References
- (a) Neog, K.; Gogoi, P. Recent Advances in the Synthesis of Organophosphorus Compounds via Kobayashi’s Aryne Precursor: A Review. Org. Biomol. Chem. 2020, 18, 9549–9561. DOI: https://doi.org/10.1039/D0OB01988G. (b) Kuzmin, I. S.; Yuriev, D. Y.; Toporkov, G. A.; Kalistratova, A. V.; Kovalenko, L. V. Synthesis and Biological Activity of N-Phosphonacetyl-L-Aspartate’s Structural Analogs N-(α-Dietoxyphosphorylcyclopropylcarbonyl)-Amino Acids. Fine Chem. Technol. 2020, 15, 26–35. DOI: https://doi.org/10.32362/2410-6593-2020-15-5-26-35. (c) Tang, Z.; Kong, N.; Ouyang, J.; Feng, C.; Kim, Y. N.; Ji, X.; Wang, C.; Farokhzad, O. C.; Zhang, H.; Tao, W. Phosphorus Science-Oriented Design and Synthesis of Multifunctional Nanomaterials for Biomedical Applications. Matter 2020, 2, 297–322. DOI: https://doi.org/10.1016/j.matt.2019.12.007.
- (a). Demkowicz, S.; Rachon, J.; Daśko, M.; Kozak, W. Selected Organophosphorus Compounds with Biological Activity. RSC Adv. 2016, 6, 7101–7112. DOI: https://doi.org/10.1039/C5RA25446A. . (b). Chen, L.; Liu, X.-Y.; Zou, Y.-X. Recent Advances in the Construction of Phosphorus-Substituted Heterocycles, 2009–2019. Adv. Synth. Catal. 2020, 362, 1724–1818. DOI: https://doi.org/10.1002/adsc.201901540.
- (a). Arribata, M.; Cavelier, F.; Rémond, E. B. Phosphorus-Containing Amino Acids with a P–C Bond in the Side Chain or a P–O, P–S or P–N Bond From Synthesis to Applications. RSC Adv. 2020, 10, 6678–6724. DOI: https://doi.org/10.1039/C9RA10917J. (b) Khadir, F. S. A.; Boukhssas, S.; Achamlale, S.; Aouine, Y.; Nakkabi, A.; Faraj, H.; Alami, A. Synthesis and Characterization of the Structure of Diethyl [(4-{(1H-Benzo[d]Imidazol-1-yl)Methyl}-1H-1,2,3-Triazol-1-yl)(Benzamido)Methyl]Phosphonate Using 1D and 2D NMR Experiments. Euro. J. Adv. Chem. Res. 2021, 2, 1–7. DOI: https://doi.org/10.24018/ejchem.2021.2.1.42.
- Abdou, W. M.; Barghash, R. F.; Bekheit, M. S. Carbodiimides in the Synthesis of Enamino- and α-Aminophosphonates as Peptidomimetics of Analgesic/Antiinflammatory and Anticancer Agents. Arch. Pharm. 2012, 345, 884–895. DOI: https://doi.org/10.1002/ardp.201200142.
- Schweiker, S. S.; Tauber, A. L.; Kam, C. M.; Eyckens, D. J.; Henderson, L. C.; Levonis, S. M. Levonis, S. M. α-Aminophosphonates as Potential PARP1 Inhibitors. ChemistrySelect 2020, 5, 4205–4209. DOI: https://doi.org/10.1002/slct.202000520.
- Sabbaghzadeh, R. Physicochemical Properties of Analogs α-Aminophosphonates Drugs Determined via Molecular Dynamics Simulation. Asian Pac. J. Cancer Biol. 2019, 4, 47–50. DOI: https://doi.org/10.31557/apjcb.2019.4.3.47-50.
- Quntar, A. A.; Dweik, H.; Jabareen, A.; Gloriozova, T. A.; Dembitsky, V. M. An Aminopyrrolidinyl Phosphonates-A New Class of Antibiotics: Facile Synthesis and Predicted Biological Activity. Int. J. Org. Chem. 2020, 10, 170–181. DOI: https://doi.org/10.4236/ijoc.2020.104013.
- Poola, S.; Nagaripati, S.; Tellamekala, S.; Chintha, V.; Kotha, P.; Yagani, J. R.; Golla, N.; Cirandur, S. R. Green Synthesis, Antibacterial, Antiviral and Molecular Docking Studies of α-Aminophosphonates. Synth. Commun. 2020, 50, 2655–2672. DOI: https://doi.org/10.1080/00397911.2020.1753079.
- Xie, D.; Zhang, A.; Liu, D.; Yin, L.; Wan, J.; Zeng, S.; Hu, D. Synthesis and Antiviral Activity of Novel α-Aminophosphonates Containing 6-Fluorobenzothiazole Moiety. Phosphorus, Sulfur, and Silicon 2017, 192, 1061–1067. DOI: https://doi.org/10.1080/10426507.2017.1323895.
- (a). Gundluru, M.; Badavath, V. N.; Haroon, Y. S.; Sudileti, M.; Nemallapudi, B. R.; Gundala, S.; Zyryanov, G. V.; Cirandur, S. R. Design, Synthesis, Cytotoxic Evaluation and Molecular Docking Studies of Novel Thiazolyl α-Aminophosphonates. Res. Chem. Intermed. 2021, 47, 1139–1160. DOI: https://doi.org/10.1007/s11164-020-04321-6. . (b). Aita, S.; Badavath, V. N.; Gundluru, M.; Sudileti, M.; Nemallapudi, B. R.; Gundala, S.; Zyryanov, G. V.; Chamarti, N. R.; Cirandur, S. R. Novel α-Aminophosphonates of Imatinib Intermediate: Synthesis, Anticancer Activity, Human Abl Tyrosine Kinase Inhibition and Drug-Likeness Prediction. Bioorg. Chem. 2021, 109, 104718. DOI: https://doi.org/10.1016/j.bioorg.2021.104718.
- Shaik, M. S.; Nadiveedhi, M. R.; Gundluru, M.; Poola, S.; Allagadda, R.; Chippada, A. R.; Cirandur, S. R. Green Synthesis of Diethyl((2-Iodo-4-(Trifluoromethyl)Phenyl) Amino) (Aryl) Methyl) Phosphonates as Potent α-Glucosidase Inhibitors. Synth. Commun. 2020, 50, 587–601. DOI: https://doi.org/10.1080/00397911.2019.1709208.
- Nayab, R. S.; Maddila, S.; Krishna, M. P.; Titinchi, S. J. J.; Thaslim, B. S.; Chintha, V.; Wudayagiri, R.; Nagam, V.; Tartte, V.; Chinnam, S.; et al. 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: https://doi.org/10.1080/10799893.2020.1722166.
- Sudileti, M.; Chintha, V.; Nagaripati, S.; Gundluru, M.; Yasmin, S. H.; Wudayagiri, R.; Cirandur, S. R. Green Synthesis, Molecular Docking, Anti-Oxidant and Anti-Inflammatory Activities of α-Aminophosphonates. Med. Chem. Res. 2019, 28, 1740–1754. DOI: https://doi.org/10.1007/s00044-019-02411-8.
- Sujatha, B.; Mohan, S.; Subramanyam, C.; Rao, K. P. Microwave-Assisted Synthesis and anti-Inflammatory Activity Evaluation of Some Novel α-Aminophosphonates. Phosphorus, Sulfur, and Silicon 2017, 192, 1110–1113. DOI: https://doi.org/10.1080/10426507.2017.1331233.
- Elsherbiny, D. A.; Abdelgawad, A. M.; El-Naggar, M. E.; El-Sherbiny, R. A.; El-Rafie, M. H.; El-Sayed, I. E. Synthesis, Antimicrobial Activity, and Sustainable Release of Novel α-Aminophosphonate Derivatives Loaded Carrageenan Cryogel. Int. J. Biol. Macromol. 2020, 163, 96–107. DOI: https://doi.org/10.1016/j.ijbiomac.2020.06.251.
- An, T. N. M.; Cuong, N. V.; Quang, N. M.; Thanh, T. V.; Alam, M. Green Synthesis Using PEG-400 Catalyst, Antimicrobial Activities, Cytotoxicity and in Silico Molecular Docking of New Carbazole Based on α-Aminophosphonate. ChemistrySelect 2020, 5, 6339–6349. DOI: https://doi.org/10.1002/slct.202000855.
- Mohan, G.; Kuma, S.; Sudileti, M.; Sridevi, C.; Venkatesu, P.; Reddy, C. S. Excellency of Pyrimidinyl Moieties Containing α-Aminophosphonates over Benzthiazolyl Moieties for Thermal and Structural Stability of Stem Bromelain. Int. J. Biol. Macromol. 2020, 165, 2010–2021. DOI: https://doi.org/10.1016/j.ijbiomac.2020.10.065.
- Lewkowski, J.; Morawska, M.; Karpowicz, R.; Rychter, P.; Rogacz, D.; Lewicka, K. Novel (5-Nitrofurfuryl)-Substituted Esters of Phosphonoglycine - Their Synthesis and Phyto- and Ecotoxicological Properties. Chemosphere 2017, 188, 618–632. DOI: https://doi.org/10.1016/j.chemosphere.2017.09.031.
- Reddy, N. M.; Poojith, N.; Mohan, G.; Reddy, Y. M.; Saritha, K. V.; Rao, P. V.; Reddy, A. V. K.; Swetha, V.; Zyryanov, G. V.; Krishna, B. S.; et al. Green Synthesis, Antioxidant, and Plant Growth Regulatory Activities of Novel α-Furfuryl-2-alkylaminophosphonates. ACS Omega. 2021, 6, 2934–2948. DOI: https://doi.org/10.1021/acsomega.0c05302.
- Li, Y.; Geng, J.; Liu, Y.; Yu, S.; Zhao, G. Thiadiazole-A Promising Structure in Medicinal Chemistry. ChemMedChem 2013, 8, 27–41. DOI: https://doi.org/10.1002/cmdc.201200355.
- (a). Sahu, S.; Sahu, T.; Kalyani, G.; Gidwani, B. Synthesis and Evaluation of Antimicrobial Activity of 1, 3, 4-Thiadiazole Analogues for Potential Scaffold. J. Pharmacopuncture. 2021, 24, 32–40. DOI: https://doi.org/10.3831/KPI.2021.24.1.32. . (b). Abo-Bakr, A. M.; Hashem, H. E. New 1,3,4-Thiadiazole Derivatives: Synthesis, Characterization, and Antimicrobial Activity. J. Het. Chem. 2019, 56, 1038–1047. DOI: https://doi.org/10.1002/jhet.3489. DOI: https://doi.org/10.1002/jhet.3489.
- Szeliga, M. Thiadiazole Derivatives as Anticancer Agents. Pharmacol. Rep. 2020, 72, 1079–1100. DOI: https://doi.org/10.1007/s43440-020-00154-7.
- El Ashry, E. H.; Ramadan, E. S.; Amer, M. R.; El Kilany, Y.; Badawy, M. E. I.; Rabea, E. I. Synthesis and Antioxidant Activity of Novel 5-Amino-2-Alkyl/Glycosylthio-1,3,4-Thiadiazoles: Regioselective Alkylation and Glycosylation of the 5-Amino-1,3,4-Thiadiazole-2-Thiol Scaffold. Curr. Org. Synth. 2019, 16, 801–809. DOI: https://doi.org/10.2174/1570179416666190415113847.
- Serban, G. Synthetic Compounds with 2-Amino-1,3,4-Thiadiazole Moiety against Viral Infections. Molecules 2020, 25, 942. DOI: https://doi.org/10.3390/molecules25040942.
- Bhattacharya, S.; Kashaw, V. Design, Synthesis and Anticonvulsant Potential of (E)-3-(5-(Substituted Aminomethyl)-1,3,4-Thiadiazol-2-yl)-2-Substituted Styrylquinazolin-4-(3H)-One. J. Drug Deliv. Ther. 2019, 9, 591–602. DOI: https://doi.org/10.22270/jddt.v9i2.2705.
- Oruc, E. E.; Rollas, S.; Kandemirli, F.; Shvets, N.; Dimoglo, A. S. 1,3,4-thiadiazole Derivatives. Synthesis, Structure Elucidation, and Structure-Antituberculosis Activity Relationship Investigation. J. Med. Chem. 2004, 47, 6760–6767. DOI: https://doi.org/10.1021/jm0495632.
- Omar, Y. M.; Abdel-Moty, S. G.; Abdu-Allah, H. H. M. Further Insight into the Dual COX-2 and 15-LOX anti-Inflammatory Activity of 1,3,4-Thiadiazole-Thiazolidinone Hybrids: The Contribution of the Substituents at 5th Positions is Size Dependent. Bioorg. Chem. 2020, 97, 103657. DOI: https://doi.org/10.1016/j.bioorg.2020.103657.
- Luszczki, J. J.; Karpińska, M.; Matysiak, J.; Niewiadomy, A. Characterization and Preliminary Anticonvulsant Assessment of Some 1,3,4-Thiadiazole Derivatives. Pharmacol. Rep. 2015, 67, 588–592. DOI: https://doi.org/10.1016/j.pharep.2014.12.008.
- Amira, A.; Aouf, Z.; K’tir, H.; Chemam, Y.; Ghodbane, R.; Zerrouki, R.; Aouf, N. Recent Advances in the Synthesis of α-Aminophosphonates: A Review. ChemistrySelect 2021, 6, 6137–6149. DOI: https://doi.org/10.1002/slct.202101360.
- Petra, R.; Varga, P. R.; Keglevich, G. Synthesis of α-Aminophosphonates and Related Derivatives; the Last Decade of the Kabachnik–Fields Reaction. Molecules 2021, 26, 2511. DOI: https://doi.org/10.3390/molecules26092511.
- Sravya, G.; Balakrishna, A.; Zyryanov, G. V.; Mohan, G.; Reddy, C. S.; Reddy, N. B. Synthesis of α-Aminophosphonates by the Kabachnik-Fields Reaction. Phosphorus, Sulfur, and Silicon 2021, 196, 353–381. DOI: https://doi.org/10.1080/10426507.2020.1854258.
- Shastri, R. A. Review on the Synthesis of α-Aminophosphonate Derivatives. Chem. Sci. Trans. 2019, 8, 359–367. DOI: https://doi.org/10.7598/cst2019.1585.
- Erika, B.; Adam, T.; Ladanyi-Para, K.; Toth, N.; Mátravölgyi, B.; Keglevich, G. Continuous Flow Synthesis of α-Aryl-α-Aminophosphonates. Pure Appl. Chem. 2019, 91, 67–76. DOI: https://doi.org/10.1515/pac-2018-0923.
- Adam, T.; Erika, B.; Keglevich, G. Microwave-Assisted Synthesis of α-Aminophosphonates and Related Derivatives by the Kabachnik-Fields Reaction. Phosphorus, Sulfur, and Silicon 2019, 194, 379–381. DOI: https://doi.org/10.1080/10426507.2018.1547729.
- Kaur, G.; Shamim, M.; Bhardwaj, V.; Gupta, V. K.; Banerjee, B. Acid Catalyzed One-Pot Three-Component Synthesis of α-Aminonitriles and α-Aminophosphonates under Solvent-Free Conditions at Room Temperature. Synth. Commun. 2020, 50, 1545–1560. DOI: https://doi.org/10.1080/00397911.2020.1745844.
- Ravi, N.; Venkatanarayana, M.; Sharathbabu, H.; Babu, K. R. Synthesis of Novel α-Aminophosphonates by Methanesulfonic Acid Catalyzed Kabachnik–Fields Reaction. Phosphorus, Sulfur, and Silicon 2021, 196, 1018–1024. DOI: https://doi.org/10.1080/10426507.2021.1960834.
- Maheswari, C. S.; Shanmugapriya, C.; Revathy, K.; Lalitha, A. SnO2 Nanoparticles as an Efficient Heterogeneous Catalyst for the Synthesis of 2H-Indazolo[2,1-B]Phthalazine-Triones. J. Nanostruct. Chem. 2017, 7, 283–291. DOI: https://doi.org/10.1007/s40097-017-0238-1.
- Bhattacharjee, A.; Ahmaruzzaman, M.; Sinha, T. A Novel Approach for the Synthesis of SnO2 Nanoparticles and Its Application as a Catalyst in the Reduction and Photodegradation of Organic Compounds. Spectrochim. Acta Part A: Mol. Biomol. Spectr. 2015, 136, 751–760. DOI: https://doi.org/10.1016/j.saa.2014.09.092.
- Dehbashi, M.; Aliahmad, M.; Shafiee, M. R. M.; Ghashang, M. Nickel-Doped SnO2 Nanoparticles: Preparation and Evaluation of Their Catalytic Activity in the Synthesis of 1-Amido Alkyl-2-Naphtholes. Synth. React. Inorg., Metal-Org., Nano-Metal Chem. 2013, 43, 1301–1306. DOI: https://doi.org/10.1080/15533174.2012.757753.
- Sapkal, B. M.; Labhane, P. K.; Disale, S. T.; More, D. H. ZnO@SnO2 Mixed Metal Oxide as an Efficient and Recoverable Nanocatalyst for the Solvent Free Synthesis of Hantzsch 1,4-Dihydropyridines. Loc. 2019, 16, 139–144. DOI: https://doi.org/10.2174/1570178615666180907150307.
- Baghernejad, B.; Fiuzat, M. Synthesis of 2-Amino-4H-Pyran Derivatives in Aqueous Media with Nano-SnO2 as Recyclable Catalyst. Asian J. Nanosci. Mater. 2021, 4, 171–177. DOI: https://doi.org/10.26655/AJNANOMAT.2021.2.7.
- Shaikh, S.; Yellapurkar, I.; Ramana, M. M. V. Ultrasound Assisted One-Pot Synthesis of Novel Antipyrine Based α-Aminophosphonates Using TiO2/Carbon Nanotubes Nanocomposite as a Heterogeneous Catalyst. Reaction Kinetics, Mech. Catal. 2021, 134, 917–936. DOI: https://doi.org/10.1007/s11144-021-02110-9.
- Kolli, M. K.; Palani, E.; Govindasamy, C.; Katta, V. R. Highly Efficient One-Pot Synthesis of α-Aminophosphonates Using Nanoporous AlSBA-15 Catalyst in a Three-Component System. Res. Chem. Intermed. 2020, 46, 1047–1064. DOI: https://doi.org/10.1007/s11164-018-3458-1.
- Zandieh, H.; Mokhtari, J.; Larijani, K. Synthesis of α-Amino Phosphonates Catalyzed by Copper-Based Metal Organic Frameworks. J. Organomet. Chem. 2022, 957, 122156. DOI: https://doi.org/10.1016/j.jorganchem.2021.122156.
- Balouiri, M.; Sadiki, M.; Ibnsouda, S. K. Methods for in Vitro Evaluating Antimicrobial Activity: A Review. J. Pharm. Anal. 2016, 6, 71–79. DOI: https://doi.org/10.1016/J.JPHA.2015.11.005.
- Pobiega, K.; Kraśniewska, K.; Derewiaka, D.; Gniewosz, M. Comparison of the antimicrobial activity of Propolis Extracts Obtained by Means of Various Extraction Methods. J. Food Sci. Technol. 2019, 56, 5386–5395. DOI: https://doi.org/10.1007/s13197-019-04009-9.
- Abdollahzadeh, E.; Nematollahi, A.; Hosseini, H. Composition of Antimicrobial Edible Films and Methods for Assessing Their Antimicrobial Activity: A Review. Trends Food Sci. Tech. 2021, 110, 291–303. DOI: https://doi.org/10.1016/j.tifs.2021.01.084.