714970-66-8

Basic information

• Product Name: ((S)-1-(4-Hydroxy-2,6-dimethyl-benzyl)-2-oxo-2-{(S)-2-[(S)-2-phenyl-1-(pyridin-3-ylcarbamoyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-ethyl)-carbamic acid tert-butyl ester
• Synonyms: ((S)-1-(4-Hydroxy-2,6-dimethyl-benzyl)-2-oxo-2-{(S)-2-[(S)-2-phenyl-1-(pyridin-3-ylcarbamoyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-ethyl)-carbamic acid tert-butyl ester
• CAS NO: 714970-66-8
• Molecular Weight: 629.756
• Mol File: 714970-66-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ((S)-1-(4-Hydroxy-2,6-dimethyl-benzyl)-2-oxo-2-{(S)-2-[(S)-2-phenyl-1-(pyridin-3-ylcarbamoyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-ethyl)-carbamic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: ((S)-1-(4-Hydroxy-2,6-dimethyl-benzyl)-2-oxo-2-{(S)-2-[(S)-2-phenyl-1-(pyridin-3-ylcarbamoyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-ethyl)-carbamic acid tert-butyl ester(714970-66-8)
• EPA Substance Registry System: ((S)-1-(4-Hydroxy-2,6-dimethyl-benzyl)-2-oxo-2-{(S)-2-[(S)-2-phenyl-1-(pyridin-3-ylcarbamoyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-ethyl)-carbamic acid tert-butyl ester(714970-66-8)

Safety Data

• Hazardous Substances Data: 714970-66-8(Hazardous Substances Data)

Upstream product

• 714970-09-9 (S)-2-[(S)-2-Phenyl-1-(pyridin-3-ylcarbamoyl)-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 88932-75-6 3-(L-phenylalanylamino)pyridine 
• 88932-69-8 3-<amino>pyridine 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 462-08-8 pyridin-3-ylamine 
• 99953-00-1 (S)-N-Boc-2,6-dimethyltyrosine 

Relevant articles and documents

Development of potent bifunctional endomorphin-2 analogues with mixed μ-/δ-opioid agonist and δ-opioid antagonist properties

The C terminus of endomorphin-2 (EM-2) analogues (Tyr-Pro-Phe-NH-X) was modified with aromatic, heteroaromatic, or aliphatic groups (X = phenethyl,benzyl, phenyl, naphthyl, pyridyl, quinolyl, isoquinolyl, tert-butyl, cyclohexyl, or adamantyl; 3-18) to study their effect on opioid activity. Only 9 (1-naphthyl), 11 (5-quinolyl), 16 (cyclohexyl), and 18 (2-adamantyl) exhibited μ-opioid receptor affinity in the nanomolar range (Ki = 2.41-6.59 nM), which, however, was 3-to 10-fold less than the parent peptide. Replacement of Tyr1 by Dmt (2′,6′-dimethyl-L-tyrosine) (19-32) exerted profound effects: (i) acquisition of high μ-opioid receptor affinity (Ki = 0.11-0.52 nM) except 23 (Ph); (ii) presence of potent functional μ-opioid receptor agonism (IC50 1]EM-2), 27 (1-naphthyl), 29 (5-quinolyl), and 32 (5-isolquinolyl); (iii) association of weak δ-opioid antagonist activity (pA2 = 5.41-7.18) except 19 ([Dmt1]EM-2), 20 (H), 27 (1-naphthyl), and in particular 29 (5-quinolyl) with its potent δ-agonism (IC50 = 0.62 nM, pA2 = 5.88); (iv) production of antinociception after ic administration of 32 (5-isoquinolyl) in mice, a bioactivity absent in the corresponding Tyr1 analogue (14); and (v) preferential cis orientation (cis/trans = 3:2 to 7:3) at the Dmt-Pro amide bond, in contrast to the Tyr-Pro amide trans orientation (cis/trans = 1:2 to 1:3). Thus, [Dmt1]EM-2 analogues with hydrophobic C-terminal extensions provide model compounds with potent μ-opioid receptor bioactivity and dual functional agonism.