127819-97-0

Basic information

• Product Name: N-{(2S,3S)-1-[(2S)-1-{3-[2,2-bis(piperidin-1-ylcarbonyl)-2H-imidazol-4-yl]-D-alanyl}-2-formylpyrrolidin-2-yl]-3-methyl-1-oxopentan-2-yl}-3-naphthalen-2-yl-L-alaninamide
• Synonyms: L 366948;Cyclo[L-Pro-3-(2-naphtyl)-D-Ala-L-Ile-D-Pip-L-Pip-D-His-];Cyclo[L-Pro-3-(2-naphthalenyl)-D-Ala-L-Ile-D-Hpr-L-Hpr-D-His-];Cyclo[L-Ile-D-Hpr-L-Hpr-D-His-L-Pro-3-(2-naphthalenyl)-D-Ala-];cyclo-
• CAS NO: 127819-97-0
• Molecular Formula: C₄₂H₅₆N₈O₆
• Molecular Weight: 768.944
• Mol File: 127819-97-0.mol

Chemical Properties

• Density: 1.35g/cm³
• Refractive Index: 1.666
• CAS DataBase Reference: N-{(2S,3S)-1-[(2S)-1-{3-[2,2-bis(piperidin-1-ylcarbonyl)-2H-imidazol-4-yl]-D-alanyl}-2-formylpyrrolidin-2-yl]-3-methyl-1-oxopentan-2-yl}-3-naphthalen-2-yl-L-alaninamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-{(2S,3S)-1-[(2S)-1-{3-[2,2-bis(piperidin-1-ylcarbonyl)-2H-imidazol-4-yl]-D-alanyl}-2-formylpyrrolidin-2-yl]-3-methyl-1-oxopentan-2-yl}-3-naphthalen-2-yl-L-alaninamide(127819-97-0)
• EPA Substance Registry System: N-{(2S,3S)-1-[(2S)-1-{3-[2,2-bis(piperidin-1-ylcarbonyl)-2H-imidazol-4-yl]-D-alanyl}-2-formylpyrrolidin-2-yl]-3-methyl-1-oxopentan-2-yl}-3-naphthalen-2-yl-L-alaninamide(127819-97-0)

Safety Data

• Hazardous Substances Data: 127819-97-0(Hazardous Substances Data)

Upstream product

• 138775-65-2 D-2-Nal-Ile-D-Pip-L-Pip-D-His-Pro-NHNH₂ 
• 121428-29-3 Boc-D-His-OH 
• 138775-65-2 H-D-β-Nal-Ile-D-Pip-Pip-D-His-Pro-NH-NH2 

Relevant articles and documents

Development of a Novel Class of Cyclic Hexapeptide Oxytocin Antagonists Based on a Natural Product

A new structural class of cyclic hexapeptide oxytocin antagonists derived from Streptomyces silvensis and typified by L-365,209(cyclo-1-D-phenylalanyl2-L-isoleucyl3-D-dehydropiperazyl4-L-dehydropiperazyl5-D-(N-methyl)phenylalanyl6> was recently reported.In this paper we further delineate the structure-activity profile for this new class by systematic study of L-365,209 analogs obtained by total synthesis.The optimal combination of cyclic amino acid ring sizes at positions 1, 4, and 5 and the role of the N-alkyl substituent at position 6 was elucidated.The lipophilic amino acids at position 2 and 3 and the unusual amino acid D-dehydropiperazic acid at position 4 were found to be the most critical residues for obtaining good oxytocin receptor affinity.Analogs containing a basic side chain at the less critical 5- and 6-positions maintained good receptor affinity and also had useful levels of water solubility for intravenous formulation.By combining potency- and solubility-enhancing substitutions, several analogs were identified that have the desired combination of properties in vitro (22, cyclo-; 25, cyclo-; 26, cyclo-; 33, cyclo-; 34, cyclo-).Unexpectedly, compound 33 was found to stimulate contractions of the isolated rat uterus via activation of the uterine bradykinin receptor.Compounds 22, 25, 26, 33, and 34 were found to be potent antagonists of oxytocin-stimulated contraction of the rat uterus in vitro and in vivo.Compounds 22 and 25 were additionally characterized as potent antagonists of oxytocin-stimulated uterine contractions in the near-term pregnant rhesus monkey.These studies thus demonstrate the selectivity and efficacy of certain members of this novel class of antagonists and suggest their use as pharmacological tools in further defining the role of oxytocin in both term and preterm labor.

Use of N-Fmoc Amino Acid Chlorides and Activated 2-(Fluorenylmethoxy)-5(4H)-oxazolones in Solid-Phase Peptide Synthesis. Efficient Syntheses of Highly N-Alkylated Cyclic Hexapeptide Oxytocin Antagonists Related to L-365,209

Fmoc amino acid chlorides have been shown to be useful reagents in the solid-phase synthesis of hexapeptides containing up to four sequential secondary amino acids.The oxytocin antagonist cyclo-(D-Phe-Ile-D-Pip-Pip-D-(N-Me)Phe-Pro) (1) was prepared in 70p