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Medicinal Chemistry Research

, Volume 28, Issue 10, pp 1740–1754 | Cite as

Green synthesis, molecular docking, anti-oxidant and anti-inflammatory activities of α-aminophosphonates

  • Murali Sudileti
  • Venkataramaiah Chintha
  • Saichaithanya Nagaripati
  • Mohan Gundluru
  • Shaik Haroon Yasmin
  • Rajendra Wudayagiri
  • Suresh Reddy CirandurEmail author
Original Research
  • 44 Downloads

Abstract

The naturally viable α-amino acid surrogates have been synthesised via Kabachnik–Fields reaction by the condensation of 2-aminothiazole with various aldehydes and dialkyl phosphites in the presence of Caffeine hydrogen sulfate (CHS) as eco-friendly and reusable catalyst under microwave irradiation and solvent-free conditions. The title compounds were characterised by IR, 1H, 13C, 31P NMR and mass spectral data. All the synthesised (4aj) compounds were screened for their insilico and in vitro studies. The results revealed that, out of all the titled compounds 4a, 4e, 4h and 4i have exhibited significant activity in terms of antioxidant and anti-inflammatory activity. In addition, molecular docking studies were also carried out against Cox-2 with celocoxib as the standard.

Keywords

α-aminophosphonates Caffeine hydrogen sulfate Antioxidant Anti-inflammatory activity Molecular docking studies 

Notes

Acknowledgements

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

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

44_2019_2411_MOESM1_ESM.doc (2 mb)
Supplementary Item

References

  1. Agarwal S, Kidwai M, Nath M (2019) A facile and green pathway for one pot multi component synthesis of functionalized spiroxy indoles using caffeinium hydrogen sulfate as a catalyst. Chem Sel 4:2135–2139Google Scholar
  2. Ananda K, Kasumbwe K, Ramesh M, Gengan RM (2017) Catalytic synthesis of α-amino chromone phosphonates and their antimicrobial, toxicity and potential HIV-1 RT inhibitors based on silico screening. J Photochem Photobio B Biol 166:136–147CrossRefGoogle Scholar
  3. Antipin IS, Stoikov II, Konovalov AI (1999) α-Aminophosphonates: effective carriers for the membrane transport of bio relevant species. Phosphorus Sulfur Silicon 144:347–350CrossRefGoogle Scholar
  4. Anzini M, Chelini A, Mancini A, Cappelli A, Frosini M, Ricci L, Valoti M, Magistretti J, Castelli L, Giordani A, Makovec F, Vomero S (2010) Synthesis and biological evaluation of amidine, guanidine, and thiourea derivatives of 2-amino-(6-trifluoromethoxy)benzothiazole as neuroprotective agents potentially useful in brain diseases. J Med Chem 53:734–744CrossRefGoogle Scholar
  5. Azizi N, Saidi MR (2003) Lithium perchlorate-catalyzed three-component coupling: a facile and general method for the synthesis of α-aminophosphonates under solvent-free conditions. Eur J Org Chem 23:4630–4633CrossRefGoogle Scholar
  6. Bakr F, Wahab A, Mohamed SF, Amr EEA, Abdalla MM (2008) Synthesis and reactions of thiosemicarbazides, triazoles, and Schiff bases as antihypertensive α-blocking agents. Mon Chem 139:1083–1090CrossRefGoogle Scholar
  7. Bhagat S, Chakraborti AK (2007) An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik-Fields Reaction) for the synthesis of α-aminophosphonates catalyzed by magnesium Perchlorate. J Org Chem 72:1263–1270CrossRefGoogle Scholar
  8. Bhattacharya AK, Raut DS, Rana KC, Polanki IK, Khan MS, Iram SE (2013) Diversity-oriented synthesis of α-aminophosphonates: a new class of potential anticancer agents. J Med Chem 66:146–152CrossRefGoogle Scholar
  9. Boughabaa S, Bouacidab S, Aoufa Z, Bechiric O, Aouf NE (2018) H6P2W18O62.14H2O Catalyzed synthesis, spectral characterization and X-ray study of α-aminophosphonates containing aminothiazole moiety. Cur Org Chem 22:1–7CrossRefGoogle Scholar
  10. Chea JY, Xu XY, Tang ZL, Gu YC, Shi DQ (2016) Synthesis and herbicidal activity evaluation of novel α-amino phosphonate derivatives containing a uracil moiety. Bioorg Med Chem Lett 26:1310–1313CrossRefGoogle Scholar
  11. Damiche R, Chafaa S (2017) Synthesis of new bioactive aminophosphonates and study of their antioxidant, anti-inflammatory and antibacterial activities as well the assessment of their toxicological activity. J Mol Struct 1130:1009–1017CrossRefGoogle Scholar
  12. Esalah J, Husein MM (2008) Removal of heavy metals from aqueous solutions by precipitation-filtration using novel organo-phosphorus ligands. Sep Sci Tec 43:3461–3475CrossRefGoogle Scholar
  13. Firouzabadi H, Iranpoor N, Sobhani S (2004) Metal Triflate-Catalyzed One-Pot synthesis of α-Aminophosphonates from carbonyl compounds in the absence of solvent. Synthesis 16:2692–2696CrossRefGoogle Scholar
  14. Forlani G, Berlicki L, Duo M, Dziedziola G, Giberti S, Bertazzini M, Kafarski P (2013) Synthesis and evaluation of effective inhibitors of plant δ 1-pyrroline-5-carboxylate reductase. J Agric Food Chem 61:6792–6798CrossRefGoogle Scholar
  15. Gundluru M, Sarva S, Reddy KMK, Netala VR, Vijaya T, Reddy CS (2016) Phosphosulfonic acid-catalyzed green synthesis and bioassay of α-aryl-α-1,3,4-thiadiazolyl aminophosphonates. Heteroat Chem 27:269–278CrossRefGoogle Scholar
  16. Hirschmann R, Smith III AB, Taylor CM, Benkovic PA, Taylor SD, Yager KM, Sprengler PA, Benkovic S (1994) Peptide synthesis catalyzed by an antibody containing a binding site for variable amino acids. Science 265:234–237CrossRefGoogle Scholar
  17. Kafarski P, Lejczak B (1991) Biological activity of aminophosphonic acids. Phosphorus Sulfur Silicon 63:193–215CrossRefGoogle Scholar
  18. Kandula MKR, Sadik SM, Peddanna K, Reddy NB, Sravya G, Reddy CS (2018) Microwave assisted synthesis and anti-microbial activity of new diethyl ((dialkoxyphosphoryl) (2-hydroxyphenyl) methyl) phosphoramidates. Phosphorous Sulfur Silicon 193:329–334CrossRefGoogle Scholar
  19. Kudrjasova J, Herckens R, Penxten H, Adriaensens P, Lutsen L, Vanderzande D, Maes W (2014) Direct arylation as a versatile tool towards thiazolo-[5,4-d]thiazole-based semi conducting materials. Org Biomol Chem 12:4663–4672CrossRefGoogle Scholar
  20. Lajczak B, Kafarski P, Sztajer H, Mastalerz P (1986) Antibacterial activity of phosphono dipeptides related to alafosfalin. J Med Chem 29:2212–2217CrossRefGoogle Scholar
  21. Maier L (1990) Organic phosphorus compounds 91.1 synthesis and properties of 1-amino-2-arylethylphosphonic and -phosphinic acids as well as -phosphine oxides. Phosphorous Sulfur Silicon 53:43–67CrossRefGoogle Scholar
  22. Malamiri F, Khaksar S (2014) Pentafluorophenylammonium triflate (PFPAT): A new organo catalyst for the one-pot three-component synthesis of α-aminophosphonates. J Chem Sci 126:807–801CrossRefGoogle Scholar
  23. Matsubara N, Fuchimoto S, Iwagaki H, Nonaka Y, Kimura T, Kashino H, Edamatsu R, Hiramatsu M, Orita K (1991) The possible involvement of free radical scavenging properties in the action of cytokines. Res Commun Chem Pathol Pharm 71:239–242Google Scholar
  24. Meyer JH, Barlett PA (1998) Macrocyclic inhibitors of penicillopepsin. 1. Design, synthesis, and evaluation of an inhibitor bridged between P1 and P3. J Am Chem Soc 120:4600–4609CrossRefGoogle Scholar
  25. Mulla SAR, Pathan MY, Chavan SS, Gample SP, Sarkar D (2014) Highly efficient one-pot multi-component synthesis of α-aminophosphonates and bis-α-aminophosphonates catalyzed by heterogeneous reusable silica supported dodeca tungsto phosphoric acid (DTP/SiO2) at ambient temperature and their anti-tubercular evaluation against Mycobactrium Tuberculosis. RSC Adv 4:7666–7672CrossRefGoogle Scholar
  26. Park JS, Park EM, kim DH, Jung K, Jung JS, Lee EJ, Hyun JW, Kang JL, Kim HS (2009) Anti- inflammatory mechanism of ginseng saponins in activated microglia. J Neuroimmunol 209:40–49CrossRefGoogle Scholar
  27. Pekarova M, Kralova J, Kubala L, Ciz M, Papezikova I, Macickova T, Pecivova J, Nosal R, Lojek A (2009) Carvedilol and adrenergic agonists suppress the lipopolysaccharide induced NO production in RAW 264.7 macrophages via the adrenergic receptors. J Physiol Pharm 60:143–150Google Scholar
  28. Qian C, Huang T (1998) One-Pot synthesis of α-Aminophosphonates from aldehydes using lanthanide triflate as a catalyst. Org Chem 63:4125–4128CrossRefGoogle Scholar
  29. Ranu BC, Hajra A, Jana U (1999) General procedure for the synthesis of α-amino phosphonates from aldehydes and ketones using Indium (III) chloride as a catalyst. Org Lett 8:1141–1143CrossRefGoogle Scholar
  30. Raquel P, Bravo L, Saura Calixto F (2000) Antioxidant activity of dietary polyphenols As determined by a modified ferric reducing/antioxidant power assay. J Agric Food Chem 48:3396–3402CrossRefGoogle Scholar
  31. Shalini A, Roona P, Mazaahir K, Mahendra N (2018) Caffeinium hydrogen sulfate: a green solid acid catalyst for selective One-Pot domino knoevenagel michael-transformations. Chem Sel 3:10909–10914Google Scholar
  32. Sharma PC, Sinhmar A, Sharma A, Rajak H, Pathak DP (2013) Medicinal significance of benzothiazole scaffold: an insight view. J Enzym Inhib Med Chem 28:240–266CrossRefGoogle Scholar
  33. Smith III AB, Taylor CM, Benkovic SJ, Hirschmann R (1994) Peptide bond formation via catalytic antibodies: synthesis of a novel phosphonate diester hapten. Tetahedron Lett 35:6853–6856CrossRefGoogle Scholar
  34. Sreekanth T, Mohan G, Santhisudha S, Nadiveedhi MR, Murali. S, Rajasekhar A, Chippada AR, Reddy CS (2018) Meglumine sulfate-catalyzed one-pot green synthesis and antioxidant activity of α-aminophosphonates. Synth Commun 49:563–575Google Scholar
  35. Stowasser B, Budt KH, Peyman A, Ruppert D (1992) New hybrid transition slate analog inhibitors of HIV protease with peripheric C2-Symmetry. Tetahedron Lett 33:6625–6628CrossRefGoogle Scholar
  36. Tibhe GD, Lagunas-Rivera S, Vargas-Diaz E, Garcia-Barradas O, Ordonz M (2010) Un-catalyzed One-Pot diastereo selective synthesis of α-Aminophosphonates under solvent-Free conditions. Eur J Org Chem 14:6573–6581CrossRefGoogle Scholar
  37. Tzanopoulou S, Sagnou M, Petsotas MP, Gourni E, Loudos G, Xanthopoulos S, Lafkas D, Kiaris H, Varvarigou A, Pirmettis IC, Papadopoulos M, Pelecanou M (2010) Evaluation of Re and 99mTc Complexes of 2-(40-Aminophenyl)benzothiazole as potential breast cancer Radiopharmaceuticals. J Med Chem 53:4633–4641CrossRefGoogle Scholar
  38. Vilar S, Cozza G, Moro S (2008) Medicinal chemistry and the molecular operating environment (MOE): application of QSAR and molecular docking to drug discovery. Curr Top Med Chem 8:1555–1572CrossRefGoogle Scholar
  39. Xie D, Zhang A, Liu D, Yin L, Wan J, Zeng S, Hu D (2017) Synthesis and antiviral activity of novel α-aminophosphonates containing 6-fluorobenzothiazole moiety. Phosphorous Sulphur Silicon 192:1061–1067CrossRefGoogle Scholar
  40. Xu F, Luo Y, Deng M, Shen Q (2003) One-Pot synthesis of α-amino phosphonates using samarium diiodide as a catalyst Precursor. Eur J Org Chem 24:4728–4730CrossRefGoogle Scholar
  41. Xu Y, Yan K, Song B, Xu G, Yang S, Xue W, Hu D, Lu P, Ouyang G, Jin L, Chen Z (2006) Synthesis and antiviral bioactivities of α-aminophosphonates containing alkoxy ethyl moieties. Molecules 11:666–676CrossRefGoogle Scholar
  42. Ugwu DI, Okoro UC, Ukoha PO, Gupta A, Okafor SN (2018) Novel anti-inflammatory and analgesic agents: synthesis, molecular docking and in vivo studies. J Enzyme Inhib Med Chem 33:405–415CrossRefGoogle Scholar
  43. Zhan ZP, Li JP (2005) Bismuth(III) chloride–catalyzed three-component coupling: synthesis of α-Amino phosphonates. Synth Commun 35:2501–2508CrossRefGoogle Scholar
  44. Zuo Y, Wu Q, Su SW, Niu CW, Xi Z, Yang GF (2016) Synthesis, Herbicidal activity and QSAR of novel N-Benzothiazolyl-pyrimidine-2,4-diones as protoporphyrinogen oxidase inhibitors. J Agric Food Chem 64:552–562CrossRefGoogle Scholar

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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of ChemistrySri Venkateswara UniversityTirupatiIndia
  2. 2.Department of ZoologySri Venkateswara UniversityTirupatiIndia
  3. 3.DST-PURSE CentreSri Venkateswara UniversityTirupatiIndia
  4. 4.Institute of Food Security and Sustainable AgricultureUniversiti Malaysia Kelantan Kampus JeliJeliMalaysia

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