Synthesis of new 2-naphthyl ethers and their protective activities against DNA damage induced by bleomycin-iron.
The reaction of 2-naphthaloxyacetic acid with thiosemicarbazide in the presence of phosphoryl chloride, followed by treatment with phenacylbromides, led to the formation of imidazo[2,1-b][1,3,4]thiadiazoles 3a-c. 2-(Naphthalen-3-yloxy)acetohydrazide 4 on treatment with ethyl 2-(2-arylhydrazono)-3-oxobutanoates (5a-c), 2-methoxymethylene)malononitrile, or ethyl 2-cyano-3,3-bis(methylthio)acrylate led to the formation of substituted pyrazoles 6-8. The reaction of the hydrazide 4 with hydrazonoyl chlorides 9a-c and 1,2,4,5-benzene tetracarboxylic-1,2:4,5-dianhydride produced bis-diazo compounds 10a-c and dimide 11 respectively. All new compounds were tested for their protective activity against DNA damage induced by bleomycin-iron complex. Compound 2 showed the greatest protection against DNA damage, thus diminishing chromogen formation between the damaged DNA and thiobarbituric acid.
Abdel-Wahab
Bakr F
BF
Applied Organic Chemistry Department, National Research Center, Dokki, Giza, Egypt. Bakrfatehy@yahoo.com
El-Ahl
Abdel-Aziz S
AA
Badria
Farid A
FA
D001761:Bleomycin / Q000031:analogs & derivatives* / Q000633:toxicity; D004249:DNA Damage / Q000187:drug effects*; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D004987:Ethers; D009281:Naphthalenes; D013830:Thiadiazoles; C023503:iron bleomycin; D001761:Bleomycin