Synthesis of thioridazine-VLA-4 antagonist hybrids using N-propargyl northioridazine enantiomers

References

• Guillon, J.; Petit, C.; Toutain, B.; Guette, C.; Lelièvre, E.; Coqueret, O. Chemotherapy-Induced Senescence, an Adaptive Mechanism Driving Resistance and Tumor Heterogeneity. Cell Cycle 2019, 18, 2385–2397. DOI: 10.1080/15384101.2019.1652047.
   PubMed Web of Science ®Google Scholar
• Meads, M. B.; Gatenby, R.; Dalton, W. S. Environment-Mediated Drug Resistance: A Major Contributor to Minimal Residual Disease. Nat. Rev. Cancer 2009, 9, 665–674. DOI: 10.1038/nrc2714.
   PubMed Web of Science ®Google Scholar
• Meads, M. B.; Hazlehurst, L. A.; Dalton, W. S. The Bone Marrow Microenvironment as a Tumor Sanctuary and Contributor to Drug Resistance. Clin. Cancer Res. 2008, 14, 2519–2526. DOI: 10.1158/1078-0432.CCR-07-2223.
   PubMed Web of Science ®Google Scholar
• Lim, A. B. M.; Curley, C.; Fong, C. Y.; Bilmon, I.; Beligaswatte, A.; Purtill, D.; Getta, B.; Johnston, A. M.; Armytage, T.; Collins, M.; et al. Acute Myeloid Leukaemia Relapsing after Allogeneic Haemopoietic Stem Cell Transplantation: Prognostic Factors and Impact of Initial Therapy of Relapse. Intern. Med. J. 2018, 48, 276–285. DOI: 10.1111/imj.13522.
   PubMed Web of Science ®Google Scholar
• Shain, K. H.; Dalton, W. S. Environmental-Mediated Drug Resistance: A Target for Multiple Myeloma Therapy. Expert Rev. Hematol. 2009, 2, 649–662. DOI: 10.1586/ehm.09.55.
   PubMed Web of Science ®Google Scholar
• Damiano, J. S.; Cress, A. E.; Hazlehurst, L. A.; Shtil, A. A.; Dalton, W. S. Cell Adhesion Mediated Drug Resistance (CAM-DR): Role of Integrins and Resistance to Apoptosis in Human Myeloma Cell Lines. Blood 1999, 93, 1658–1667. DOI: 10.1182/blood.V93.5.1658.405a19_1658_1667.
   PubMed Web of Science ®Google Scholar
• Doherty, G. A.; Yang, G. X.; Borges, E.; Tong, S.; McCauley, E. D.; Treonz, K. M.; Van Riper, G.; Pacholok, S.; Si, Q.; Koo, G. C.; et al. N-Isonicotinoyl-(L)-4-Aminophenylalanine Derivatives as Tight Binding VLA-4 Antagonists. Bioorg. Med. Chem. Lett. 2003, 13, 1891–1895. DOI: 10.1016/s0960-894x(03)00308-1.
   PubMed Web of Science ®Google Scholar
• Chigaev, A.; Wu, Y.; Williams, D. B.; Smagley, Y.; Sklar, L. a. Discovery of Very Late Antigen-4 (VLA-4, alpha4beta1 Integrin) Allosteric Antagonists. J. Biol. Chem. 2011, 286, 5455–5463. DOI: 10.1074/jbc.M110.162636.
   PubMed Web of Science ®Google Scholar
• Spengler, G.; Molnar, J.; Viveiros, M.; Amaral, L. Thioridazine Induces Apoptosis of Multidrug-Resistant Mouse Lymphoma Cells Transfected with the Human ABCB1 and Inhibits the Expression of P-Glycoprotein. Anticancer Res. 2011, 31, 4201–4205.
   PubMed Web of Science ®Google Scholar
• Kang, S.; Dong, S. M.; Kim, B. R.; Park, M. S.; Trink, B.; Byun, H. J.; Rho, S. B. Thioridazine Induces Apoptosis by Targeting the PI3K/Akt/mTOR Pathway in Cervical and Endometrial Cancer Cells. Apoptosis 2012, 17, 989–997. DOI: 10.1007/s10495-012-0717-2.
   PubMed Web of Science ®Google Scholar
• Sachlos, E.; Risueño, R. M.; Laronde, S.; Shapovalova, Z.; Lee, J. H.; Russell, J.; Malig, M.; McNicol, J. D.; Fiebig-Comyn, A.; Graham, M.; et al. Identification of Drugs Including a Dopamine Receptor Antagonist that Selectively Target Cancer Stem Cells. Cell 2012, 149, 1284–1297. DOI: 10.1016/j.cell.2012.03.049.
   PubMed Web of Science ®Google Scholar
• Bonig, H.; Wundes, A.; Chang, K. H.; Lucas, S.; Papayannopoulou, T. Increased Numbers of Circulating Hematopoietic Stem/Progenitor Cells Are Chronically Maintained in Patients Treated with the CD49d Blocking Antibody Natalizumab. Blood 2008, 111, 3439–3441. DOI: 10.1182/blood-2007-09-112052.
   PubMed Web of Science ®Google Scholar
• Zohren, F.; Toutzaris, D.; Klärner, V.; Hartung, H. P.; Kieseier, B.; Haas, R. The Monoclonal anti-VLA-4 Antibody Natalizumab Mobilizes CD34+ Hematopoietic Progenitor Cells in Humans. Blood 2008, 111, 3893–3895. DOI: 10.1182/blood-2007-10-120329.
   PubMed Web of Science ®Google Scholar
• Lapidot, T.; Petit, I. Current Understanding of Stem Cell Mobilization: The Roles of Chemokines, Proteolytic Enzymes, Adhesion Molecules, Cytokines, and Stromal Cells. Exp. Hematol. 2002, 30, 973–981. DOI: 10.1016/S0301-472X(02)00883-4.
   PubMed Web of Science ®Google Scholar
• Lin, L. S.; Lanza, T.; Jewell, J. P.; Liu, P.; Jones, C.; Kieczykowski, G. R.; Treonze, K.; Si, Q.; Manior, S.; Koo, G.; et al. Discovery of N-{N-[(3-Cyanophenyl)Sulfonyl]-4(R)-Cyclobutylamino-(L)-Prolyl}-4-[(3′,5′-Dichloroisonicotinoyl) Amino]-(L)-Phenylalanine (MK-0668), an Extremely Potent and Orally Active Antagonist of Very Late Antigen-4. J. Med. Chem. 2009, 52, 3449–3452. DOI: 10.1021/jm900257b.
   PubMed Web of Science ®Google Scholar
• Markiewicz, J. T.; Wiest, O.; Helquist, P. Synthesis of Primary Aryl Amines through a Copper-Assisted Aromatic Substitution Reaction with Sodium Azide. J. Org. Chem. 2010, 75, 4887–4890. DOI: 10.1021/jo101002p.
   PubMed Web of Science ®Google Scholar
• Xu, S.; Zhuang, X.; Pan, X.; Zhang, Z.; Duan, L.; Liu, Y.; Zhang, L.; Ren, X.; Ding, K. 1-Phenyl-4-Benzoyl-1H-1,2,3-Triazoles as Orally Bioavailable Transcriptional Function Suppressors of Estrogen-Related Receptor α. J. Med. Chem. 2013, 56, 4631–4640. DOI: 10.1021/jm4003928.
   PubMed Web of Science ®Google Scholar
• Lin, L.; Doherty, G.; Shah, S. N-arylsulfonyl aza-bicyclic derivatives as potent cell adhesion inhibitors. US Patent 20030008861A1, Jan 9, 2003.
   Google Scholar
• Choi, S.; Haggart, D.; Toll, L.; Cuny, G. D. Synthesis, Receptor Binding and Functional Studies of Mesoridazine Stereoisomers. Bioorg. Med. Chem. Lett. 2004, 14, 4379–4382. DOI: 10.1016/j.bmcl.2004.06.078.
   PubMed Web of Science ®Google Scholar
• Antonsen, S.; Monsen, E. B.; Ovchinnikov, K.; Nolsøe, J. M. J.; Ekeberg, D.; Kristiansen, J. E.; Diep, D. B.; Stenstrøm, Y. Synthesis of the Enantiomers of Thioridazine. SynOpen 2020, 04, 12–16. DOI: 10.1055/s-0039-1690834.
   Google Scholar
• Patrick, K. S.; Singletary, J. L. Relative Configuration of Thioridazine Enantiomers. Chirality 1991, 3, 208–211. DOI: 10.1002/chir.530030312.
   Web of Science ®Google Scholar
• Bender, C.; Liebscher, J. Stereoselective 1-arylation of isoquinolines via chiral N-acylisoquinolinium salts. Arkivoc 2009, vi, 2009, 111.
   Google Scholar
• CrysAlis PRO, Version 1.171.37.33d (release 23.04.2014 CrysAlis171. NET) (compiled Apr 23, 2014,17:37:27), Agilent Technologies, Santa Clara, CA, 2014.
   Google Scholar
• Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. SIR 92 – a Program for Automatic Solution of Crystal Structures by Direct Methods. J. Appl. Crystallogr. 1994, 27, 435–435. DOI: 10.1107/S002188989400021X.
   Web of Science ®Google Scholar
• Betteridge, P. W.; Carruthers, J. R.; Cooper, R. I.; Prout, K.; Watkin, D. J. CRYSTALS Version 12: Software for Guided Crystal Structure Analysis. J. Appl. Crystallogr. 2003, 36, 1487–1487. DOI: 10.1107/S0021889803021800.
   Web of Science ®Google Scholar