A novel series of cannabimimetic aminoalkylindole‐based sulfonamide derivatives was synthesized. These new compounds were synthesized by reacting acyl chlorides of naphthoic acids with deacetylated acetazolamide in the presence of N‐ethyl‐morpholine to give structures incorporating 1‐naphthoyl groups of cannabimimetic aminoalkylindoles and a five‐membered heteroring typical of antiglaucoma sulfa drugs. The synthesized compounds were characterized using standard techniques. Photoluminescence of these derivatives was also studied, where more electron‐donating groups on the aromatic ring at the para‐position caused an increase in the intensity of the main peaks and shifts to higher emission wavelengths. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:707–714, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20738