Skip to main content

Advertisement

SpringerLink
Log in

Design, synthesis, cytotoxic evaluation and molecular docking studies of novel thiazolyl α-aminophosphonates

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

A new class of thiazolyl α-aminophosphonate derivatives was synthesized by one-pot Kabachnik–Fields reaction of ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate with various aryl amines and diethyl phosphite under solvent-free conditions using β-cyclodextrin supported sulfonic acid (β-CD-SO3H) as an efficient, reusable and heterogeneous solid acid catalyst. The products were obtained in good to excellent yields at shorter reaction time. All the title compounds were screened for cytotoxic activity against human breast cancer (MCF-7 and MDA-MB-231), prostate cancer (DU-145) liver cancer (HepG2) and HeLa cancer cell lines using sulfarodamine-B (SRB assay). Compounds (8b, –4OMe), (8h, –4NO2) and (8j, –2I, –4CF3) showed better anticancer activity when compared with standard drug Adriamycin. Further in-silico target hunting reveals the anticancer activity of the designed compounds by inhibiting DNA topoisomerase II.

Graphical abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2
Scheme 3
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. G. Mohan, S. Santhisudha, S. Murali, N.B. Reddy, G. Sravya, Z.V. Grigory, C.S. Reddy, Res. Chem. Intermed. 44, 3475 (2018)

    CAS  Google Scholar 

  2. G. Mohan, S. Santhisudha, N.M. Reddy, S. Murali, T. Sreekanth, C.S. Reddy, Monatsh. Chem. 148, 1843 (2017)

    CAS  Google Scholar 

  3. G. Mohan, S. Santhisudha, S. Murali, T. Sreekanth, Y.S. Rao, N.B. Reddy, C.S. Reddy, J. Heterocyclic Chem. 57, 1414 (2020)

    Google Scholar 

  4. S. Murali, C. Venkataramaiah, N. Saichaithanya, G. Mohan, S.H. Yasmin, W. Rajendra, S.R. Cirandur, Med. Chem. Res. 28, 1740 (2019)

    Google Scholar 

  5. P. Sreelakshmi, M.R. Nadiveedhi, S. Santhisudha, G. Mohan, N. Saichaithanya, M. Sadik, K. Peddanna, S.R. Cirandur, Med. Chem. Res. 28, 528 (2019)

    Google Scholar 

  6. G. Mohan, S. Kumar, M. Sudileti, C. Sridevi, P. Venkatesu, C.S. Reddy, Int. J. Biol. Macromol. 165, 2010 (2020)

    CAS  PubMed  Google Scholar 

  7. K.M.K. Reddy, S. Santhisudha, G. Mohan, K. Peddanna, C.A. Rao, C.S. Reddy, Phosphorus Sulfur Silicon 191, 933 (2016)

    CAS  Google Scholar 

  8. P. Dinéra, M. Amedjkouh, Org. Biomol. Chem. 4, 2091 (2006)

    Google Scholar 

  9. W.R. Gemmill, M.D. Smith, B.A. Reisner, J. Solid State Chem. 178, 2658 (2005)

    CAS  Google Scholar 

  10. L. Tusek-Bozic, Current. Med. Chem. 20, 2096 (2013)

    CAS  Google Scholar 

  11. A. Mucha, P. Kafarski, L. Berlicki, J. Med. Chem. 54, 5955 (2011)

    CAS  PubMed  Google Scholar 

  12. M. Sienczyk, J. Oleksyszyn, Curr. Med. Chem. 16, 1673 (2009)

    CAS  PubMed  Google Scholar 

  13. R. Damiche, S. Chafaa, J. Mol. Struct. 1130, 1009 (2017)

    CAS  Google Scholar 

  14. C. Jin-Long, W. Tang, C. Jian-Yi, C. Kai, Y. Gang, G. Yu-Cheng, S. De-Qing, J. Agri. Food Chem. 63, 7219 (2015)

    Google Scholar 

  15. Z.L. Ren, J. Zhang, H.D. Li, M.J. Chu, L.S. Zhang, X.K. Yao, Y. Xia, X.H. Lv, H.Q. Cao, Chem. Pharm. Bull. 64, 1755 (2016)

    CAS  Google Scholar 

  16. P. Kafarski, B. Lejczak, E. Slesak, J. Przetocki, Pest. Manag. Sci. 25, 137143 (1989)

    Google Scholar 

  17. L. Gu, C. Cheng, Org. Biomol. Chem. 10, 7098 (2012)

    CAS  PubMed  Google Scholar 

  18. B. Sujatha, S. Mohan, Ch. Subramanyam, K.P. Rao, Phosphorus Sulfur Silicon 192, 1110 (2017)

    CAS  Google Scholar 

  19. S. Murali, G. Mohan, S. Santhisudha, T. Sreekanth, H. Balaji, M. Balaji C. S. Reddy, Monatsh. Chem. 150, 1101 (2019)

    Google Scholar 

  20. T. Sreekanth, G. Mohan, S. Santhisudha, N.M. Reddy, S. Murali, A. Rajasekhar, C.A. Rao, C.S. Reddy, Synth. Commun. 49, 563 (2019)

    Google Scholar 

  21. Y. Xu, K. Yan, B. Song, G. Xu, S. Yang, W. Xue, D. Hu, P. Lu, G. Ouyang, L. Jin, Z. Chen, Molecules 11, 666 (2006)

    CAS  PubMed  PubMed Central  Google Scholar 

  22. S.A.R. Mulla, M.Y. Pathan, S.S. Chavan, S.P. Gample, D. Sarkar, RSC Adv. 4, 7666 (2014)

    CAS  Google Scholar 

  23. R.R. Chinthaparthi, I. Bhatnagar, C.S. Gangireddy, S.C. Syama, S.R. Cirandur, Archive. Pharm Chem. Life Sci. 346, 667 (2013)

    CAS  Google Scholar 

  24. C.B. Reddy, K.S. Kumar, M.A. Kumar, M.V.N. Reddy, B.S. Krishna, M. Naveen, M.K. Arunasree, C.S. Reddy, C.N. Raju, C.D. Reddy, Eur. J. Med. Chem. 47, 553 (2012)

    CAS  PubMed  Google Scholar 

  25. S.J. Kashyap, V.J. Garg, P.K. Sharma, N. Kumar, R. Dudhe, J.K. Gupta, Med. Chem. Res. 21, 2123 (2012)

    CAS  Google Scholar 

  26. C.A. Calderón-Ospina, M.O. Nava-Mesa, CNS Neurosci. Ther. 26, 5 (2020)

    PubMed  Google Scholar 

  27. G.M. Reddy, J.R. Garcia, V.H. Reddy, A.M. Andrade, A. Camilo Jr., R.A.P. Ribeiro, S.R. Lazaro, Eur. J. Med. Chem. 123, 508 (2016)

    CAS  PubMed  Google Scholar 

  28. N. Siddiqui, W. Ahsan, Eur. J. Med. Chem. 45, 1536 (2010)

    CAS  PubMed  Google Scholar 

  29. M.H.M. Helal, M.A. Salem, M.S.A. El-Gaby, M. Aljahdali, Eur. J. Med. Chem. 65, 517 (2013)

    CAS  PubMed  Google Scholar 

  30. P. Singh, S. Gupta, S. Kumar, Med. Chem. 16, 4 (2020)

    CAS  PubMed  Google Scholar 

  31. H. Yu, Z. Qin, H. Dai, X. Zhang, X. Qin, T. Wang, J. Fang, J. Agric. Food Chem. 56, 11356 (2008)

    CAS  PubMed  Google Scholar 

  32. V. Jaishree, N. Ramdas, J. Sachin, B. Ramesh, J. Saudi. Chem. Soc. 16, 371 (2012)

    CAS  Google Scholar 

  33. M. Bagheri, M. Shekarchi, M. Jorjani, M.H. Ghahremani, M. Vosooghi, A. Shafiee, Archive. Pharm. Chem. Life Sci. 337, 25 (2004)

    CAS  Google Scholar 

  34. S. Anuradha, R. Patel, P. Patle, A. Parameswaran, J.A. Shard, Eur. J. Pharma. Sci. 134, 20 (2019)

    CAS  Google Scholar 

  35. R.G. Kalkhambkar, G.M. Kulkarni, H. Shivkumar, R.N. Rao, European. J. Med. Chem. 42, 1272 (2007)

    CAS  Google Scholar 

  36. T.K. Venkatachalam, E.A. Sudbeck, C. Mao, F.M. Uckun, Bioorg. Med. Chem. Lett. 11, 523 (2001)

    CAS  PubMed  Google Scholar 

  37. K.V. Sashidhara, K.B. Rao, V. Kushwaha, R.K. Modukuri, R. Verma, P.K. Murthy, Eur. J. Med. Chem. 81, 473 (2014)

    CAS  PubMed  Google Scholar 

  38. F. Delmas, A. Avellaneda, C.D. Giorgio, M. Robin, E.D. Clercq, P. Timon-David, J.P. Galy, Eur. J. Med. Chem. 39, 685 (2004)

    CAS  PubMed  Google Scholar 

  39. P. Makam, P.K. Thakur, T. Kannan, Eur. J. Pharma Sci. 52, 138 (2014)

    CAS  Google Scholar 

  40. H. Zhao, G. Cui, J. Jin, X. Chen, B. Xu, Bioorg. Med. Chem. 24, 5911 (2016)

    CAS  PubMed  Google Scholar 

  41. S. Kumar, R. Aggarwal, Mini Rev. Org. Chem. 16, 26 (2019)

    CAS  Google Scholar 

  42. T.K. Khatab, A.M. Abdelghany, E.M. Kandil, D.E. Elsefy, A. El-Mekabaty, Biointer. Res. Appl. Chem. 10, 5182 (2020)

    CAS  Google Scholar 

  43. T.K. Khatab, A.M. Abdelghany, H.A. Soliman, Silicon 10, 703 (2018)

    CAS  Google Scholar 

  44. H.A. Soliman, T.K. Khatab, Silicon 10, 229 (2018)

    CAS  Google Scholar 

  45. R.M.F. Batista, S.P.G. Costa, E.L. Malheiro, M. Belsley, M.M.M. Raposo, Tetrahedron 63, 4258 (2007)

    CAS  Google Scholar 

  46. P.V.G. Reddy, Y.W. Lin, H.T. Chang, Arkivoc 16, 113 (2007)

    Google Scholar 

  47. D. Xie, A. Zhang, D. Liu, L. Yin, J. Wan, S. Zeng, D. Hu, Phosphorus Sulfur Silicon 192, 1061 (2017)

    CAS  Google Scholar 

  48. D. Ravikumar, S. Mohan, Ch. Subramanyam, K.P. Rao, Phosphorus Sulfur Silicon 193, 400 (2018)

    CAS  Google Scholar 

  49. F. Tamaddon, S.E. Tadayonfar, J. Mol. Liq. 283, 51 (2019)

    CAS  Google Scholar 

  50. N. Grimblat, A.M. Sarotti, T.S. Kaufmanaand, S.O. Simonetti, Org. Biomol. Chem. 14, 10496 (2016)

    CAS  PubMed  Google Scholar 

  51. S. Lianyong, Z. Haibo, H. Tao, C. Lingwu, Chin. J. Pharma. 47, 22 (2016)

    Google Scholar 

  52. V. Vichai, K. Kirtikara, Nature Proto. 1, 1112 (2006)

    CAS  Google Scholar 

  53. S. Munusamy, V.N. Badavath, S. Maji, M. Sekar, M.N. Shabbir, New J. Chem. 44, 17231 (2019)

    Google Scholar 

  54. C. Nath, V.N. Badavath, A. Thakur, G. Ucar, O. Acevedo, M.U.M. Siddique, V. Jayaprakash, Med. Chem. Commun. 9, 1164 (2018)

    CAS  Google Scholar 

  55. B.V. Nayak, S. Ciftci-Yabanoglu, S. Bhakat, A.K. Timiri, B.N. Sinha, G. Ucar, M.E.S. Soliman, V. Jayaprakash, Bioorg. Chem. 58, 72 (2015)

    PubMed  Google Scholar 

  56. V.N. Badavath, C. Nath, N.M. Ganta, G. Ucar, B.N. Sinha, V. Jayaprakash, Chin. Chem. Lett. 28, 1528 (2017)

    CAS  Google Scholar 

  57. V.N. Badavath, I. Baysal, G. Ucar, B.N. Sinha, V. Jayaprakash, A.C.S. Med, Chem. Lett. 7, 56 (2016)

    CAS  Google Scholar 

  58. V.N. Badavath, G. Ucar, B.N. Sinha, S.K. Mondal, V. Jayaprakash, Chem. Select. 1, 5879 (2016)

    CAS  Google Scholar 

  59. V.B. Nayak, S. Ciftci-Yabanoglu, S.S. Jadav, M. Jagrat, B.N. Sinha, G. Ucar, V. Jayaprakash, Eur. J. Med. Chem. 69, 762 (2013)

    Google Scholar 

  60. H. Wei, A.J. Ruthenburg, S.K. Bechis, G.L. Verdine, J. Biol. Chem. 280, 37041 (2005)

    CAS  PubMed  Google Scholar 

  61. M. Mantipally, M.R. Gangireddy, R. Gundla, V.N. Badavath, S.R. Mandha, V.C. Maddipati, Bioorg. Med. Chem. Lett. 29, 2248 (2019)

    CAS  PubMed  Google Scholar 

  62. G.M. Reddy, M. Mantipally, R. Gundla, B.V. Nayak, K. Paidikondala, A. Yamala, Chem.Select. 4, 13622 (2019)

    Google Scholar 

  63. B.V. Kumbhar, D. Panda, A. Kunwar, PLoS ONE 13, e0194934 (2018)

    PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgments

The author G. Mohan thanks to Prof. C. Devendranath Reddy, Department of Chemistry, S.V. University, Tirupati for his helpful discussions and acknowledges DST-PURSE 2nd Phase Programme facilitated in S.V. University, Tirupati funded by DST, New Delhi, India for providing instrumentation facility and funding (File No: 17118-UGC-III(3)/DST-PURSE 2nd Phase/2017, Dt: 23-08-2018). One of the authors S.H. Yasmin acknowledges DST, New Delhi, India for the financial support under DST-INSPIRE Fellowship Programme (File No. DST/INSPIRE Fellowship/2017/IF170317, Dated: 24/05/2017).

Author information

Authors and Affiliations

  1. Department of Chemistry, Sri Venkateswara University, Tirupati, Andhra Pradesh, 517 502, India

    Mohan Gundluru, Haroon Yasmin Shaik, Murali Sudileti & Suresh Reddy Cirandur

  2. DST-PURSE Centre, Sri Venkateswara University, Tirupati, Andhra Pradesh, 517 502, India

    Mohan Gundluru

  3. Institute for Drug Research, School of Pharmacy, The Hebrew University, 91120, Jerusalem, Israel

    Vishnu Nayak Badavath

  4. Department of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, 19 Mira Street, Yekaterinburg, Russian Federation, 620002

    Bakthavatchala Reddy Nemallapudi, Sravya Gundala & Grigory V. Zyryanov

  5. I.Ya, Postovskiy Institute of Organic Synthesis, Ural Division of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, Yekaterinburg, Russian Federation, 620219

    Grigory V. Zyryanov

Authors
  1. Mohan Gundluru
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Vishnu Nayak Badavath
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Haroon Yasmin Shaik
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Murali Sudileti
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Bakthavatchala Reddy Nemallapudi
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Sravya Gundala
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Grigory V. Zyryanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Suresh Reddy Cirandur
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Suresh Reddy Cirandur.

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 file1 (DOCX 4301 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gundluru, M., Badavath, V.N., Shaik, H.Y. et al. Design, synthesis, cytotoxic evaluation and molecular docking studies of novel thiazolyl α-aminophosphonates. Res Chem Intermed 47, 1139–1160 (2021). https://doi.org/10.1007/s11164-020-04321-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-020-04321-6

Keywords

Search

Navigation