Synthesis and Antimicrobial Activity of Some of Isoindolin-1-One-3-Phosphonates under Mild and Solvent-Free Conditions

References

• V. Pace, F. Martínez, C. I. Nova, M. Fernández, J. V. Sinisterra, and A. R. Alcántara, “Efficient Horner–Wadsworth–Emmons Intramolecular Cyclisation of a N-Substituted Phthalimide Promoted by KF-Alumina: A General Tool for the Synthesis of Functionalised Isoindolinones,” Tetrahedron Letters 50, no. 25 (2009): 3050–3.
   Web of Science ®Google Scholar
• Nagendra Prasad Muddala, Baskar Nammalwar, and Richard A. Bunce, “Expeditious Synthesis of (+-)-Diethyl 2-Alkyl-and 2-Aryl-(3-Oxoisoindolin-1-yl) Phosphonates Catalysed by OSU-6,” RSC Advances 5, no. 36 (2015): 28389–93.
   Google Scholar
• Y. Nozawa, K. Yamamoto, M. Ito, N. Sakai, K. Mizoue, F. Mizobe, K. Hanada, and C. Stachybotrin, “Stachybotrin C and Parvisporin, Novel Neuritogenic Compounds. I. Taxonomy, Isolation, Physico-Chemical and Biological Properties,” The Journal of Antibiotics 50, no. 8 (1997): 635–40.
   PubMedGoogle Scholar
• S. M. Allin, C. J. Northfield, M. I. Page, and A. M. Slawin, “A Highly Diastereoselective Synthesis of 3-Substituted Isoindolin-1-One Dericatives,” Tetrahedron Letters 40, no. 1 (1999): 143–6.
   Google Scholar
• I. Al Nasr, J. Jentzsch, I. Winter, R. Schobert, K. Ersfeld, W. S. Koko, A. A. Mujawah, T. A. Khan, and B. Biersack, “Antiparasitic Activities of New Lawsone Mannich Bases,” Archiv Der Pharmazie 352, no. 11 (2019): 1900128.
   Google Scholar
• I. Al Nasr, N. Touj, W. Koko, T. Khan, I. Özdemir, S. Yaşar, and N. Hamdi, “Biological Activities of NHC–Pd (II) Complexes Based on Benzimidazolylidene N-Heterocyclic Carbene (NHC) Ligands Bearing Aryl Substituents,” Catalysts 10, no. 10 (2020): 1190.
   Google Scholar
• P. Antico, V. Capaccio, A. Di. Mola, A. Massa, and L. Palombi, “Electrochemically Initiated Tandem and Sequential Conjugate Addition Processes: One-Pot Synthesis of Diverse Functionalized Isoindolinones,” Advanced Synthesis & Catalysis 354, no. 9 (2012): 1717–24.
   Google Scholar
• K. Arakawa, T. Nishimura, Y. Sugimoto, H. Takahashi, and T. Shimamura, US Patent 8362052 (B2), 2013.
   Google Scholar
• A. R. Katritzky, C. A. Ramsden, E. F. Scriven, and R. J. Taylor, Comprehensive Heterocyclic Chemistry III (Amsterdam: Elsevier Science Oxford, 2008), 3.
   Google Scholar
• R. Bonnett and S. A. North, “The Chemistry of the Isoindoles,” Advances in Heterocyclic Chemistry 29 (1981): 341–99.
   Google Scholar
• Jaco C. Breytenbach, Sandra van Dyk, Ilse van den Heever, Steven M. Allin, Claire C. Hodkinson, Christopher J. Northfield, and Micheal I. Page, “Synthesis and Antimicrobial Activity of Some Isoindolin-1-Ones Derivatives,” Bioorganic & Medicinal Chemistry Letters 10, no. 15 (2000): 1629–31.
   PubMed Web of Science ®Google Scholar
• Marina Büchert, Sebastian Meinke, Alexander H. G. P. Prenzel, Nina Deppermann, and Wolfgang Maison, “Azabicycloalkenes as Synthetic Intermediates-Synthesis of Azabicyclo[X.3.0]Alkane Scaffolds,” Organic Letters 8, no. 24 (2006): 5553–6.
   PubMedGoogle Scholar
• R. D. Dally and T. A. Woods, US Patent 0275121 (A1), 2014.
   Google Scholar
• T. J. Donohoe, “Product Class 14: 1H- and 2H-Isoindoles,” Science of Synthesis 10 (2001): 653–92.
   Google Scholar
• V. Dubois, C. V. Ginneken, H. D. Cock, A. M. Lambeir, P. V. Veken, K. Augustyns, X. Chen, S. Scharpé, and I. D. Meester, “Enzyme Activity and Immunohistochemical Localization of Dipeptidyl Peptidase 8 and 9 in Male Reproductive Tissues,” The Journal of Histochemistry and Cytochemistry 57, no. 6 (2009): 531–41.
   PubMedGoogle Scholar
• D. Enders, A. A. Narine, F. Toulgoat, and T. Bisschops, “Asymmetric Brønsted Acid Catalyzed Isoindoline Synthesis: Enhancement of Enantiomeric Ratio by Stereoablative Kinetic Resolution,” Angewandte Chemie International Edition 47, no. 30 (2008): 5661–5.
   PubMedGoogle Scholar
• A. J. Frank, H. W. Man, C. Ge, and M. Saindane, US Patent 8415485 (B2), 2013.
   Google Scholar
• S. Fustero, L. Herrera, R. Lázaro, E. Rodríguez, M. A. Maestro, N. Mateu, and P. Barrio, “Base-Dependent Stereodivergent Intramolecular Aza-Michael Reaction: Asymmetric Synthesis of 1,3-disubstituted isoindolines,” Chemistry (Weinheim an Der Bergstrasse, Germany) 19, no. 35 (2013): 11776–85.
   PubMedGoogle Scholar
• P. Gomes, M. J. Araújo, M. Rodrigues, N. Vale, Z. Azevedo, J. Iley, P. Chambel, J. Morais, and R. Moreira, “Synthesis of Imidazolidin-4-One and 1H-Imidazo [2, 1-a] Isoindole-2, 5 (3H, 9bH)-Dione Derivatives of Primaquine: Scope and Limitations,” Tetrahedron 60, no. 26 (2004): 5551–55562.
   Google Scholar
• K. R. Guertin, US Patent 6482951 (B2), 2002.
   Google Scholar
• C. Hemmert, A. Fabié, A. Fabre, F. Benoit-Vical, and H. Gornitzka, “Synthesis, Structures, and Antimalarial Activities of Some Silver(I), Gold(I) and Gold(III) Complexes Involving N-Heterocyclic Carbene Ligands,” European Journal of Medicinal Chemistry 60 (2013): 64–75.
   PubMed Web of Science ®Google Scholar
• M. Ignasik, M. Bajda, N. Guzior, M. Prinz, U. Holzgrabe, and B. Malawska, “Design, Synthesis and Evaluation of Novel 2-(Aminoalkyl)-Isoindoline-1,3-Dione Derivatives as Dual-Binding Site Acetylcholinesterase Inhibitors,” Archiv Der Pharmazie 345, no. 7 (2012): 509–16.
   PubMedGoogle Scholar
• C. Intaraudom, N. Bunbamrung, A. Dramae, N. Boonyuen, P. Kongsaeree, K. Srichomthong, S. Supothina, and P. Pittayakhajonwut, “Terphenyl Derivatives and drimane - Phathalide/isoindolinones from Hypoxylon Fendleri BCC32408,” Phytochemistry 139 (2017): 8–17.
   PubMed Web of Science ®Google Scholar
• J. Jentzsch, W. S. Koko, I. S. Al Nasr, T. A. Khan, R. Schobert, K. Ersfeld, and B. Biersack, “New Antiparasitic Bis-Naphthoquinone Derivatives,” Chemistry & Biodiversity 17, no. 2 (2020): e1900597.
   PubMedGoogle Scholar
• W. T. Jiaang, Y. S. Chen, T. Hsu, S. H. Wu, C. H. Chien, C. N. Chang, S. P. Chang, S. J. Lee, and X. Chen, “Novel Isoindoline Compounds for Potent and Selective Inhibition of Prolyl Dipeptidase DPP8,” Bioorganic & Medicinal Chemistry Letters 15, no. 3 (2005): 687–91.
   PubMed Web of Science ®Google Scholar
• G. O. Kachkovskyi and O. I. Kolodiazhnyi, “Synthesis of Phosphonic Acids Possessing Isoindolin-1-One Moiety: Unexpected Acid-Catalyzed CP-Bond Cleavage,” Phosphorus, Sulfur, and Silicon 184, no. 4 (2009): 890–907.
   Web of Science ®Google Scholar
• W. S. Koko, J. Jentzsch, H. Kalie, R. Schobert, K. Ersfeld, I. S. Al Nasr, T. A. Khan, and B. Biersack, “Evaluation of the Antiparasitic Activities of Imidazol-2-Ylidene-Gold(I) Complexes,” Archiv Der Pharmazie 353, no. 5 (2020): e1900363.
   PubMedGoogle Scholar
• M. Ordonez, G. D. Tibhe, A. Zamudio-Medina, and J. L. Viveros-Ceballos, “An Easy Approach for the Synthesis of N-Substituted Isoindolin-1-Ones,” Synthesis 2012, no. 04 (2012): 569–74.
   Google Scholar
• M. A. Reyes-González, A. Zamudio-Medina, and M. Ordóñez, “Practical and High Stereoselective Synthesis of 3-(Arylmethylene) Isoindolin-1-Ones from 2-Formylbenzoic Acid,” Tetrahedron Letters 53, no. 43 (2012): 5756–8.
   Google Scholar
• V. Gutierrez, E. Mascaró, F. Alonso, Y. Moglie, and G. Radivoy, “Direct Synthesis of β-Ketophosphonates and Vinyl Phosphonates from Alkenes or Alkynes Catalyzed by CuNPs/ZnO,” RSC Advances 5, no. 81 (2015): 65739–44.
   Google Scholar
• L. Li, W. Huang, L. Chen, J. Dong, X. Ma, and Y. Peng, “Silver-Catalyzed Oxidative C (sp3)− P Bond Formation through C − C and P − H Bond Cleavage,” Angewandte Chemie 129, no. 35 (2017): 10675–80.
   Google Scholar
• D. Nellisara and S. Shashikumar, “Preparation of New α-Aminophosphonate Derivatives by Kabachnik-Fields Reaction Using a Recyclable Catalyst,” Journal of Chemistry. 2013 (2013): 1–8.
   Google Scholar
• M. B. Gawande, S. Disale, S. Kale, G. Abraham, S. Kahandal, and A. Sawarkar, “A Sustainable and Efficient Synthesis of Benzyl Phosphonates Using PEG/KI Catalytic System,” Frontiers in Chemistry 4 (2016): 35.
   PubMedGoogle Scholar
• Y. Qian, Q. Dai, Z. Li, Y. Liu, and J. Zhang, “O-Phosphination of Aldehydes/Ketones toward Phosphoric Esters: Experimental and Mechanistic Studies,” Organic Letters 22, no. 12 (2020): 4742–8.
   PubMedGoogle Scholar
• H. Jelali, I. S. Al Nasr, W. S. Koko, T. A. Khan, E. Deniau, M. Sauthier, F. Alresheedi, and N. Hamdi, “Synthesis, Characterization and In Vitro Bioactivity Studies of Isoindolin-1-3-Phosophonate Compounds,” Journal of Heterocyclic Chemistry (2021): 2021.
   Google Scholar
• A. Mantovani, “In Vitro and In Vivo Cytotoxicity of Adriamycin and Daunomycin for Murine Macrophages,” Cancer Research 37, no. 3 (1977): 815–20.
   PubMedGoogle Scholar
• N. A. Johnson, M. R. Southerland, and W. J. Youngs, “Recent Developments in the Medicinal Applications of Silver-NHC Complexes and Imidazolium Salts,” Molecules 22, no. 8 (2017): 1263.
   Web of Science ®Google Scholar
• K. Güven, E. Yücel, and F. Cetintaş, “Antimicrobial Activities of Fruits of Crataegus. and Pyrus. Species,” Pharmaceutical Biology 44, no. 2 (2006): 79–83.
   Web of Science ®Google Scholar
• J. R. Badgujar, D. H. More, and J. S. Meshram, “Synthesis, Antimicrobial and Antioxidant Activity of Pyrazole Based Sulfonamide Derivatives,” Indian Journal of Microbiology 58, no. 1 (2018): 93–9.
   PubMedGoogle Scholar
• M. Lamblin, A. Couture, E. Deniau, and P. Grandclaudon, “Alternative and Complementary Approaches to the Asymmetric Synthesis of C3 Substituted NH Free or N-Substituted Isoindolin-1-Ones,” Tetrahedron: Asymmetry 19, no. 1 (2008): 111–23.
   Google Scholar
• K. Li, X. Fu, Y. Zhao, W. Gao, and Y. Li, “ A Facile Synthesis of Novel Pyrrolo [3, 4-b] Quinolin-1-One Derivatives,” Research on Chemical Intermediates 42, no. 5 (2016): 4273–87.
   Web of Science ®Google Scholar
• Mátyás Milen, András Dancsó, Tamás Földesi, Péter Slégel, and Balázs Volk, “Propylphosphonic Anhydride (T3P®) Mediated One-Pot Three-Component Synthesis of Racemic Dialkyl (2-Substituted-3-Oxo-2, 3-Dihydro-1H-Isoindol-1-yl) Phosphonates,” Tetrahedron 72, no. 33 (2016): 5091–9.
   Google Scholar
• H. Miyabe, K. Yoshida, Y. Kobayashi, A. Matsumura, and Y. Takemoto, “Synthesis of Azacycles Based on Iridium-Catalyzed Sequential Allylic Amination,” Synlett, no. 7 (2003): 1031–3.
   Google Scholar
• Y. Nozawa, M. Ito, K. Sugawara, K. Hanada, and K. Mizoue, “Stachybotrin C and Parvisporin, Novel Neuritogenic Compounds II. Structure Determination,” The Journal of Antibiotics 50, no. 8 (1997): 641–5.
   PubMed Web of Science ®Google Scholar