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Signposts to Chiral Drugs pp 83–102Cite as

Sertraline

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Abstract

Biological target: Sertraline is an aryl-substituted tetrahydronaphthalene derivative which selectively inhibits the plasma membrane serotonin transporter (SERT) and thereby blocks serotonin re-uptake from the neuronal synapse.

Therapeutic profile: As a selective serotonin reuptake inhibitor (SSRI), sertraline is a widely used drug for the treatment of depression and anxiety-related disorders.

Synthetic highlights: A variety of pathways have been taken in the synthetic approach to sertraline. These include stereoselective reduction of ketones and imines under kinetic and thermodynamic control, using diastereoselective or enantioselective catalysts and reagents, desymmetrization of oxabenzonorbornadiene followed by the Suzuki coupling of arylboronic acids and vinyl halides and Pd-Catayzed (Tsuji-Trost) coupling of arylboronic acids and allylic esters. For the production of sertraline, the simulated moving bed (SMB), a cost-effective technology, has been introduced.

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References

  1. McRae AL, Brady KT (2001) Exp Opin Pharmacother 5:883–892

    Article  Google Scholar 

  2. Chen Z, Skolnick P (2007) Exp Opin Pharmacother 9:1365–1377

    Google Scholar 

  3. Ban TA (2001) J Neural Trans 108:707–716

    Article  CAS  Google Scholar 

  4. Skolnik P, Basile AS (2006) Drug Descov Today Ther Strateg 3:489–494

    Article  Google Scholar 

  5. Welch WM, Kraska AR, Sarges R, Koe BK (1984) J Med Chem 27:1508–1515

    Article  PubMed  CAS  Google Scholar 

  6. Roman DL, Walline CC, Rodrigez GJ, Barker EL (2003) Eur J Pharmacol 479:53–63

    Article  PubMed  CAS  Google Scholar 

  7. Ives JL, Heym J (1989) Ann Rept Med Chem 24:21

    Article  CAS  Google Scholar 

  8. Zhou Z, Zhen J, Karpowich NK, Law CJ, Reith MEA, Wang D-N (2009) Nature Struct Mol Biol 16:652–658

    Article  CAS  Google Scholar 

  9. Yamashita A, Singh SK, Kawate T, Jin Y, Gouaux E (2005) Nature 437:215–223

    Article  PubMed  CAS  Google Scholar 

  10. Caruso F, Besmer A, Rossi M (1999) Acta Crystallogr C 55:1712–1714

    Article  Google Scholar 

  11. Quallich GJ (2005) Chirality 17:120–126

    Article  Google Scholar 

  12. Welch WM, Krasak AR, Sarges R, Koe BK (1984) J Med Chem 27:1508–1515

    Article  PubMed  CAS  Google Scholar 

  13. Taber GP, Pfisterer DM, Colberg C (2004) Or Proc Res Develop 8:385–388

    Article  CAS  Google Scholar 

  14. Yun J, Buchwald SL (2000) J Org Chem 65:767–774

    Article  PubMed  CAS  Google Scholar 

  15. Yun J, Buchwald SL (1999) J Am Chem Soc 121:5640–5644

    Article  CAS  Google Scholar 

  16. Verdauger X, Lange UEW, Buchwald SL (1998) Angew Chem Int Ed 37:1103–1107

    Article  Google Scholar 

  17. Verdauger X, Lange UEW, Reding MT, Buchwald SL (1996) J Am Chem Soc 118:6784–6785

    Article  Google Scholar 

  18. Fujita K, Furukawa S, Yamaguchi R (2002) J Organomet Chem 649:289–292

    Article  CAS  Google Scholar 

  19. Cshernyik G, Bogar K, Backwall J (2004) Tetrathedron Lett 36:6799–6802

    Article  Google Scholar 

  20. Ell AH, Samec JSM, Brasse C, Backvall JE (2002) Chem Commun. 1144–1145

    Google Scholar 

  21. Samec JSM, Ell AH, Backvall JE (2005) Chem-Eur J 11:2327–2334

    Article  PubMed  CAS  Google Scholar 

  22. Blacker AJ, Stirling MJ, Page MI (2007) Org Process Res Develop 11:642–648

    Google Scholar 

  23. Berkessel A, Goroger H (2005) Asymmetric reduction of ketones by organocatalysis, Chap. 11. In: Asymmetric organocatalysis. Wiley-VCH, Weinheim, pp. 314–322

  24. Pozzi G (2008) Handbook of asymmetric heterogeneous catalysis. Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim, Germany, pp 181–208

    Book  Google Scholar 

  25. Kuang Y, Islam NM, Nabae Y, Hayakawa T, Kakimoto M (2010) Angew Chem Int Ed 49:436–440

    Article  CAS  Google Scholar 

  26. Figiel PJ, Leskela M, Repo T (2007) Adv Synth Catal 349:1173–1179

    Article  CAS  Google Scholar 

  27. Quallich GJ, Blake JF, Woodall TM (1994) J Am Chem Soc 116:8516–8525

    Article  CAS  Google Scholar 

  28. Lautens M, Rovis T (1997) J Org Chem 62:5246–5247

    Article  CAS  Google Scholar 

  29. Lautens M, Rovis T (1999) Tetrahedron 55:8967–8976

    Article  CAS  Google Scholar 

  30. Thompson LA, Ellman JA (1996) Chem Rev 96:555–572

    Article  PubMed  CAS  Google Scholar 

  31. Patchett AA, Nargund RP (2000) Ann Rep Med Chem 35:289–298

    Google Scholar 

  32. Miyaura N, Suzuki A (1995) Chem Rev 95:2457–2483

    Google Scholar 

  33. Thompson AS, Humphrey GR, Demarco AM, Mathre DJ, Grabowski EJJ (1993) J Org Chem 58:6886–5890

    Article  Google Scholar 

  34. Trost BM, Van Vranken DL (1996) Chem Rev 96:395–422

    Article  PubMed  CAS  Google Scholar 

  35. Trost BM, Crawley ML (2003) Chem Rev 103:2921–2943

    Article  PubMed  CAS  Google Scholar 

  36. Ohmiya H, Makida Y, Tanaka T, Sawamura M (2008) J Am Chem Soc 130:17276–17277

    Article  PubMed  CAS  Google Scholar 

  37. Ohmiya H, Makida Y, Li D, Tanabe M, Sawamura M (2010) J Am Chem Soc 132:879–889

    Article  PubMed  CAS  Google Scholar 

  38. D Enders, M Bartsch, D Backhaus (1995) Synlett; 869–870

    Google Scholar 

  39. Juza M, Mazzotti M, Morbidelli M (2000) Simulated moving-bed chromatography and its application to chirotechnology. Tibtech 18:108–118

    Article  CAS  Google Scholar 

  40. Abel S, Juza M (2007) Less common applications of enantioselective HPLC using the SMB technology in the pharamaceutical industry. In: Subramanian G (ed) Chiral separation techniques, 3rd edn. Wiley-VCH, Weinheim, pp 203–273

    Google Scholar 

  41. Cox GB (2005) Preparative enantioselective chromatography. Blackwell, Oxford/Ames, IA

    Book  Google Scholar 

  42. Guiochon G, Fellinger A, Shirazi SG, Katti AM (2006) Fundamentals of preparative and nonlinear chromatography. Academic, Boston, MA

    Google Scholar 

  43. Schmidt-Traub H (2005) Preparative chromatography of fine chemicals and pharmaceutical agents. Wiley-VCH, Weinheim

    Book  Google Scholar 

  44. Blaser H-U, Pugin B, Spindler F (2005) J Mol Catal A 231:1–20

    Article  CAS  Google Scholar 

  45. Farina V, Reeves JT, Senanayake CH, Song JJ (2006) Chem Rev 106:2734–2793

    Article  PubMed  CAS  Google Scholar 

  46. Toumi A, Engell S, Diehl M, Bock HG, Schloder J (2007) Chem Eng Process 46:1067–1084

    Article  CAS  Google Scholar 

  47. Araujo JMM, Rodrigues RCR, Eusebio MFJ, Mota JPB (2008) J Chromatogr A 1189:292–301

    Article  PubMed  CAS  Google Scholar 

  48. Lode A, Houmard M, Miglioroni C, Mazotti M, Morbidelli M (2001) Chem Eng Sci 56:269–291

    Article  CAS  Google Scholar 

  49. Barker PE, Ganetsos G, Ajongwen J, Akintoye A (1992) Chem Eng J 50:B23–B28

    Article  CAS  Google Scholar 

  50. Barker PE, Ganetsos G, Ajongwen J (1993) J Chem Technol Biotechnol 57:21–26

    Article  PubMed  CAS  Google Scholar 

  51. O Dapremont, F Geiser, T Zhang, SG Subramanian, RM Guinn, GJ Quallich (2002) U.S. Pat. 6,444, 854

    Google Scholar 

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Authors and Affiliations

  1. Faculty of Natural Sciences and Mathematics Department of Organic Chemistry, University of Zagreb, Horvatovac 102A, HR-10000, Zagreb, Croatia

    Prof. Dr. Vitomir Šunjić

  2. Research and Clinical Immunology Departments, University Hospital for Infectious Diseases “Dr. Fran Mihaljevic”, Mirogojska cesta 8, HR-10000, Zagreb, Croatia

    Prof. Dr. Michael J. Parnham

Authors
  1. Prof. Dr. Vitomir Šunjić
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  2. Prof. Dr. Michael J. Parnham
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Correspondence to Vitomir Šunjić .

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Šunjić, V., Parnham, M.J. (2011). Sertraline. In: Signposts to Chiral Drugs. Springer, Basel. https://doi.org/10.1007/978-3-0348-0125-6_7

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