Novel advances in the synthesis of bisphosphonates, containing heterocyclic and macrocyclic structure

References

• Russel, R. G. G. Bisphosphonates: From Bench to Bedside. Ann. N. Y. Acad. Sci. 2006, 1068, 367–401. DOI: 10.1196/annals.1346.041.
   PubMed Web of Science ®Google Scholar
• Green, G.; Lipton, A. Anticancer Properties of Zoledronic Acid. Cancer Invest. 2010, 28, 944–957. DOI: 10.3109/07357907.2010.512598.
   PubMed Web of Science ®Google Scholar
• Rodrigues-Poveda, C. A.; Gonzalez-Pacanowska, D.; Szajnman, S. H.; Rodriguez, J. B. 2-Alkylaminoethyl-1,1-Bisphosphonic Acids Are Potent Inhibitors of the Enzymatic Activity of Trypanosoma Cruzi Squalene Synthase. Antimicrob. Agents Chemother. 2012, 56, 4483–4486. http://dx.doi.org/10.1128/AAC.00796-12.
   PubMed Web of Science ®Google Scholar
• Ghosh, S.; Chan, J. M. W.; Lea, C. R.; Meints, G. A.; Lewis, J. C.; Tovian, Z. S.; Flessner, R. M.; Loftus, T. C.; Bruchhaus, I.; Kendrick, H.; et al. Effects of Bisphosphonates on the Growth of Entamoeba Histolytica and Plasmodium Species in Vitro and in Vivo. J. Med. Chem. 2004, 47, 175–187. DOI: 10.1021/jm030084x.
   PubMed Web of Science ®Google Scholar
• Das, H.; Wang, L.; Kamath, A.; Bukowski, J. F. Vgamma2Vdelta2 T-Cell Receptor-Mediated Recognition of Aminobisphosphonates. Blood 2001, 98, 1616–1618. DOI: 10.1182/blood.V98.5.1616.
   PubMed Web of Science ®Google Scholar
• Bhushan, K. R.; Tanaka, E.; Frangioni, J. V. Synthesis of Conjugatable Bisphosphonates for Molecular Imaging of Large Animals. Angew. Chem. Int. Ed. 2007, 46, 7969–7971. DOI: 10.1002/anie.200701216.
   PubMed Web of Science ®Google Scholar
• Xu, K.; Ge, W.; Liang, G.; Wang, L.; Yang, Z.; Wang, Q.; Hsing, I.-M.; Xu, B. Bisphosphonate-Containing Supramolecular Hydrogels for Topical Decorporation of Uranium-Contaminated Wounds in Mice. Int. J. Radiat. Biol. 2008, 84, 353–362. DOI: 10.1080/09553000802029902.
   PubMed Web of Science ®Google Scholar
• Pradeep, A. R.; Sharma, A.; Rao, N. S.; Bajaj, P.; Naik, S. B.; Kumari, M. Local Drug Delivery of Alendronate Gel for the Treatment of Patients with Chronic Periodontitis with Diabetes Mellitus: A Double-Masked Controlled Clinical Trial. J. Periodontol. 2012, 83, 1322–1328. DOI: 10.1902/jop.2012.110292.
   PubMed Web of Science ®Google Scholar
• Rodriguez, J. B. Tetraethyl Vinylidenebisphosphonate: A Versatile Synthon for the Preparation of Bisphosphonates. Synthesis 2014, 46, 1129–1142. DOI: 10.1055/s-0033-1340952.
   Web of Science ®Google Scholar
• Reznikov, A. N.; Skomorokhov, M. Y.; Leonova, M. V.; Klimochkin, Y. N. Synthesis of Adamantyl-Containing Cidofovir Analogs as Potential Antiviral Prodrugs with High Bioavailability Parameters. Russ. J. Gen. Chem. 2015, 85, 402–408. DOI: 10.1134/S1070363215020097.
   Web of Science ®Google Scholar
• Galmarini, C. M.; Mackey, J. R.; Dumontet, C. Nucleoside Analogues and Nucleobases in Cancer Treatment. Lancet Oncol. 2002, 3, 415–424. DOI: 10.1016/S1470-2045(02)00788-X.
   PubMed Web of Science ®Google Scholar
• Vagapova, L. I.; Smolobochkin, A. V.; Gazizov, A. S.; Burilov, A. R.; Bogdanov, A. A.; Pudovik, M. A.; Sinyashin, O. G. Synthesis of New Nucleoside Analogs Containing Amino Bisphosphonic Groups. Russ. J. Org. Chem. 2016, 52, 1335–1338. DOI: 10.1134/S1070428016090141.
   Web of Science ®Google Scholar
• Vagapova, L. I.; Smolobochkin, A. V.; Gazizov, A. S.; Burilov, A. R.; Bogdanov, A. A.; Pudovik, M. A. Synthesis of New Phosphorylated Analogs of Nucleotides Containing Adenine and Ethylidene-1,1-Bisphosphoryl Moieties. Russ. J. Gen. Chem. 2017, 87, 2119–2121. DOI: 10.1134/S1070363217090353.
   Web of Science ®Google Scholar
• Smolobochkin, A. V.; Gazizov, A. S.; Vagapova, L. I.; Burilov, A. R.; Bogdanov, A. A.; Pudovik, M. A. Reaction of 9-[2-(1,3-Dioxolan-2-yl)Ethyl]-9H-Purin-6-Amine with Phenols. Synthesis of Diarylpropanes. Russ. J. Org. Chem. 2017, 53, 96–98. DOI: 10.1134/S1070428017010171.
   Web of Science ®Google Scholar
• Vagapova, L. I.; Burilov, A. R.; Amirova, L. R.; Voronina, J. K. Garyfzyanov A. R.; Abdrachmanova, N. F.; Pudovik, M. A. New Aminophosphonates (Aminophosphine Oxides) Containing Acetal Groups in Reactions with Polyatomic Phenols. Phosphorus, Sulfur, Silicon, Relat. Elem. 2016, 191, 1527–1529. http://dx.doi.org/10.1080/10426507.2016.1212349.
   Web of Science ®Google Scholar
• Vagapova, L. I.; Makhrus, E. M.; Burilov, A. R.; Pudovik, M. A. Synthesis of New Diarylmethanes on the Basis of Resorcinol Derivatives and Amino Acetals Containing an Aminoethylidenebisphosphonate Fragment. Russ. J. Gen. Chem. 2017, 87, 2103–2106. DOI: 10.1134/S1070363217090316.
   Web of Science ®Google Scholar
• Yang, X.; Akhtar, S.; Rubino, S.; Leifer, K.; Hilborn, J.; Ossipov, D. Direct “Click” Synthesis of Hybrid Bisphosphonate–Hyaluronic Acid Hydrogel in Aqueous Solution for Biomineralization. Chem. Mater. 2012, 24, 1690–1697. DOI: 10.1021/cm300298n.
   Web of Science ®Google Scholar
• Alanne, A. L.; Lahtinen, M.; Lofman, M.; Turhanen, P.; Kolehmainen, E.; Vepsäläinen, J.; Sievänen, E. First Bisphosphonate Hydrogelators: Potential Composers of Biocompatible Gels. J. Mater. Chem. B 2013, 1, 6201–6211. DOI: 10.1039/C3TB20957A.
   PubMed Web of Science ®Google Scholar
• Chen, S.-P.; Hu, L.; Zhang, Y.-Q.; Deng, P.; Li, C.; Chen, X.; Yuan, L. (AEDPH 3 )·(BtaH): A Novel Supramolecular Plaster with Formaldehyde Adsorption and Formaldehyde/Ultraviolet Ray-Induced Luminescence Switching Performance. J. Chem. Commun. 2012, 48, 552–554. DOI: 10.1039/C1CC16415E.
   PubMed Web of Science ®Google Scholar
• Chen, S.-P.; Yuan, Y.-X.; Pan, L.-L.; Xu, S.-Q.; Xia, H.; Yuan, L.-J. A Novel Supramolecular Plaster Based on An Organic Acid − Base Compound: Synthesis, Structure, Mechanical Properties, and Sterilizing Performance. Cryst. Growth Des. 2009, 9, 874–879. DOI: 10.1021/cg800552s.
   Web of Science ®Google Scholar
• Chen, S.-P.; Hu, L.; Hu, X.-J.; Yuan, Y.-X.; Pan, L.-L.; Yuan, L. (AEDPH 3)·(ureaH)·(H2O): A Novel Organic Supramolecular Plaster with Gas Adsorption Performance. J. Cryst. Growth Des. 2009, 9, 3835–3839. DOI: 10.1021/cg9004483.
   Google Scholar
• Vagapova, L. I.; Gazizov, A. S.; Burilov, A. R.; Bogdanov, A. A.; Pudovik, M. A. New Nucleoside Analogs Derived from Adenosine and Methylenebisphosphonic Acids. Russ. J. Gen. Chem. 2016, 86, 2564–2566. DOI: 10.1134/S1070363216110281.
   Web of Science ®Google Scholar
• Jang, Y. M.; Yu, C. J.; Kim, J. S.; Kim, S. U. Ab Initio Design of Drug Carriers for Zoledronate Guest Molecule Using Phosphonated and Sulfonated Calix[4]Arene and Calix[4]Resorcinarene Host Molecules. J. Mater. Sci. 2018, 53, 5125–5139. https://doi.org/10.1007/s10853-017-1930-8.
   Web of Science ®Google Scholar
• Mokhtari, B.; Pourabdollah, K. Applications of Calixarene Nano-Baskets in Pharmacology. J. Incl. Phenom. Macrocycl. Chem. 2012, 73, 1–15. DOI: 10.1007/s10847-011-0062-z.
   Web of Science ®Google Scholar
• Vagapova, L. I.; Nasirova, Z. A.; Burilova, E. A.; Zobov, V. V.; Burilov, A. R.; Amirov, R. R.; Pudovik, M. A. New Salt Structures Based on Aminomethylated Calix[4]-Resorcinarenes and (1-Hydroxyethane-1,1-Diyl)Bisphosphonic Acid. Russ. J. Org. Chem. 2017, 53, 312–314. DOI: 10.1134/S1070428017020324.
   Web of Science ®Google Scholar
• Zakharova, L. Y.; Kashapov, R. R.; Pashirova, T. N.; Mirgorodskaya, A. B.; Sinyashin, O. G. Self-Assembly Strategy for the Design of Soft Nanocontainers with Controlled Properties. Mendeleev Commun. 2016, 26, 457–468. DOI: 10.1016/j.mencom.2016.11.001.
   Web of Science ®Google Scholar
• . Schühle, D. T.; van Rijn, P.; Laurent, S.; Vander, E. L.; Muller, R. N.; Stuart, M. C.; Schatz, J.; Peters, J. A. Liposomes with Conjugates of a Calix[4]Arene and a Gd-DOTA Derivative on the outside Surface; An Efficient Potential Contrast Agent for MRI. Chem. Commun. 2010, 46, 4399–4401. DOI: 10.1039/c0cc00107d.
   PubMed Web of Science ®Google Scholar