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Combined palladium/eosin Y-catalysed direct synthesis of anticancer biarylquinolinooxazocino-quinoxaline-1-ones under visible light in one-pot sequence: a revisited proof of concept

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Abstract

A novel, efficient, and green catalytic system under visible light irradiation has been introduced for the synthesis of anticancer biarylquinolooxazocino-quinoxaline-1-ones in one-pot sequence. The developed synthetic approach will be successfully utilized for the synthesis of various bioactive biarylquinolone in near future. Also, the cytotoxicity profile of these scaffolds has unveiled their superb cytoselectivity in HeLa and MCF-7 cell line compared to cisplatin.

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References

  1. Seiyaku D (1983) Drugs Fut 8:395

    Google Scholar 

  2. Hayakawa I, Hiramitsu T, Tanaka Y (1984) Chem Pharm Bull 32:4907

    CAS  PubMed  Google Scholar 

  3. Tanaka Y, Sujuki N, Hayakawa I, Sujuki K (1984) Chem Pharm Bull 32:4923

    CAS  PubMed  Google Scholar 

  4. Koga H, Itoh A, Murayama S, Suzue S, Irikura T (1980) J Med Chem 23:1358

    CAS  PubMed  Google Scholar 

  5. Chu DTW, Maleczka REJ (1987) J Heterocycl Chem 24:453

    CAS  Google Scholar 

  6. Dell A, William DH, Morris HR, Smith GA, Feeney J, Roberts GCK (1975) J Am Chem Soc 97:2497

    CAS  PubMed  Google Scholar 

  7. Bailly C, Echepare S, Gago F, Waring M (1999) Anti-Cancer Drug Des 14:291

    CAS  Google Scholar 

  8. Sato S, Shiratori O, Katagiri KJ (1967) Antibiot 20:270

    CAS  Google Scholar 

  9. Gonzalez M, Cerecetto H (2012) Expert Opin Ther Pat 22:1289

    CAS  PubMed  Google Scholar 

  10. Carta A, Piras S, Loriga G, Paglietti G (2006) Mini-Rev Med Chem 6:1179

    CAS  PubMed  Google Scholar 

  11. Padmavathy K, Nagendrappa G, Geetha KV (2011) Tetrahedron Lett 52:544

    CAS  Google Scholar 

  12. Lee H, Cho S, Namgoong K, Jung JK, Cho J, Yang S (2004) Bioorg Med Chem Lett 14:1235

    CAS  PubMed  Google Scholar 

  13. Kim YB, Kim YH, Park JY, Kim SK (2004) Bioorg Med Chem Lett 14:541

    CAS  PubMed  Google Scholar 

  14. Toshima K, Ozawa T, Kimura T, Matsumura S (2004) Bioorg Med Chem Lett 14:2777

    CAS  PubMed  Google Scholar 

  15. Tanimori S, Nishimura T, Kirihata M (2009) Bioorg Med Chem Lett 19:4119

    CAS  PubMed  Google Scholar 

  16. Shibinskaya MO, Lyakhov SA, Mazepa AV, Andronati SA, Turov AV, Zholobak NM, Spivak NY (2010) Eur J Med Chem 45:1237

    CAS  PubMed  Google Scholar 

  17. Shibinskaya MO, Karpenko AS, Lyakhov SA, Andronati SA, Zholobak NM, Spivak NY, Samochina NA, Shafran LM, Zubritsky MJ, Galat VF (2011) Eur J Med Chem 46:794

    CAS  PubMed  Google Scholar 

  18. Heerden LV, Cloete TT, Breytenbach JW, Kock CD, Smith PJ, Breytenbach JC, Da DDN (2012) Eur J Med Chem 55:335

    PubMed  Google Scholar 

  19. Ramalingam P, Ganapaty S, Rao CB (2010) Bioorg Med Chem Lett 20:406

    CAS  PubMed  Google Scholar 

  20. Torres E, Moreno E, Ancizu S, Barea C, Galiano S, Aldana I, Monge A, Silanes SP (2011) Bioorg Med Chem Lett 21:3699

    CAS  PubMed  Google Scholar 

  21. Abid M, Azam A (2006) Bioorg Med ChemLett 16:2812

    CAS  Google Scholar 

  22. Kotharkar SA, Shinde DB (2006) Bioorg Med Chem Lett 16:6181

    CAS  PubMed  Google Scholar 

  23. Khan SA, Asiri AM (2011) Arab J Chem 4:349

    CAS  Google Scholar 

  24. Parhi AK, Zhang Y, Saionz KW, Pradhan P, Kaul M, Trivedi K, Pilch DS, Lavoie EJ (2013) Bioorg Med Chem Lett 23:4968

    CAS  PubMed  PubMed Central  Google Scholar 

  25. Kalinin AA, Voloshina AD, Kulik NV, Zobov VV, Mamedova VA (2013) Eur J Med Chem 66:345

    CAS  PubMed  Google Scholar 

  26. Zhang M, Dai ZC, Qian SS, Liu JY, Xiao Y, Lu AM, Zhu HL, Wang JX, Ye YH (2014) J Agric Food Chem 62:9637

    CAS  PubMed  Google Scholar 

  27. Peraman R, Varma RV, Reddy YP (2015) Bioorg Med Chem Lett 25:4314

    CAS  PubMed  Google Scholar 

  28. Burguete A, Pontiki E, Litina DH, Villar R, Vicente E, Solano B, Ancizu S, Silanes SP, Aldanaa I, Monge A (2007) Bioorg Med Chem Lett 17:6439

    CAS  PubMed  Google Scholar 

  29. Guillon J, Mouray E, Moreau S, Mullié C, Forfar I, Desplat V, Belisle-Fabre S, Pinaud N, Ravanello F, Le-Naour A, Léger JM, Gosmann G, Jarry C, Déléris G, Sonnet P, Grellier P (2011) Eur J Med Chem 46:2310

    CAS  PubMed  Google Scholar 

  30. Tanis SP, Strohbach JW, Parker TT, Moon MW, Thaisrivongs S, Perrault WR, Hopkins TA, Knechtel ML, Oien NL, Wieber JL, Stephanski KJ, Wathen MW (2010) Bioorg Med Chem Lett 20:1994

    CAS  PubMed  Google Scholar 

  31. Bhosale RS, Sarda SR, Andhapure SS, Jadhav WN, Bhusare SR, Pawar RP (2005) Tetrahedron Lett 46:7183

    CAS  Google Scholar 

  32. More SV, Sastry MNV, Yao CF (2006) Green Chem 8:91

    CAS  Google Scholar 

  33. Mahesh R, Devadoss T, Pandey DK, Bhatt S (2011) Bioorg Med Chem Lett 21:1253

    CAS  PubMed  Google Scholar 

  34. Vicente E, Duchowicz PR, Benítez D, Castro EA, Cerecetto H, González M, Monge A (2010) Bioorg Med Chem Lett 20:831

    Google Scholar 

  35. Torres E, Viguri EM, Galiano S, Devarapally G, Crawford PW, Azqueta A, Arbillaga L, Varela J, Birriel E, Maio RD, Cerecetto H, González M, Aldana I, Monge A, Silanes SP (2013) Eur J Med Chem 66:324

    CAS  PubMed  Google Scholar 

  36. Khattab SN, Hassan SY, Bekhit AA, Massry AME, Langer V (2010) Eur J Med Chem 45:4479

    CAS  PubMed  Google Scholar 

  37. Brock ED, Lewis DM, Yousaf TI, Harper HH (1999) Reactive dyes and their use. Patent WO 9951688, Oct 14, 1999; (1999) Chem Abstr 131:287743

  38. Dailey S, Feast JW, Peace RJ, Sage IC, Till S, Wood EL (2001) J Mater Chem 11:2238

    CAS  Google Scholar 

  39. Sascha O, Rudiger F (2004) Synlett 1509

  40. Peter PC, Gang Z, Grace AM, Carlos H, Linda MGT (2004) Org Lett 6:333

    Google Scholar 

  41. Zheng H, Jiang C, Chiu MH, Covey JM, Chan KK (2002) Drug Metab Dispos 30:344

    CAS  PubMed  Google Scholar 

  42. Zarrouk A, Dafali A, Hammouti B, Zarrok H, Boukhris S, Zertoubi M (2010) Int J Electrochem Sci 5:46

    CAS  Google Scholar 

  43. Barchechath SD, Tawatao RI, Corr M, Carson DA, Cottam HB (2005) Bioorg Med Chem Lett 15:1785

    CAS  PubMed  Google Scholar 

  44. Brana MF, Cacho M, Gradillas A, Pascual-Teresa B, Ramos A (2001) Curr Pharm Des 7:1745

    CAS  PubMed  Google Scholar 

  45. Bringmann G, Gunther C, Ochse M, Schupp O, Tasler S (2001) In: Herz W, Falk H, Kirby GW, Moore RE, Tamm C (eds) Progress in the chemistry of organic natural products, vol 82. Springer, Wien

    Google Scholar 

  46. Bringmann G, Feineis D (2000) Acta Chim Ther 26:151

    Google Scholar 

  47. Wang Z, Wang B, Wu J (2007) J Comb Chem 9:811

    CAS  PubMed  Google Scholar 

  48. Bai L, Wang JX, Zhang Y (2003) Green Chem 5:615

    CAS  Google Scholar 

  49. Pironti V, Colonna S (2005) Green Chem 7:43

    CAS  Google Scholar 

  50. Nüchter M, Ondruschka B, Bonrath W, Gum A (2004) Green Chem 6:128

    Google Scholar 

  51. Sheldon RA (2000) C R Acad Sci Ser IIc: Chim 3:541

    CAS  Google Scholar 

  52. Paira P, Paira R, Hazra A, Sahu KB, Naskar S, Saha P, Mondal S, Maity A, Banerjee S, Mondal NB (2009) Tetrahedron Lett 50:5505

    CAS  Google Scholar 

  53. Saha P, Naskar S, Paira P, Hazra A, Sahu KB, Paira R, Banerjee S, Mondal NB (2009) Green Chem 11:931

    CAS  Google Scholar 

  54. Nicewicz DA, MacMillan DWC (2008) Science 77:322

    Google Scholar 

  55. Prier CK, Rankic DA, MacMillan DWC (2013) Chem Rev 113:5322

    CAS  PubMed  PubMed Central  Google Scholar 

  56. Narayanam JMR, Stephenson CRJ (2011) Chem Soc Rev 40:102

    CAS  PubMed  Google Scholar 

  57. Yoon TP, Ischay MA, Du J (2010) Nat Chem 2:527

    CAS  PubMed  Google Scholar 

  58. Schultz DM, Yoon TP (2014) Science 343:6174

    Google Scholar 

  59. Shi L, Xia W (2012) Chem Soc Rev 41:7687

    CAS  PubMed  Google Scholar 

  60. Xuan J, Xiao WJ (2012) Angew Chem Int Ed 51:6828

    CAS  Google Scholar 

  61. Hari DP, König B (2013) Angew Chem Int Ed 52:4734

    CAS  Google Scholar 

  62. Xuan J, Lu LQ, Chen JR, Xiao WJ (2013) Eur J Org Chem 6755

  63. Xi Y, Yi H, Lei A (2013) Org Biomol Chem 11:2387

    CAS  PubMed  Google Scholar 

  64. Zhang G, Bian C, Lei A (2015) Chin J Cat 36:1428

    Google Scholar 

  65. Yadav AK, Yadav LDS (2014) Tetrahedron Lett 55:2065

    CAS  Google Scholar 

  66. Pan Y, Kee CW, Chen L, Tan CH (2011) Green Chem 13:2682

    CAS  Google Scholar 

  67. Xiao T, Li L, Lin G, Wang Q, Zhang P, Mao Z, Zhou L (2014) Green Chem 16:2418

    CAS  Google Scholar 

  68. Pan Y, Wang S, Kee CW, Dubuisson E, Yang Y, Loh KP, Tan CH (2011) Green Chem 13:3341

    CAS  Google Scholar 

  69. Liu H, Feng W, Kee CW, Zhao Y, Leow D, Pan Y, Tan CH (2010) Green Chem 12:953

    CAS  Google Scholar 

  70. Hari DP, Schroll P, König B (2012) J Am Chem Soc 134:2958

    CAS  PubMed  Google Scholar 

  71. Guo W, Lu LQ, Wang Y, Wang YN, Chen JR, Xiao WJ (2015) Angew Chem Int Ed 54:2265

    CAS  Google Scholar 

  72. Neumann M, Füldner S, König B, Zeitler K (2011) Angew Chem Int Ed 50:951

    CAS  Google Scholar 

  73. Luo K, Chen YZ, Yang WC, Zhu J, Wu L (2016) Org Lett 18:452

    CAS  PubMed  Google Scholar 

  74. Zhu X, Xie X, Li P, Guo J, Wang L (2016) Org Lett 18:1546

    CAS  PubMed  Google Scholar 

  75. Yang D, Huang B, Wei W, Li J, Lin G, Liu Y, Ding J, Sun P, Wang H (2016) Green Chem 18:5630

    CAS  Google Scholar 

  76. Srivastavaa V, Singh PP (2017) RSC Adv 7:31377

    Google Scholar 

  77. Paira P, Hazra A, Sahu KB, Banerjee S, Mondal NB, Sahu NP, Weber M, Luger P (2008) Tetrahedron 64:4026

    CAS  Google Scholar 

  78. Sarkar B, Mondal A, Madaan Y, Roy N, Moorthy A, Kuo Y-C, Paira P (2019) Dalton Trans 48:12257

    CAS  PubMed  Google Scholar 

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Acknowledgements

The authors gratefully acknowledge VIT for providing ‘VIT SEED GRANT’, Vellore for the support through Seed Grant for Research. We acknowledge DST, New Delhi, India for DST-FIST project.

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Correspondence to Priyankar Paira.

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Roy, N., Paira, P. Combined palladium/eosin Y-catalysed direct synthesis of anticancer biarylquinolinooxazocino-quinoxaline-1-ones under visible light in one-pot sequence: a revisited proof of concept. Monatsh Chem 151, 1163–1172 (2020). https://doi.org/10.1007/s00706-020-02641-2

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