Synthesis and biological evaluation of novel hydroquinone dimethyl ethers as potential anticancer and antimicrobial agents
The synthesis of two novel series of quinol dimethyl ethers linked to either various functionalities or to some biologically active nitrogenous heterocycles is described. Nine of the newly synthesized quinol dimethyl ethers 5a , b , 9b , 10a , d , 12a , b, and 13a , b were selected by the NCI and we...
Saved in:
Published in | Medicinal chemistry research Vol. 22; no. 8; pp. 3760 - 3778 |
---|---|
Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
New York
Springer-Verlag
01.08.2013
|
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | The synthesis of two novel series of quinol dimethyl ethers linked to either various functionalities or to some biologically active nitrogenous heterocycles is described. Nine of the newly synthesized quinol dimethyl ethers
5a
,
b
,
9b
,
10a
,
d
,
12a
,
b,
and
13a
,
b
were selected by the NCI and were tested initially at a single high dose (10 μM) in the full NCI 60 cell panel. Four of the screened quinol dimethyl ethers bearing unsubstituted phenylhydrazone
5a
, 4-chlorophenylhydrazone
5b
, 4-chlorophenyl-3-sulfanyl-1,2,4-triazole
9b
, as well as 4-chloroanilino-1,3,4-oxadiazole
12b
moieties satisfied the threshold antitumor screen. 4-Chlorophenylhydrazone
5b
showed very promising results and accordingly was chosen for in vivo antitumor screening. Thus, compound
5b
of the series could be considered as the potential lead for development of novel anticancer agents. In addition, compounds
5a–c
,
6a–c
,
9a–c
,
10a, b, d, e, g, h
,
11a–c
,
12a–c,
and
13a–c
were screened for their in vitro antimicrobial activity. Some of the tested compounds exhibited special high activity comparable to the reference ampicillin against
Pseudomonas aeruginosa
and
Escherichia coli
. |
---|---|
ISSN: | 1054-2523 1554-8120 |
DOI: | 10.1007/s00044-012-0337-y |