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An efficient multicomponent synthesis of fused pyrido-dipyrimidines containing tranexamic acid under green conditions

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Abstract

An efficient protocol was exploited to synthesize pyrido-dipyrimidines containing tranexamic acid moiety as a pharmaceutically interesting core via facile, highly efficient one-pot multicomponent reactions. The products were formed within a short time from the reaction of barbituric acid, tranexamic acid, and a variety of aryl aldehydes in water at room temperature under air conditions.

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References

  1. Roberts I, Ageron F-X (2022) Nat Rev Dis Primers 8:1

    Article  Google Scholar 

  2. Katsuta Y, Yoshida Y, Kawai E, Suetsugu M, Kohno Y, Inomata S, Kitamura K (2005) J Dermatol Sci 40:218

    Article  CAS  PubMed  Google Scholar 

  3. Wang J, Zhang Z, Li J, Huang B, Jiang Z, Pan Y, He T, Hu Y, Wang L (2022) Sci Rep 12:1

    Article  Google Scholar 

  4. Svahn CM, Merenyi F, Karlson L (1986) J Med Chem 29:448

    Article  CAS  PubMed  Google Scholar 

  5. Costanzo MJ, Almond HR, Hecker LR, Schott MR, Yabut SC, Zhang H-C, Andrade-Gordon P, Corcoran TW, Giardino EC, Kauffman JA (2005) J Med Chem 48:1984

    Article  CAS  PubMed  Google Scholar 

  6. Hom RK, Gailunas AF, Mamo S, Fang LY, Tung JS, Walker DE, Davis D, Thorsett ED, Jewett NE, Moon JB (2004) J Med Chem 47:158

    Article  CAS  PubMed  Google Scholar 

  7. Palanki MSS, Bhat A, Lappe RW, Liu B, Oates B, Rizzo J, Stankovic N, Bradshaw C (2012) Bioorg Med Chem Lett 22:4249

    Article  CAS  PubMed  Google Scholar 

  8. Betti M, Genesio E, Panico A, Sanna Coccone S, Wiedenau P (2013) Org Process Res Dev 17:1042

    Article  CAS  Google Scholar 

  9. Cervi G, Magnaghi P, Asa D, Avanzi N, Badari A, Borghi D, Caruso M, Cirla A, Cozzi L, Felder E (2014) J Med Chem 57:10443

    Article  CAS  PubMed  Google Scholar 

  10. Galiano S, Erviti O, Perez S, Moreno A, Juanenea L, Aldana I, Monge A (2005) Arzneimittelforschung 55:81

    CAS  PubMed  Google Scholar 

  11. Juanenea L, Galiano S, Erviti O, Moreno A, Pérez S, Aldana I, Monge A (2004) Bioorg Med Chem 12:4717

    Article  CAS  PubMed  Google Scholar 

  12. Suresh J, Sandhu S (2012) ARKIVOC 2012:66

    Article  Google Scholar 

  13. Wang Q, Mgimpatsang KC, Li X, Dömling A (2021) J Org Chem 86:9771

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  14. Sharma M, Borah P, Bhuyan PJ (2015) Synth Commun 45:1792

    Article  CAS  Google Scholar 

  15. Panahi F, Niknam E, Sarikhani S, Haghighi F, Khalafi-Nezhad A (2017) New J Chem 41:12293

    Article  CAS  Google Scholar 

  16. Demirci T, Çelik B, Yildiz Y, Eriş S, Arslan M, Sen F, Kilbas B (2016) RSC Adv 6:76948

    Article  CAS  Google Scholar 

  17. Yan X, Ling F, Zhang Y, Ma C (2015) Org Lett 17:3536

    Article  CAS  PubMed  Google Scholar 

  18. Hantzsch A (1881) Ber Dtsch Chem Ges 14:1637

    Article  Google Scholar 

  19. Abdella AM, Abdelmoniem AM, Abdelhamid IA, Elwahy AHM (2020) J Heterocycl Chem 57:1476

    Article  CAS  Google Scholar 

  20. Jindal D, Singh Sohal H, Singh Malhi D (2022) Mater Today: Proc 68:950

    CAS  Google Scholar 

  21. Bialer M (2012) Adv Drug Deliv Rev 64:887

    Article  CAS  PubMed  Google Scholar 

  22. Cain CK, Kleis J (1959) J Med Pharm Chem 1:31

    Article  CAS  PubMed  Google Scholar 

  23. Smissman EE, Robinson RA, Buckwalter MA (1971) J Med Chem 14:853

    Article  CAS  PubMed  Google Scholar 

  24. Janser I, Janser R (2012) Barbituric acid-based GABA(A) receptor modulators for the treatment of sleep disorder and epilepsy and as anesthetics. In: Lamberth C, Dinges J (eds) Bioactive heterocyclic compound classes: pharmaceuticals. Viley-VCH, p 51

    Chapter  Google Scholar 

  25. Mahmudov KT, Kopylovich MN, Maharramov AM, Kurbanova MM, Gurbanov AV, Pombeiro AJL (2014) Coord Chem Rev 265:1

    Article  CAS  Google Scholar 

  26. Varun DN, Manjunatha JG, Hareesha N, Sandeep S, Mallu P, Karthik CS, Prinith NS, Sreeharsha N, Asdaq SMB (2021) Monatsh Chem 152:1183

    Article  CAS  Google Scholar 

  27. Boukis AC, Reiter K, Frölich M, Hofheinz D, Meier MA (2018) Nat Commun 9:1

    Article  CAS  Google Scholar 

  28. Younus HA, Al-Rashida M, Hameed A, Uroos M, Salar U, Rana S, Khan KM (2021) Expert Opin Ther Pat 31:267

    Article  CAS  PubMed  Google Scholar 

  29. Balalaie S, Ramezanpour S, Bararjanian M, Gross JH (2008) Synth Commun 38:1078

    Article  CAS  Google Scholar 

  30. Ramezanpour S, Balalaie S, Rominger F, Alavijeh NS, Bijanzadeh HR (2013) Tetrahedron 69:10718

    Article  CAS  Google Scholar 

  31. Fathi Vavsari V, Mohammadi Ziarani G, Balalaie S, Badiei A, Golmohammadi F, Ramezanpour S, Rominger F (2017) ChemistrySelect 2:3496

    Article  CAS  Google Scholar 

  32. Litvić M, Cepanec I, Vinković V (2003) Heterocycl Commun 9:385

    Article  Google Scholar 

  33. Katritzky AR, Ostercamp DL, Yousaf TI (1986) Tetrahedron 42:5729

    Article  CAS  Google Scholar 

  34. Rostami H, Shiri L (2021) Appl Organomet Chem 35:e6293

    CAS  Google Scholar 

  35. Brahmachari G, Nurjamal K, Karmakar I, Begam S, Nayek N, Mandal B (2017) ACS Sustain Chem Eng 5:9494

    Article  CAS  Google Scholar 

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Acknowledgements

We are grateful to Dr. Hooman Kaghazian (Director of Celltech Accelerator) for helping us with financial support.

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Correspondence to Sorour Ramezanpour or Seyed Abdulmajid Ayatollahi.

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Yazdian, F., Ramezanpour, S., Ayatollahi, S.A. et al. An efficient multicomponent synthesis of fused pyrido-dipyrimidines containing tranexamic acid under green conditions. Monatsh Chem 154, 223–229 (2023). https://doi.org/10.1007/s00706-022-03027-2

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  • DOI: https://doi.org/10.1007/s00706-022-03027-2

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