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Journal articles on the topic 'Cyclic α-Aminophosphonates'

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Published: 6 September 2023

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1

Odinets, Irina L., Oleg I. Artyushin, Konstantin A. Lyssenko, Nikolay E. Shevchenko, Valentin G. Nenajdenko, and Gerd-Volker Röschenthaler. "Facile synthesis of cyclic α-perfluoroalkyl-α-aminophosphonates." Journal of Fluorine Chemistry 130, no. 7 (July 2009): 662–66. http://dx.doi.org/10.1016/j.jfluchem.2009.05.002.

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2

Odinets, Irina, Oleg Artyushin, Nikolay Shevchenko, Pavel Petrovskii, Valentin Nenajdenko, and Gerd-Volker Röschenthaler. "Efficient Synthesis of Substituted Cyclic α-Aminophosphonates." Synthesis 2009, no. 04 (February 2009): 577–82. http://dx.doi.org/10.1055/s-0028-1083349.

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3

Sobhani, Sara, Elham Safaei, Mozaffar Asadi, Fariba Jalili, and Zahra Tashrifi. "Efficient synthesis of secondary and primary dialkyl α-aminophosphonates catalyzed by tetramethyl-tetra-3,4-pyridinoporphyrazinato copper(II) methyl sulfate under solvent-free conditions." Journal of Porphyrins and Phthalocyanines 12, no. 07 (July 2008): 849–56. http://dx.doi.org/10.1142/s1088424608000248.

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An efficient method for the synthesis of secondary and primary dialkyl α-aminophosphonates under solvent-free conditions by one-pot reaction of aldehydes/ketones, amines/ammonium acetate and trialkyl/diethyl phosphite in the presence of a low catalytic amount of [ Cu (3,4-tmtppa)]( MeSO 4)4(0.16 mol%) as a highly stable and reusable catalyst, is described. By this method, aromatic, aliphatic, cyclic and heterocyclic aldehydes, hindered and cage ketones are converted into their corresponding α-aminophosphonates in good to excellent yields.

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4

Ray Choudhury, Abhijnan, and Santanu Mukherjee. "Enantioselective dearomatization of isoquinolines by anion-binding catalysis en route to cyclic α-aminophosphonates." Chemical Science 7, no. 12 (2016): 6940–45. http://dx.doi.org/10.1039/c6sc02466a.

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An enantioselective dearomatization of isoquinolines has been developed using chiral anion-binding catalysis. This transformation makes use of silyl phosphite as a nucleophile and generates cyclic α-aminophosphonates.

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5

Yan, Zhong, Bo Wu, Xiang Gao, and Yong-Gui Zhou. "Enantioselective synthesis of quaternary α-aminophosphonates by Pd-catalyzed arylation of cyclic α-ketiminophosphonates with arylboronic acids." Chemical Communications 52, no. 72 (2016): 10882–85. http://dx.doi.org/10.1039/c6cc04096a.

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6

Xu, Bo, Gerald Hammond, Junbin Han, and Robert Paton. "Synthesis of Cyclic α-Aminophosphonates through Copper-Catalyzed Enamine Activation." Synthesis 45, no. 04 (January 17, 2013): 463–70. http://dx.doi.org/10.1055/s-0032-1317984.

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7

Yuan, Chengye, Qianyi Chen, and Jinfeng Li. "Sulfinimine-Mediated Asymmetric Synthesis of Acyclic and Cyclic α-Aminophosphonates." Synthesis 2008, no. 18 (September 2008): 2986–90. http://dx.doi.org/10.1055/s-2008-1067247.

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8

Han, Junbin, Robert S. Paton, Bo Xu, and Gerald B. Hammond. "ChemInform Abstract: Synthesis of Cyclic α-Aminophosphonates Through Copper-Catalyzed Enamine Activation." ChemInform 44, no. 26 (June 6, 2013): no. http://dx.doi.org/10.1002/chin.201326176.

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9

Yan, Zhong, Xiang Gao, and Yong-Gui Zhou. "Enantioselective synthesis of quaternary α-aminophosphonates by organocatalytic Friedel–Crafts reactions of indoles with cyclic α-ketiminophosphonates." Chinese Journal of Catalysis 38, no. 5 (May 2017): 784–91. http://dx.doi.org/10.1016/s1872-2067(17)62804-3.

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10

Liu, Yong-Jie, Jin-Shan Li, Jing Nie, and Jun-An Ma. "Organocatalytic Asymmetric Decarboxylative Mannich Reaction of β-Keto Acids with Cyclic α-Ketiminophosphonates: Access to Quaternary α-Aminophosphonates." Organic Letters 20, no. 12 (May 31, 2018): 3643–46. http://dx.doi.org/10.1021/acs.orglett.8b01422.

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11

Luo, Zhi, Zhong‐Hua Gao, Chun‐Lin Zhang, Kun‐Quan Chen, and Song Ye. "Enantioselective Synthesis of Cyclic α‐Aminophosphonates through N‐Heterocyclic Carbene‐Catalyzed [4+2] Annulation of Enals with α‐Iminophosphonates." Asian Journal of Organic Chemistry 7, no. 12 (November 5, 2018): 2452–55. http://dx.doi.org/10.1002/ajoc.201800604.

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12

Dehnel, André, Jolanta M. Kanabus-Kaminska, and Gilbert Lavielle. "α-Aminophosphonates. III. Cycloaddition anionique-1,3 des esters α,β-insaturés: Préparation et transformations des Δ1-pyrrolines." Canadian Journal of Chemistry 66, no. 2 (February 1, 1988): 310–18. http://dx.doi.org/10.1139/v88-054.

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The anions of the 2-azaallylphosphonates 1 react with the α,β-unsaturated esters 2 to yield the intermediates 4′. These intermediates form the 2-diethoxyphosphonyl-4-ethoxycarbonylpyrrolidines 4 following a protonation while an elimination of the anion of the diethylphosphonate leads to the 4-ethoxycarbonyl-Δ1-pyrrolines 5. The proportions of these two products vary with the experimental conditions and the bulkiness of the substrates. The formation of the cyclic products has been studied for numerous substrates and in the presence of a number of bases. The reaction is regioselective and stereospecific and on the basis of the formation of the kinetically more strained diastereoisomer it is possible to conclude that the cycloaddition is a concerted one. The thermodynamically less strained diastereoisomers 6 and 7 are obtained from the compounds 4 and 5 respectively when they are subjected to the action of a base in a protic media. The other epimers of 4, the compounds 8 and 9, have been obtained by the addition of diethylphosphite to the pyrrolines 5 and 7. The pyrrolines 5 have been reduced to the 3-ethoxycarbonylpyrrolidines 12. The isomerization of the pyrrolines 5 with a phenyl substituent in position 5 leads to the formation of the 3-ethoxycarbonyl-2-phenyl-Δ1-pyrrolines 10. The latter spontaneously oxidize with atmospheric oxygen to yield the 3-ethoxycarbonyl-3-hydroxy-2-phenyl-Δ1-pyrrolines 11. [Journal translation]

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13

Kumara Swamy, K. C., Sudha Kumaraswamy, K. Senthil Kumar, and C. Muthiah. "Cyclic chlorophosphites as scaffolds for the one-pot synthesis of α-aminophosphonates under solvent-free conditions." Tetrahedron Letters 46, no. 19 (May 2005): 3347–51. http://dx.doi.org/10.1016/j.tetlet.2005.03.080.

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14

Ramírez-Marroquín, Oscar Abelardo, Iván Romero-Estudillo, José Luis Viveros-Ceballos, Carlos Cativiela, and Mario Ordóñez. "Convenient Synthesis of Cyclic α-Aminophosphonates by Alkylation-Cyclization Reaction of Iminophosphoglycinates Using Phase-Transfer Catalysis." European Journal of Organic Chemistry 2016, no. 2 (November 17, 2015): 308–13. http://dx.doi.org/10.1002/ejoc.201501203.

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15

Harger, Martin J. P., and Andrew Williams. "Evidence for cyclic azaphosphiridine oxide intermediates in the methoxide-induced rearrangements of N-alkyl α-chlorophosphonamidates: formation of phosphoramidates as well as α-aminophosphonates." J. Chem. Soc., Perkin Trans. 1, no. 3 (1989): 563–69. http://dx.doi.org/10.1039/p19890000563.

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16

Salem, Mounir A. I., Tarik E. Ali, and Magda I. Marzouk. "Electron Ionization Mass Spectra of Organophosphorus Compounds Part I: The Mass Fragmentation Pathways of Cyclic α-Aminophosphonates Monoester Containing 1,2,4-Triazinone Moiety." Phosphorus, Sulfur, and Silicon and the Related Elements 187, no. 3 (January 31, 2012): 336–42. http://dx.doi.org/10.1080/10426507.2011.610851.

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17

Ali, Tarik E., and Somaia M. Abdel-Kariem. "Electron ionization mass spectra of organophosphorus compounds Part V: Mass fragmentation modes of some azolyl, azinyl, and azepinyl phosphonates as cyclic α-aminophosphonates." Phosphorus, Sulfur, and Silicon and the Related Elements 191, no. 9 (June 29, 2016): 1223–28. http://dx.doi.org/10.1080/10426507.2016.1160241.

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18

Ma, Yi, Jian-Guo Wang, Bin Wang, and Zheng-Ming Li. "Integrating molecular docking, DFT and CoMFA/CoMSIA approaches for a series of naphthoquinone fused cyclic α-aminophosphonates that act as novel topoisomerase II inhibitors." Journal of Molecular Modeling 17, no. 8 (November 25, 2010): 1899–909. http://dx.doi.org/10.1007/s00894-010-0898-y.

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19

H. Ouf, Nabil, Mohamed A.Hamed, Ibrahim El Sayed, and Mohamed Ibrahim Sakran. "Anti-cancer, Anti-inflammatory, Cytotoxic and Biochemical Activities of a Novel Phosphonotripeptide Synthesized from Formyl Pyrazolofuran using TUBU as Condensing Agent." JOURNAL OF ADVANCES IN CHEMISTRY 6, no. 3 (December 7, 2010): 1093–102. http://dx.doi.org/10.24297/jac.v6i3.2647.

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A novel and mild protocol for the synthesis of phosphonotripeptide 16 were achieved from novel formylpyrazolofuran 3, benzyl carbamate 5, triphenyl phosphite 6 by Birum-Oleksyszyn reaction using copper (II) trifliate as Lewis acid catalyst in dry dichloromethane at room temperature which synthesis of novel N-benzyloxy-α-aminophosphonate 7 . A mechanism for this condensation reaction is proposed. Cleavage of the N-benzyloxy carbonyl group under acid hydrolysis afford the free α-aminophosphonate 9 in quantitative yield. This in turn, by reaction with N-phthaloylglycine 12 via TUBU to phthalimido group 13.Cleavage of phthalimido group under hydrazinedihydrochloride afford free peptide 14 .the result phosphonotripeptide 16 obtained by the reaction of free peptide with bioactive cyclic moiety-COCl 15. The structures of all new compounds were established by IR,1HNMR and mass spectral data. Also anti-cancer, anti-inflammatory and biochemical activities of all these compounds were reported.

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20

Sabbaghzadeh, Reihaneh. "Physicochemical Properties of analogs α-Aminophosphonates Drugs Determined via Molecular Dynamics Simulation." Asian Pacific Journal of Cancer Biology 4, no. 3 (September 8, 2019): 47–50. http://dx.doi.org/10.31557/apjcb.2019.4.3.47-50.

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Cyclin-dependent kinases (CDKs, play important roles in cell cycle regulation. Since deregulation of cyclins and/or alteration or absence of inhibitors has been associated with many cancers, there is strong interest in CDKs inhibitors that could play an necessary role in the discovery of a new family of antitumor agents. molecular modeling is used to design new materials, which the correct prediction of physical properties of realistic systems is required. Gromacs is an tool to perform molecular dynamics simulations and energy minimization of bimolecular systems which commonly consists of several tens to thousands of amino acid residues. From the simulations the first 100 ps were regarded as equilibration, leaving 900 ps for analysis purposes. Thermodynamic properties density, potential energy, temperature, and pressure are given. In this results tetramethyl((1,4-phenylenebis(azanediyl))bis((4-chlorophenyl)methylene))bis(phosphonate) was found to be the better selective known inhibitor for cyclin-dependent kinase2 because it shown lowest energy. The phosphoric acid moiety is considered to bind to the affected protein more actively than the corresponding carboxylic acid because of its di anionic character.

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21

Iwanejko, Jakub, Mahzeiar Samadaei, Matthias Pinter, Daniel Senfter, Sibylle Madlener, Andrzej Kochel, Nataliya Rohr-Udilova, and Elżbieta Wojaczyńska. "Cytotoxic Activity of Piperazin-2-One-Based Structures: Cyclic Imines, Lactams, Aminophosphonates, and Their Derivatives." Materials 14, no. 9 (April 22, 2021): 2138. http://dx.doi.org/10.3390/ma14092138.

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N-Heterocycles are considered as desirable scaffolds for the development of novel lead compounds for anticancer drug research. Among them, phosphorus-containing amino-derivatives play a crucial role. A series of imines and products of their further reactions with P-nucleophiles were obtained starting from vicinal bisamines. Reaction of ethylenediamine and α-carbonyl esters yielded in novel unexpected products, which structures were confirmed by crystallographic measurements. The cytotoxic activity evaluation was done on a variety of cell lines including HUH7, AKH12, DAOY, UW228-2, D283, D425, and U251. Human umbilical vein endothelial cells (HUVECs) were used as control. Two of the tested compounds, bearing TADDOL-derived, and trifluoromethyl substituents showed a significant effect on cell viability, though comparable to nonmalignant cells.

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22

Arsanious, Mona, Shaban Darwish, El-Sayed Shalaby, and Dina El-Ghwas. "Synthesis, X-ray, DFT Studies and Antimicrobial Properties of New Quinolinylphosphonates." Letters in Organic Chemistry 16, no. 8 (June 18, 2019): 668–75. http://dx.doi.org/10.2174/1570178616666181231161801.

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The phosphorus atom in hexamethyl phosphorus triamide 5 attacks the carbonyl function in 2-chloroquinoline-3-carbaldehyde 4a to give the bis-quinolinyl ethanone product 6. On the other hand, quinoline ring-attack proceeds by the same phosphorus reagent upon reaction with 2-chloroquinoline- 3-aldoxime 4b yielding phosphonate 7. Meanwhile, the reaction of the tris-aminophosphine reagent 5 with 2-chloroquinoline- 3-(p-chlorophenyl)imine 4c affords the respective α-aminophosphonate 8. Moreover, the attack by phosphine 5 on 2-chloroquinoline-3-imines 4d and 4e produces the respective cyclic azophosphole derivatives 9a and 9b. [(2-chloroquinolin-3-yl)methylidene]propane dinitrile 4f reacts with phosphine 5 to yield [(2-chloroquinolinen-3-yl) 2,2-dicyanoethyl]tetramethylphosphonic diamide 10. Structural elucidations for the new products were based on compatible analytical and spectroscopic data. Moreover, the structures assigned for compounds 7 and 9a were unambiguously confirmed by X-ray crystallographic measurements. Biological evaluations indicated that compounds 4a,c exhibit antibacterial potency against Gram-positive bacteria and 4a,c and 9a show activity against Candida albicans strain.

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23

Ali, Tarik E. "Synthesis of Some New 1,3,2-Oxazaphosphinine, 1,3,2-Diazaphosphinine, Acyclic, and/or Cyclic α-Aminophosphonate Derivatives Containing the Chromone Moiety." Phosphorus, Sulfur, and Silicon and the Related Elements 185, no. 1 (December 28, 2009): 88–96. http://dx.doi.org/10.1080/10426500802713309.

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24

Mirzaei, Mahdi, Hossein Eshghi, Maede Hasanpour, and Reihaneh Sabbaghzadeh. "Synthesis, characterization, and application of [1-methylpyrrolidin-2-one-SO3H]Cl as an efficient catalyst for the preparation of α-aminophosphonate and docking simulation of ligand bond complexes of cyclin-dependent kinase 2." Phosphorus, Sulfur, and Silicon and the Related Elements 191, no. 10 (July 21, 2016): 1351–57. http://dx.doi.org/10.1080/10426507.2016.1206101.

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25

Odinets, Irina L., Oleg I. Artyushin, Konstantin A. Lyssenko, Nikolay E. Shevchenko, Valentin G. Nenajdenko, and Gerd-Volker Roeschenthaler. "ChemInform Abstract: Facile Synthesis of Cyclic α-Perfluoroalkyl-α-aminophosphonates." ChemInform 40, no. 46 (November 17, 2009). http://dx.doi.org/10.1002/chin.200946183.

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26

Wang, Bin, Zhiwei Miao, You Huang, and Ruyu Chen. "Synthesis of Novel Naphthoquinone Fused Cyclic α-Aminophosphonates." ChemInform 38, no. 7 (February 13, 2007). http://dx.doi.org/10.1002/chin.200707152.

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27

Chen, Qianyi, Jinfeng Li, and Chengye Yuan. "ChemInform Abstract: Sulfinimine-Mediated Asymmetric Synthesis of Acyclic and Cyclic α-Aminophosphonates." ChemInform 40, no. 4 (January 27, 2009). http://dx.doi.org/10.1002/chin.200904171.

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28

Swamy, K. C. Kumara, Sudha Kumaraswamy, K. Senthil Kumar, and C. Muthiah. "Cyclic Chlorophosphites as Scaffolds for the One-Pot Synthesis of α-Aminophosphonates under Solvent-Free Conditions." ChemInform 36, no. 37 (September 13, 2005). http://dx.doi.org/10.1002/chin.200537169.

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29

Ramirez-Marroquin, Oscar Abelardo, Ivan Romero-Estudillo, Jose Luis Viveros-Ceballos, Carlos Cativiela, and Mario Ordonez. "ChemInform Abstract: Convenient Synthesis of Cyclic α-Aminophosphonates by Alkylation-Cyclization Reaction of Iminophosphoglycinates Using Phase-Transfer Catalysis." ChemInform 47, no. 22 (May 2016). http://dx.doi.org/10.1002/chin.201622158.

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30

HARGER, M. J. P., and A. WILLIAMS. "ChemInform Abstract: Evidence for Cyclic Azaphosphiridine Oxide Intermediates in the Methoxide-Induced Rearrangements of N-Alkyl α-Chlorophosphonamidates: Formation of Phosphoramidates as Well as α-Aminophosphonates." ChemInform 20, no. 25 (June 20, 1989). http://dx.doi.org/10.1002/chin.198925067.

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31

Mirzaei, Mahdi, Hossein Eshghi, and Reihaneh Sabbaghzadeh. "LaCl3⋅7H2O as an Effective Catalyst for the Synthesis of α-Aminophosphonates under Solvent-Free Conditions and Docking Simulation of Ligand Bond Complexes of Cyclin-Dependent Kinase 2." Polycyclic Aromatic Compounds, August 11, 2021, 1–11. http://dx.doi.org/10.1080/10406638.2021.1962926.

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