N-propargyl-2-alkynylbenzothiazolium aza-enediynes: role of the 2-alkynylbenzothiazolium functionality in DNA cleavage.
The 2-alkynylbenzothiazolium salts 3a-d incorporating an N-propargyl moiety have been prepared as aza-enediyne analogues. While these aza-enediynes are shown to be modest DNA cleavage agents, DNA cleavage was also observed with the N-methyl-2-alkynylbenzothiazolium salt 4, which lacks the aza-enediyne moiety. The structural requirements for DNA cleavage, and the correlation of DNA cleavage efficiency with the propensity of these compounds to undergo nucleophilic addition by methanol support a proposed DNA cleavage mechanism involving DNA alkylation by appropriate 2-alkynyl-substituted benzothiazolium salts.
Kumar
D
D
Division of Medicinal Chemistry, College of Pharmacy, University of Texas at Austin, Austin, TX 78712, USA.
David
W M
WM
Kerwin
S M
SM
D001372:Aza Compounds / Q000138:chemical synthesis / Q000494:pharmacology*; D004247:DNA / Q000737:chemistry / Q000187:drug effects*
D001372:Aza Compounds; D004247:DNA