Structure-Activity Relationship in the Mutagenic Effect of Chiral or Racemic 2-Bromo-2-propanamides on Salmonella typhimurium

Some 2‐bromo‐propanamides were prepared and tested for direct mutagenicity in Salmonella typhimurium TA 100. Results confirm the mutagenic activity of 2‐bromo‐N‐benzyl‐propanamide and indicate that it is independent of enantiomeric configuration. A variation in the chemical structure, namely, the addition of a methyl group at the benzylic carbon, causes the four resulting diastereomers to be devoid of any activity. Conversely, some racemic ring‐substituted methoxy and/or hydroxy derivatives of the parent compound displayed mutagenic properties, causing an increase in the number of his+ revertants up to 524 per milligram per plate. Copyright © 1992 Wiley‐Liss, Inc., A Wiley Company