1213338-17-0

Basic information

• Product Name: Boc-3,5-Dimethy-D-Phenylalanine
• Synonyms: Boc-3,5-Dimethy-D-Phenylalanine;Boc-D-Phe(3,5-Me2)-OH;BOC-3,5-DIMETHYL-D-PHENYLALANINE
• CAS NO: 1213338-17-0
• Molecular Formula: C16H23NO4
• Molecular Weight: 293.35812
• Mol File: 1213338-17-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Boc-3,5-Dimethy-D-Phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-3,5-Dimethy-D-Phenylalanine(1213338-17-0)
• EPA Substance Registry System: Boc-3,5-Dimethy-D-Phenylalanine(1213338-17-0)

Safety Data

• Hazardous Substances Data: 1213338-17-0(Hazardous Substances Data)

Upstream product

• 1241680-65-8 3',5'-dimethyl-L-phenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 27129-86-8 1-bromomethyl-3,5-dimethylbenzene 
• 102831-44-7 diethyl tert-butoxycarbonylaminomalonate 

Downstream Products

• 1229620-64-7 Nα-(tert-butoxycarbonyl)-N-(cyanomethyl)-3,5-dimethyl-L-phenylalaninamide 
• 1352542-97-2 C₃₂H₄₃N₅O₄S₂ 

Relevant articles and documents

CATHEPSIN B INHIBITORS

Compounds of formula I, including individual diastereomers thereof and pharmaceutically acceptable salts and hydrates thereof, are selective inhibitors of cathepsin B, and are useful in treating pathological conditions that are treated by inhibiting cathepsin B.

Bifunctional [2′,6′-dimethyl-L-tyrosine1] endomorphin-2 analogues substituted at position 3 with alkylated phenylalanine derivatives yield potent mixed μ-agonist/δ-antagonist and dual μ-agonist/δ-agonist opioid ligands

Endomorphin-2 (H-Tyr-Pro-Phe-Phe-NH2) and [Dmt1]EM-2 (Dmt = 2′,6′-dimethyl-L-tyrosine) analogues, containing alkylated Phe3 derivatives, 2′-monomethyl (2, 2′), 3′,5′- and 2′,6′-dimethyl (3, 3′, and 4′, respectively), 2′,4′,6′-trimethyl (6, 6′), 2′-ethyl-6′-methyl (7, 7′), and 2′-isopropyl-6′- methyl (8, 8′) groups or Dmt (5, 5′), had the following characteristics: (i) [Xaa3]EM-2 analogues exhibited improved μ- and δ-opioid receptor affinities. The latter, however, were inconsequential (Kiδ = 491-3451 nM). (ii) [Dmt 1,-Xaa3]EM-2 analogues enhanced μ- and δ-opioid receptor affinities (Kiμ = 0.069-0.32 nM; K iδ = 1.83-99.8 nM) without κ-opioid receptor interaction. (iii) There were elevated μ-bioactivity (IC50 = 0.12-14.4 nM) and abolished δ-agonism (IC50 > 10 μM in 2′, 3′, 4′, 5′, 6′), although 4′ and 6′ demonstrated a potent mixed μ-agonism/δ-antagonism (for 4′, IC50μ = 0.12 and pA2 = 8.15; for 6′, IC50μ = 0.21 nM and pA2 = 9.05) and 7′ was a dual μ-agonist/δ-agonist (IC50 μ = 0.17 nM; IC50δ = 0.51 nM).

Identification of dipeptidyl nitriles as potent and selective inhibitors of cathepsin B through structure-based drug design

Cathepsin B is a member of the papain superfamily of cysteine proteases and has been implicated in the pathology of numerous diseases, including arthritis and cancer. As part of an effort to identify potent, reversible inhibitors of this protease, we examined a series of dipeptidyl nitriles, starting with the previously reported Cbz-Phe-NH-CH2CN (19, IC50 = 62 μM). High-resolution X-ray crystallographic data and molecular modeling were used to optimize the P1, P2, and P3 substituents of this template. Cathepsin B is unique in its class in that it contains a carboxylate recognition site in the S2′ pocket of the active site. Inhibitor potency and selectivity were enhanced by tethering a carboxylate functionality from the carbon α to the nitrile to interact with this region of the enzyme. This resulted in the identification of compound 10, a 7 nM inhibitor of cathepsin B, with excellent selectivity over other cysteine cathepsins.