Facile Synthesis of Dispiroheterocycles through One-Pot [3+2] Cycloaddition, and Their Antiviral Activity

Abstract

A facile synthesis of novel dispiroheterocycles has been developed through one-pot [3+2] cycloaddition between isatins, amino acids, and aurones. Thirty different dispiroheterocycles were synthesized eusing this method which features mild conditions, convenient operation, and high efficacy. Evaluation of the bioactivity of these dispiroheterocyclic products revealed antiviral activity against tobacco mosaic virus (TMV).

Key words

cycloaddition - isatins - aurones - dispiroheterocycles - antiviral activity

• References

• 1a Hein CD, Liu X.-M, Wang D. Pharm. Res. 2008; 25: 2216
• 1b van Dijk M, Rijkers DT. S, Liskamp RM. J, van Nostrum CF, Hennink WE. Bioconjugate Chem. 2009; 20: 2001
• 1c Porta R, Benaglia M, Puglisi A. Org. Process Res. Dev. 2016; 20: 2
• 2a Binder WH, Sachsenhofer R. Macromol. Rapid Commun. 2007; 28: 15
• 2b Binder WH, Sachsenhofer R. Macromol. Rapid Commun. 2008; 29: 952
• 2c Nair DP, Podgorski M, Chatani S, Gong T, Xi WX, Fenoli CR, Bowman CN. Chem. Mater. 2014; 26: 724
• 3a Dömling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083
• 3b Thirumurugan P, Matosiuk D, Jozwiak K. Chem. Rev. 2013; 113: 4905
• 4a Ruiz-Sanchis P, Savina SA, Albericio F, Álvarez M. Chem. Eur. J. 2011; 17: 1388
• 4b Narayan R, Potowski M, Jia Z.-J, Antonchick AP, Waldmann H. Acc. Chem. Res. 2014; 47: 1296
• 5a Panda SS, Jones RA, Bachawala P, Mohapatra PP. Mini-Rev. Med. Chem. 2017; 17: 1515
• 5b Yu B, Zheng Y.-C, Shi X.-J, Qi P.-P, Liu H.-M. Anti-Cancer Agents Med. Chem. 2016; 16: 1315
• 5c Mei G.-J, Shi F. Chem. Commun. 2018; 54: 6607
• 6a Kazmierski WM, Maynard A, Duan M, Baskaran S, Botyanszki J, Crosby R, Dickerson S, Tallant M, Grimes R, Hamatake R, Leivers M, Roberts CD, Walker J. J. Med. Chem. 2014; 57: 2058
• 6b Dang Q, Zhang Z, Tang B, Song Y, Wu L, Chen T, Bogen S, Girijavallabhan V, Olsen DB, Meinke PT. Tetrahedron Lett. 2014; 55: 3813
• 7a Dandia A, Khan S, Soni P, Indora A, Mahawar DK, Pandya P, Chauhan CS. Bioorg. Med. Chem. Lett. 2017; 27: 2873
• 7b Hassaneen HM. E, Eid EM, Eid HA, Farghaly TA, Mabkhot YN. Molecules 2017; 22: 357
• 8 García Giménez D, García Prado E, Sáenz Rodríguez T, Fernández Arche A, De la Puerta R. Planta Med. 2010; 76: 133
• 9 Edmondson S, Danishefsky SJ, Sepp-Lorenzino L, Rosen N. J. Am. Chem. Soc. 1999; 121: 2147
• 10a von Nussbaum F, Danishefsky SJ. Angew. Chem. Int. Ed. 2000; 39: 2175
• 10b Sebahar PR, Williams RM. J. Am. Chem. Soc. 2000; 122: 5666
• 11a Stephen MR, Rahman MT, Tiruveedhula VV. N. P. B, Fonseca GO, Deschamps JR, Cook JM. Chem. Eur. J. 2017; 23: 15805
• 11b Wearing XZ, Cook JM. Org. Lett. 2002; 4: 4237
• 12a Zaima K, Koga I, Iwasawa N, Hosoya T, Hirasawa Y, Kaneda T, Ismail IS, Lajis NH, Morita H. J. Nat. Med. 2013; 67: 9
• 12b Kam TS, Lek IH, Choo YM. Phytochemistry 1999; 51: 839
• 13a Zhang WB, Chen CX, Sim SM, Kwan CY. N.-S. Naunyn-Schmiedeberg’s Arch. Pharmacol. 2004; 369: 232
• 13b Deiters A, Pettersson M, Martin SF. J. Org. Chem. 2006; 71: 6547

Reviews:
• 14a Borthwick AD. Chem. Rev. 2012; 112: 641
• 14b Shi JS, Yu JX, Chen XP, Xu RX. Acta Pharmacol. Sin. 2003; 24: 97
• 14c Yu B, Yu D.-Q, Liu H.-M. Eur. J. Med. Chem. 2015; 97: 673

Selected examples:
• 14d Kumar A, Gupta G, Srivastava S, Bishnoi AK, Saxena R, Kant R, Khanna RS, Maulik PR, Dwivedi A. RSC Adv. 2013; 3: 4731
• 14e Girgis AS, Mabied AF, Stawinski J, Hegazy L, George RF, Farag H, Shalaby EM, Farag IS. A. New J. Chem. 2015; 39: 8017
• 14f Wang H.-J, Pan B.-W, Zhang W.-H, Yang C, Liu X.-L, Zhao Z, Feng T.-T, Zhou Y, Yuan W.-C. Tetrahedron 2015; 71: 8131
• 14g Kelemen AA, Satala G, Bojarski AJ, Keseru GM. Bioorg. Med. Chem. Lett. 2018; 28: 2418
• 14h Kornet MJ, Thio AP. J. Med. Chem. 1976; 19: 892

Reviews:
• 15a Le Marquand P, Tam W. Angew. Chem. Int. Ed. 2008; 47: 2926
• 15b Shibata T, Tsuchikama K. Org. Biomol. Chem. 2008; 6: 1317
• 15c Cao Z.-Y, Zhou F, Zhou J. Acc. Chem. Res. 2018; 51: 1443
• 15d Fang X, Wang C.-J. Org. Biomol. Chem. 2018; 16: 2591
• 15e Ball-Jones NR, Badillo JJ, Franz AK. Org. Biomol. Chem. 2012; 10: 5165

Selected examples:
• 15f You Y, Lu W.-Y, Wang Z.-H, Chen Y.-Z, Xu X.-Y, Zhang X.-M, Yuan W.-C. Org. Lett. 2018; 20: 4453
• 15g Yan J, Shi K, Zhao C, Ding L, Jiang S, Yang L, Zhong G. Chem. Commun. 2018; 54: 1567
• 15h Huang N, Zou L, Peng Y. Org. Lett. 2017; 19: 5806
• 15i Liu J.-Y, Zhao J, Zhang J.-L, Xu P.-F. Org. Lett. 2017; 19: 1846
• 15j Wagner B, Hiller W, Ohno H, Krause N. Org. Biomol. Chem. 2016; 14: 1579
• 15k Trost BM, Cramer N, Silverman SM. J. Am. Chem. Soc. 2007; 129: 12396
• 15l Selvakumar K, Vaithiyanathan V, Shanmugam P. Chem. Commun. 2010; 46: 2826
• 15m Awata A, Arai T. Chem. Eur. J. 2012; 18: 8278
• 16a El-Ahl A.-AS. Heteroat. Chem. 2002; 13: 324
• 16b Hazra A, Paira P, Sahu KB, Naskar S, Saha P, Paira R, Mondal S, Maity A, Luger P, Weber M, Mondal NB, Banerjee S. Tetrahedron Lett. 2010; 51: 1585
• 16c Babu SR, Raghunathan R. Tetrahedron Lett. 2008; 49: 4618
• 16d Wu G, Ouyang L, Liu J, Zeng S, Huang W, Han B, Wu F, He G, Xiang M. Mol. Diversity 2013; 17: 271
• 16e Fokas D, Ryan WJ, Casebier DS, Coffen DL. Tetrahedron Lett. 1998; 39: 2235
• 16f Revathy K, Lalitha A. RSC Adv. 2014; 4: 279
• 16g Dutta K, Kumar M, Ghosh SK, Das A, Chowdhury R. Synth. Commun. 2019; 49: 444
• 16h Girgis AS, Panda SS, Srour AM, Farag H, Ismail NS. M, Elgendy M, Abdel-Aziz AK, Katritzky AR. Org. Biomol. Chem. 2015; 13: 6619
• 16i Manikandan S, Mohamed Ashraf M, Raghunathan R. Synth. Commun. 2001; 31: 3593
• 17a Tabatabaei Rezaei SJ, Nabid MR, Yari A, Ng SW. Ultrason. Sonochem. 2011; 18: 49
• 17b Tiwari KN, Pandurang TP, Pant S, Kumar R. Tetrahedron Lett. 2016; 57: 2286
• 18a Naga Siva Rao J, Raghunathan R. Tetrahedron Lett. 2012; 53: 854
• 18b Bakthadoss M, Kannan D, Sivakumar D. Synthesis 2012; 44: 793
• 19a Poornachandran M, Raghunathan R. Synth. Commun. 2007; 37: 2507
• 19b Poornachandran M, Muruganantham R, Raghunathan R. Synth. Commun. 2006; 36: 141
• 20 Pavlovskaya TL, Yaremenko FG, Lipson VV, Shishkina SV, Shishkin OV, Musatov VI, Karpenko AI. Beilstein J. Org. Chem. 2014; 10: 117
• 21a Kumar RS, Rajesh SM, Perumal S, Banerjee D, Yogeeswari P, Sriram D. Eur. J. Med. Chem. 2010; 45: 411
• 21b Prasanna P, Balamurugan K, Perumal S, Yogeeswari P, Sriram D. Eur. J. Med. Chem. 2010; 45: 5653
• 21c Ranjith KR, Perumal S, Senthilkumar P, Yogeeswari P, Sriram D. Eur. J. Med. Chem. 2009; 44: 3821
• 21d Filatov AS, Knyazev NA, Molchanov AP, Panikorovsky TL, Kostikov RR, Larina AG, Boitsov VM, Stepakov AV. J. Org. Chem. 2017; 82, 959
• 21e Yue J, Chen S, Zuo X, Liu X.-L, Xu S.-W, Zhou Y. Tetrahedron Lett. 2019; 60: 137

Review:
• 22a Sanchez LM, Thomas HJ, Romanelli GP. Mini-Rev. Org. Chem. 2015; 12: 115

Selected examples:
• 22b Royes J, Ni S, Farré A, La Cascia E, Carbó JJ, Cuenca AB, Maseras F, Fernández E. ACS Catal. 2018; 8: 2833
• 22c Lanka S, Thennarasu S, Perumal PT. Tetrahedron Lett. 2012; 53: 7052
• 22d Muthusamy S, Kumar SG. Tetrahedron 2016; 72: 2392
• 22e Sun Y.-H, Xiong Y, Peng C.-Q, Li W, Xiao J.-A, Yang H. Org. Biomol. Chem. 2015; 13: 7907
• 23a Ding Y, Zhang T, Chen Q.-Y, Zhu C. Org. Lett. 2016; 18: 4206
• 23b Zhu C, Bi B, Ding Y, Zhang T, Chen Q.-Y. Tetrahedron 2015; 71: 9251
• 23c Zhu C, Bi B, Ding Y, Zhang T, Chen Q.-Y. Org. Biomol. Chem. 2015; 13: 6278
• 23d Zhang M, Yang W.-B, Qian M, Zhao T, Yang L.-Q, Zhu C. Tetrahedron 2018; 74: 955
• 23e Zhang M, Li T, Qian M, Li K, Qin Y, Zhao T, Yang L.-Q. J. Heterocycl. Chem. 2018; 55: 1574
• 24a Rehn S, Bergman J, Stensland B. Eur. J. Org. Chem. 2004; 413
• 24b Amornraksa K, Grigg R, Gunaratne HQ. N, Kemp J, Sridharan V. J. Chem. Soc., Perkin Trans. 1 1987; 2285
• 25a Wang KL, Su B, Wang ZW, Wu M, Li Z, Hu YN, Fan ZJ, Mi N, Wang QM. J. Agric. Food Chem. 2010; 58: 2703
• 25b Chen LW, Xie JL, Song HJ, Liu YX, Gu YC, Wang LZ, Wang QM. J. Agric. Food Chem. 2016; 64: 6508