Skip to main content

Flow Chemistry as a Drug Discovery Tool: A Medicinal Chemistry Perspective

  • Chapter
  • First Online:
Flow Chemistry for the Synthesis of Heterocycles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 56))

Abstract

The applications of flow chemistry in a drug discovery environment are discussed within. The development of integrated synthesis–bioassay platforms is discussed in the context of enabling medicinal chemistry programs, as is the use of flow chemistry to facilitate intermediate scale-up in a lead optimization setting. Emerging chemical technologies are also discussed, highlighting the use of high temperatures, hazardous gases, and photochemistry in flow to support medicinal chemistry efforts.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 229.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 299.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 299.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. DiMasi JA, Faden LB (2011) Nat Rev Drug Discov 10:23–27

    Article  CAS  PubMed  Google Scholar 

  2. Plutschack MB, Pieber B, Gilmore K, Seeberger PH (2017) Chem Rev. https://doi.org/10.1021/acs.chemrev.7b00183

  3. Porta R, Benaglia M, Puglisi A (2016) Org Process Res Dev 20:2–25

    Article  CAS  Google Scholar 

  4. McQuade DT, Seeberger PH (2013) J Org Chem 78:6384–6389

    Article  CAS  PubMed  Google Scholar 

  5. Pastre JC, Browne DL, Ley SV (2013) Chem Soc Rev 42:8849–8869

    Article  CAS  PubMed  Google Scholar 

  6. Wegner J, Ceylan S, Kirschning A (2011) Chem Commun 47:4583–4592

    Article  CAS  Google Scholar 

  7. Mason BP, Price KE, Steinbacher JL, Bogdan AR, McQuade DT (2007) Chem Rev 107:2300–2318

    Article  CAS  PubMed  Google Scholar 

  8. Hessel V, Lowe H (2005) Chem Eng Technol 28:267–284

    Article  CAS  Google Scholar 

  9. Ahmed-Omer B, Brandt JC, Wirth T (2007) Org Biomol Chem 5:733–740

    Article  CAS  PubMed  Google Scholar 

  10. Gutmann B, Cantillo D, Kappe CO (2015) Angew Chem Int Ed 54:6688–6728

    Article  CAS  Google Scholar 

  11. Malet-Sanz L, Flavien SJ (2012) Med Chem 55:4062–4098

    Article  CAS  Google Scholar 

  12. Baxendale IR, Deeley J, Griffiths-Jones CM, Ley SV, Saaby S, Tranmer GK (2006) Chem Commun:2566–2568

    Google Scholar 

  13. Adamo A, Beignessner RL, Behnam M, Chen J, Jamison TF, Jensen KF, Monbaliu J-CM, Myerson AS, Revalor EM, Snead DR, Stelzer T, Weeranoppanant N, Wong SY, Zhang P (2016) Science 352:61–67

    Article  CAS  PubMed  Google Scholar 

  14. Thompson CM, Poole JL, Cross JL, Akritopoulou-Zanze I, Djuric SW (2011) Molecules 16:9161–9177

    Article  CAS  PubMed  Google Scholar 

  15. Bogdan AR, Sach NW (2009) Adv Synth Catal 351:849–854

    Article  CAS  Google Scholar 

  16. Lange PP, Bogdan AR, James K (2012) Adv Synth Catal 354:2373–2379

    Article  CAS  Google Scholar 

  17. Lange PP, James K (2012) ACS Comb Sci 14:570–578

    Article  CAS  PubMed  Google Scholar 

  18. Hochlowski JE, Searle PA, Tu NP, Pan JY, Spanton SG, Djuric SW (2011) J Flow Chem 2:56–61

    Article  CAS  Google Scholar 

  19. Sutherland JD, Tu NP, Nemcek TA, Searle PA, Hochlowski JE, Djuric SW, Pan JY (2014) J Lab Autom 19:176–182

    Article  CAS  PubMed  Google Scholar 

  20. Bogdan AR, Wang Y (2015) RSC Adv 5:79264–79269

    Article  CAS  Google Scholar 

  21. Guetzoyan L, Nikbin N, Baxendale IR, Ley SV (2013) Chem Sci 4:764–769

    Article  CAS  Google Scholar 

  22. Petersen TP, Mirsharghi S, Rummel PC, Thiele S, Rosenkilde MM, Ritzen A, Ulven T (2013) Chem Eur J 19:9343–9350

    Article  CAS  PubMed  Google Scholar 

  23. Wong Fawkes SYF, Chapela MJV, Montembault M (2005) QSAR Combi Sci 24:712–717

    Article  CAS  Google Scholar 

  24. Desai B, Dixon K, Farrant E, Feng Q, Gibson KR, van Hoorn WP, Mills J, Morgan T, Parry DM, Ramjee MK, Selway CN, Tarver GJ, Whitlock G, Wright AG (2013) J Med Chem 56:3033–3047

    Article  CAS  PubMed  Google Scholar 

  25. Czechtizky W, Dedio J, Desai B, Dixon K, Farrant E, Feng Q, Morgan T, Parry DM, Ramjee MK, Selway CN, Schmidt T, Tarver GJ, Wright AG (2013) ACS Med Chem Lett 4:768–772

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. Werner M, Kuratli C, Martin RE, Hochstrasser R, Wechsler D, Enderle T, Alanine AI, Vogel H (2014) Angew Chem Int Ed 53:1704

    Article  CAS  Google Scholar 

  27. O’Brien AG, Levesque F, Seeberger PH (2011) Chem Commun 47:2688–2690

    Article  Google Scholar 

  28. Wilson NS, Osuma AT, Van Camp JA, Xu X (2012) Tetrahedron Lett 53:4498–4501

    Article  CAS  Google Scholar 

  29. Ullah F, Samarakoon T, Rolfe A, Kurtz RD, Hanson PR, Organ MG (2010) Chem Eur J 16:10959–10962

    Article  CAS  PubMed  Google Scholar 

  30. Martin RE, Morawitz F, Kuratli C, Alker AM, Alanine AI (2012) Eur J Org Chem:47–52

    Google Scholar 

  31. Lehmann J, Alzieu T, Martin RE, Britton R (2013) Org Lett 15:3550–3553

    Article  CAS  PubMed  Google Scholar 

  32. Charaschanya M, Bogdan AR, Wang Y, Djuric SW (2016) Tetrahedron Lett 57:1035–1039

    Article  CAS  Google Scholar 

  33. Lengyel L, Nagy TZ, Sipos G, Jones R, Dorman G, Urge L, Darvas F (2012) Tetrahedron Lett 53:738–743

    Article  CAS  Google Scholar 

  34. Tsoung J, Bogdan AR, Kantor S, Wang Y, Charaschanya M, Djuric SW (2017) J Org Chem 82:1073–1084

    Article  CAS  PubMed  Google Scholar 

  35. Tsoung J, Wang Y, Djuric SW (2017) React Chem Eng 2:458–461

    Article  CAS  Google Scholar 

  36. Bogdan AR, Charaschanya M, Dombrowski AW, Wang Y, Djuric SW (2016) Org Lett 18:1732–1735

    Article  CAS  PubMed  Google Scholar 

  37. Shore G, Yoo W-J, Li C-J, Organ MG (2010) Chem Eur J 16:126–133

    Article  CAS  PubMed  Google Scholar 

  38. Mallia CJ, Baxendale IR (2016) OPRD 20:327–360

    Article  CAS  Google Scholar 

  39. Brzozowski M, O’Brien M, Ley SV, Polyzos A (2015) Acc Chem Res 48:349–362

    Article  CAS  PubMed  Google Scholar 

  40. Koolman HF, Kantor S, Bogdan AR, Wang Y, Pan JY, Djuric SW (2016) Org Biomol Chem 14:6591–6596

    Article  CAS  PubMed  Google Scholar 

  41. Mastronardi F, Gutmann B, Kappe CO (2013) Org Lett 15:5590–5593

    Article  CAS  PubMed  Google Scholar 

  42. Dallinger D, Pinho VD, Gutmann B, Kappe CO (2016) J Org Chem 81:5814–5823

    Article  CAS  PubMed  Google Scholar 

  43. Polyzos A, O’Brien M, Baxendale IR, Ley SV (2010) Org Lett 12:1596–1598

    Article  CAS  Google Scholar 

  44. Ciriminna R, Delisi R, Xu Y-J, Pagliaro M (2016) OPRD 20:403–408

    Article  CAS  Google Scholar 

  45. Su Y, Straathof NJW, Hessel V, Noel T (2014) Chem Eur J 20:10562–10589

    Article  CAS  PubMed  Google Scholar 

  46. Gilmore K, Seeberger PH (2014) Chem Rec 14:410–418

    Article  CAS  PubMed  Google Scholar 

  47. Elliott LD, Knowles JP, Koovits PJ, Maskill KG, Ralph MJ, Lejeune G, Edwards LJ, Robinson RI, Clemens IR, Cox B, Pascoe DD, Koch G, Eberle M, Berry MB, Booker-Milburn KI (2014) Chem Eur J 20:15226–15232

    Article  CAS  PubMed  Google Scholar 

  48. Vasudevan A, Villamel C, Trumbull J, Olson J, Sutherland D, Pan J, Djuric S (2010) Tetrahedron Lett 51:4007–4009

    Article  CAS  Google Scholar 

  49. Koolman HF, Braje WM, Haupt A (2016) Synlett 27:2561–2566

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Andrew R. Bogdan .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2018 Springer International Publishing AG

About this chapter

Check for updates. Verify currency and authenticity via CrossMark

Cite this chapter

Bogdan, A.R., Organ, M.G. (2018). Flow Chemistry as a Drug Discovery Tool: A Medicinal Chemistry Perspective. In: Sharma, U., Van der Eycken, E. (eds) Flow Chemistry for the Synthesis of Heterocycles. Topics in Heterocyclic Chemistry, vol 56. Springer, Cham. https://doi.org/10.1007/7081_2018_24

Download citation

Publish with us

Policies and ethics