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Original Articles

Synthesis and anti-diabetic activity evaluation of phosphonates containing thiazolidinedione moiety

, , , &
Pages 586-591 | Received 23 Aug 2019, Accepted 27 Feb 2020, Published online: 16 Mar 2020

References

  • Global status report on noncommunicable diseases 2014. World Health Organization: Geneva, 2015.
  • Greenfield, J. R.; Chisholm, D. Thiazolidine-2,4-Diones-Mechanism of Action. Aust. Prescr. 2004, 27, 67–70. DOI: 10.18773/austprescr.2004.059.
  • (a) Naim, M.J.; Alam, O.; Alam, M.J.; Zaman, M. S.; Alam, M.M.; Naidu, V.G.M. Synthesis, docking, in vitro and in vivo antidiabetic activity of pyrazole‐based 2,4‐thiazolidinedione derivatives as PPAR‐γ modulators Arch Pharm Chem Life Sci. 2018, 351, 1–15. (b) Naim, M.J.; Alam, O.; Alam, M.J.; Hassan, M.Q.; Siddiqui, N.; Naidu, V.G.M. Design, synthesis and molecular docking of thiazolidinedione based benzene sulphonamide derivatives containing pyrazole core as potential anti-diabetic agents. Bioorg. Chem. 2018, 76, 98–112. DOI: 10.1016/j.bioorg.2017.11.010. (c) Naim, M.J.; Alam, O.; Alam, M.J.; Nawaz, F.; Naidu, V.G.M.; Aaghaz, S.; Siddiqui, N.; Alam, O. Synthesis, molecular docking and anti-diabetic evaluation of 2, 4-thiazolidinedione based amide derivatives. Bioorg. Chem. 2017, 73, 24–36. DOI:10.1016/j.bioorg.2017.05.007. (d) Naim, M. J.; Alam, M. J.; Ahmad, S.; Nawaz, F.; Shrivastava, N.; Sahu, M.; Alam, O. Therapeutic journey of 2,4-thiazolidinediones as a versatile scaffold: An insight into structure activity relationship. Eur. J. Med. Chem. 2017, 129, 218–250. DOI: 10.1002/ardp.201700223.
  • (a) Engel, R.; Cohen, J. I. Synthesis of Carbon-phosphorous Bonds, 2nd ed.; CRC Press: Boca Raton, 2004. (b) Metcalf W. W.; Van der Donk, W. A. Biosynthesis of Phosphonic and Phosphinic Acid Natural Products, Ann. Rev. Biochem. 2009, 78, 65–94. DOI: 10.1146/annurev.biochem.78.091707.1002. (c).Bock, T.; Moehwald H.; Muelhaupt, R, Arylphosphonic Acid‐Functionalized Poly-electrolytes as Fuel Cell Membrane Material. Macromol. Chem. Phys. 2007, 208, 1324–1340. DOI:10.1002/macp.200700193. (d) Quntar, A.; Baum, O.; Reich R.; Srebnik, M. Recently Synthesized Class of Vinylphosphonates as Potent Matrix Metalloproteinase (MMP-2) Inhibitors., Arch. Pharm. 2004, 337, 76–80, DOI: 10.1002/ardp.200300828. (e) Abbas, S.; Bertram, R. D.; Hayes, Commercially Available 5’-DMT Phosphoramidites as Reagents for the Synthesis of Vinylphosphonate-Linked Oligonucleic Acids. J. Org. Lett. 2001, 3, 3365–3367. DOI: 10.1021/ol0166045. (f) Zmudzka, K.; Johansson, T.; Wojcik, M.; Janicka, M.; Nowak, M.; Stawinski, J.; Nawrot, B. Novel DNA Analogues with 2-, 3- and 4-Pyridylphosphonate Internucleotide Bonds: Synthesis and Hybridization Properties, New J. Chem. 2003, 27, 1698–1705. DOI:10.1039/B305689A.
  • Savignac, P.; Iorga, B. Modern Phosphonate Chemistry, CRC Press: Boca Raton: FL 2003.
  • Mori, I.; Fonne-Pfister, R.; Matsunaga, S.; Tada, S.; Kimura, Y.; Iwasaki, G.; Mano, J.; Hatano, M.; Nakano, T.; Koizumi, S.; et al. A Novel Class of Herbicides (Specific Inhibitors of Imidazoleglycerol Phosphate Dehydratase). Plant Physiol. 1995, 107, 719–723. DOI: 10.1104/pp.107.3.719.
  • Deluchat, V.; Lacour, S.; Serpaud, B.; Bollinger, J. C. Washing Powders and the Environment: has TAED Any Influence on the Complexing Behaviour of Phosphonic Acids? Water Res 2002, 36, 4301–4306. DOI: 10.1016/S0043-1354(02)00160-4.
  • Subramanyam, C.; Madhava, G.; Thaslim Basha, S. K.; Rasheed, S.; Uday Sankar, A.; Naga Raju, C. Bismuth(III) Chloride Mediated Michaelis-Arbuzov Reaction: A Facile Synthesis of Substituted Arylphosphonates/Phosphinates and Bioactivity Evaluation. Phosphorus, Sulfur, Silicon Relat. Elem 2015, 190, 1948–1957. DOI: 10.1080/10426507.2015.1043048.
  • Wafaa Abdou, M.; Neven Ganoub, A.; Reham, F. B. Synthesis and Bioactivity of Benzothiazaphosphepines and Relevant Phosphonates as Antioxidant/Antidiabetic Agents. Synth. Commun 2014, 44, 2669–2678. DOI: 10.1080/00397911.2014.912329.
  • Clercq, E. D.; Holý, A.; Rosenberg, I.; Sakuma, T.; Balzarini, J.; Maudgal, P. C. A Novel Selective Broad-Spectrum anti-DNA Virus Agent. Nature 1986, 323, 464–467. DOI: 10.1038/323464a0.
  • Reiser, H.; Wang, J.; Chong, L.; Watkins, W. J.; Ray, A.; Shibata, R.; Birkus, G.; Cihlar, T.; Wu, S.; Li, B.; et al. GS-9219. A Novel Acyclic Nucleotide Analogue with Potent Antineoplastic Activity in Dogs with Spontaneous Non-Hodgkin’s Lymphoma. Clin. Cancer Res 2008, 14, 2824–2832. DOI: 10.1158/1078-0432.CCR-07-20610432.
  • Kononova, S. V.; Nesmeyanova, M. A. Phosphonates and Their Degradation by Microorganisms. Biochemistry (Moscow) 2002, 67, 184–195. DOI: 10.1023/A:101440992.
  • 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.
  • Prashantha Kumar, B. R.; Soni, M.; Kumar, S. S.; Singh, K.; Patil, M.; Baig, R. B. N.; Laxmi, A. Synthesis, Glucose Uptake Activity and Structure-Activity Relationships of Some Novel Glitazones Incorporated with Glycine, Aromatic and Alicyclic Amine Moieties via Two Carbon Acyl Linker. Eur. J. Med. Chem 2011, 46, 835–844. DOI: 10.1016/j.ejmech.2010.12.019.
  • Prasanna, A. D.; Sainath, B. A. Design and Synthesis of Novel Thiazolidine-2,4-Diones as Hypoglycemic Agents. J. Saud. Chem. Soc 2016, 20, S196. S201. DOI: 10.1016/j.jscs.2012.10.010.
  • Moorthy, P.; Priya Ekambaram, S.; Selvan Perumal, S. Synthesis, Characterization and Antimicrobial Evaluation of Imidazolyl Thiazolidinedione Derivatives. Arab. J. Chem 2019, 12, 413–419. DOI: 10.1016/j.arabjc.2014.08.010.
  • Sucheta, S. T.; Prabhakar Kumar, V. Biological Potential of Thiazolidinedione Derivatives of Synthetic Origin. Chem. Cen. J 2017, 11, 1–29. DOI: 10.1186/s13065-017-0357-2.
  • Vilar, S.; Cozza, G.; Moro, S. Medicinal Chemistry and the Molecular Operating Environment (MOE): Application of QSAR and Molecular Docking to Drug Discovery. Ctmc. 2008, 8, 1555–1572. DOI: 10.2174/156802608786786624.
  • Nickavar, B. Amin, Enzyme Assay Guided Isolation of an α-Amylase Inhibitor Flavonoid from Vaccinium Arctostaphylos Leaves. G. Iran J. Pharm Res 2011, 10, 849–853. PMCID: PMC3813050.
  • Patil, V. S.; Nandre, K. P.; Ghosh, S.; Rao, V. J.; Chopade, B. A.; Sridhar, B.; Bhosale, S. V.; Bhosale, S. V. Synthesis, Crystal Structure and Antidiabetic Activity of Substituted (E)-3-(Benzo [d]Thiazol-2-Ylamino) Phenylprop-2-en-1-One. Eur. J. Med. Chem 2013, 59, 304–309. DOI: 10.1016/j.ejmech.2012.11.020.

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