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Tungstosulfonic acid-catalyzed green synthesis and bioassay of α-aminophosphonates

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Abstract

An eco-friendly green synthetic procedure was accomplished through the one-pot three-component synthesis of α-aminophosphonates having –CF3 moiety in good to excellent yields, under ultrasonication and solvent-free conditions in the presence of tungstosulfonic acid as an efficient, reusable, heterogeneous solid acid catalyst. All the title compounds were evaluated for their antioxidant activity using DPPH, H2O2 methods and antimicrobial activity by disc diffusion method. The bio-activity revealed that all the title compounds showed significant antioxidant and antimicrobial activities.

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References

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

    Article  CAS  PubMed  Google Scholar 

  2. Kafarski P, Lejczak B (1991) Phosphorus Sulfur Silicon Relat Elem 63:193

    Article  CAS  Google Scholar 

  3. Grembecka J, Mucha A, Cierpicki T, Kafarski P (2003) J Med Chem 46:2641

    Article  CAS  PubMed  Google Scholar 

  4. Liu W, Rogers CJ, Fischer AJ, Toney MD (2002) J Biol Chem 41:12320

    CAS  Google Scholar 

  5. Beers SA, Schwender CF, Loughney A, Malloy E, Demarest KJ (1996) Bioorg Med Chem 4:1693

    Article  CAS  PubMed  Google Scholar 

  6. Wang Q, Zhu MD, Zhu R, Lu L, Yuan C, Xing S, Fu X, Mei Y, Hang Q (2012) Eur J Med Chem 49:354

    Article  CAS  PubMed  Google Scholar 

  7. Prasad SS, Kumar KS, Jayaprakash SH, Krishna BS, Sundar CS, Rao PV, Babu TM, Rajendra W, Reddy CS (2013) Arch Pharm Chem Life Sci 346:380

    Article  CAS  Google Scholar 

  8. Bhagat S, Shah P, Garg KS, Mishra S, Kaur PK, Singh S, Chakraborti AK (2014) Med Chem Commun 5:665

    Article  CAS  Google Scholar 

  9. Zhou D, Staake M, Patterson SE (2008) Org Lett 10:2179

    Article  CAS  PubMed  Google Scholar 

  10. Virieux D, Volle JN, Pirat JL (2012) Arkivoc 4:264

    Google Scholar 

  11. Reddy CB, Kumar SK, Kumar MA, Reddy MV, Krishna BS, Naveen M, Anushree K, Reddy CS, Nagaraju C, Reddy CD (2012) Eur J Med Chem 47:553

    Article  CAS  PubMed  Google Scholar 

  12. Santhisudha S, Reddy KMK, Kumar YN, Selvarajan E, Mohansrinivasan V, Nayak SK, Reddy CS (2017) Lett Drug Des Discov 14:139

    Article  CAS  Google Scholar 

  13. Reddy KMK, Sadik SM, Chaithanya NS, Peddanna K, Reddy NB, Sravya G, Grigory ZV, Reddy CS (2017) Res Chem Intermed 43:7087

    Article  CAS  Google Scholar 

  14. Mulla SAR, Pathan MY, Chavan SS, Gample SP, Sarkar D (2014) RSC Adv 4:7666

    Article  CAS  Google Scholar 

  15. Atherton FR, Hassall CH, Lambert RW (1986) J Med Chem 29:29

    Article  CAS  PubMed  Google Scholar 

  16. Hirschmann R, Smith AB, Taylor CM, Benkovic PA, Taylor SD, Yager KM, Sprengler PA, Benkovic SJ (1994) Science 265:234

    Article  CAS  PubMed  Google Scholar 

  17. Smith AB III, Taylor CM, Benkovic SJ, Hirschmann R (1994) Tetrahedron Lett 35:6853

    Article  CAS  Google Scholar 

  18. Kenawy ERS, Azaam MM, Saad-Allah KM (2015) Arabian J Chem 8:427

    Article  CAS  Google Scholar 

  19. Reddy SS, Rao VK, Krishna BS, Reddy CS, Rao PV, Raju CN (2011) Phosphorus Sulfur Silicon Relat Elem 186:1411

    Article  CAS  Google Scholar 

  20. Prasad GS, Krishna JR, Manjunath M, Reddy OVS, Krishnaiah M, Reddy CS, Puranikd VG (2007) Arkivoc 13:131

    Google Scholar 

  21. Reddy NB, Sundar CS, Rani CR, Rao KUM, Nayak SK, Reddy CS (2016) Arabian J Chem 9:S685

    Article  CAS  Google Scholar 

  22. Reddy KMK, Sadik SM, Peddanna K, Reddy NB, Sravya G, Grigory ZV, Reddy CS (2017) Phosphorus Sulfur Silicon Relat Elem 193:329

    Article  CAS  Google Scholar 

  23. Kafarski P, Lejczak B, Tyka R, Koba L, Pliszczak E, Wiecczorek P (1995) J Plant Growth Regul 14:199

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Reddy GS, Rao KUM, Krishna BS, Reddy CSS, Santhisudha S, Haritha B, Swapna S, Reddy CS (2014) Arabian J Chem 7:833

    Article  CAS  Google Scholar 

  26. Naidu KRM, Kumar KS, Aruselvan P, Reddy CB, Lasekan O (2012) Arch Pharm Chem Life Sci 345:957

    Article  CAS  Google Scholar 

  27. Rao KUM, Swapna S, Manidhar DM, Reddy KMK, Reddy CS (2015) Phosphorus Sulfur Silicon Relat Elem 190:232

    Article  CAS  Google Scholar 

  28. Rao AJ, Rao PV, Rao VK, Mohan C, Raju CN, Reddy CS (2010) Bull Korean Chem Soc 31:1863

    Article  CAS  Google Scholar 

  29. Forlani G, Giberti S, Berlicki L, Petrollino D, Kafarski P (2007) J Agric Food Chem 55:4340

    Article  CAS  PubMed  Google Scholar 

  30. Maier L (1990) Phosphorus Sulfur Silicon Relat Elem 53:43

    Article  CAS  Google Scholar 

  31. Hayashi S, Ueno N, Murase A, Nakagawa Y, Takada J (2012) Eur J Med Chem 50:179

    Article  CAS  PubMed  Google Scholar 

  32. Jashim UM, Elleman AV, Ghebreselasie K, Daniel CK, Crews BC, Nance KD, Huda T, Marnett LJ (2014) Med Chem Lett 5:1254

    Article  CAS  Google Scholar 

  33. Wenthur CJ, Bennet MR, Lindsley CW (2014) ACS Chem Neurosci 5:14

    Article  CAS  Google Scholar 

  34. Shengguo S, Adeboye A (2006) Curr Top Med Chem 6:1457

    Article  Google Scholar 

  35. Vorobyeva DV, Peregudov AS, Schenthaler GR, Osipov SN (2015) J Fluor Chem 175:60

    Article  CAS  Google Scholar 

  36. Rosen TC, Yoshida S, Frohlich R, Kirk KL, Haufe G (2004) J Med Chem 47:5860

    Article  CAS  PubMed  Google Scholar 

  37. Deshmukh SU, Kharath KR, Yadav AR, Shisodia SU, Damale MG, Sangshetti JN, Pawar RP (2018) ChemistrySelect 3:5552

    Article  CAS  Google Scholar 

  38. Arrendale A, Kim K, Young Choi J, Li W, Geahlen RL, Borch RF (2012) Chem Biol 19:666

    Article  CAS  Google Scholar 

  39. Panigrahi K, Eggen MJ, Maeng JH, Shen Q, Berkowitz DB (2009) Chem Biol 16:928

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. Buer BC, Marsh ENG (2012) Protein Sci 21:453

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  41. Danielson MA, Falke JJ (1996) Annu Rev Biophys Biomol Struct 25:163

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. Marsh EG (2014) Acc Chem Res 47:2878

    Article  CAS  PubMed  Google Scholar 

  43. Chen H, Viel S, Ziarellic F, Peng L (2013) Chem Soc Rev 42:7971

    Article  CAS  PubMed  Google Scholar 

  44. Shen MG, Shang SB, Song ZQ, Wang D, Rao XP, Gao H, Wang JS (2014) Synth Commun 44:361

    Article  CAS  Google Scholar 

  45. Heo Y, Cho DH, Mishra MK, Jang DO (2012) Tetrahedron Lett 53:3897

    Article  CAS  Google Scholar 

  46. Qian C, Huang T (1998) J Org Chem 63:4125

    Article  CAS  Google Scholar 

  47. Sobhani S, Tashrifi Z (2009) Synth Commun 39:120

    Article  CAS  Google Scholar 

  48. Ranu BC, Hajra A, Jana U (1999) Org Lett 1:1141

    Article  CAS  Google Scholar 

  49. Xu F, Luo Y, Wu J, Shen Q, Chen H (2006) Heteroat Chem 17:389

    Article  CAS  Google Scholar 

  50. Li XC, Gong SS, Zeng DY, You YH, Sun Q (2016) Tetrahedron Lett 57:1782

    Article  CAS  Google Scholar 

  51. Xu F, Luo Y, Deng M, Shen Q (2003) Eur J Org Chem 24:4728

    Article  CAS  Google Scholar 

  52. Zhan ZP, Li JP (2005) Synth Commun 35:2501

    Article  CAS  Google Scholar 

  53. Akiyama T, Sanada M, Fuchibe K (2003) Synlett 10:1463

    Article  Google Scholar 

  54. Kalbasi RJ, Massah AR, Shafiei A (2011) J Mol Catal A Chem 335:51

    Article  CAS  Google Scholar 

  55. Kumar KS, Krishna BS, Reddy CB, Reddy MVN, Reddy CS (2017) Arabian J Chem 10:S368

    Article  CAS  Google Scholar 

  56. Kalla RMN, Bae J, Kim I (2017) New J Chem 41:6653

    Article  CAS  Google Scholar 

  57. Santhisudha S, Sreekanth T, Murali S, Kumar BV, Devi MA, Reddy CS (2017) Cardiovasc Hematol Agents Med Chem 14:167

    Article  CAS  PubMed  Google Scholar 

  58. Ravikumar D, Mohan S, Subramanyam CH, Prasada Rao K (2018) Phosphorus Sulfur Silicon Relat Elem 193:400

    Article  CAS  Google Scholar 

  59. Agawane SM, Nagarkar JM (2011) Tetrahedron Lett 52:3499

    Article  CAS  Google Scholar 

  60. Dar B, Singh A, Sahu A, Patidar P, Chakraborty A, Sharma M, Singh B (2012) Tetrahedron Lett 53:5497

    Article  CAS  Google Scholar 

  61. Kalla RMN, Kim MR, Kim YN, Kim I (2016) New J Chem 40:687

    Article  CAS  Google Scholar 

  62. Karami B, Eskandari K, Gholipour S, Jamshidi M (2013) Org Prep Proced Int 45:220

    Article  CAS  Google Scholar 

  63. Karami B, Montazerozohori M, Habibi MH (2006) Phosphorus Sulfur Silicon Relat Elem 181:2825

    Article  CAS  Google Scholar 

  64. Burits M, Bucar F (2000) Phytother Res 14:323

    Article  CAS  PubMed  Google Scholar 

  65. Yen GC, Chen HY (1995) J Agric Food Chem 43:27

    Article  CAS  Google Scholar 

  66. Goni P, Lopez P, Sánchez C, Gómez-Lus R, Becerril R (2009) Food Chem 116:982

    Article  CAS  Google Scholar 

  67. Isloor AM, Kalluraya B, Shetty P (2009) Eur J Med Chem 44:3784

    Article  CAS  PubMed  Google Scholar 

  68. Lamb DC, Kelly DE, Schunk WH (1997) J Biol Chem 272:5682

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are grateful to Prof. C. Devendranath Reddy, Department of Chemistry, S.V. University, Tirupati, for his helpful discussions and acknowledge DST-PURSE 2nd Phase Programme in S.V. University, Tirupati, funded by DST, New Delhi, India, for providing instrumental analysis and funding (SRF) for one of the co-authors, Mr. Gundluru Mohan (File no. 17118-UGC-III (3)/DST-PURSE-2nd phase/2017, dated 23/08/2018).

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Authors and Affiliations

  1. Organic and Medicinal Chemistry Division, Department of Chemistry, Sri Venkateswara University, Tirupati, 517 502, Andhra Pradesh, India

    Murali Sudileti, Mohan Gundluru, Santhisudha Sarva, Sreekanth Tellamekala & Suresh Reddy Cirandur

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

    Mohan Gundluru

  3. Department of Bio-Chemistry, Sri Venkateswara University, Tirupati, 517 502, Andhra Pradesh, India

    Balaji Hari & Balaji Meriga

  4. Institute of Food Security and Sustainable Agriculture, Universiti Malaysia Kelantan Kampus Jeli, Locked Bag 100, 17600, Jeli, Kelantan, Malaysia

    Suresh Reddy Cirandur

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  1. Murali Sudileti
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Correspondence to Suresh Reddy Cirandur.

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Sudileti, M., Gundluru, M., Sarva, S. et al. Tungstosulfonic acid-catalyzed green synthesis and bioassay of α-aminophosphonates. Monatsh Chem 150, 1101–1109 (2019). https://doi.org/10.1007/s00706-019-2385-1

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  • DOI: https://doi.org/10.1007/s00706-019-2385-1

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