14477-64-6Relevant academic research and scientific papers
Anti-influenza active and low toxic N-phenyl-substituted β-amidoamidines structurally related to natural antibiotic amidinomycin
Korshin, Edward E.,Zakharova, Lyubov G.,Levin, Yakov A.,Shulaeva, Marina P.,Pozdeev, Oskar K.
supporting information, p. 2357 - 2361 (2013/05/09)
A set of racemic N-phenyl-substituted β-amidoamidines hydrochlorides 4, which are structurally related to natural antiviral agent amidinomycin (1), was synthesized in four steps starting from methacryloyl anilide (5). In the final step of the synthetic route, an uncommon monoacylation of β-aminoamidine 8 at the less reactive β-phenylamino-group took place. To rationalize this result, a mechanism which involves initial acylation at the more active amidine-function followed by intramolecular acyl-group transfer to β-phenylamino-group was suggested. All three β-amidoamidines 4d-f bearing long linear aliphatic chain (from n-C8H17 to n-C12H25) revealed significant in vitro activity against influenza A virus (H3N2) and modest cytotoxicity. The in vitro antiviral potency of 4d,e is 6-20 times greater than that of commercial rimantadine with lower EC50 values and higher therapeutic index. The non-toxic in vivo compounds 4d-f showed a beneficial protective effect in influenza A (H3N2) infected mice.
AMINOAMIDINES III. ACYLATION OF N1,N2-DIARYL-N-ARYLGLYCINEAMIDINES
Korshin, E. E.,Soboleva, G. I.,Levin, Ya. A.,Zakharova, L. G.,Litvinov, I. A.,et al.
, p. 973 - 985 (2007/10/02)
The reaction of aryl-substituted α-aminoamidines with acetic anhydride, the acid chlorides of aromatic and mono- and dichloroacetic acids, and ethoxalyl chloride leads to the products from acylation at the α-amino group.The structure of the N1,
A Versatile New Synthesis of Quinolines and Related Fused Pyridines. Part 11. Conversion of Acylanilides into α-Iminopyridines
Meth-Cohn, Otto,Westwood, Keith T.
, p. 2089 - 2092 (2007/10/02)
The Vilsmeier formylation of enamidines, readily derived by treatment of acetanilides with PCl5, allowed the synthesis of 6-chloro-1-aryl-2-iminopyridines.Similarly other acylanilides (RCH2CONHAr) gave 3,5-R2 disubstituted analogues.
