Ancient city street associated with duke's historic dare (5)
I believe the answer is:
durst
'historic dare' is the definition.
(archaic word for 'dare')
'ancient city street associated with duke's' is the wordplay.
'ancient city' becomes 'ur' (ancient Sumerian city state).
'street' becomes 'st' (abbreviation).
'associated with' means one lot of letters go next to another.
'duke' becomes 'd' (abbreviation).
'ur'+'st'='urst'
'urst' put after 'd' is 'DURST'.
(Other definitions for durst that I've seen before include "Dared to venture" , "defied once" .)