Skip to main content
Log in

Application of Cu (II)-Guanine Complexes Anchored on SBA-15 and MCM-41 as Efficient Nanocatalysts for One-Pot, Four-Component Domino Synthesis of Phenazine Derivatives and Investigation of Their Antimicrobial Behavior

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

A one-pot, two-step, four-component synthesis of benzo[c]pyrano[3,2-a]phenazine and bis-benzo[c]pyrano[3,2-a]phenazine derivatives was carried out by the reaction of 2-hydroxy-1,4-naphthoquinone, benzene-1,2-diamine, carbonyl compounds and alkylmalonates using new copper (II) ions complexes of guanine (2-amino-1H-purin-6(9H)-one) supported into MCM-41 (Cu-guanine-MCM-41) and SBA-15 (Cu-guanine-SBA-15) channels as efficient and heterogeneous catalysts in PEG. The desired products were obtained in good to excellent yields. The prepared catalysts have been extensively characterized by different methods and can be reused for several times without any significant loss of their catalytic activities. The phenazine derivatives were also tested for their antimicrobial activities.

Graphic Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Scheme 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Scheme 2
Scheme 3
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Fig. 15
Fig. 16
Fig. 17

Similar content being viewed by others

References

  1. Nikoorazm M, Khanmoradi M, Mohammadi M (2020) Appl Organometal Chem 34:e5504

    CAS  Google Scholar 

  2. Khanmoradi M, Nikoorazm M, Ghorbani-Choghamarani A (2017) Catal Lett 147:1114

    CAS  Google Scholar 

  3. Kazemi M, Mohammadi M (2020) Appl Organometal Chem 34:e5400

    CAS  Google Scholar 

  4. Ghorbani-Choghamarani A, Mohammadi M, Hudson RHE, Tamoradi T (2019) Appl Organometal Chem 33:e4977

    Google Scholar 

  5. Mohammadi M, Ghorbani-Choghamarani A (2020) New J Chem 44:2919

    CAS  Google Scholar 

  6. Tamoradi T, Mousavi SM, Mohammadi M (2020) New J Chem 44:3012

    CAS  Google Scholar 

  7. Zabeti M, Wan Daud WMA, Aroua MK (2015) Fuel Process Technol 90:770

    Google Scholar 

  8. Khanmoradi M, Nikoorazm M, Ghorbani-Choghamarani A (2017) Appl Organomet Chem 31:3693

    Google Scholar 

  9. Tadic M, Kralj S, Lalatonne Y, Motte L (2019) Appl Surf Sci 476:641

    CAS  Google Scholar 

  10. Shi F, Shan H, Li D, Yin X, Yu J, Ding B (2019) J Colloid Interface Sci 538:620

    CAS  PubMed  Google Scholar 

  11. Ghorbani-Choghamarani A, Mohammadi M, Taherinia Z (2019) J Iran Chem Soc 16:411

    CAS  Google Scholar 

  12. You S, Xiao R, Liu H, Cai M (2017) New J Chem 41:13862

    CAS  Google Scholar 

  13. Nikoorazm M, Ghorbani-Choghamarani A, Khanmoradi M (2016) Appl Organomet Chem 30:236

    CAS  Google Scholar 

  14. Yao N, Lu M, Liu XB, Tan J, Hu YL (2018) J Mol Liq 262:328

    Google Scholar 

  15. Tan J, Liu X, Yao N, Hu YL, Li XH (2019) New J Chem 43:2583

    Google Scholar 

  16. Tan J, Liu X, Yao N, Hu YL, Li X (2019) ChemistrySelect 4:2475

    CAS  Google Scholar 

  17. Wang HB, Yao N, Wang L, Hu YL (2017) New J Chem 41:10528

    CAS  Google Scholar 

  18. Hu YL, Wang HB, Chen ZW, Li XG (2018) ChemistrySelect 3:5087

    CAS  Google Scholar 

  19. Appaturi JN, Selvaraj M, Bee Abdul Hamid S (2018) Microporous Mesoporous Mater 260:260

    CAS  Google Scholar 

  20. Venkatesan C, Singh AP (2003) Catal Lett 88:3

    Google Scholar 

  21. Ghorbani-Choghamarani A, Mohammadi M, Tamoradi T, Ghadermazi M (2019) Polyhedron 158:25

    CAS  Google Scholar 

  22. Safaei-Ghomi J, Bakhtiari A (2019) RSC Adv 9:19662

    CAS  Google Scholar 

  23. Safaei-Ghomi J, Bakhtiari A (2018) ChemistrySelect 44:12704

    Google Scholar 

  24. Ying Y, Mehnert CP, Wong MS (1999) Angew Chem Int Ed 38:56

    CAS  Google Scholar 

  25. Nikoorazm M, Ghorbani-Choghamarani A, Khanmoradi M (2016) RSC Adv 6:56549

    CAS  Google Scholar 

  26. Beck J, Vartuli J, Roth W, Leonowicz M, Kresge C, Schmitt K, Chu C, Olson D, Sheppard E, McCullen S, Higgins J, Schlenker J (1992) J Am Chem Soc 114:10834

    CAS  Google Scholar 

  27. Anastas PT, Kirchhoff MM, Williamson TC (2001) Appl Catal A 221:3

    CAS  Google Scholar 

  28. Nikoorazm M, Ghorbani-Choghamarani A, Khanmoradi M (2016) Appl Organomet Chem 30:705

    CAS  Google Scholar 

  29. Habib M, Hafida M, Abdelkader T, Caroline B, Anne B (2019) Sep Purif Technol 209:359

    Google Scholar 

  30. Nikoorazm M, Ghorbani-Choghamarani A, Panahi A, Tahmasbi B, Noori N (2018) J Iran Chem Soc 15:181

    CAS  Google Scholar 

  31. Marın-Astorga N, Pecchi G, Fierro JLG, Reyes P (2005) J Mol Catal A 231:67

    Google Scholar 

  32. Zhao D, Sun J, Li Q, Stucky GD (2000) Chem Mater 12:275

    CAS  Google Scholar 

  33. Huo Q, Margolese DI, Stucky GD (1996) Chem Mater 8:1147

    CAS  Google Scholar 

  34. Vartuli JC, Schmitt KD, Kresge CT, Roth WJ, Leonowicz ME, McCullen SB, Hellring SD, Beck JS, Schlenker JL (1994) Chem Mater 6:2317

    CAS  Google Scholar 

  35. Kappe CO (2000) Chem Res 33:879

    CAS  Google Scholar 

  36. Martínez JJ, Romero-Vega S, Abeja-Cruz R, Álvarez-Toledano C, Miranda R (2013) Int J Mol Sci 14:2903

    PubMed  PubMed Central  Google Scholar 

  37. Rajanarendar E, Venkateshwarlu P, Rama Krishna S, Govardhan Reddy K, Thirupathaiah K (2015) Green Sustain Chem 5:107

    CAS  Google Scholar 

  38. Nikoorazm M, Ghorbani-Choghamarani A, Khanmoradi M (2016) J Porous Mater 23:761

    CAS  Google Scholar 

  39. Biggs-Houck JE, Younai A, Shaw JT (2010) Curr Opin Chem Biol 14:371

    CAS  PubMed  Google Scholar 

  40. Moosavi-Zare AR, Zolfigol MA, Derakhshan-Panah F, Balalaie S (2018) Mol Catal 449:142

    CAS  Google Scholar 

  41. Varadi A, Palmer TC, Notis Dardashti R, Majumdar S (2016) Molecules 21:19

    Google Scholar 

  42. Weber L (2002) Curr Med Chem 9:2085

    CAS  PubMed  Google Scholar 

  43. Mehmood A, Ghafar H, Yaqoob S, Gohar UF, Ahmad B (2017) J Dev Drugs 6:2

    Google Scholar 

  44. Abbasi Pour S, Yazdani-Elah-Abadi A, Afradi M (2017) Appl Organomet Chem 31:3791

    Google Scholar 

  45. Safaei-Ghomi J, Bakhtiari A (2019) Appl Organomet Chem 33:1

    Google Scholar 

  46. Safaei-Ghomi J, Teymuri R (2019) Appl Organomet Chem 33:1

    Google Scholar 

  47. Filian H, Kohzadian A, Mohammadi M, Ghorbani-Choghamarani A, Karami A (2020) Appl Organometal Chem. https://doi.org/10.1002/aoc.5579

    Article  Google Scholar 

  48. Rho YS, Kim SA, Jung JC, Shin CC, Chang SG (2002) Int J Oncol 20:929

    CAS  PubMed  Google Scholar 

  49. Sultana C, Rahman MAA, Al-Bari MAA, Banu MLA, Islam MS, Khatune NA, Sadik G (2003) Pak J Biol Sci 6:525

    Google Scholar 

  50. Brown DB, Khokhar AR, Hacker MP, Lokys L, Burchenal JH, Newman RA, McCormack JJ, Frost D (1982) J Med Chem 25:952

    CAS  PubMed  Google Scholar 

  51. Zhu S, Matilla A, Tercero JM, Vijayaragavan V, Walmsley JA (2004) Inorg Chim Acta 357:411

    CAS  Google Scholar 

  52. Ghorbani-Choghamarani A, Tahmasbi B, Hudson RHE, Heidari A (2019) Microporous Mesoporous Mater 284:366

    CAS  Google Scholar 

  53. Lee-Thorp JA, Rüede JE, Thornton DA (1978) J Mol Struct 50:65

    CAS  Google Scholar 

  54. Hosseini-Sarvari M, Moeini F (2014) RSC Adv 4:321

    Google Scholar 

  55. Mohamed GG, Hosny WM, Abd-El-Rahim MA, Jain PC (2002) Gazz Chim Ital 32:1501

    CAS  Google Scholar 

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

    CAS  PubMed  Google Scholar 

  57. Yazdani Elah Abadi A, Maghsoodlou M-T, Heydari R, Mohebat R (2016) Res Chem Intermed 42:1227

    Google Scholar 

  58. Hasaninejad A, Firoozi S (2013) Mol Divers 17:499

    CAS  PubMed  Google Scholar 

  59. Yazdani Elah Abadi A, Maghsoodlou M-T, Heydari R, Mohebat R (2017) Chin Chem Lett 28:446

    CAS  Google Scholar 

  60. Ghorbani-Choghamarani A, Mohammadi M, Shiri L, Taherinia Z (2019) Res Chem Intermed 45:5705

    CAS  Google Scholar 

  61. Shaterian HR, Moradi F, Mohammadnia M (2012) C R Chim 15:1055

    CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the Iran National Science Foundation and research facilities of Ilam University, Ilam, Iran.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mohsen Nikoorazm.

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.

Supplementary file 1 (DOCX 1221 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nikoorazm, M., Khanmoradi, M. Application of Cu (II)-Guanine Complexes Anchored on SBA-15 and MCM-41 as Efficient Nanocatalysts for One-Pot, Four-Component Domino Synthesis of Phenazine Derivatives and Investigation of Their Antimicrobial Behavior. Catal Lett 150, 2823–2840 (2020). https://doi.org/10.1007/s10562-020-03185-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-020-03185-0

Keywords

Navigation