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Nobilamide B, a TRPV1 antagonist, and a series of Ala-substituted analogues were synthesized and their neuroactivity was assessed in a primary culture of dorsal root ganglion (DRG) neurons. Analogues 4 , 6 , and 7 showed comparable activity, affecting capsaicin response in neurons, in contrast to 2 , 3 , and 5 which showed minimal blocking. Compounds 2 , 3 , and 5 correspond to analogues in which d-Phe, d-Leu and d- allo -Thr have been substituted with Ala, respectively. The observed loss of bioactivity in these three analogues highlights the importance of d amino acids in the primary structure of nobilamide B.

On the inhibition of capsaicin response in dorsal root ganglion neurons by nobilamide B and analogues: a structure–activity relationship study