351
Views
0
CrossRef citations to date
0
Altmetric
Research Article

Synthesis of novel alkylphosphonates as promising antimicrobial drugs: Computational molecular docking studies

, ORCID Icon, , , , ORCID Icon & show all
Pages 722-730 | Received 04 Nov 2020, Accepted 14 Mar 2021, Published online: 31 Mar 2021

References

  • Sampath, C.; Naga Raju, C.; Venkata Rao, C. An Efficient Synthesis, Spectral Characterization, Antimicrobial, and Antioxidant Activities of Novel α-Hydroxyphosphonates and α-Hydroxyphosphinates. Phosphorus Sulfur Silicon Relat. Elem 2016, 191, 95–99. DOI: 10.1080/10426507.2015.1032412.
  • Sampath, C.; Harika, P.; Revaprasadu, N. Design, Green Synthesis, anti-Microbial, and anti-Oxidant Activities of Novel α-Aminophosphonates via Kabachnik-Fields Reaction. Phosphorus, Sulfur, Silicon Relat. Elem 2016, 191, 1081–1085. DOI: 10.1080/10426507.2015.1035379.
  • Sampath, C.; Vani, K. V.; Kotaiah, Y.; Krishna, N. H.; Raju, C. N.; Rao, C. V. A Facile and Efficient One-Pot Three Component Reaction (Kabachinik-Fields Reaction) for the Synthesis of Novel α-Aminophosphonates by 1, 4-Dimethylpiperazine as a New Catalyst. J. Chem. Pharm. Res 2012, 4, 1375–1382.
  • Sampath, C.; Naga Raju, C.; Venkata Rao, C. Synthesis, Spectral Characterization, anti-Microbial and anti-Oxidant Activities of Novel Phosphorylated Derivatives of Amlodipine. Phosphorus, Sulfur. Silicon Relat. Elem 2015, 190, 11–19. DOI: 10.1080/10426507.2014.909429.
  • De Clercq, E. The Discovery of Antiviral Agents: Ten Different Compounds, Ten Different Stories. Med. Res. Rev. 2008, 28, 929–953. DOI: 10.1002/med.20128.
  • a) Engel, R. Synthesis of carbon-phosphorus bonds, 2nd ed.; CRC Press: Boca Raton, FL, 2003. b) Savignac, P.; Iorga, B. Modern phosphonate chemistry, 1st ed.; CRC Press: Boca Raton, FL, 2003. DOI: 10.1021/ja033620j.
  • Freedman, L. D.; Doak, G. O. The Preparation and Properties of Phosphonic Acids. Chem. Rev. 1957, 57, 479–523. DOI: 10.1021/cr50015a003.
  • Murai, T.; Tomizawa, C. Chemical Transformation of S-benzyl O-ethyl phenylphosphonothiolate (Inezin) by ultraviolet light. J. Environ. Sci. Health. B. 1976, 11, 185–197. DOI: 10.1080/03601237609372034.
  • Nayab, R. S.; Maddila, S.; Krishna, M. P.; Salam, J. J. T.; Thaslim, B. S.; Chintha, V.; Wudayagiri, R.; Nagam, V.; Tartte, V.; Chinnam, S.; Chamarthi, N. R. In Silico Molecular Docking and in vitro antioxidant activity studies of novel α-aminophosphonates bearing 6-amino-1,3-dimethyl uracil. J Recept Signal Transduct Res. 2020, 40, 166–172. DOI: 10.1080/10799893.2020.1722166.
  • Harika, P.; Abbo, H. S.; Krishnamurthy, P.; Titinchi, S. J.; Sampath, C. Polyethylene Glycol (PEG-400): an Efficient One-Pot Green Synthesis and anti-Viral Activity of Novel α-Diaminophosphonates. Phosphorus, Sulfur. Silicon Relat. Elem 2019, 194, 1035–1039. DOI: 10.1080/10426507.2019.1597365.
  • Kononova, S. V.; Nesmeyanova, M. A. Phosphonates and Their Degradation by Microorganisms. Biochem. (Moscow) 2002, 67, 184–195. DOI: 10.1023/A:1014409929875.
  • Papazoglou, E. S. Flame Retardants for Plastics. In Handbook of Building Materials for Fire Protection. McGraw-Hill New York. 2004; pp. 1–4.
  • Weil, E. D. Phosphorus-Containing Polymers and Oligomers. John Wiley: New York, 1996, 10, 976–998. DOI: 10.1002/0471440264.pst237.pub2.
  • Maryanoff, B. E.; Reitz, A. B. The Wittig Olefination Reaction and Modifications Involving Phosphoryl-Stabilized Carbanions. Stereochemistry, Mechanism, and Selected Synthetic Aspects. Chem. Rev. 1989, 89, 863–927. DOI: 10.1021/cr00094a007.
  • Engel, R. Phosphonates as Analogues of Natural Phosphates. Chem. Rev. 1977, 77, 349–367. DOI: 10.1021/cr60307a003.
  • Freeman, G. A.; Rideout, J. L.; Miller, W. H.; Reardon, J. E. 3'-Azido-3', 5'-Dideoxythymidine-5'-Methylphosphonic Acid Diphosphate: synthesis and HIV-1 Reverse Transcriptase Inhibition. J. Med. Chem. 1992, 35, 3192–3196. DOI: 10.1021/jm00095a014.
  • Alberti, G.; Costantino, U.; Allulli, S.; Tomassini, N. Crystalline Zr (R-PO3)2 and Zr (R-OPO3)2 Compounds (R = Organic Radical): a New Class of Materials Having Layered Structure of the Zirconium Phosphate Type. J. Inorg. Nucl. Chem 1978, 40, 1113–1117. DOI: 10.1016/0022-1902(78)80520-X.
  • Cheetham, A. K.; Rao, C. N. R.; Feller, R. K. Structural Diversity and Chemical Trends in Hybrid Inorganic-Organic Framework Materials. Chem. Commun 2006, 46, 4780–4795. DOI: 10.1039/b610264f.
  • Villemin, D.; Moreau, B.; Siméon, F.; Maheut, G.; Fernandez, C.; Montouillout, V.; Jaffrès, P. A. A One Step Process for Grafting Organic Pendants on Alumina via the Reaction of Alumina and Phosphonate under Microwave Irradiation. Chem. Commun 2001, 20, 2060–2061. DOI: 10.1039/B105240N.
  • Amar, H.; Benzakour, J.; Derja, A.; Villemin, D.; Moreau, B. A Corrosion Inhibition Study of Iron by Phosphonic Acids in Sodium Chloride Solution. J. Electroanal. Chem 2003, 558, 131–139. DOI: 10.1016/S0022-0728(03)00388-7.
  • Richard A. J. O Hair; Gas-phase positive and negative ion chemistry of organophosphorus compounds via mass spectrometric techniques. Wiley: Chichester, UK, 1996. DOI: 10.1002/0470034351.ch8.
  • Minardi, R. M.; Schulz, P. C.; Vuano, B. The Aggregation Ofn-Dodecanephosphonic Acid in Water. Colloid Polym. Sci. 1996, 274, 1089–1093. 1996, DOI: 10.1007/BF00658374.
  • Guénin, E.; Hervé, A.-C.; Floch, V.; Loisel, S.; Yaouanc, J.-J.; Clément, J.-C.; Férec, C.; Des Abbayes, H. Des Abbayes, H. Cationic Phosphonolipids Containing Quaternary Phosphonium and Arsonium Groups for DNA Transfection with Good Efficiency and Low Cellular Toxicity. Angew. Chem. Int. Ed 2000, 39, 629–631. DOI: 10.1002/(SICI)1521-3773(20000204)39:3 < 629::AID-ANIE629 > 3.0.CO;2-K.
  • Bhattacharya, A. K.; Thyagarajan, G. Michaelis-Arbuzov Rearrangement. Chem. Rev. 1981, 81, 415–430. DOI: 10.1021/cr00044a004.
  • a) Michaelis, A.; Kaehene, R., Chem. Ber. 1898, 31, 1408. DOI: 10.1002/cber.189803101190. b) Arbuzov, A. E. On the structure of phosphonic acid and its derivates: Isometization and transition of bonds from trivalent to pentavalent phosphorus. J. Russ. Phys. Chem. Soc. 1906, 38, 687. DOI: 10.1011/jrpc.18980310.
  • a) Kosolapov, G. Organophosphorus Compounds; Wiley: New York; Chapter 7, 1950. b) Harvey, R. G.; DeSombre, E. R. Topics in Phosphorus Chemistry. Vol. I, Grayson, M.; Griffith, E. J.; Ed.; Interscience: New York, p 57, 1964. c) Arbuzov, B. A. Pure Appl. Chem. 1964, 9, 307. DOI: 10.1351/pac196409020307. d) Henning, H. G.; Hilgetag, G. Z. Chem. 1967, 7, 169. e) Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415–430. DOI: 10.1021/cr00044a004.
  • Munichandrareddy, S.; Venkataramana, C.; Krishnamurthy, P.; Sampath, C.; Nagaraju, C. In Silico Docking Studies and Synthesis of New Phosphoramidate Derivatives of 6-Fluoro-3-(Piperidin-4-yl) Benzo [d] Isoxazole as Potential Antimicrobial Agents. J. Recep. Sig. Transd 2020, 40, 486–492. DOI: 10.1080/10799893.2020.1752719.
  • Potla, K. M.; Poojith, N.; Osório, F. A. P.; Valverde, C.; Chinnam, S.; Suchetan, P. A.; Vankayalapati, S. An Analysis of Spectroscopic, Computational and Biological Activity Studies of L-Shaped Sulfamoylbenzoic Acid Derivatives: A Third Order Non-Linear Optical Material. J. Mol. Struct 2020, 1210, 128070. DOI: 10.1016/j.molstruc.2020.128070.
  • Kavitha, C.; Narendra, K.; Ratnakar, A.; Poojith, N.; Sampath, C.; Banik, S.; Suchetan, P. A.; Potla, K. M.; Naidu, N. V. An Analysis of Structural, Spectroscopic Signatures, Reactivity and anti-Bacterial Study of Synthetized 4-Chloro-3-Sulfamoylbenzoic Acid. J. Mol. Struct 2020, 1202, 127176. DOI: 10.1016/j.molstruc.2019.127176.
  • Krishnamurthy, P.; Sampath, C.; Poojith, N.; Usharani, N.; Suneetha, N.; Venkatasubbanaidu, N. An Analysis of Spectroscopic Signatures, DFT Calculations and anti-Bacterial Activity of Newly Synthesized Cu (II) and Pd (II) Complexes of 2-Aminoquinolin-8-ol and 2-(Naphthalen-1-Ylmethyl)-4,5-Dihydro-1H-Imidazole. J. Ind. Chem. Soc 2019, 96, 569–576.
  • Cherukupalli, S.; Hampannavar, G. A.; Chinnam, S.; Chandrasekaran, B.; Sayyad, N.; Kayamba, F.; Reddy Aleti, R.; Karpoormath, R. An Appraisal on Synthetic and Pharmaceutical Perspectives of pyrazolo[4,3-d]pyrimidine scaffold. Bioorg. Med. Chem. 2018, 26, 309–339. DOI: 10.1016/j.bmc.2017.10.012.
  • Suresh, M.; Sridevi, G.; Sampath, C.; Lavanya, P. Synthesis and anti-Inflammatory Activity of Some New 1, 3, 4-Thiadiazoles Containing Pyrazole and Pyrrole Nucleus. J. Saudi. Chem. Soc 2016, 20, S306–S312. DOI: 10.1016/j.jscs.2012.11.007.
  • Nagaraju, K.; Kotaiah, Y.; Sampath, C.; Harikrishna, N.; Rao, C. V. A Facile Synthesis of Some Novel Fused [1,2,4] Triazolo [3,4-b][1,3,4] Thiadiazol Derivatives. J. Sulf. Chem 2013, 34, 264–275. DOI: 10.1080/17415993.2012.734306.
  • Chung, K. T.; Thomasson, W. R.; Wu‐Yuan, C. D. Growth Inhibition of Selected food-borne bacteria, particularly Listeria monocytogenes, by plant extracts. J. Appl. Bacteriol. 1990, 69, 498–503. DOI: 10.1111/j.1365-2672.1990.tb01541.x.
  • Paul, H. M.; Philip, W.; Sosthenes, C. S.; Kanakani, W. S. Antibacterial Effects of Crude Extract of Azadirachta Indica against Escherichia coli, Salmonella Spp and Staphylococcus aureus. Int. J. Med. Med. Sci 2013, 5, 14–18. DOI: 10.5897/IJMMS12.017.
  • Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. AutoDock4 and AutoDockTools4: Automated Docking with Selective Receptor Flexibility. J. Comput. Chem. 2009, 30, 2785–2791. DOI: 10.1002/jcc.21256.
  • Ter Haar, E.; Coll, J. T.; Austen, D. A.; Hsiao, H. M.; Swenson, L.; Jain, J. Structure of GSK3beta reveals a primed phosphorylation mechanism. Nat. Struct. Biol. 2001, 8, 593–596. DOI: 10.1038/89624.
  • Pettersen, E. F.; Goddard, T. D.; Huang, C. C.; Couch, G. S.; Greenblatt, D. M.; Meng, E. C.; Ferrin, T. E. UCSF Chimera-a Visualization System for Exploratory Research and Analysis. J. Comput. Chem. 2004, 25, 1605–1612. DOI: 10.1002/jcc.20084.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.