. J. Med., 2017, 377(5), 454-464. doi: 10.1056/NEJMoa1614359 PMID: 28644114
  12. Theoharides, T.C.; Valent, P.; Akin, C. Mast cells, mastocytosis, and related disorders. N. Engl. J. Med., 2015, 373(19), 1884-1886. doi: 10.1056/NEJMc1510021 PMID: 26535528
  13. Arnán Sangerman, M.; Fernández Moreno, A.; García Quintana, A.; García-Vidal, C.; Olave Rubio, M.T.; Del Mar Tormo Díaz, M.; Vendranas, M.; Rodriguez Macias, G. Practical tips for managing FLT3 mutated acute myeloid leukemia with midostaurin. Expert Rev. Hematol., 2022, 15(3), 203-214. doi: 10.1080/17474086.2022.2054801 PMID: 35332831
  14. Cerchione, C.; Peleteiro Raíndo, A.; Mosquera Orgueira, A.; Mosquera Torre, A.; Bao Pérez, L.; Marconi, G.; Isidori, A.; Pérez Encinas, M.M.; Martinelli, G. Safety of FLT3 inhibitors in patients with acute myeloid leukemia. Expert Rev. Hematol., 2021, 14(9), 851-865. doi: 10.1080/17474086.2021.1969911 PMID: 34424108
  15. Roboz, G.J.; Strickland, S.A.; Litzow, M.R.; Dalovisio, A.; Perl, A.E.; Bonifacio, G.; Haines, K.; Barbera, A.; Purkayastha, D.; Sweet, K. Updated safety of midostaurin plus chemotherapy in newly diagnosed FLT3 mutation–positive acute myeloid leukemia: The RADIUS-X expanded access program. Leuk. Lymphoma, 2020, 61(13), 3146-3153. doi: 10.1080/10428194.2020.1805109 PMID: 32812818
  16. Men, Y.; Hu, Z.; Dong, J.; Xu, X.; Tang, B. Formal 1 + 2 + 3 annulation: Domino access to carbazoles and indolocarbazole alkaloids. Org. Lett., 2018, 20(17), 5348-5352. doi: 10.1021/acs.orglett.8b02266 PMID: 30110173
  17. Faul, M.M.; Winneroski, L.L.; Krumrich, C.A. A new one step synthesis of maleimides by condensation of glyoxylate esters with acetamides. Tetrahedron Lett., 1999, 40(6), 1109-1112. doi: 10.1016/S0040-4039(98)02594-5
  18. Faul, M.M.; Winneroski, L.L.; Krumrich, C.A. A new, efficient method for the synthesis of bisindolylmaleimides. J. Org. Chem., 1998, 63(17), 6053-6058. doi: 10.1021/jo980513c PMID: 11672217
  19. Zhang, D.; Wang, G.; Yu, X.; Wei, T.; Farbiak, L.; Johnson, L.T.; Taylor, A.M.; Xu, J.; Hong, Y.; Zhu, H.; Siegwart, D.J. Enhancing CRISPR/Cas gene editing through modulating cellular mechanical properties for cancer therapy. Nat. Nanotechnol., 2022, 17(7), 777-787. doi: 10.1038/s41565-022-01122-3 PMID: 35551240
  20. Zhou, Z.; Liu, Y.; Jiang, X.; Zheng, C.; Luo, W.; Xiang, X.; Qi, X.; Shen, J. Metformin modified chitosan as a multi-functional adjuvant to enhance cisplatin-based tumor chemotherapy efficacy. Int. J. Biol. Macromol., 2023, 224, 797-809. doi: 10.1016/j.ijbiomac.2022.10.167 PMID: 36283555
  21. Zhen, C.; Luo, W.; Liu, Y.; Chen, J.; Deng, H.; Zhou, Z.; Shen, J. Killing three birds with one stone: Multi-stage metabolic regulation mediated by clinically usable berberine liposome to overcome photodynamic immunotherapy resistance. Chem. Eng. J., 2023, 454(2), 140164. doi: 10.1016/j.cej.2022.140164

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2023 Bentham Science Publishers