I'm not sure I entirely understand your requirements, but /t(?!est\b)\w*t/ would match any 't' not followed by 'est' and a word break then match 0 or more word characters and then match one last 't'. For example (anchors added):
#!/usr/bin/perl -w
use strict;
/^t(?!est\b)\w*t$/ and print while <DATA>;
__DATA__
test
testset
tot
tesset
tt
prints everything but 'test'.
Adapting it slightly for your original problem like this
#!/usr/bin/perl -lw
use strict;
$_ = "thought test tot 1 2 3 tesset";
s/t(?!est\b)\w*t\s*//g;
print;
prints " test 1 2 3" just as you want.
-sauoq
"My two cents aren't worth a dime.";
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