Skip to main content

Advertisement

SpringerLink
Log in

Synthesis, single-crystal X-ray diffraction, and in vitro biological evaluation of sodium, cobalt, and tin complexes of o-nitro-/o-methoxyphenylacetic acid: experimental and theoretical investigation

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Four new metal carboxylates with o-nitro- and o-methoxyphenylacetic acid were synthesized and well characterized using single-crystal XRD. The synthesized complexes were evaluated for their biological potentials (antibacterial, antifungal, antioxidant, and enzyme inhibition) according to reported methods. Four bacterial and two fungal strains were targeted in this study and it was concluded that the synthesized compounds showed activities comparable to standard drugs. Co complex of nitro and tin complex of methoxy substituent are more active against bacterial as well as fungal strains. Enzyme inhibition activity of the synthesized compound was evaluated against acetylcholine esterase, butyrylcholine esterase, and trypsin. The maximum activity was depicted by Co complex of nitro, while all other tested compounds had moderate to good activity. DFT calculations were performed to gain further insight into the spectral properties. Docking model was also used to check the interaction of most active compound on the active site of the enzyme. All theoretical parameters supported the practical calculation and our findings that such compounds may be the best molecules in the near future against infectious as well as Alzheimer disease.

Graphic 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
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Štarha P, Trávníček Z, Popa I, Dvořák Z (2014) Molecules 19:10832

    PubMed  PubMed Central  Google Scholar 

  2. Ali N, Tahir MN, Ali S, Iqbal M, Munawar KS, Perveen S (2014) J Coord Chem 67:1290

    CAS  Google Scholar 

  3. Pedireddi V, Varughese S (2004) Inorg Chem 43:450

    CAS  PubMed  Google Scholar 

  4. Wang R, Jiang F, Zhou Y, Han L, Hong M (2005) Inorg Chim Acta 358:545

    CAS  Google Scholar 

  5. Zhang W-M, Li M-H, Sun J, Lv P-C, Zhu H-L (2014) J Coord Chem 67:3519

    CAS  Google Scholar 

  6. Casarin M, Corvaja C, Di Nicola C, Falcomer D, Franco L, Monari M, Pandolfo L, Pettinari C, Piccinelli F (2005) Inorg Chem 44:6265

    CAS  PubMed  Google Scholar 

  7. Kuai H-W, Cheng X-C, Zhu X-H (2011) J Coord Chem 64:1636

    CAS  Google Scholar 

  8. Kamel S, Abu Ali H, Abu Shamma A (2017) J Coord Chem 70:1910

    CAS  Google Scholar 

  9. Gao X, Gao E, Zhu M (2019) J Struct Chem 60:1180

    CAS  Google Scholar 

  10. Manna P, Seth SK, Das A, Hemming J, Prendergast R, Helliwell M, Choudhury SR, Frontera A, Mukhopadhyay S (2012) Inorg Chem 51:3557

    CAS  PubMed  Google Scholar 

  11. Mitra M, Manna P, Seth SK, Das A, Meredith J, Helliwell M, Bauzá A, Choudhury SR, Frontera A, Mukhopadhyay S (2013) Cryst Eng Comm 15:686

    CAS  Google Scholar 

  12. Seth SK, Saha I, Estarellas Martín C, Frontera Beccaria A, Kar T, Mukhopadhyay S (2018) Cryst Growth Des 11:3250

    Google Scholar 

  13. Mitra M, Manna P, Das A, Seth SK, Helliwell M, Bauzá A, Choudhury SR, Frontera A, Mukhopadhyay S (2013) J Phys Chem A 117:5802

    CAS  PubMed  Google Scholar 

  14. Sharma P (2011) J Chem Pharm Res 3:403

    CAS  Google Scholar 

  15. Danish M, Ali S, Mazhar M, Badshah A, Choudhary MI, Alt HG, Kehr G (1995) Polyhedron 14:3115

    CAS  Google Scholar 

  16. Mitra M, Manna P, Bauzá A, Ballester P, Seth SK, Ray Choudhury S, Frontera A, Mukhopadhyay S (2014) J Phys Chem B 118:14713

    CAS  PubMed  Google Scholar 

  17. Seth SK (2018) Crystals 8:455

    Google Scholar 

  18. Maity T, Mandal H, Bauzá A, Samanta BC, Frontera A, Seth SK (2018) New J Chem 42:10202

    CAS  Google Scholar 

  19. Manna P, Choudhury SR, Mitra M, Seth SK, Helliwell M, Bauzá A, Frontera A, Mukhopadhyay S (2014) J Solid State Chem 220:149

    CAS  Google Scholar 

  20. Mitra M, Seth SK, Choudhury SR, Manna P, Das A, Helliwell M, Bauzá A, Frontera A, Mukhopadhyay S (2013) Eur J Inorg Chem 2013:4679

    CAS  Google Scholar 

  21. Bhirud R, Srivastava T (1990) Inorg Chim Acta 173:121

    CAS  Google Scholar 

  22. Ikram M, Rehman S, Faiz A (2010) Bull Chem Soc Ethiop 24:201

    Google Scholar 

  23. Rosenberg B, VanCamp L (1970) Cancer Res 30:1799

    CAS  PubMed  Google Scholar 

  24. Keppler B, Berger M, Klenner T, Heim M (1990) Adv Drug Res 19:243

    CAS  Google Scholar 

  25. Hussain S, Ali S, Shahzadi S, Sharma SK, Qanungo K, Shahid M (2014) BioinorgChemAppl 2014:1

    Google Scholar 

  26. Rocha C, De Morais B, Rodrigues B, Donnici C, De Lima G, Ardisson J, Takahashi J, Bitzer R (2017) Appl Organomet Chem 31:e3645

    Google Scholar 

  27. Yousif E, Mehdi BI, Yusop R, Salimon J, Salih N, Abdullah BM (2014) J Taibah Univ Sci 8:276

    Google Scholar 

  28. Ghazi D, Rasheed Z, Yousif E (2018) Arc Org Inorg Chem Sci 3:344

    Google Scholar 

  29. Javed F, Ali S, Shahzadi S, Khalid N, Tabassum S, Khan I, Sharma SK, Qanungo K (2015) J Chin Chem Soc 62:728

    CAS  Google Scholar 

  30. Savithri K, Kumar B, Vivek H, Revanasiddappa H (2018) Int J Spectrosc 2018:1

    Google Scholar 

  31. Rocamora-Reverte L, Carrasco-García E, Ceballos-Torres J, Prashar S, Kaluđerović GN, Ferragut JA, Gómez-Ruiz S (2012) ChemMedChem 7:301

    CAS  PubMed  Google Scholar 

  32. Gielen M (2002) Appl Organomet Chem 16:481

    CAS  Google Scholar 

  33. Sirajuddin M, Ali S, McKee V, Zaib S, Iqbal J (2014) RSC Adv 4:57505

    CAS  Google Scholar 

  34. Danish M, Tahir MN, Iftikhar S, Raza MA, Ashfaq M (2015) Acta Cryst E71:m59

    Google Scholar 

  35. Danish M, Tahir MN, Iftikhar S, Raza MA, Ashfaq M (2015) Acta CrystE 71:m52

    CAS  Google Scholar 

  36. Mahon MF, Molloy KC, Stanley JE, Rankin DW, Robertson HE, Johnston BF (2005) Appl Organomet Chem 19:658

    CAS  Google Scholar 

  37. Danish M, Bibi A, Gilani K, Raza MA, Ashfaq M, Arshad MN, Asiri AM, Ayub K (2019) J Mol Struct 1175:379

    CAS  Google Scholar 

  38. Lobo V, Patil A, Phatak A, Chandra N (2010) Pharmacog Rev 4:118

    CAS  Google Scholar 

  39. Zhang Y-J, Gan R-Y, Li S, Zhou Y, Li A-N, Xu D-P, Li H-B (2015) Molecules 20:21138

    CAS  PubMed  PubMed Central  Google Scholar 

  40. Colovic MB, Krstic DZ, Lazarevic-Pasti TD, Bondzic AM, Vasic VM (2013) Curr Neuropharmacol 11:315

    CAS  PubMed  PubMed Central  Google Scholar 

  41. Gráf L, Szilágyi LA, Venekei I (2013) Chymotrypsin. In: Handbook of proteolytic enzymes. Elsevier Ltd, Amsterdam, p 2626

  42. Shahwar D, Raza MA, Rehman SU, Abbasi MA, Rahman AU (2012) Nat Prod Res 26:1087

    CAS  PubMed  Google Scholar 

  43. Shahwar D, Raza MA, Saeed A, Riasat M, Chattha FI, Javaid M, Ullah S (2012) Afr J Biotechnol 11:4288

    Google Scholar 

  44. Ellman GL, Courtney KD, Andres V Jr, Featherstone RM (1961) Biochem Pharmacol 7:88

    CAS  PubMed  Google Scholar 

  45. Raza MA, Shahwar D (2013) MedChem Res 22:3698

    CAS  Google Scholar 

  46. Shahid S, Raza MA, Ur-Rehman S (2009) Afr J Biotechnol 8:5116

    CAS  Google Scholar 

  47. Ali M, Ali S, Khan M, Rashid U, Ahmad M, Khan A, Al-Harrasi A, Ullah F, Latif A (2018) Bioorg Chem 80:472

    CAS  PubMed  Google Scholar 

  48. Iftikhar F, Yaqoob F, Tabassum N, Jan MS, Sadiq A, Tahir S, Batool T, Niaz B, Ansari FL, Choudhary MI (2018) Bioorg Chem 80:99

    CAS  PubMed  Google Scholar 

  49. Tanoli ST, Ramzan M, Hassan A, Sadiq A, Jan MS, Khan FA, Ullah F, Ahmad H, Bibi M, Mahmood T (2019) Bioorg Chem 83:336

    CAS  PubMed  Google Scholar 

  50. Pilot P (2016) Dassault Systèmes BIOVIA, discovery studio modelling environment

  51. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Rev C01. Gaussian Inc, Wallingford, CT

    Google Scholar 

  52. Xu X, Goddard WA (2004) Proc Natl Acad Sci 101:2673

    CAS  PubMed  Google Scholar 

  53. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785

    CAS  Google Scholar 

  54. Hariharan PC, Pople JA (1973) Theor Chim Acta 28:213

    CAS  Google Scholar 

  55. Ilyas A, Muhammad N, Gilani MA, Ayub K, Vankelecom IF, Khan AL (2017) J Membr Sci 543:301

    CAS  Google Scholar 

  56. Sherzaman S, Ahmed MN, Khan BA, Mahmood T, Ayub K, Tahir MN (2017) J Mol Struct 1148:388

    CAS  Google Scholar 

  57. Mahmood T, Kosar N, Ayub K (2017) Tetrahedron 73:3521

    CAS  Google Scholar 

  58. Bibi S, Ullah H, Ahmad SM, Ali Shah AUH, Bilal S, Tahir AA, Ayub K (2015) JPhysChem C 119:15994

    CAS  Google Scholar 

Download references

Acknowledgements

Muhammad Danish is thankful to the University of Gujrat for funding this project, while Umer Rashid is thankful to Higher Education Commission for financial support under the HEC-NRPU project 5291/Federal/NRPU/R&D/HEC/2016.

Author information

Authors and Affiliations

  1. Department of Chemistry, Hafiz Hayat Campus, University of Gujrat, Gujrat, Pakistan

    Muhammad Danish, Muhammad Asam Raza, Sana Iftikhar & Muhammad Waseem Mumtaz

  2. Department of Physics, University of Sargodha, Sargodha, Pakistan

    Muhammad Nawaz Tahir

  3. Department of Chemistry, COMSATS University Islamabad, Abbottabad Campus, Abbottabad, 22060, KPK, Pakistan

    Umer Rashid & Khurshid Ayub

Authors
  1. Muhammad Danish
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Muhammad Asam Raza
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Sana Iftikhar
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Muhammad Waseem Mumtaz
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Muhammad Nawaz Tahir
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Umer Rashid
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Khurshid Ayub
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Muhammad Danish.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Danish, M., Raza, M.A., Iftikhar, S. et al. Synthesis, single-crystal X-ray diffraction, and in vitro biological evaluation of sodium, cobalt, and tin complexes of o-nitro-/o-methoxyphenylacetic acid: experimental and theoretical investigation. Monatsh Chem 151, 1727–1736 (2020). https://doi.org/10.1007/s00706-020-02699-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-020-02699-y

Keywords

Search

Navigation