317357-42-9

Basic information

• Product Name: (2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-(2-NAPHTHYLOXY)-2-PYRROLIDINECARBOXYLIC ACID
• Synonyms: (2S,4S)-BOC-4-(2-NAPHTHYLOXY)-PYRROLIDINE-2-CARBOXYLIC ACID;(2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-(2-NAPHTHYLOXY)-2-PYRROLIDINECARBOXYLIC ACID;(2S,4S)-Boc-4-(naphthalen-2-yloxy)-pyrrolidine-2-carboxylic acid;(2S,4S)-Boc-4-(2-naphthyloxy)-Pro-OH;N-BOC-cis-4-Naphthyloxy-L-proline
• CAS NO: 317357-42-9
• Molecular Formula: C₂₀H₂₃NO₅
• Molecular Weight: 357.4
• Mol File: 317357-42-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 537.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.263±0.06 g/cm3(Predicted)
• PKA: 3.70±0.40(Predicted)
• CAS DataBase Reference: (2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-(2-NAPHTHYLOXY)-2-PYRROLIDINECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-(2-NAPHTHYLOXY)-2-PYRROLIDINECARBOXYLIC ACID(317357-42-9)
• EPA Substance Registry System: (2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-(2-NAPHTHYLOXY)-2-PYRROLIDINECARBOXYLIC ACID(317357-42-9)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 317357-42-9(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Upstream product

• 135-19-3 β-naphthol 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 317357-41-8 methyl 1-(tert-butoxycarbonyl)-(4S)-(2-naphthyloxy)-(2S)-pyrrolidinylcarboxylate 

Downstream Products

• 317357-46-3 methyl 4-[(2S,4S)-1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-4-(2-naphthyloxy)-2-pyrrolidinyl]methoxybenzoate 
• 317357-44-1 methyl 4-[1-tert-butoxycarbonyl-(4S)-(2-naphthyloxy)-(2S)-pyrrolidinylmethoxy]benzoate 
• 317357-45-2 methyl 4-[(4S)-(2-naphthyloxy)-(2S)-pyrrolidinyl]methoxybenzoate 

Relevant articles and documents

Synthesis, biological evaluation, and pharmacokinetic study of prolyl-1-piperazinylacetic acid and prolyl-4-piperidinylacetic acid derivatives as VLA-4 antagonists

A series of prolyl-1-piperazinylacetic acid and prolyl-4-piperidinylacetic acid derivatives were synthesized and evaluated for their activity as VLA-4 antagonists. Of 22 compounds synthesized, 19 compounds showed potent activity with low nanomolar IC50 values. In addition, the representative compounds 11o and 11p with a hydroxy group in the pyrrolidine ring showed moderate plasma clearance in rats (11o, 30 ml/min/kg and 11p, 21 ml/min/kg) and in dogs (11o, 12 ml/min/kg and 11p, 9 ml/min/kg).

VLA-4 INHIBITORS

The present invention relates to a compound represented by the following formula (I): (wherein, W represents WA-A1 -WB - (in which, WA is substituted or unsubstituted aryl, etc., A1 is -NR1-, single bond, -C(O)-, etc., and WB is substituted or unsubstituted arylene, etc.), R is single bond, -NH-, -OCH2-, alkenylene, etc., X is -C(O) -CH2-, etc., and M is, for example, the following formula: (in which, R11, R12 and R13 each independently represents hydrogen, hydroxyl, amino, halogen, etc., R14 is hydrogen or lower alkyl, Y represents -CH2-O-, etc., Z is substituted or unsubstituted arylene, etc., A2 is single bond, etc, and R10 is hydroxyl or lower alkoxy)), or salt thereof; and a medicament containing the same. This compound or salt thereof selectively inhibits binding of cell adhesion molecules to VAL-4 and exhibits high bioavailability so that it is useful as a preventive and/or remedy for inflammatory diseases, autoimmune diseases, metastasis, bronchial asthma, rhinostenosis, diabetes, and the like.