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Bioorg Med Chem Lett ; 17(5): 1346-8, 2007 Mar 01.
Article in English | MEDLINE | ID: mdl-17188865

ABSTRACT

Quaternized chlorpromazine, triflupromazine, and promethazine derivatives were synthesized and examined as antitubercular agents against both actively growing and non-replicating Mycobacterium tuberculosis H37Rv. Impressively, several compounds inhibited non-replicating M. tuberculosis at concentrations equal to or double their MICs against the actively growing strain. All active compounds were non-toxic toward Vero cells (IC50 > 128 microM). N-Allylchlorpromazinium bromide was only weakly antitubercular, but replacing allyl with benzyl or substituted benzyl improved potency. An electron-withdrawing substituent on the phenothiazine ring was also essential. Branching at the carbon chain decreased antitubercular activity. The optimum antitubercular structures possessed N-(4- or 3-chlorobenzyl) substitution on triflupromazine.


Subject(s)
Antitubercular Agents/chemical synthesis , Antitubercular Agents/pharmacology , Chlorpromazine/chemical synthesis , Chlorpromazine/pharmacology , Mycobacterium tuberculosis/drug effects , Promazine/chemical synthesis , Promazine/pharmacology , Promethazine/chemical synthesis , Promethazine/pharmacology , Quaternary Ammonium Compounds/chemical synthesis , Quaternary Ammonium Compounds/pharmacology , Structure-Activity Relationship , Triflupromazine/chemical synthesis , Triflupromazine/pharmacology
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