2005
DOI: 10.1002/chin.200545180
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Abstract: Purine derivatives R 0540Synthesis of 3-Benzylxanthine and Lumazine Analogues. -Xanthine and lumazine derivatives exhibit a wide range of biological activities and they are potential anti-HIV drugs. -(EL ASHRY, E. S. H.; YOUSSIF*, S.; EL AHWANY, M.; EL SANAN, M.; J. Chem. Res. 2005, 4, 262-266; Dep. Chem., Fac. Sci., Zagazig Univ., Zagazig, Egypt; Eng.) -K. Woydowski 45-180

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Cited by 3 publications
(6 citation statements)
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“…To our endeavor toward developing new uracil-based architectures of potential pharmacological significance, 5,6-diamino-1-(2-chlorobenzyl)uracil 3 [ 30 ] was chosen as scaffold for annulations of the target congeners. This substrate was prepared from 1-(2-chlorobenzyl)urea by consecutive cyclization with ethylcyanoacetate in the presence of sodium ethoxide [ 31 – 33 ], nitrosation with in situ prepared HNO 2 [ 30 , 34 ] then reduction with (NH 4 ) 2 S [ 30 ] (Scheme 1 ). Series 5a – e was prepared in moderate yield (49–66%) by refluxing compound 3 with different arylidene ethylcyanoacetates in DMF containing TEA for 6–7 h. All derivatives were recrystallized from DMF/EtOH.…”
Section: Resultsmentioning
confidence: 99%
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“…To our endeavor toward developing new uracil-based architectures of potential pharmacological significance, 5,6-diamino-1-(2-chlorobenzyl)uracil 3 [ 30 ] was chosen as scaffold for annulations of the target congeners. This substrate was prepared from 1-(2-chlorobenzyl)urea by consecutive cyclization with ethylcyanoacetate in the presence of sodium ethoxide [ 31 – 33 ], nitrosation with in situ prepared HNO 2 [ 30 , 34 ] then reduction with (NH 4 ) 2 S [ 30 ] (Scheme 1 ). Series 5a – e was prepared in moderate yield (49–66%) by refluxing compound 3 with different arylidene ethylcyanoacetates in DMF containing TEA for 6–7 h. All derivatives were recrystallized from DMF/EtOH.…”
Section: Resultsmentioning
confidence: 99%
“…This compound was prepared according to a reported method [ 30 , 34 ], yield 95%, m.p. 236 °C [lit 235 °C].…”
Section: Methodsmentioning
confidence: 99%
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“…The nitrosation of 6-aminouracils 1 [26][27][28][29][30][31][32][33][34] yielded 5-nitroso derivatives 2 which upon reduction with (NH 4 ) 2 S afforded 5,6-diaminouracils 3-e. [30][31][32][33][34] 6-Aminouracils and 5,6-diaminouracils used as direct starting materials for the synthesis of our target compounds.…”
Section: Resultsmentioning
confidence: 99%
“…7-Hydroxyxanthine and its 8-alkyl or 8-aryl derivatives have been prepared from 6-amino-5-nitrosouracils by the reaction with aliphatic or aromatic aldehydes [17 -21]. Due to the various biological activities [18] exhibited by these compounds, we present herein a versatile synthetic procedure for 8-aryl-7-hydroxy-3-methyl-2-thioxanthines [22] 27 -32 via a transamination process using aldehyde-anils 21 -26. Thus, refluxing of 21 -26 with 6-amino-1-methyl-5-nitroso-2-thiouracil [23] (20) in acetic acid took place by the elimination of aniline to give 27 -32 (Scheme 3) in 36 -55 % yield.…”
Section: Resultsmentioning
confidence: 99%