40510-88-1Relevant articles and documents
Synthesis and antimicrobial activities of N4-(2-acetoxyethoxymethyl)thiosemicarbazones and N3-(2-acetoxyethoxymethyl)thioureas
Foye,Banijamali,Patarapanich
, p. 1180 - 1184 (1986)
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Diversity oriented efficient access of trisubstituted purines via sequential regioselective Mitsunobu coupling and SNAr based C 6 functionalizations
Manvar, Atul,Shah, Anamik
, p. 680 - 691 (2013/07/25)
An efficient protocol for the syntheses of diverse 2,6,7- and 2,6,9-trisubstituted purines is reported starting from the guanine precursor, 2amino-6-chloropurine nucleoside through subsequent regioselective, high yielding Mitsunobu coupling and nucleophilic substitutions at C6 with versatile primary and secondary amines. A wide range of 2,6,7- and 2,6,9-trisubstituted purines were accessible in good to excellent yields with remarkable functional group tolerance. Moreover, solvent-free, large scale synthesis of precursors 2 & 3 and facile preparation of organophosphorus side chains 4 & 5 were also accomplished with excellent yields.
Novel 5-(N -alkylaminouracil) acyclic nucleosides
Boncel, Sawomir,Gondela, Andrzej,McZka, MacIej,Tuszkiewicz-Kuznik, Magdalena,Grec, Przemysaw,Hefczyc, Barbara,Walczak, Krzysztof
experimental part, p. 603 - 610 (2011/04/12)
Protocols for the two-step syntheses of new 5-(N-hydroxyalkyl- and 5-N-benzylamino)uracil acyclic nucleosides bearing various functional groups (alkoxy/hydroxy and cyano/ester) are presented. Two groups of the title compounds were synthesised via aminolysis of 5-bromouracil and, subsequently, either coupling with an alkylating agent (2-chloromethoxyethyl acetate), or Michael-type addition to acrylonitrile/methyl acrylate. The reverse sequences for both syntheses were also studied. The target molecules were designed as non-nucleoside reverse transcriptase inhibitors (NNRTI) and are analogues of 1-(hydroxyethoxymethyl)-6-thiophenylthymine (HEPT) and 3-benzyl-1- cyanomethyluracils. The obtained compounds will be used in screening tests for anti-HIV-1 activity. Georg Thieme Verlag Stuttgart New York.
A novel, simple cyclocondensation reaction towards glycosyl triazines
Kikelj, Vincent,Julienne, Karine,Janvier, Pascal,Meslin, Jean-Claude,Deniaud, David
scheme or table, p. 3453 - 3460 (2009/05/26)
Sugars bearing an isothiocyanate moiety at C-1 react with diazadienium iodide to afford glycosyl triazines that represent, through an easy cyclocondensation reaction step, a flexible entry to different nucleoside analogues. We herein demonstrate that this [4+2] cycloaddition reaction occurs with total regiocontrol and good yields. Subsequent transformation of the thiocarbonyl into a carbonyl, and nucleophilic substitution of the methylsulfanyl group by ammonia, yields the 5-azacytidine analogues. All compounds were fully characterised by IR, HRMS, and 13C and 1H NMR (COSY, HMBC and HMQC). Georg Thieme Verlag.
