Green synthesis of phosphoramidates and evaluation of their α-amylase activity by in silico and in vitro studies

References

• Richard Pon, T. Nucleoside Phosphoramidites Containing Cleavable Linkers. Nucleic Acid Chem. 2006, 26, 3.12.1–3.12.24. DOI: 10.1002/0471142700.nc0312s23.
   Google Scholar
• Keunsoo, K.; Venkateshwarlu, P.; Phaneendrasai, K.; Ramanarayanan, K. Synthesis of Phosphoramidites of isoGNA, an Isomer of Glycerol Nucleic Acid. Beilstein J. Org. Chem. 2014, 10, 2131–2138. DOI: 10.3762/bjoc.10.220.
   PubMed Web of Science ®Google Scholar
• Johannes, F.; Teichert Ben, L. Feringa, Phosphoramidites: Privileged Ligands in Asymmetric Catalysis. Angew. Chem. Int. Ed. 2010, 14, 2486–2528. DOI: 10.1002/anie.200904948.
   Web of Science ®Google Scholar
• Katagi, T. Photochemistry of Organophosphorus Herbicide Butamifos. J. Agric. Food Chem. 1993, 41, 496–501. DOI: 10.1021/jf00027a028.
   Web of Science ®Google Scholar
• Oliveira, F. M.; Barbosa, L. C. A.; Teixeira, R. R.; Demuner, A. J.; Maltha, C. R. Á.; Picanço, M. C.; Silva, G. A.; Paula, V. F. d. Synthesis and Insecticidal Activity of New Phosphoramidates. J. Pestic. Sci. 2012, 37, 85–88. DOI: 10.1584/jpestics.D11-014.
   Web of Science ®Google Scholar
• Paula, V. F.; Barbosa, L. C. A.; Teixeira, R. R.; Picanço, M. C.; Silva, G. A. Synthesis and Insecticidal Activity of New 3-Benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate Derivatives. Pest. Manag. Sci. 2008, 64, 863–872. DOI: 10.1002/ps.1559.
   PubMed Web of Science ®Google Scholar
• Oliveira, F. M.; Barbosa, L. C. A.; Ismail, F. M. D. The Diverse Pharmacology and Medicinal Chemistry of Phosphoramidates–a Review. RSC Adv. 2014, 4, 18998–19012. DOI: 10.1039/C4RA01454E.
   Web of Science ®Google Scholar
• Phillips, D. R.; Uramoto, M.; Isono, K.; McCloskey, J. A. Structure of the Antifungal Nucleotide Antibiotic Phosmidosine. J. Org. Chem. 1993, 58, 854–859. DOI: 10.1021/jo00056a017.
   Web of Science ®Google Scholar
• Cho, A.; Zhang, L.; Xu, J.; Lee, R.; Butler, T.; Metobo, S.; Aktoudianakis, V.; Lew, W.; Ye, H.; Clarke, M.; et al. Discovery of the First C-Nucleoside HCV Polymerase Inhibitor (GS-6620) with Demonstrated Antiviral Response in HCV Infected Patients. J. Med. Chem. 2014, 57, 1812–1831. DOI: 10.1021/jm400201a.
   PubMed Web of Science ®Google Scholar
• Roberts, W. P.; Tate, M. E.; Kerr, A. Agrocin 84 is a 6-N-Phosphoramidate of an Adenine Nucleotide Analogue. Nature 1977, 265, 379–381. DOI: 10.1038/265379a0.
   PubMed Web of Science ®Google Scholar
• Charlton, M.; Gane, E.; Manns, M. P.; Brown, R. S.; Curry, M. P.; Kwo, P. Y.; Fontana, R. J.; Gilroy, R.; Teperman, L.; Muir, A. J.; et al. Sofosbuvir and Ribavirin for Treatment of Compensated Recurrent Hepatitis C Virus Infection after Liver Transplantation. Gastroenterology 2015, 148, 108–117. DOI: 10.1053/j.gastro.2014.10.001.
   PubMed Web of Science ®Google Scholar
• WHO Drug Information. Proposed INN: List 111. 2014, 28, 2.
   Google Scholar
• Yadav, L. D. S.; Srivastava, V. P.; Patel, R. An Easy Access to Functionalized Allyl Dithiocarbamates from Baylis–Hillman Adducts in Water. Tetrahedron Lett. 2009, 50, 1335–1339. DOI: 10.1016/j.tetlet.2009.01.023.
   Web of Science ®Google Scholar
• Yadav, L. D. S.; Awasthi, C.; Rai, V. K.; Rai, A. A Convenient Synthesis of 1,2,4-Trisubstituted Azetidines by Reductive Cyclization of Aza-Michael Adducts of Chalcones. Tetrahedron Lett. 2007, 48, 8037–8039. DOI: 10.1016/j.tetlet.2007.09.044.
   Web of Science ®Google Scholar
• Minami, T.; Ogata, M.; Hirao, I.; Tanaka, M.; Agawa, T. Synthesis of a 3,1-Benzoxazin-4-One, 2,4(1H,3H)-Quinolinediones, and 2,4(1H,3H)-Quinazolinediones from the Reaction of Phosphoryl-Stabilized Anions Containing No a-Hydrogen Atoms with Isatoic Anhydride. Synthesis 1982, 5, 231–233. DOI: 10.1055/s-1982-29760.
   Google Scholar
• Mével, M.; Breuzard, G.; Yaouanc, J.-J.; Clément, J.-C.; Lehn, P.; Pichon, C.; Jaffrès, P.-A.; Midoux, P. Synthesis and Transfection Activity of New Cationic Phosphoramidate Lipids: High Efficiency of an Imidazolium Derivative. Chembiochem 2008, 9, 1462–1471. DOI: 10.1002/cbic.200700727.
   PubMed Web of Science ®Google Scholar
• Jaffres, P. A.; Fraix, A.; Lorilleux, C.; Berchel, M.; Couthon, H.; Haelters, J. P.; Montier, T. New Lipo-Phosphoramidates for Gene Delivery. Phosphorus Sulphur Silicon 2011, 186, 918–920. DOI: 10.1080/10426507.2010.522639.
   Web of Science ®Google Scholar
• Winkler, J. Oligonucleotide Conjugates for Therapeutic Applications. Chem. Biodivers. 2010, 7, 791–809. DOI: 10.4155/tde.13.47.
   Google Scholar
• Mottais, A.; Berchel, M.; Sibiril, Y.; Laurent, V.; Gill, D.; Hyde, S.; Jaffrès, P. A.; Montier, T.; Le, G. T. Antibacterial Effect and DNA Delivery Using a Combination of an Arsonium-Containing Lipophosphoramide with an N-Heterocyclic Carbene-Silver Complex – Potential Benefits for Cystic Fibrosis Lung Gene Therapy. Int. J. Pharm. 2017, 1, 29–41. DOI: 10.1016/j.ijpharm.2017.11.022.
   Web of Science ®Google Scholar
• Yasunori, T.; Maren, P.; Johnston, J. N. Brønsted Acid Catalyzed Phosphoramidic Acid Additions to Alkenes: Diastereo- and Enantioselective Halogenative Cyclizations for the Synthesis of C- and P-Chiral Phosphoramidates. J. Am. Chem. Soc. 2014, 42, 14734–14737. DOI: 10.1021/ja5088584.
   Web of Science ®Google Scholar
• Gao, X.; Tang, Z.; Lu, M.; Liu, H.; Jiang, Y.; Zhao, Y.; Cai, Z. Suppression of Matrix Ions by N-Phosphorylation Labeling Using Matrix-Assisted Laser Desorption–Ionization Time-of-flight Mass Spectrometry. Chem. Commun. 2012, 12, 10198–10200. DOI: 10.1039/c2cc36091h.
   Web of Science ®Google Scholar
• Le Corre, S. S.; Berchel, M.; Gourvès, H. C.; Haelters, J. P.; Jaffrès, P. BeilsteinAtherton-Todd Reaction: Mechanism, Scope and Applications. Beilstein. J. Org. Chem. 2014, 10, 1166–1196. DOI: 10.3762/bjoc.10.117.
   PubMed Web of Science ®Google Scholar
• Li, S. O. Synthesis of N-Phosphoryl Amino Acid Esters. J. Am. Chem. Soc. 1952, 74, 5959–5961. DOI: 10.1021/ja01143a041.
   Web of Science ®Google Scholar
• Cho, A.; Zhang, L.; Xu, J.; Lee, R.; Butler, T.; Metobo, S.; Aktoudianakis, V.; Lew, W.; Ye, H.; Clarke, M.; et al. Discovery and Synthesis of C-Nucleosides as Potential New anti-HCV Agents. J. Med. Chem. 2014, 5, 679–684. DOI: 10.1021/ml500077j.
   Web of Science ®Google Scholar
• Bohrsch, V.; Mathew, T.; Zieringer, M.; Vallee, M. R. J.; Artner, L. M.; Dernedde, J.; Haag, R.; Hackenberger, C. P. Chemoselective Staudinger-Phosphite Reaction of Symmetrical Glycosyl-Phosphites with Azido-Peptides and Polygycerols. Org. Biomol. Chem. 2012, 10, 6211–6216. DOI: 10.1039/C2OB25207D.
   PubMed Web of Science ®Google Scholar
• Serwa, R.; Wilkening, I.; Del Signore, G.; Mühlberg, M.; Claussnitzer, I.; Weise, C.; Gerrits, M.; Hackenberger, C. P. R. Chemoselective Staudinger-Phosphite Reaction of Azides for the Phosphorylation of Proteins. Angew. Chem. Int. Ed. Engl. 2009, 48, 8234–8239. DOI: 10.1002/anie.200902118.
   PubMed Web of Science ®Google Scholar
• Nischan, N.; Chakrabarti, A.; Serwa, R. A.; Bovee-Geurts, P. H.; Brock, R.; Hackenberger, C. P. Stabilization of Peptides for Intracellular Applications by Phosphoramidate-Linked Polyethylene Glycol Chains. Angew. Chem. Int. Ed. Engl. 2013, 52, 11920–11924. DOI: 10.1002/anie.201303467.
   PubMed Web of Science ®Google Scholar
• Kontoyianni, M.; McClellan, L. M.; Sokol, G. S. Evaluation of Docking Performance: Comparative Data on Docking algorithms. J. Med. Chem. 2004, 47, 558–565. DOI: 10.1021/jm0302997.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Rhabasa-Lhoret, R.; Chiasson, J. L. International Textbook of Diabetes Mellitus, John Wiley & Sons Ltd: Chichester, 2004; p 901.
   Google Scholar
• Tamil, I. G.; Dineshkumar, B.; Nandhakumar, M.; Senthilkumar, M.; Mitra, A. Inmaculada Fuertes Isidoro Caraballo Antonia Miranda Mónica Millán Study of Critical Points of Drugs with Different Solubilities in Hydrophilic Matrices. Ind. J. Pharm. 2010, 42, 138–146. DOI: 10.1016/j.ijpharm.2009.09.019.
   Google Scholar
• Sales, P. M.; de Souza, P. M.; Simeoni, L. A.; Magalhaes, P. O.; 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.
   PubMed Web of Science ®Google Scholar
• Qin, L.; Ren, X.; Yang, X.; Bai, F.; Wang, L.; Geng, P.; Bai, G.; Shen, Y. Structures of Human Pancreatic α-amylase in Complex with Acarviostatins: Implications for Drug Design Against Type II Diabetes. J. Struct. Biol. 2011, 174, 196–202. DOI: 10.1016/j.jsb.2010.11.020.
   PubMed Web of Science ®Google Scholar
• Danny, C.; Lenstra, J. J.; Wolf, Jasmin, M. Catalytic Staudinger Reduction at Room Temperature. J. Org. Chem. 2019, 10, 6536–6545. DOI: 10.1021/acs.joc.9b00831.
   Web of Science ®Google Scholar