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Palladium acetate-catalysed one-pot green synthesis of bis α-aminophosphonates

  • Shaik Mahammad Sadik
  • Sarva Santhisudha
  • Gundluru Mohan
  • Nadiveedhi Maheshwara Reddy
  • Poola Sree Lakshmi
  • Allagadda Rajasekhar
  • Chippada Appa Rao
  • Cirandur Suresh Reddy
Article
  • 12 Downloads

Abstract

A simple and effective green method has been developed for the synthesis of a series of novel bis α-aminophosphonate derivatives (4a–j) by the reaction of 1,4-diaminonaphthalene, various aryl/heteroaryl aldehydes and dialkyl phosphites under neat and microwave irradiation conditions using palladium acetate as catalyst. The products are characterized by elemental analysis, IR, 1H, 13C, 31P-NMR and mass spectra and their antioxidant activities are evaluated by DPPH, NO and H2O2 methods and molecular docking studies. The compounds 4d and 4h exhibited the highest radical scavenging activity in the DPPH method, while compounds 4a, 4e and 4f showed good NO scavenging activity. The compound 4g showed remarkably higher H2O2 scavenging activity than even the standard ascorbic acid, and compound 4h has stronger inhibiting activity on DNA gyrase enzyme.

Keywords

Bis α-aminophosphonates Palladium acetate Antioxidant activity Molecular docking DNA gyrase 

Notes

Acknowledgements

The authors express thanks to Prof. C. Devendranath Reddy, Department of Chemistry, Sri Venkateswara University, Tirupati, for his helpful discussions, and acknowledge the University Grants Commission (UGC), New Delhi, providing funding (BSR-RFSMS) to Mr. Shaik Mahammad Sadik [Letter no. F. 25-1/2014-15 (BSR)/7-187/2007(BSR), dated 13-03-2015]. One of the co-authors, Mr. G. Mohan (SRF), expresses his sincere thanks to DST-PURSE 2nd Phase Programme in S.V. University, Tirupati, funded by DST, New Delhi, India [17118-UGC-III(3)/DST-PURSE 2nd Phase/2017, Dt: 23-08-2018].

Supplementary material

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Supplementary material 1 (DOC 3239 kb)

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Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  • Shaik Mahammad Sadik
    • 1
  • Sarva Santhisudha
    • 1
  • Gundluru Mohan
    • 1
    • 2
  • Nadiveedhi Maheshwara Reddy
    • 1
  • Poola Sree Lakshmi
    • 1
  • Allagadda Rajasekhar
    • 3
  • Chippada Appa Rao
    • 3
  • Cirandur Suresh Reddy
    • 1
  1. 1.Department of ChemistrySri Venkateswara UniversityTirupatiIndia
  2. 2.DST-PURSE CentreSri Venkateswara UniversityTirupatiIndia
  3. 3.Department of BiochemistrySri Venkateswara UniversityTirupatiIndia

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