New catechol derivatives derived from amino acids have siderophore activity and are useful as growth factors in bacterial cultures and as prodrugs for iron chelators

摘要

Catechol derivatives derived from amino acids are new. Catechol derivatives are of formula (I) as free acids, salts and readily cleavable esters are new. R1 = H or alkyl or aryl (each optionally substituted); R2 and R3 = H, CO-alkyl or COO-alkyl; X = direct bond, (CH2)qNH or CO(CH2)qNH; q = 1-6; or R2 + X = (a) or (b); R4 = H; halo; or alkyl, aryl or alkoxy (each optionally substituted); R5 = H; OH; O-alkyl; O-acyl; O-aryl; or alkyl or aryl (each optionally substituted); R6 = (c), (d) or (e); R8 = H; CO-alkyl; or COO-alkyl; R7 and R8 = -CO-; o = 1-10; R6 and/or R7 = (f) or (g); p = 2-10; R7 = H; alkyl or aryl (each optionally substituted); or -(CH2)s-N(Ra)(Rb); s = 2-4; Ra = (g); Rb = (c); n = 0-8; m = 0-3 Y = OA; A = H; alkali metal; or optionally substituted ammonium; Z' = direct bond; -(CH2)r-; or optionally substituted arylene; and r = 0-10. Provided that: (i) compounds are excluded when R7 and R8 together are CO; (ii) R5 is H when Z is a direct bond; and (iii) R7 is group (f) when R6 is group (c), R5 is H and X and Z are direct bonds.