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Synthesis of novel γ-butyrolactone-based phenazine compounds via microwave-assisted multicomponent domino reactions

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Chemistry of Heterocyclic Compounds Aims and scope

A series of new and significative γ-butyrolactone-based phenazines were synthesized through two-step one-pot five-component reactions of 2-hydroxy-1,4-naphthoquinone, a variety of aromatic aldehydes, benzene-1,2-diamine, tetronic acid, and ammonium acetate in glacial acetic acid. The synthesis proceeded via condensation, Michael addition, tautomerization sequence of steps. All the synthesized compounds were fully characterized by spectral data.

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References

  1. Choudhary, M. I.; Yousuf, S.; Samreen; Ahmed, S.; Atta-Ur-Rahman Nat. Prod. Res. 2007, 21, 877.

    Article  CAS  Google Scholar 

  2. Watanabe, I.; Koike, K.; Satou, T.; Nikaido, T. Biol. Pharm. Bull. 1999, 22, 1310.

    Article  CAS  Google Scholar 

  3. Thanh, N. H.; Phuong, H. T.; Tu Anh, L. T.; Thuy, G. L. N.; Quynh Giang, N. T.; Anh, N. T.; Tuyet Anh, D. T.; Van Kiem, P. Nat. Prod. Commun. 2022, 17, 1934578X2211331.

  4. Nguyen, H. T.; Le-Nhat-Thuy, G.; Thi, P. H.; Thi, Q. G. N.; Nguyen, T. A.; Thi, T. H. N.; Thi, T. A. D.; Nguyen, T. V. Chem. Biodiversity 2022, 19, e202200359.

    CAS  Google Scholar 

  5. Nguyen Thi, Q. G.; Le-Nhat-Thuy, G.; Dang Thi, T. A.; Thi, P. H.; Anh, N. T.; Nguyen Thi, T. H.; Nguyen, T. T.; Nguyen, H. T.; Hoang, M. H.; Nguyen, T. V. Bioorg. Med. Chem. Lett. 2021, 37, 127841.

    Article  CAS  Google Scholar 

  6. Haritakun, R.; Rachtawee, P.; Chanthaket, R.; Boonyuen, N.; Isaka, M. Chem. Pharm. Bull. 2010, 58, 1545.

    Article  CAS  Google Scholar 

  7. Wang, Y.; Zheng, J.; Liu, P.; Wang, W.; Zhu, W. Mar. Drugs 2011, 9, 1368.

    Article  CAS  Google Scholar 

  8. Bai, Z.-Q.; Lin, X.; Wang, Y.; Wang, J.; Zhou, X.; Yang, B.; Liu, J.; Yang, X.; Wang, Y.; Liu, Y. Fitoterapia 2014, 95, 194.

    Article  CAS  Google Scholar 

  9. Thi, T. A. D.; Le-Nhat-Thuy, G.; Thi, Q. G. N.; Thi, P. H.; Tuan, A. N.; Mai, H. H.; Ha, T. N.; Le, T. A.; Nguyen, T. V. Chem. Heterocycl. Compd. 2021, 57, 137.

    Article  CAS  Google Scholar 

  10. Chen, L. Z.; Wu, J.; Li, K.; Wu, Q. Q.; Chen, R.; Liu, X. H.; Ruan, B. F. Eur. J. Med. Chem. 2020, 206, 112722.

    Article  CAS  Google Scholar 

  11. Tran, Q. T. N.; Wong, W. S. F.; Chai, C. L. L. Eur. J. Med. Chem. 2019, 174, 33.

    Article  CAS  Google Scholar 

  12. Salaski, E. J.; Krishnamurthy, G.; Ding, W.-D.; Yu, K.; Insaf, S. S.; Eid, C.; Shim, J.; Levin, J. I.; Tabei, K.; Toral-Barza, L.; Zhang, W.-G.; McDonald, L. A.; Honores, E.; Hanna, C.; Yamashita, A.; Johnson, B.; Li, Z.; Laakso, L.; Powell, D.; Mansour, T. S. J. Med. Chem. 2009, 52, 2181.

    Article  CAS  Google Scholar 

  13. Nguyen, H. T.; Nguyen Thi, Q. G.; Nguyen Thi, T. H.; Thi, P. H.; Le-Nhat-Thuy, G.; Thi, T. A. D.; Le-Quang, B.; Pham-The, H.; Nguyen, T. V. RSC Adv. 2022, 12, 22004.

    Article  CAS  Google Scholar 

  14. Sugiyama, Y.; Yoshida, K.; Abe, N.; Hirota, A. Biosci., Biotechnol., Biochem. 2010, 74, 881.

    Article  CAS  Google Scholar 

  15. Lohézic-Le Dévéhat, F.; Tomasi, S.; Elix, J. A.; Bernard, A.; Rouaud, I.; Uriac, P.; Boustie, J. J. Nat. Prod. 2007, 70, 1218.

    Article  Google Scholar 

  16. (a) Kitagawa, M.; Okabe, T.; Ogino, H.; Matsumoto, H.; Suzuki-Takahashi, I.; Kokubo, T.; Higashi, H.; Saitoh, S.; Taya, Y.; Yasuda, H.; Ohba, Y.; Nishimura, S.; Tanaka, N.; Okuyama, A. Oncogene 1993, 8, 2425. (b) Nishio, K.; Ishida, T.; Arioka, H.; Kurokawa, H.; Fukuoka, K.; Nomoto, T.; Fukumoto, H.; Yokote, H.; Saijo, N. Anticancer Res. 1996, 16, 3387. (c) Schimmel, T. G.; Coffman, A. D.; Parsons, S. J. Appl. Environ. Microbiol. 1998, 64, 3707. d Fischer, P. M.; Lane, D. P. Curr. Med. Chem. 2000, 7, 1213.

  17. Vivino, F. B.; Al-Hashimi, I.; Khan, Z.; LeVeque, F. G.; Salisbury, P. L. 3rd; Tran-Johnson, T. K.; Muscoplat, C. C.; Trivedi, M.; Goldlust, B.; Gallagher, S. C. Arch. Intern. Med. 1999, 159, 174.

  18. Krattenmacher, R. Contraception 2000, 62, 29.

  19. Kagawa, C. M.; Cella, J. A.; Van Arman, C. G. Science 1957, 126, 1015.

    Article  CAS  Google Scholar 

  20. Jayatilake, G. S.; Thornton, M. P.; Leonard, A. C.; Grimwade, J. E.; Baker, B. J. J. Nat. Prod. 1996, 59, 293.

    Article  CAS  Google Scholar 

  21. Brisbane, P. G.; Janik, L. J.; Tate, M. E.; Warren, R. F. Antimicrob. Agents Chemother. 1987, 31, 1967.

    Google Scholar 

  22. Hussain, H.; Specht, S.; Sarite, S. R.; Saeftel, M.; Hoerauf, A.; Schulz, B.; Krohn, K. J. Med. Chem. 2011, 54, 4913.

    Article  CAS  Google Scholar 

  23. Le-Nhat-Thuy, G.; Thi, T. A. D.; Nguyen Thi, Q. G.; Thi, P. H.; Nguyen, T. A.; Nguyen, H. T.; Nguyen Thi, T. H.; Nguyen, H. S.; Nguyen, T. V. Bioorg. Med. Chem. Lett. 2021, 43, 128054.

    Article  CAS  Google Scholar 

  24. Wang, S.-L.; Wu, F.-Y.; Cheng, C.; Zhang, G.; Liu, Y.-P.; Jiang, B.; Shi, F.; Tu, S.-J. ACS Comb. Sci. 2011, 13, 135.

    Article  CAS  Google Scholar 

  25. Wang, J.; Zhi, X.; Yu, X.; Xu, H. J. Agric. Food Chem. 2013, 61, 6336.

    Article  CAS  Google Scholar 

  26. Rewcastle, G. W.; Denny, W. A.; Baguley, B. C. J. Med. Chem. 1987, 30, 843.

    Article  CAS  Google Scholar 

  27. Kondratyuk, T. P.; Park, E.-J.; Yu, R.; Van Breemen, R. B.; Asolkar, R. N.; Murphy, B. T.; Fenical, W.; Pezzuto, J. M. Mar. Drugs 2012, 10, 451.

    Article  CAS  Google Scholar 

  28. Marler, L.; Conda-Sheridan, M.; Cinelli, M. A.; Morrell, A. E.; Cushman, M.; Chen, L.; Huang, K.; Van Breemen, R.; Pezzuto, J. M. Anticancer Res. 2010, 30, 4873.

    CAS  Google Scholar 

  29. Makgatho, M. E.; Anderson, R.; O'Sullivan, J. F.; Egan, T. J.; Freese, J. A.; Cornelius, N.; van Rensburg, C. E. J. Drug Dev. Res. 2000, 50, 195.

    Article  CAS  Google Scholar 

  30. De Andrade-Neto, V. F.; Goulart, M. O. F.; Da Silva Filho, J. F.; Da Silva, M. J.; Pinto, M. D. C. F. R.; Pinto, A. V.; Zalis, M. G.; Carvalho, L. H.; Krettli, A. U. Bioorg. Med. Chem. Lett. 2004, 14, 1145.

    Article  Google Scholar 

  31. Neves-Pinto, C.; Malta, V. R. S.; Pinto, M. D. C. F. R.; Santos, R. H. A.; De Castro, S. L.; Pinto, A. V. J. Med. Chem. 2002, 45, 2112.

    Article  CAS  Google Scholar 

  32. Ghorbani-Choghamarani, A.; Mohammadi, M.; Shiri, L.; Taherinia, Z. Res. Chem. Intermed. 2019, 45, 5705.

    Article  CAS  Google Scholar 

  33. Wang, S.; Miller, W.; Milton, J.; Vicker, N.; Stewart, A.; Charlton, P.; Mistry, P.; Hardick, D.; Denny, W. A. Bioorg. Med. Chem. Lett. 2002, 12, 415.

    Article  Google Scholar 

  34. Vicker, N.; Burgess, L.; Chuckowree, I. S.; Dodd, R.; Folkes, A. J.; Hardick, D. J.; Hancox, T. C.; Miller, W.; Milton, J.; Sohal, S.; Wang, S.; Wren, S. P.; Charlton, P. A.; Dangerfield, W.; Liddle, C.; Mistry, P.; Stewart, A. J.; Denny, W. A. J. Med. Chem. 2002, 45, 721.

    Article  CAS  Google Scholar 

  35. Zhuo, S.-T.; Li, C.-Y.; Hu, M.-H.; Chen, S.-B.; Yao, P.-F.; Huang, S.-L.; Ou, T.-M.; Tan, J.-H.; An, L.-K.; Li, D.; Gu, L.-Q.; Huang, Z.-S. Org. Biomol. Chem. 2013, 11, 3989.

    Article  CAS  Google Scholar 

  36. Naeimi, H.; Zarabi, M. F. RSC Adv. 2019, 9, 7400.

    Article  CAS  Google Scholar 

  37. Abadi, A. Y. E.; Maghsoodlou, M.-T.; Heydari, R.; Mohebat, R. Res. Chem. Intermed. 2016, 42, 1227.

    Article  CAS  Google Scholar 

  38. Abadi, A. Y. E.; Mohebat, R.; Kangani, M. J. Chin. Chem. Soc. 2017, 64, 690.

    Article  Google Scholar 

  39. Gao, J.; Chen, M.; Tong, X.; Zhu, H.; Yan, H.; Liu, D.; Li, W.; Qi, S.; Xiao, D.; Wang, Y.; Lu, Y.; Jiang, F. Comb. Chem. High Throughput Screening 2015, 18, 960.

    Article  CAS  Google Scholar 

  40. Thanh, N. H.; Anh, D. T. T.; Phuong, H. T.; Le-Nhat-Thuy, G.; Nguyen Thi, Q. G.; Anh, N. T.; Le Thi, T. A.; Van Nguyen, T. Tetrahedron Lett. 2021, 81, 153337.

    Article  Google Scholar 

  41. Nguyen, T. Q.; Le Nhat, T. G.; Vu Ngoc, D.; Dang Thi, T. A.; Nguyen, H. T.; Hoang Thi, P.; Nguyen, H. H.; Cao, H. T.; Abbaspour Tehrani, K.; Nguyen, T. V. Tetrahedron Lett. 2016, 57, 4352.

    Article  CAS  Google Scholar 

  42. Thanh, N. H.; Phuong, H. T.; Giang, L. N. T.; Giang, N. T. Q.; Ha, N. T. T.; Anh, D. T. T.; Cuong, V. D.; Van Tuyen, N.; Van Kiem, P. Nat. Prod. Commun. 2021, 16, 1934578X2110539.

  43. Tuyet Anh, D. T.; Cuc, D. T.; Le-Nhat-Thuy, G.; Hien, N. T.; Doan, V. N.; Thanh, N. H.; Tuyen, N. V.; Van Kiem, P. Nat. Prod. Commun. 2020, 15, 1934578X2093196.

  44. Thuy, G. L. N.; Van Dinh, T.; Pham-The, H.; Quang, H. N.; Thi, N. N.; Thi, T. A. D.; Thi, P. H.; Thi, T. A. L.; Nguyen, H. T.; Thanh, P. N.; Duc, T. L.; Nguyen, T. V. Bioorg. Med. Chem. Lett. 2018, 28, 3741.

    Article  Google Scholar 

  45. Pham-The, H.; Le-Nhat-Thuy, G.; Thi, T. A. D.; Thi, P. H.; Nguyen, T. A.; Nguyen, T. H.; Nguyen, T. D.; Ngo, H. T.; Le, T. A.; Nguyen, T. V. Chem. Heterocycl. Compd. 2020, 56, 1167.

    Article  Google Scholar 

  46. Rehberg, G. M.; Rutherford, J. L. J. Heterocycl. Chem. 1995, 32, 1643.

    Article  CAS  Google Scholar 

  47. Choudhary, A. S.; Malik, M. K.; Patil, S. R.; Prabhu, K. H.; Deshmukh, R. R.; Sekar, N. Can. Chem. Trans. 2014, 2, 365.

    Google Scholar 

  48. Kanakaraju, S.; Prasanna, B.; Basavoju, S.; Chandramouli, G. V. P. Arab. J. Chem. 2017, 10, S2705.

    Article  CAS  Google Scholar 

  49. Dabiri, M.; Tisseh, Z. N.; Bahramnejad, M.; Bazgir, A. Ultrason. Sonochem. 2011, 18, 1153.

    Article  CAS  Google Scholar 

  50. Youseftabar-Miri, L.; Hosseinjani-Pirdehi, H.; Akrami, A.; Hallajian, S. J. Iran. Chem. Soc. 2020, 17, 2179.

    Article  CAS  Google Scholar 

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The authors are indebted to Vietnam Academy of Science and Technology, grant No. NCVCC06.01/22-23 for financial support.

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Authors and Affiliations

  1. Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay, Hanoi, Vietnam

    Ha-Thanh Nguyen, Phuong Hoang Thi, Giang Le-Nhat-Thuy, Quynh Giang Nguyen Thi, Tuan Anh Nguyen, Tuyet Anh Dang Thi & Tuyen Van Nguyen

  2. Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St., Cau Giay, Hanoi, Vietnam

    Ha-Thanh Nguyen, Giang Le-Nhat-Thuy, Quynh Giang Nguyen Thi, Tuyet Anh Dang Thi & Tuyen Van Nguyen

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  1. Ha-Thanh Nguyen
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  2. Phuong Hoang Thi
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Correspondence to Ha-Thanh Nguyen or Tuyen Van Nguyen.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(12), 749–755

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Nguyen, HT., Thi, P.H., Le-Nhat-Thuy, G. et al. Synthesis of novel γ-butyrolactone-based phenazine compounds via microwave-assisted multicomponent domino reactions. Chem Heterocycl Comp 58, 749–755 (2022). https://doi.org/10.1007/s10593-023-03152-8

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