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两种氟磷苯基化合物的合成及其抑菌活性研究
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Abstract:
为设计并合成新的含磷氟键的化合物,并研究其性质,以二苯基氯化膦,苯基二氯化膦为反应物,通过简单的卤素交换反应合成两种化合物PhP(O)F2、Ph2P(O)F,并通过单晶X-射线衍射仪,1H、31P、19F NMR对其结构进行表征。同时对其进行抑菌活性筛选,发现二者对于两种革兰氏菌(大肠杆菌、金黄色葡萄球菌)均具有良好的抑菌活性,并得到了最小抑菌浓度。
To design and synthesize new phosphorus-fluorine-containing compounds, and to study their properties, two compounds, PhP(O)F2 and Ph2P(O)F, were synthesized from diphenylphosphine chloride and phenylphosphorus dichloride through a simple halogen exchange reaction. Their structures were characterized by single-crystal X-ray diffraction, 1H, 31P, and 19F NMR spectroscopies. Additionally, their antibacterial activity was screened against two Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli), revealing that both compounds exhibited good antibacterial activity with minimum inhibitory concentrations determined.
[1] | Gouverneur, V. (2024) Fluorine Chemistry: An Outlook to the Future. Advanced Synthesis & Catalysis, 366, 3404-3404. https://doi.org/10.1002/adsc.202400881 |
[2] | Attique, I., Hussain, S., Amjad, M., Nazir, K. and Nazir, M.S. (2020) The Therapeutic and Diagnostic Value of Fluorine. Scientific Inquiry and Review, 4, 17-29. https://doi.org/10.32350/sir.41.02 |
[3] | Gozdalik, J.T., Adamczyk-Woźniak, A. and Sporzyński, A. (2017) Influence of Fluorine Substituents on the Properties of Phenylboronic Compounds. Pure and Applied Chemistry, 90, 677-702. https://doi.org/10.1515/pac-2017-1009 |
[4] | Adamczyk-Woźniak, A., Gozdalik, J.T., Wieczorek, D., Madura, I.D., Kaczorowska, E., Brzezińska, E., et al. (2020) Synthesis, Properties and Antimicrobial Activity of 5-Trifluoromethyl-2-Formylphenylboronic Acid. Molecules, 25, Article 799. https://doi.org/10.3390/molecules25040799 |
[5] | Ravindra, M., Wilson, M.R., Tong, N., O’Connor, C., Karim, M., Polin, L., et al. (2018) Fluorine-Substituted Pyrrolo[2, 3-d]Pyrimidine Analogues with Tumor Targeting via Cellular Uptake by Folate Receptor α and the Proton-Coupled Folate Transporter and Inhibition of de Novo Purine Nucleotide Biosynthesis. Journal of Medicinal Chemistry, 61, 4228-4248. https://doi.org/10.1021/acs.jmedchem.8b00408 |
[6] | Partyka, D.V., Washington, M.P., Updegraff, J.B., Chen, X., Incarvito, C.D., Rheingold, A.L., et al. (2009) Surveying the {AuCl} Adducts of Bulky Phosphines Bearing the 2,6-Dimesitylphenyl Group. Journal of Organometallic Chemistry, 694, 1441-1446. https://doi.org/10.1016/j.jorganchem.2008.12.051 |
[7] | Huang, Y. and Chen, Q. (2017) Fluorination Reaction of P(Ⅲ) Compounds with the Electrophilic Fluorinating Reagent Selectfluor. Chinese Journal of Organic Chemistry, 37, 2751. https://doi.org/10.6023/cjoc201704001 |
[8] | Kawaguchi, S., Saga, Y., Sato, Y., Minamida, Y., Nomoto, A. and Ogawa, A. (2017) P-Fluorous Phosphines as Electron-Poor/Fluorous Hybrid Functional Ligands for Precious Metal Catalysts: Synthesis of Rh(I), Ir(I), Pt(II), and Au(I) Complexes Bearing P-Fluorous Phosphine Ligands. Inorganics, 5, Article 5. https://doi.org/10.3390/inorganics5010005 |
[9] | Delgado Calvo, F., Mirabello, V., Caporali, M., Oberhauser, W., Raltchev, K., Karaghiosoff, K., et al. (2016) A Straightforward Access to Ruthenium-Coordinated Fluorophosphines from Phosphorous Oxyacids. Dalton Transactions, 45, 2284-2293. https://doi.org/10.1039/c5dt04624f |
[10] | Ullah, E., McNulty, J., Sliwinski, M. and Robertson, A. (2012) Cheminform Abstract: One‐Step Synthesis of Reusable, Polymer‐Supported Trialkyl Phosphine Ligands. Application in Suzuki—Miyaura and Alkoxycarbonylation Reactions. ChemInform, 43, 3990-3993. https://doi.org/10.1002/chin.201245101 |
[11] | Ullah, E., McNulty, J., Sliwinski, M. and Robertson, A. (2012) One-Step Synthesis of Reusable, Polymer-Supported Tri-Alkyl Phosphine Ligands. Application in Suzuki-Miyaura and Alkoxycarbonylation Reactions. Tetrahedron Letters, 53, 3990-3993. https://doi.org/10.1016/j.tetlet.2012.05.091 |
[12] | Sheldrick, G.M. (2015) SHELXT—Integrated Space-Group and Crystal-Structure Determination. Acta Crystallographica Section A Foundations and Advances, 71, 3-8. https://doi.org/10.1107/s2053273314026370 |
[13] | Sheldrick, G. (2014) SHELXT: Integrating Space Group Determination and Structure Solution. Acta Crystallographica Section A Foundations and Advances, 70, C1437-C1437. https://doi.org/10.1107/s2053273314085623 |
[14] | Leão, C., Borges, A. and Simões, M. (2020) NSAIDs as a Drug Repurposing Strategy for Biofilm Control. Antibiotics, 9, Article 591. https://doi.org/10.3390/antibiotics9090591 |