Mokotoff, Michael; Ren, Kaijun; Wong, Lan K.; LeFever, Ann V.; Lee, Ping C. published their research in Journal of Medicinal Chemistry on December 11 ,1992. The article was titled 《Synthesis and biological evaluation of novel potent antagonists of the bombesin/gastrin releasing peptide receptor》.Synthetic Route of C13H26N2O4 The article contains the following contents:
The solid-phase synthesis and antagonist activity of 20 C-terminal analogs of gastrin releasing peptide (GRP) are reported.. The ability of each analog to inhibit bombesin (BN)-stimulated amylase release from rat pancreatic acini was determined, and those showing antagonist activity were further evaluated for their ability to inhibit BN stimulated [3H]-thymidine uptake in serum-starved 3T3 cells. The assays also included two known peptide antagonists, ([Leu14,ψ13,14]BN) (I) and (N-pivaloyl-GRP20-25-(R)-2-methyl-4-nonylamide) (II), as pos. controls. On the basis of these assays we suggest that a des-Met27,Leu26-ψ[CH2NHCOCH3]GRP C-terminal octapeptide imparts antagonist activity. The two most active compounds are peptides [D-Phe19,Leu26-ψ(CH2NHCOCH3)]GRP19-26 (III) and [D-Phe19,Gln20,Leu26-ψ(CH2NHCOCH3)]GRP19-26 (IV). In their ability to inhibition BN stimulated [3H]-thymidine uptake, the IC50 of peptides I, II, III, and IV were 43, 31, 3, and 33 nM, resp. In conclusion, the novel C-terminal ψ[CH2NHCOCH3] bond promises to be a useful peptide backbone modification for imparting antagonism in GRP/BN analogs. The experimental part of the paper was very detailed, including the reaction process of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Synthetic Route of C13H26N2O4)
(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Synthetic Route of C13H26N2O4 The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds.
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics