Stable hemiaminals attached to PAMAM dendrimers

Tetrahedron Letters

Volumn 50, Issue 47, 2009, Pages 6512-6514

  Subik, Paweł ^a   Welc, Barbara ^a   Wisz, Beata ^b   Wołowiec, Stanisław ^a,b  

^a UNIVERSITY OF INFORMATION TECHNOLOGY AND MANAGEMENT   (Poland)

^b RZESZOW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINE; DENDRIMER; METHANOL; METHANOLAMINE DERIVATIVE; POLYAMIDOAMINO; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SURFACE PROPERTY;

EID: 78649891960     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.031     Document Type: Article

References (19)

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8. In a typical protocol G48 (0.125 g) (containing 64 surface amine groups corresponding to 0.56 mmol of NH2) and of ethyl iodide (1.53 mmol) (EtI) or iso-propyl iodide (14.1 mmol) (iPrI) in methanol (5 cm ) were kept at rt for 48 h (Etl) or heated at 50 °C for 2 h (iPrI). The G4 dendrimers were substituted at an average level of 85% with Et groups (G485Et) and 72% with iPr groups (G472iPr) based upon the integral intensity of the methyl group proton resonances in the 1H NMR spectra of the derivatives in methanol-d4. Later the level of substitution was confirmed by quantitative conversion of G485Et and G472iPr into Schiff bases by reaction with the aldehydes used throughout these studies. The acetyl derivative G435Ac was obtained by the reaction of G4 (0.075 mmol) (5.44 mmol of surface amine groups) with acetyl chloride (3.1 mmol) at rt for 24 h. The excess alkylating and acylating reagents were removed by vacuum evaporation, while the modified dendrimers were further purified by dialysis (12 h) of their methanolic solutions against MeOH through a cellulose membrane (ZelluTrans Roth 3.5; molecular weight cut-off 4-6 kD) to remove traces of HI. In analogous procedures, a series of GInEt,GImiPr, and GIkAc derivatives were obtained (n, m, or k are variable within 30-85%, and I = 3 or 4).
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