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Original Articles

Synthesis, α-amylase inhibitory activity evaluation and in silico molecular docking study of some new phosphoramidates containing heterocyclic ring

, &
Pages 389-397 | Received 13 Jul 2020, Accepted 30 Oct 2020, Published online: 23 Nov 2020

References

  • Engel, R. Phosphonates as Analogues of Natural Phosphates. Chem. Rev. 1977, 77, 349–367. DOI: 10.1021/cr60307a003. (b) Hiratake, J.; Oda, J. Aminophosphonic and Aminoboronic Acids as Key Elements of a Transition State Analogue Inhibitor of Enzymes. Biosci. Biotechnol. Biochem. 1997, 61, 211–218. DOI: 10.1271/bbb.61.211. (c) Schug, K. A.; Lindner, W. Noncovalent Binding between Guanidinium and Anionic Groups: Focus on Biological- and Synthetic-Based Arginine/Guanidinium Interactions with Phosph[on]ate and Sulf[on]ate Residues. Chem. Rev. 2005, 105, 67–114. DOI: 10.1021/cr040603j.
  • (a) Manfredini, S.; Baraldi, P. G.; Durini, E.; Vertuani, S.; Balzarini, J.; De Clercq, E.; Karlsson, A.; Buzzoni, V.; Thelander, L. 5,5′-Phosphoramidates and 5′-Diphosphates of 2′-O-Allyl-Beta-D-Arabinofuranosyluracil, -Cytosine, and -Adenine: Inhibition of Ribonucleotide Reductase. J. Med. Chem. 1999, 42, 3243–3250. DOI: 10.1021/jm9807095. (b) Yang, K. W.; Brandt, J. J.; Chatwood, L. L.; Crowder, M. W. Phosphonamidate and Phosphothioate Dipeptides as Potential Inhibitors of VanX. Bioorg. Med. Chem. Lett. 2000, 10, 1085–1087. DOI: 10.1016/S0960-894X(00)00186-4.
  • (a) Mc Guigan, C.; Swords, B. Preparation of Novel N-Substituted Phospholipids via Phosphoramidite Intermediates. J. Chem. Soc. Perkin Trans. 1992, 1, 51–55. (b) Egron, D.; Imbach, J. L.; Gosselin, G.; Aubertin, A. M.; Perigaud, C. S-Acyl-2-Thioethyl Phosphoramidate Diester Derivatives as Mononucleotide Prodrugs. J. Med. Chem. 2003, 46, 4564–4571. DOI: 10.1021/jm0308444. (c) Meyers, C. L. F.; Borch, R. F. Activation Mechanisms of Nucleoside Phosphoramidate Prodrugs. J. Med. Chem. 2000, 43, 4319–4327. DOI: 10.1021/jm000302b. (d) Chang, S. L.; Griesgraber, G. W.; Southern, P. J.; Wagner, C. R. Amino Acid Phosphoramidate Monoesters of 3′-Azido-3′-Deoxythymidine: Relationship Between Antiviral Potency and Intracellular Metabolism. J. Med. Chem. 2001, 44, 223–231. DOI: 10.1021/jm000260r.
  • Kaur, R.; Dahiya, L.; Kumar, M. Fructose-1,6-Bisphosphatase Inhibitors: A New Valid Approach for Management of Type 2 Diabetes Mellitus. Eur. J. Med. Chem. 2017, 141, 473–505. DOI: 10.1016/j.ejmech.2017.09.029.
  • (a) Dirven, H. A. A. M.; Van Ommen, B.; Van Bladeren, P. Glutathione Conjugation of Alkylating Cytostatic Drugs with a Nitrogen Mustard Group and the Role of Glutathione S-Transferases. Chem. Res. Toxicol. 1996, 9, 351–360. DOI: 10.1021/tx950143c. (b) Niculescu-Duvaz, I.; Spooner, R.; Marais, R.; Springer, C. J. Gene-Directed Enzyme Prodrug Therapy. Bioconjug. Chem. 1998, 9, 4–22. DOI: 10.1021/bc970116t.
  • Patocka, J. Acetylcholinesterase Inhibitors – From Nervous Gas to Alzheimer’s Disease Therapeutics. Chem. Listy 1998, 92, 1018–1019.
  • (a) Congiatu, C.; McGuigan, C.; Jiang, W. G.; Davies, G.; Mason, M. D. Naphthyl Phosphoramidate Derivatives of BVdU as Potential Anticancer Agents: Design, Synthesis and Biological Evaluation. Nucleosides Nucleotides Nucleic Acids 2005, 24, 485–489. DOI: 10.1081/ncn-200061774. (b) Mc Guigan, C.; Cahard, D.; Sheeka, H. M.; De Clercq, E.; Balzarini, J. Aryl Phosphoramidate Derivatives of d4T Have Improved anti-HIV Efficacy in Tissue Culture and May Act by the Generation of a Novel Intracellular Metabolite. J. Med. Chem. 1996, 39, 1748–1753. DOI: 10.1021/jm950605j. (c) McGuigan, C.; Harris, S. A.; Daluge, S. M.; Gudmundsson, K. S.; McLean, E. W.; Burnette, T. C.; Marr, H.; Hazen, R.; Condreay, L. D.; Johnson, L.; et al. Application of Phosphoramidate Pronucleotide Technology to Abacavir Leads to a Significant Enhancement of Antiviral Potency. J. Med. Chem. 2005, 48, 3504–3515. DOI: 10.1021/jm0491400. (d) Perrone, P.; Luoni, G. M.; Kelleher, M. R.; Daverio, F.; Angell, A.; Mulready, S.; Congiatu, C.; Rajyaguru, S.; Martin, J. A.; Le Pogam, S.; et al. Application of the Phosphoramidate ProTide Approach to 4′-Azidouridine Confers Sub-Micromolar Potency Versus Hepatitis C Virus on an Inactive Nucleoside. J. Med. Chem. 2007, 50, 1840–1849. DOI: 10.1021/jm0613370.
  • Adams, L. A.; Cox, R. J.; Gibson, J. S.; Mayo-Martín, M. B.; Walter, M.; Whittingham, W. A New Synthesis of Phosphoramidates: Inhibitors of the Key Bacterial Enzyme Aspartate Semi-Aldehyde Dehydrogenase. Chem. Commun. 2002, 18, 2004–2005. DOI: 10.1039/B206199F.
  • (a) Munichandra Reddy, S.; Subba Rao, D.; Sudhamani, H.; Gnana Kumari, P.; Naga Raju, C. New Phosphoramidate Derivatives of 5-Nitroquinolin-8-ol: Synthesis, Spectral Characterization, and Evaluation of Biological Activity. Phosphorus, Sulfur Silicon Relat. Elem. 2015, 190, 2005–2012. DOI: 10.1080/10426507.2015.1054484. (b) Thaslim Basha, S. K.; Subba Rao, D.; Madhava, G.; Thahir Basha, S. K.; Devamma, M. N.; Madhu, S. S.; Usha, R. A.; Naga Raju, C. N. Phosphorylated Derivatives of 5-Nitroindazole as Antimicrobial and Antioxidant Agents and Docking Study against DNA Gyrasea. Phosphorus, Sulfur Silicon Relat. Elem. 2015, 190, 1064–1074. DOI: 10.1080/10426507.2014.965818.
  • Subramanyam, C.; Venkata Ramana, K.; Rasheed, S.; Adam, S.; Naga Raju, C. Synthesis and Biological Activity of Novel Diphenyl N-Substituted Carbamimidoylphosphoramidate Derivatives. Phosphorus, Sulfur Silicon Relat. Elem. 2013, 188, 1228–1235. DOI: 10.1080/10426507.2012.745075.
  • Mc Guigan, C.; Pathirana, R. N.; Balzarini, J.; De Clercq, E. Intracellular Delivery of Bioactive AZT Nucleotides by Aryl Phosphate Derivatives of AZT. J. Med. Chem. 1993, 36, 1048–1052. DOI: 10.1021/jm00060a013.
  • Letsinger, R. L.; Singman, C. N.; Histand, G.; Salunkhe, M. Cationic Oligonucleotides. J. Am. Chem. Soc. 1988, 110, 4470–4471. DOI: 10.1021/ja00221a089.
  • Majoral, Jean-Pierre (Ed.), New Aspects in Phosphorus Chemistry; Springer: Heidelberg, 2002.
  • Ashok, M.; Holla, B. S. Synthesis and Antimicrobial Evaluation of Some New Thiadiazinotriazinones Carrying 4-Methylthiobenzyl Moiety. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 1599–1608. DOI: 10.1080/10426500701263778.
  • Quin, L. D. A Guide to Organophosphorus Chemistry; Wiley-Interscience: New York, 2000.
  • Meltzer-Mats, E.; Babai-Shani, G.; Pasternak, L.; Uritsky, N.; Getter, T.; Viskind, O.; Eckel, J.; Cerasi, E.; Senderowitz, H.; Sasson, S.; Gruzman, A. Synthesis and Mechanism of Hypoglycemic Activity of Benzothiazole Derivatives. J. Med. Chem. 2013, 56, 5335–5350. DOI: 10.1021/jm4001488.
  • Naim, M. J.; Alam, O.; Alam, M. J.; Shaquiquzzaman, M.; 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, 1700223–1700224. DOI: 10.1002/ardp.201700223.
  • Datar, P. A.; Jadhav, S. R. Design and Synthesis of Pyrazole-3-One Derivatives as Hypoglycaemic Agents. Int. J. Med. Chem. 2015, 2015, 1–10. DOI: 10.1155/2015/670181.
  • Qinyuan, X.; Li, H.; Juan, L.; Liang, M.; Tao, C.; Jinying, C.; Fei, P.; Dong, C.; Zhuang, Y.; Neng, Q.; et al. Design, Synthesis and Biological Evaluation of Thiazole- And Indole-Based Derivatives for the Treatment of Type II Diabetes. Eur. J. Med. Chem. 2012, 52, 70–81. DOI: 10.1016/j.ejmech.2012.03.006.
  • Mariappan, G.; Saha, B. P.; Datta, S.; Deepak, K.; Haldar, P. K. Design, Synthesis and Antidiabetic Evaluation of Oxazolone Derivatives. J. Chem. Sci. 2011, 123, 335–341. DOI: 10.1007/s12039-011-0079-2.
  • Tanushree, S.; Jagadish, S.; Arup, N.; Tirtha, G.; Arijit, M.; Mrityunjoy, K.; Ranjit, K. H.; Tapan Kumar, M. Synthesis and Evaluation of Antiproliferative Activity of 1,2,4-Triazole Derivatives against EAC Bearing Mice Model. Ind. J. Pharm. Edu. Res. 2012, 46, 346–351.
  • Sandip, S.; Biplab, D.; Easwari, T. S. Synthesis and Biological Evaluation of Some Novel Furan Derivatives. Pak. J. Pharm. Sci. 2014, 27, 1747–1760. PMID: 25362600.
  • (a) Naim, M. J.; Alam, O.; Alam, M. J.; Hassan, M. Q.; Siddiqui, N.; Naidu, V. G. M.; Alam, M. I. 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. (b) 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. (c) 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: 10.1016/j.ejmech.2017.02.031.
  • Sales, P. M.; Souza, P. M.; Simeoni, L. A.; Silveira, D. α-Amylase Inhibitors: A Review of Raw Material and Isolated Compounds from Plant Source. J. Pharm. Pharm. Sci. 2012, 15, 141–183. DOI: 10.18433/j35s3k.
  • Konig, V.; Vertesy, L.; Schneider, T. R. Structure of the Alpha-Amylase Inhibitor Tendamistat at 0.93 A. Acta Crystallogr. D Biol. Crystallogr. 2003, 59, 1737–1743. DOI: 10.1107/s0907444903015828.
  • Chiasson, J. L.; Josse, R. G.; Gomis, R.; Hanefeld, M.; Karasik, A.; Laakso, M. Acarbose for Prevention of Type 2 Diabetes Mellitus: The STOP-NIDDM Randomised Trial. Lancet 2002, 359, 2072–2077. DOI: 10.1016/S0140-6736(02)08905-5.
  • Murai, A.; Iwamura, K.; Takada, M.; Ogawa, K.; Usui, T.; Okumura, J. Control of Postprandial Hyperglycaemia by Galactosyl Maltobionolactone and its Novel Anti-Amylase Effect in Mice. Life Sci. 2002, 71, 1405–1415. DOI: 10.1016/s0024-3205(02)01844-1.
  • Pogano, G.; Marena, S.; Corgiat-Mansin, L.; Cravero, F.; Giorda, C.; Bozza, M.; Rossi, C. M. Comparison of Miglitol and Glibenclamide in Diet-Treated Type 2 Diabetic Patients. Diabetes Metab. J. 1995, 21, 162–167. PMID: 7556806.
  • Fujisawa, T.; Ikegami, H.; Inoue, K.; Kawabata, Y.; Ogihara, T. Effect of Two Alpha-Glucosidase Inhibitors, Voglibose and Acarbose, on Postprandial Hyperglycemia Correlates with Subjective Abdominal Symptoms. Metabolism 2005, 54, 387–390. DOI: 10.1016/j.metabol.2004.10.004.
  • Hollander, P. Safety Profile of Acarbose, an Alpha-Glucosidsase Inhibitor. Drugs 1992, 44, 47–53. DOI: 10.2165/00003495-199200443-00007..
  • Singh, S. K.; Rai, P. K.; Jaiswal, D.; Watal, G. Evidence-Based Critical Evaluation of Glycemic Potential of Cynodon Dactylon. Evid. Based Complement Alternat. Med. 2008, 5, 415–420. DOI: 10.1093/ecam/nem044.
  • World Health Organization WHO Traditional Medicine Strategy 2002–2005; WHO: Geneva, Switzerland, 2002.
  • Sujatha, B.; Subramanyam, C.; Venkataramaiah, C.; Rajendra, W.; Prasada Rao, K. Synthesis and anti-Diabetic Activity Evaluation of Phosphonates Containing Thiazolidinedione Moiety. Phosphorus, Sulfur Silicon Relat. Elem. 2020, 195, 586–591. DOI: 10.1080/10426507.2020.1737061.
  • Quin, L. D.; Verkade, J. G. Phosphorus-31 NMR Spectral Properties Compound Characterization and Structural Analysis; VCH Publishers: New York, 1994.
  • Trott, O.; Olson, A. J. AutoDock Vina: Improving the Speed and Accuracy of Docking with a New Scoring Function, Efficient Optimization, and Multithreading. J. Comput. Chem. 2010, 31, 455–461. DOI: 10.1002/jcc.21334.
  • Nickavar, B.; Amin, G. Enzyme Assay Guided Isolation of an Alpha-Amylase Inhibitor Flavonoid from Vaccinium Arctostaphylos Leaves. 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.
  • Bruno, G.; Costantino, L.; Curinga, C.; Maccari, R.; Monforte, F.; Nicolo, F.; Ottana, R.; Vigorita, M. G. Synthesis and Aldose Reductase Inhibitory Activity of 5-Arylidene-2,4-Thiazolidinediones. Bioorg. Med. Chem. 2002, 10, 1077–1084. DOI: 10.1016/S0968-0896(01)00366-2.
  • Chandra Sekhar, K.; Venkataramaiah, C.; Naga Raju, C. In Silico, in Ovo and In Vitro Antiviral Efficacy of Phosphorylated Derivatives of Abacavir: An Experimental Approach. J. Recept. Signal Transduct. Res. 2020, 40, 426–435. DOI: 10.1080/10799893.2020.1747492.
  • Madhu Kumar Reddy, K.; Peddanna, K.; Varalakshmi, M.; Bakthavatchala Reddy, N.; Sravya, G.; Grigory, V. Z.; Suresh Reddy, C. Ceric Ammonium Nitrate (CAN) Catalyzed Synthesis and α -Glucosidase Activity of Some Novel Tetrahydropyridine Phosphonate Derivatives. Phosphorus, Sulfur Silicon Relat. Elem. 2019, 194, 812–819. DOI: 10.1080/10426507.2018.1550641.

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