52697-47-9Relevant articles and documents
STRONG UTEROTONIC INHIBITORS-ANALOGS OF 1-DEAMINO-8-D-HOMOARGININE-VASOPRESSIN WITH p-SUBSTITUTED PHENYLALANINE IN POSITION 2
Zertova, Miroslawa,Prochazka, Zdenko,Barth, Tomislav,Slaninova, Jirina,Skopkova, Jana,et al.
, p. 1761 - 1767 (2007/10/02)
Solid phase methodology on benzhydrylamine or p-methylbenzhydrylamine resin was used for the synthesis of five analogs of deamino-vasopressin with non-coded amino acids, D-homoarginine, in position 8 and p-substituted D- or L-phenylalanine in position 2.Besides the mother analog, 1, D-Har8>vasopressin (I). 1, L-Phe(p-Me)2, D-Har8>vasopressin (II), 1, D-Phe(p-Me)2, D-Har8>vasopressin (III), 1,L-Phe(p-Et)2, D-Har8>vasopressin (IV) and 1, D-Phe(p-Et)2, D-Har8>vasopressin (V) were synthesized.All analogs have very low antidiuretic and pressor activities.Analogs containing p-methylphenylalanine of L-configuration and p-ethylphenylalanine of both D- and L-configuration are pressor inhibitors.All analogs substituted in position 2 were found to act as the uterotonic inhibitors, the most potent being 1, D-Phe(p-Et)2, D-Har8>vasopressin (V) with pA2 = 8.30.
