39654-32-5Relevant academic research and scientific papers
Competition between cyclisation and bisimine formation in the reaction of 1,3-diaminopropanes with aromatic aldehydes
Locke, Julie M.,Griffith, Renate,Bailey, Trevor D.,Crumbie, Robyn L.
experimental part, p. 10685 - 10692 (2010/02/28)
Condensation of 1,3-diamines with aldehydes or ketones gives rise to two major products, the hexahydropyrimidine and the bisimine. Experimental studies of the reaction between a range of aromatic aldehydes and 1,3-diaminopropane or 1,3-diamino-2-propanol establish that the hexahydropyrimidine is favoured by the less nucleophilic amine and by the presence of electron withdrawing groups on the aryl ring of the aldehyde. Calculations indicate that the electronic nature of this aryl ring substituent influences both the relative thermodynamic stability of the final products and the reactivity of the aldehyde as an electrophile.
New anti-HIV derivatives: Synthesis and antiviral evaluation
De Michelis,Rocheblave,Priem,Chermann,Kraus
, p. 1253 - 1262 (2007/10/03)
A small focused library of 18 compounds incorporating the motif 1,3-(N,N'-dibenzyl)diamino-2-propanol has been synthesized, using adapted synthetic methodologies. These series of compounds were evaluated for their in vitro anti-HIV activity on infected MT4 cells (syncytium formation observation). Some of the new synthesized compounds show potent anti-HIV activities. EC50 values for compounds (31, 40, 34, 37 and 46Scheme 3(i) Na2SO4, CH2Cl2, rt; (ii) NaBH4, EtOH, 0°C; (iii) Boc2O, CH2Cl2, 0°C; (iv) DMSO, TFAA, Et3N, CH2Cl2, -60°C; (v) TFA, CH2Cl2, rt; (vi) BOP, RCOOH, Et3N, CH2Cl2, rt.) range from 0.1 to 1μM. In order to determine at which level these new derivatives interfere with the HIV replicative cycle, inhibition assays on recombinant HIV protease and HIV integrase have been performed. None of the compounds were found active on these two enzymatic targets. Experiments are in progress in order to identify their biological target within the HIV replicative cycle. Copyright (C) 2000 Elsevier Science Ltd.
Synthesis and anti-HIV activities of symmetrical N1,N3-dibenzyl-2- hydroxy-propane derivatives
Medou,Bouygues,Rocheblave,Chermann,Kraus
, p. 1861 - 1866 (2007/10/03)
We report the synthesis and the anti-HIV activities of new C2- symmetrical and achiral N1,N3-dibenzyl-2-hydroxy-propane isosteres. Some of them showed significant inhibitory activity with respect to HIV-infected MT4 cells
Synthesis of new 7-membered α-phenylthio cyclic oxamides: HIV inhibitors
Medou,Priem,Quelever,,Camplo,Kraus
, p. 4021 - 4024 (2007/10/03)
Based on the concept of bioisosterism, we report the computer design and the synthesis of original 7-membered α-phenylthio cyclic oxamides with potent anti HIV-1 properties.
