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.
Graphic abstract
Similar content being viewed by others
References
Seiyaku D (1983) Drugs Fut 8:395
Hayakawa I, Hiramitsu T, Tanaka Y (1984) Chem Pharm Bull 32:4907
Tanaka Y, Sujuki N, Hayakawa I, Sujuki K (1984) Chem Pharm Bull 32:4923
Koga H, Itoh A, Murayama S, Suzue S, Irikura T (1980) J Med Chem 23:1358
Chu DTW, Maleczka REJ (1987) J Heterocycl Chem 24:453
Dell A, William DH, Morris HR, Smith GA, Feeney J, Roberts GCK (1975) J Am Chem Soc 97:2497
Bailly C, Echepare S, Gago F, Waring M (1999) Anti-Cancer Drug Des 14:291
Sato S, Shiratori O, Katagiri KJ (1967) Antibiot 20:270
Gonzalez M, Cerecetto H (2012) Expert Opin Ther Pat 22:1289
Carta A, Piras S, Loriga G, Paglietti G (2006) Mini-Rev Med Chem 6:1179
Padmavathy K, Nagendrappa G, Geetha KV (2011) Tetrahedron Lett 52:544
Lee H, Cho S, Namgoong K, Jung JK, Cho J, Yang S (2004) Bioorg Med Chem Lett 14:1235
Kim YB, Kim YH, Park JY, Kim SK (2004) Bioorg Med Chem Lett 14:541
Toshima K, Ozawa T, Kimura T, Matsumura S (2004) Bioorg Med Chem Lett 14:2777
Tanimori S, Nishimura T, Kirihata M (2009) Bioorg Med Chem Lett 19:4119
Shibinskaya MO, Lyakhov SA, Mazepa AV, Andronati SA, Turov AV, Zholobak NM, Spivak NY (2010) Eur J Med Chem 45:1237
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
Heerden LV, Cloete TT, Breytenbach JW, Kock CD, Smith PJ, Breytenbach JC, Da DDN (2012) Eur J Med Chem 55:335
Ramalingam P, Ganapaty S, Rao CB (2010) Bioorg Med Chem Lett 20:406
Torres E, Moreno E, Ancizu S, Barea C, Galiano S, Aldana I, Monge A, Silanes SP (2011) Bioorg Med Chem Lett 21:3699
Abid M, Azam A (2006) Bioorg Med ChemLett 16:2812
Kotharkar SA, Shinde DB (2006) Bioorg Med Chem Lett 16:6181
Khan SA, Asiri AM (2011) Arab J Chem 4:349
Parhi AK, Zhang Y, Saionz KW, Pradhan P, Kaul M, Trivedi K, Pilch DS, Lavoie EJ (2013) Bioorg Med Chem Lett 23:4968
Kalinin AA, Voloshina AD, Kulik NV, Zobov VV, Mamedova VA (2013) Eur J Med Chem 66:345
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
Peraman R, Varma RV, Reddy YP (2015) Bioorg Med Chem Lett 25:4314
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
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
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
Bhosale RS, Sarda SR, Andhapure SS, Jadhav WN, Bhusare SR, Pawar RP (2005) Tetrahedron Lett 46:7183
More SV, Sastry MNV, Yao CF (2006) Green Chem 8:91
Mahesh R, Devadoss T, Pandey DK, Bhatt S (2011) Bioorg Med Chem Lett 21:1253
Vicente E, Duchowicz PR, Benítez D, Castro EA, Cerecetto H, González M, Monge A (2010) Bioorg Med Chem Lett 20:831
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
Khattab SN, Hassan SY, Bekhit AA, Massry AME, Langer V (2010) Eur J Med Chem 45:4479
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
Dailey S, Feast JW, Peace RJ, Sage IC, Till S, Wood EL (2001) J Mater Chem 11:2238
Sascha O, Rudiger F (2004) Synlett 1509
Peter PC, Gang Z, Grace AM, Carlos H, Linda MGT (2004) Org Lett 6:333
Zheng H, Jiang C, Chiu MH, Covey JM, Chan KK (2002) Drug Metab Dispos 30:344
Zarrouk A, Dafali A, Hammouti B, Zarrok H, Boukhris S, Zertoubi M (2010) Int J Electrochem Sci 5:46
Barchechath SD, Tawatao RI, Corr M, Carson DA, Cottam HB (2005) Bioorg Med Chem Lett 15:1785
Brana MF, Cacho M, Gradillas A, Pascual-Teresa B, Ramos A (2001) Curr Pharm Des 7:1745
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
Bringmann G, Feineis D (2000) Acta Chim Ther 26:151
Wang Z, Wang B, Wu J (2007) J Comb Chem 9:811
Bai L, Wang JX, Zhang Y (2003) Green Chem 5:615
Pironti V, Colonna S (2005) Green Chem 7:43
Nüchter M, Ondruschka B, Bonrath W, Gum A (2004) Green Chem 6:128
Sheldon RA (2000) C R Acad Sci Ser IIc: Chim 3:541
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
Saha P, Naskar S, Paira P, Hazra A, Sahu KB, Paira R, Banerjee S, Mondal NB (2009) Green Chem 11:931
Nicewicz DA, MacMillan DWC (2008) Science 77:322
Prier CK, Rankic DA, MacMillan DWC (2013) Chem Rev 113:5322
Narayanam JMR, Stephenson CRJ (2011) Chem Soc Rev 40:102
Yoon TP, Ischay MA, Du J (2010) Nat Chem 2:527
Schultz DM, Yoon TP (2014) Science 343:6174
Shi L, Xia W (2012) Chem Soc Rev 41:7687
Xuan J, Xiao WJ (2012) Angew Chem Int Ed 51:6828
Hari DP, König B (2013) Angew Chem Int Ed 52:4734
Xuan J, Lu LQ, Chen JR, Xiao WJ (2013) Eur J Org Chem 6755
Xi Y, Yi H, Lei A (2013) Org Biomol Chem 11:2387
Zhang G, Bian C, Lei A (2015) Chin J Cat 36:1428
Yadav AK, Yadav LDS (2014) Tetrahedron Lett 55:2065
Pan Y, Kee CW, Chen L, Tan CH (2011) Green Chem 13:2682
Xiao T, Li L, Lin G, Wang Q, Zhang P, Mao Z, Zhou L (2014) Green Chem 16:2418
Pan Y, Wang S, Kee CW, Dubuisson E, Yang Y, Loh KP, Tan CH (2011) Green Chem 13:3341
Liu H, Feng W, Kee CW, Zhao Y, Leow D, Pan Y, Tan CH (2010) Green Chem 12:953
Hari DP, Schroll P, König B (2012) J Am Chem Soc 134:2958
Guo W, Lu LQ, Wang Y, Wang YN, Chen JR, Xiao WJ (2015) Angew Chem Int Ed 54:2265
Neumann M, Füldner S, König B, Zeitler K (2011) Angew Chem Int Ed 50:951
Luo K, Chen YZ, Yang WC, Zhu J, Wu L (2016) Org Lett 18:452
Zhu X, Xie X, Li P, Guo J, Wang L (2016) Org Lett 18:1546
Yang D, Huang B, Wei W, Li J, Lin G, Liu Y, Ding J, Sun P, Wang H (2016) Green Chem 18:5630
Srivastavaa V, Singh PP (2017) RSC Adv 7:31377
Paira P, Hazra A, Sahu KB, Banerjee S, Mondal NB, Sahu NP, Weber M, Luger P (2008) Tetrahedron 64:4026
Sarkar B, Mondal A, Madaan Y, Roy N, Moorthy A, Kuo Y-C, Paira P (2019) Dalton Trans 48:12257
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.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-020-02641-2