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4082174 
Journal Article 
Organic synthesis, antibacterial evaluation, and quantitative structure-activity relationships (QSAR) of cosmetic preservatives related to 5-bromo-5-nitro-1,3-dioxane. I. Aliphatic analogs 
Milstein, SR; Orth, DS; Lichtin, JL 
1984 
0 
Journal of the Society of Cosmetic Chemists
ISSN: 0037-9832 
35 
2 
73-93 
English 
WOS:A1984TD69800001 
An aliphatic series of 2-substituted analogs of 5-bromo-5-nitro-1,3-dioxane (Bronidox; I) was designed and synthesized, and their antibacterial activity against Staphylococcus aureus and Pseudomonas aeruginosa strains was compared with that of I and 2-bromo-2-nitropropane-1,3-diol (bronopol; II). Although most compounds exhibited rather poor activity against S. aureus, a number of the derivatives exhibited faster rates of inactivation of P. aeruginosa than either of the I or II controls. The 2-n-propyl and 2,2-diethyl analogs were the most active aliphatic analogs tested in vitro. The importance of steric and/or lipophilic influences in determining the antibacterial efficacy of the analogs against P. aeruginosa was demonstrated by the joint application of quantitative antibacterial activity data (D-values) and computer-assisted multiparameter regression analysis (Hansch QSAR). QSAR prediction of the congener with the greatest anti-Pseudomonas effect led to an analog (the 2,2-dimethyl analog), with a preservative efficacy in a white lotion formulation, which is comparable to that of the parent compound. Results show the value of using QSAR to evaluate antibacterial activity data and to predict the member of a congeneric series possessing optimal levels of activity.