One-pot Synthesis of N-Formyl-O-acyl- threo- and erythro-DL--phenylserine Ethyl Esters and their Antiviral Properties

Abstract

A series of N-formyl-O-acyl-β-phenylserine derivatives 1b -7b were prepared by the interaction of N-acylβ-phenylserine ethyl esters 1a-7a with formic acid in presence of 1.5% HF. One-pot acyl group N→O migration followed N-formylation under elaborated reaction conditions. 1.96(CH 2 ,q, J = 8.0) 3.97 q, 0.73 t, 7.42 m J = 4.0, 5.0 J = 5.0 J = 4.0, 9.0 J = 9.0 0.98(CH 3 , t, J = 7.0) J = 7.0 J = 7.0 3a CDCl 3 7.20 s 5.09 d, b ) 4.71 dd, 6.29 d, 2.02(CH 2 , q, J = 6.5) 4.04 q, 0.91 t, J = 3.0 J = 3.0, 9.0 J = 8.0 1.11(CH 3 , t, J = 7.0) J = 7.0 J = 7.3 4a (CD 3 )CO 7.06 -5.20 d, 6.18 d, 4.67 dd, 7.69 d, 2.09(CH 2 , m) 3.97 q, 0.8 t, 7.42 m J = 3.0 J = 5.0 J = 3.0, 10.0 J = 10.0 3.58(CH 2 Br, m) J = 7.0 J = 7.0 5a (CD 3 ) 2 CO 7.03 -5.15 d, b ) 4.58 dd, b ) 3.39(CH 2 , s) 3.99 q, 1.06 t, 7.24 m J = 3.2 J = 3.2; 9.0 7.03 -7.24(C 6 H 5, m) J = 7.1 J = 7.1 6a DMSO-d 6 7.09 -5.0 m b ) 4.71 dd, 5.27 d, 2.53(CH 2 , d, J = 7.0) 3.98 q, 1.1 t, 7.74 m J = 5.0, 9.0 J = 8.0 4.20(CH ,t, J = 7.0) J = 7.0 J = 7.0 7.09 -7.74 [(C 6 H 4 ) 2 C,m] 6a CDCl 3 7.09 -5.22 d, b ) 4.98 dd, 6.27 d, 2.56(CH 2 , q, J = 8,0) 4.14 q, 1.18 t, 7.83 m J = 3.0 J = 3.0, 9.0 J = 8.8 4.37(CH, t, J = 8.0) J = 7.0 J = 7.0 7.09 -7.83 [(C 6 H 4 ) 2 C, m] 7a CDCl 3 7.11-5.04 dd, b ) 4.94 dd 6.11 d, 2.56(CH 2 , d, J = 7.0) 3.98 q, 1.04 t, 7.71 m J = 3.0, 7.0 J = 3.0, 7.0 J = 7.0 4.39(CH, t, J = 7.0) J = 7.0 J = 7.0 7.11 -7.71 [(C 6 H 4 ) 2 C, m] a ) Residues R are the same as in Scheme 1 b ) Overlapped with other signals

One-pot Synthesis ofN-Formyl-O-acyl-threo- anderythro-DL-β-phenylserine Ethyl Esters and their Antiviral Properties

“…The toxicity and viral inhibition of the studied compounds were determined by methods described in [7,14]. For investigation of viral inhibition of N-formyl-O-acyl-β-phenylserine derivatives 2b -7b, vesicular stomatitis virus (VSV) (strain Indiana), coxsackievirus CVA-13 (strain Flores), echovirus ECHO-11 (strain Uppsala), and herpes simplex HSV-1 virus (strain L-2) were involved.…”

“…Earlier, we have synthesized a series of N-and O-substituted amino acids for evaluation of their antiviral properties [7]. In the course of previous work, it became evident that among different amino acids used, the non-proteinogenic amino acid β-phenylserine is a rather promising structure for chemical modifications in search of new antiviral agents.…”