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Microwave-assisted Cu-catalyzed C–C bond formation: one-pot synthesis of fully substituted 1,2,3-triazoles using nonsymmetrical iodoalkynes and their biological evaluation

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Chemistry of Heterocyclic Compounds Aims and scope

A copper-catalyzed one-pot synthesis of fused benzothiazino[1,2,3]triazolo[4,5-c]quinolinone derivatives from 1-iodoalkynes with different aryl azides via an in situ generated 5-iodotriazole intermediate in [BMIM]PF6 under microwave irradiation is reported. The reaction provided the desired fused 1,2,3-triazoles in good to excellent yields. Anticancer activity of the synthesized compounds has been screened in vitro against different cancer cell lines (MCF-7, HeLa, A-549, and IMR-32). Some of the derivatives showed remarkable anticancer activity against two cancer cell lines – MCF-7 and A-549. The remaining compounds have shown good to moderate activity against tested cell lines.

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References

  1. Alberico, D.; Scott, M. E.; Lautens, M. Chem Rev. 2007, 107, 174.

    Article  CAS  PubMed  Google Scholar 

  2. Ackermann, L.; Rajkumar, J.; Harish, K.; Potukuchi, P. N.; Lea, B. Org. Lett. 2010, 12, 2056.

    Article  CAS  PubMed  Google Scholar 

  3. Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677.

    Article  CAS  Google Scholar 

  5. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.

    Article  CAS  Google Scholar 

  6. Chuprakov, S.; Chernyak, N.; Dudnik, A. S.; Gevorgyan, V. Org.Lett. 2007, 9, 2333.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Iwasaki, M.; Yorimitsu, H.; Oshima, K. Chem.–Asian J. 2007, 2, 1430.

    Article  CAS  PubMed  Google Scholar 

  8. Ackermann, L.; Vicente, R.; Born, R. Adv. Synth. Catal. 2008,

  9. Ackermann, L.; Vicente, R. Org. Lett. 2009, 11, 4922.

    Article  CAS  PubMed  Google Scholar 

  10. Ackermann, L.; Potukuchi, H. K.; Landsberg, D.; Vicente, R. Org. Lett. 2008, 10, 3081.

    Article  CAS  PubMed  Google Scholar 

  11. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.

    Article  CAS  PubMed  Google Scholar 

  12. Thansandote, P.; Lautens, M. Chem.–Eur. J. 2009, 15, 5874.

    Article  CAS  PubMed  Google Scholar 

  13. Zhu, C.; Wang, R.; Falck, J. R. Chem.–Asian J. 2012, 7, 1502.

    Article  CAS  Google Scholar 

  14. Ackermann, L. Isr. J. Chem. 2010, 50, 652.

    Article  CAS  Google Scholar 

  15. Hickman, A. J.; Sanford, M. S. Nature 2012, 484, 177.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885.

    Article  CAS  Google Scholar 

  17. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651.

    Article  CAS  PubMed  Google Scholar 

  18. Ackermann, L.; Vicente, R. Top. Curr. Chem. 2010, 292, 211.

    Article  CAS  PubMed  Google Scholar 

  19. Ackermann, L. Pure Appl. Chem. 2010, 82, 1403.

    Article  CAS  Google Scholar 

  20. Su, Y.; Jia, W.; Jiao, N. Synthesis 2011, 1678.

  21. Yoshikai, N. Synlett 2011, 1047.

  22. Das, B.; Reddy, G. C.; Balasubramanyam, P.; Salvanna, N. Tetrahedron 2012, 68, 300.

    Article  CAS  Google Scholar 

  23. Duong, H. A.; Gilligan, R. E.; Cooke, M. L.; Phipps, R. J.; Gaunt, M. J. Angew. Chem., Int. Ed. 2011, 50, 463.

    Article  CAS  Google Scholar 

  24. Popov, I.; Lindeman, S.; Daugulis, O. J. Am. Chem. Soc. 2011, 133, 9286.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Yotphan, S.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2009, 11, 1511.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. Song, W.; Ackermann, L. Angew. Chem., Int. Ed. 2012, 51, 8251.

    Article  CAS  Google Scholar 

  27. Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. Angell, Y. L.; Burgess, K. Chem. Soc. Rev. 2007, 36, 1674.

    Article  CAS  PubMed  Google Scholar 

  29. Fournier, D.; Hoogenboom, R.; Schubert, U. S. Chem. Soc. Rev. 2007, 36, 1369.

    Article  CAS  PubMed  Google Scholar 

  30. Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249.

    Article  CAS  PubMed  Google Scholar 

  31. Giffin, M. J.; Heaslet, H.; Brik, A.; Lin, Y.-C.; Cauvi, G.; Wong, C.-H.; McRee, D. E.; Elder, J. H.; Stout, C. D.; Torbett, B. E. J. Med. Chem. 2008, 51, 6263.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  32. Hanni, K. D.; Leigh, D. A. Chem. Soc. Rev. 2010, 39, 1240.

    Article  PubMed  Google Scholar 

  33. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128.

    Article  CAS  PubMed  Google Scholar 

  34. Alvarez, R.; Velazquez, S.; San-Felix, A.; Aquaro, S.; De Clercq, E.; Perno, C.-F.; Karlsson, A.; Balzarini, J.; Camarasa, M. J. J. Med. Chem. 1994, 37, 4185.

    Article  CAS  PubMed  Google Scholar 

  35. Vennam, D. K. R.; Thatipamula, R.; Haridasyam, S. B.; Koppula, S. K. Chem. Heterocycl. Compd. 2018, 54, 630. [Khim. Geterotsikl. Soedin. 2018, 54, 630.]

    Google Scholar 

  36. Halay, E.; Ay, E.; Salva, E.; Ay, K.; Karayildirim, T. Chem. Heterocycl. Compd. 2018, 54, 158. [Khim. Geterotsikl. Soedin. 2018, 54, 158.]

    Google Scholar 

  37. Kalinina, T. A.; Bystrykh, O. A.; Pozdina, V. A.; Glukhareva, T. V.; Ulitko, M. V.; Morzherin, Yu. Yu. Chem. Heterocycl. Compd. 2015, 51, 589. [Khim. Geterotsikl. Soedin. 2015, 51, 589.]

    Google Scholar 

  38. Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210.

    Article  CAS  PubMed  Google Scholar 

  39. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org.Chem. 2002, 67, 3057.

    Article  CAS  PubMed  Google Scholar 

  40. Jeyachandran, R.; Potukuchi, H. K.; Ackermann, L. Beilstein J. Org. Chem. 2012, 8, 1771.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  41. Panteleev, J.; Geyer, K.; Aguilar-Aguilar, A.; Wang, L.; Lautens, M. Org. Lett. 2010, 12, 5092.

    Article  CAS  PubMed  Google Scholar 

  42. Banday, A. H.; Hruby, V. J. Synlett 2014, 2463.

  43. Narsimha, S.; Kumaraswamy, B.; Kumar, N. S.; Ramesh, G.; Narasimha, R. Y.; Vasudeva, R. N. RSC Adv. 2016, 6, 74332.

    Article  CAS  Google Scholar 

  44. Narsimha, S.; Kumar, T. R.; Kumar, N. S.; Yakub, S.; Reddy, N. V. Med. Chem. Res. 2014, 23, 5321.

    Article  CAS  Google Scholar 

  45. Narsimha, S.; Kumar, N. S.; Swamy, B. K.; Reddy, N. V.; Althaf Hussain, S. K.; Rao, M. S. Bioorg. Med. Chem. Lett. 2016, 26, 1639.

    Article  CAS  PubMed  Google Scholar 

  46. Reddy, N. V.; Kumar, N. S.; Narsimha, S.; Swamy, B. K.; Jyostna, T. S.; Reddy, Y. N.. Med. Chem. Res. 2016, 25, 1781.

    Article  CAS  Google Scholar 

  47. Reddy, N. V.; Narsimha, S.; Sudhakar, L.; Swamy, B. K.; Althaf Hussain, S. K. Phosphorus, Sulfur Silicon Relat. Elem. 2016, 191, 1118.

    Article  CAS  Google Scholar 

  48. Kumar, T. R.; Narsimha, S.; Swamy, B. K.; Chary, V. R.; Estari, M.; Reddy, N. V. J. Saudi Chem. Soc. 2017, 21, 795.

    Article  CAS  Google Scholar 

  49. Swamy, B. K.; Narsimha, S.; Reddy, N. V.; Priyanka, B.; Rao, M. S. J. Serb. Chem. Soc. 2016, 81, 233.

    Article  CAS  Google Scholar 

  50. Reddy, N. V.; Narsimha, S.; Swamy, B. K.; Lavudya, S.; Thatipamula, R. K. Org. Commun. 2016, 9, 32.

    Google Scholar 

  51. Swamy, B. K.; Narsimha, S.; Kumar, T. R.; Reddy, Y. N.; Reddy, N. V. ChemistrySelect 2017, 2, 4001.

    Article  CAS  Google Scholar 

  52. Swamy, B. K.; Narsimha, S.; Kumar, T. R.; Reddy, Y. N.; Reddy, N. V. ChemistrySelect 2017, 2, 9595.

    Article  CAS  Google Scholar 

  53. Narsimha, S.; Kumara, S. B.; Vasudeva, R. N. Synth. Commun. 2018, 48, 1220.

    Article  CAS  Google Scholar 

  54. Hein, J. E.; Tripp, J. C.; Krasnova, L. B.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2009, 48, 8018.

  55. Denizot, F.; Lang, R. J. Immunol. Methods 1986, 89, 271.

    Article  CAS  PubMed  Google Scholar 

  56. Kumar, J. A.; Saidachary, G.; Mallesham, G.; Sridhar, B.; Jain, N.; Kalivendi, S. V.; Rao, V. J.; Raju, B. C. Eur. J. Med. Chem. 2013, 65, 389.

    Article  CAS  PubMed  Google Scholar 

  57. Raju, B. C.; Rao, R. N.; Suman, P.; Yogeeswari, P.; Sriram, D.; Shaik, T. B.; Kalivendi, S. V. Bioorg. Med. Chem. Lett. 2011, 21, 2855.

    Article  CAS  PubMed  Google Scholar 

  58. Mubarak, H. S.; Dnyaneshwar, D. S.; Manisha, A.; Vijay, M. K.; Nandadeep, J.; Dhiman, S.; Bapurao, B. S. Bioorg. Med. Chem. Lett. 2016, 26, 561.

    Article  CAS  Google Scholar 

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The authors are thankful to the Director of Indian Institute of Chemical Technology in Hyderabad for recording 1H, 13C NMR and mass spectra. S. Narsimha thanks Council of Scientific and Industrial Research, New Delhi, for the award of senior research fellowship.

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Authors and Affiliations

  1. Department of Chemistry, Kakatiya University, Warangal, TS-506 009, India

    Sirassu Narsimha, Kumara Swamy Battula & Vasudeva Reddy Nagavelli

  2. Department of Pharmacology and Toxicology, Kakatiya University, Warangal, TS-506 009, India

    Yellu Narasimha Reddy

Authors
  1. Sirassu Narsimha
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  2. Kumara Swamy Battula
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  3. Yellu Narasimha Reddy
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  4. Vasudeva Reddy Nagavelli
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Correspondence to Vasudeva Reddy Nagavelli.

Additional information

Supplementary information file containing 1H and 13C NMR spectra of all synthesized compounds is available at the journal website at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(12), 1161–1167

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Narsimha, S., Battula, K.S., Reddy, Y.N. et al. Microwave-assisted Cu-catalyzed C–C bond formation: one-pot synthesis of fully substituted 1,2,3-triazoles using nonsymmetrical iodoalkynes and their biological evaluation. Chem Heterocycl Comp 54, 1161–1167 (2018). https://doi.org/10.1007/s10593-019-02408-6

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  • DOI: https://doi.org/10.1007/s10593-019-02408-6

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