1310050-75-9Relevant academic research and scientific papers
On the inhibition of capsaicin response in dorsal root ganglion neurons by nobilamide B and analogues: a structure-activity relationship study
Belleza, Oliver John V.,Tun, Jortan O.,Concepcion, Gisela P.,Villaraza, Aaron Joseph L.
, p. 1673 - 1678 (2018/10/26)
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.
Total syntheses of nobilamides B and D: Application of traceless Staudinger ligation
Yamashita, Tomoya,Matoba, Hiroaki,Kuranaga, Takefumi,Inoue, Masayuki
, p. 7746 - 7752 (2014/12/10)
Nobilamide B is a long-acting antagonist of transient receptor potential vanilloid-1 (TRPV1), and is expected to show therapeutic potential for treatment of pain. This linear heptapeptide possesses a Z-didehydroaminobutanoic acid moiety at the C-terminus. Stereoselective construction of the didehydroamino acid moiety was successfully achieved by application of the traceless Staudinger ligation. The combination of solid-phase peptide synthesis and the Staudinger ligation allowed rapid access to not only nobilamide B, but also its macrocyclic analogue nobilamide D.
