d-Glucose-based azacrown ethers with a phosphonoalkyl side chain: application as enantioselective phase transfer catalysts

Bakó, Péter; Novák, Tibor; Ludányi, Krisztina; Pete, Béla; Tőke, Lásʐló; Keglevich, György

doi:10.1016/s0957-4166(99)00224-4

Cited by 57 publications

(26 citation statements)

References 21 publications

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“…Diethyl aminoalkylphosphonates 2a-2d (aminomethyl-, 2-aminoethyl-, 3-aminopropyl-, and 4-aminobutylphosphonates), used in this study, are known and have already been described in the literature [19][20][21][22][23][24][25][26][27]. Thus, diethyl aminomethylphosphonate (2a) was prepared in total 90 % yield from N-(bromomethyl)phthalimide followed by the treatment with hydrazine [19][20][21] whereas xaminoalkylphosphonates 2b-2d were synthesized from the corresponding x-azidoalkylphosphonates 1b-1d [28][29][30][31][32] by catalytic hydrogenation [23,26].…”

Section: Resultsmentioning

confidence: 99%

“…Thus, diethyl aminomethylphosphonate (2a) was prepared in total 90 % yield from N-(bromomethyl)phthalimide followed by the treatment with hydrazine [19][20][21] whereas xaminoalkylphosphonates 2b-2d were synthesized from the corresponding x-azidoalkylphosphonates 1b-1d [28][29][30][31][32] by catalytic hydrogenation [23,26]. However, several literature reports [33,34] noticed the formation of significant amounts of symmetrical secondary amines as by-products during hydrogenolysis of azides depending on the azide concentration and the azide to catalyst ratio.…”

Section: Resultsmentioning

confidence: 99%

“…(E)-3-Ethoxyacryloyl chloride was obtained according to the known protocol [18]. Diethyl aminomethylphosphonate (2a) was prepared according to literature (colorless oil, yield 90 %) [19][20][21][22][23][24].…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, antiviral, cytotoxic and cytostatic evaluation of N 1-(phosphonoalkyl)uracil derivatives

et al. 2016

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A series of N 1 -(phosphonoalkyl)uracils was prepared in a two-step reaction sequence from xaminoalkylphosphonates and (E)-3-ethoxyacryloyl isocyanate followed by the uracil ring closure. Under standard conditions (NCS; NBS; I 2 /CAN) all N 1 -(phosphonoalkyl)uracils were transformed into the respective 5-halogeno derivatives to be later benzoylated at N3. All compounds were evaluated in vitro for activity against a broad variety of DNA and RNA viruses. One compound was slightly active against human cytomegalovirus in HEL cell cultures (EC 50 = 45 lM) while another showed weak activity against varicella-zoster virus (TK ? VZV strain OKA and TK -VZV strain 07-1) with EC 50 = 43 and 53 lM, respectively. In addition, several compounds exhibited noticeable inhibitory effects on the proliferation of human cervical carcinoma cells (HeLa) at a concentration lower than 200 lM. Graphical abstract

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Synthesis, antiviral, cytotoxic and cytostatic evaluation of N 1-(phosphonoalkyl)uracil derivatives

et al. 2016

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“…The bromo group of 4 was then exchanged with phthalimide, [15] yielding compound 5, which includes a chromophore that can be easily detected by UV during purification. If this reaction was allowed to proceed too long (e.g., overnight), one of the isopropyl groups was lost, [16] yielding a product mixture containing both the tetraisopropyl and triisopropyl esters of 5.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of a Novel Bisphosphonic Acid Alkene Monomer

Bala

Kashemirov

McKenna

2010

Synthetic Communications

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The convenient, scaleable synthesis of a novel h-fluorinated bisphosphonic acid, incorporating a tethered acrylamide monomer, [1-fluoro-1-phosphono-7-(prop-2-enamido)heptyl]phosphonic acid (1), is described. The a-fluorine substituent offers the advantage (compared to an a-hydroxy) of compatibility with basic conditions in tetraester intermediates (avoiding phosphonate-phosphate rearrangement) while maintaining a phosphonic acidity that mimics that of pyrophosphoric acid. Sodio tetraisopropyl methylenebis(phosphonate) was monoalkylated with 1,6-dibromohexane and fluorinated with Selectfluor. An x-nitrogen atom was introduced into the tether via incorporation of a phthalimide group, which as a UV-visible chromophore facilitated purification. Subsequent removal of the ester (HCl) and phthalimide (hydrazine) groups yielded h-F, x-aminohexyl methylenebis(phosphonic acid), which was reacted with acryloyl chloride at pH 8-9, then treated with HCl to give 1.

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“…Such receptors were used as catalysts in enantioselective Darzens and Michael reactions (Scheme 9) [27][28][29][30][31][32][33][34][35][36][37] and more recently asymmetric epoxidation [38]. The enantiomeric excess achieved in the Michael addition of 2-nitropropene anion to chalcone was as high as 85-90%, however, in most cases did not exceed 60%.…”

Section: -34mentioning

confidence: 99%