Synthesis and antitumor properties of new 2,4-dichlorophenoxy ethers

A series of new compounds incorporating 2,4-dichlorophenoxy nucleus have been synthesized. Reaction of 2,4-dichlorophenoxyacetic 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 (...

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Bibliographic Details
Published in:Pharmaceutical chemistry journal 2011-04, Vol.45 (1), p.30-35
Main Authors: Abdel-Wahab, B. F., Farghaly, M., Badria, F. A.
Format: Article
Language:English
Subjects:
Aldehydes
Antitumor activity
Antitumor agents
Ascites
Azo dyes
Carbon
Carcinoma
Chloride
Chlorides
Diazo compounds
Dichloropropane
Ethers
Medicine
Nuclei
Olefins
Organic Chemistry
Pharmacology/Toxicology
Pharmacy
pyrazoles
Schiff bases
Toy industry
Tumor cell lines
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Summary:A series of new compounds incorporating 2,4-dichlorophenoxy nucleus have been synthesized. Reaction of 2,4-dichlorophenoxyacetic 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 ( 3 ). Bischlorophenoxyallyl hydrazides ( 4 ) reacted with some of alkenes, azo dyes, aldehydes, and hydrazonoyl chlorides to produce pyrazoles, Schiff bases, and bis-diazo compounds, respectively. 1,3,4-Thiadiazole ( 10 ) was obtained by reaction of dichlorophenoxyallyl hydrazides ( 4b ) with carbon disulphide followed by hydrazonoyl chlorides. All compounds were tested for their preliminarily antitumor activity on transplantable murine tumor cell line [Ehrlich ascites carcinoma (EAC)]. Compound 2-{2-[2-(2,4-dichlorophenoxy)acetyl]hydrazono}-N'-(4-fluorophenyl)propanehydrazonoyl chloride ( 8c ) has remarkably decreased the viable EAC cell count as indicated by Trypan Blue dye exclusion test (3%) in comparison to the well known antitumor agent 5-FU (0%).
ISSN:0091-150X
1573-9031
DOI:10.1007/s11094-011-0555-5