57277-55-1

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 63-91-2 L-phenylalanine 
• 768-94-5 1-Adamantanamine 

Downstream Products

• 714970-27-1 (S)-2-[(S)-1-(Adamantan-1-ylcarbamoyl)-2-phenyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1292792-94-9 (S)-N-adamantan-1-yl-3-phenylpropane-1,2-diamine 
• 714970-55-5 [(S)-2-{(S)-2-[(S)-1-(Adamantan-1-ylcarbamoyl)-2-phenyl-ethylcarbamoyl]-pyrrolidin-1-yl}-1-(4-hydroxy-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Organocatalytic asymmetric Michael addition of aldehydes and ketones to nitroalkenes catalyzed by adamantoyl L-prolinamide

A series of adamantoyl l-prolinamides have been synthesized. These compounds have been found to be highly efficient organocatalysts for the Michael addition of aldehydes and ketones to nitroalkenes. Under the optimized reaction conditions, the correspondi

Highly enantioselective epoxidation of α,β-unsaturated ketones catalyzed by primary-secondary diamines

The asymmetric epoxidation of α,β-unsaturated ketones has been achieved by using functional and readily accessible primary-secondary diamines as the catalysts, giving the useful alkyl epoxy products with good yields and high enantioselectivities (up to 99% ee). Copyright

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.