62023-65-8

Basic information

• Product Name: N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID
• Synonyms: N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID;(2S,3R)-3-(BOC-AMINO)-2-HYDROXY-4-PHENYLBUTYRIC ACID;BOC-(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOIC ACID;BOC-(2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRIC ACID;BOC-(2S,3R)-APNS-OH;N-tert-BOC-[2S,3R]-3-amino-2-hydroxy-4-phenylbutyric acid;Boc-(2S,3R)-AHPA,
• CAS NO: 62023-65-8
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.33
• Mol File: 62023-65-8.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 499.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1 +-.0.06 g/cm3(Predicted)
• Storage Temp.: −20°C
• PKA: 3.57±0.17(Predicted)
• Water Solubility: Insoluble in water. Soluble in organic solvents.
• BRN: 5909790
• CAS DataBase Reference: N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID(62023-65-8)
• EPA Substance Registry System: N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID(62023-65-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 62023-65-8(Hazardous Substances Data)

Usage

Uses

(2S,3R)-3-(Boc-amino)-2-hydroxy-4-phenylbutyric acid, is used as a novel protected amino acid for the preparation of bestatin and analogs.

Upstream product

• 116565-03-8 N-(tert-butyloxycarbonyl)-(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 209173-80-8 2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid 
• 186393-18-0 ((S)-1-benzyl-2-cyano-2-hydroxy-ethyl)-carbamic acid tert-butyl ester 
• 290836-34-9 (3S)-1,1-dibromo-3-tert-butoxycarbonylamino-4-phenyl-2-butanone 
• 3236-56-4 dipercarbonate de O,O-t-butyle 
• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 
• 81926-51-4 N-(tert-butyloxycarbonyl)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 182699-39-4 (2S,3R)-methyl-2,3-epoxy-4-phenylbutanoic acid 
• 612096-23-8 (2R,3S)-3-Bromo-2-hydroxy-4-phenyl-butyric acid methyl ester 
• 13033-84-6 D-phenylalanine methyl ester hydrochloride 
• 19901-50-9 methyl (2R)-2-(t-butoxycarbonylamino)-3-phenylpropionate 
• 77119-85-8 N-(tert-butoxycarbonyl)-D-phenylalaninal 
• 773837-37-9 sodium cyanide 

Downstream Products

• 145986-90-9 N-Boc-(2S,3S)-AHPA-L-Leu-tert-butyl ester 
• 159000-71-2 Boc-Apns-Dmt-NHtBu 
• 246506-77-4 6-tert-butoxycarbonylamino-5-hydroxy-2-isopropyl-4-oxo-7-phenyl-3-azaheptanoic acid benzyl ester 
• 58970-76-6 bestatin 
• 187402-73-9 2-[2-(3-amino-2-hydroxy-4-phenylbutyrylamino)-3-methylbutyrylamino]-3-phenylpropionic acid 
• 612096-24-9 (S)-2-((2S,3R)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-3-methyl-butyric acid 
• 87304-15-2 (2S)-2-[[(2S,3R)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoic acid 
• 217480-76-7 (S)-2-[(S)-2-((2S,3R)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-3-methyl-butyrylamino]-3-phenyl-propionic acid 
• 123652-87-9 1-{1-[2-(3-amino-2-hydroxy-4-phenylbutyrylamino)-4-methyl-pentanoyl]pyrrolidine-2-carbonyl}-pyrrolidinme-2-carboxylic acid 
• 217480-75-6 2-(6-tert-butoxycarbonylamino-5-hydroxy-2-isopropyl-4-oxo-7-phenyl-3-azaheptanoylamino)-3-phenylpropionic acid benzyl ester 
• 612096-25-0 (S)-1-{(S)-1-[(S)-2-((2S,3R)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoyl]-pyrrolidine-2-carbonyl}-pyrrolidine-2-carboxylic acid 
• 246506-80-9 1-{1-[2-(3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyrylamino)-4-methyl-pentanoyl]pyrrolidine-2-carbonyl}-pyrrolidine-2-carboxylic acid benzyl ester 
• 145986-89-6 (S)-2-((S)-3-Amino-2-oxo-4-phenyl-butyrylamino)-4-methyl-pentanoic acid; compound with trifluoro-acetic acid 
• 223763-80-2 (2S,3S)-AHPA-L-Leu-OH trifluoroacetic acid salt 

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TUBULIN BINDING AGENTS

The invention provides combretastatin A-4 like compounds that are modified to have enhanced tubulin binding activity and in some embodiments the ability to promote accumulation in the vasculature undergoing angiogenesis (homing activity). The compounds are based on the combretastatin A-4 skeletal structure having a tubulin-binding pharmacophore comprising two fused rings (A and B rings) in which the B ring is substituted with (a) an aromatic ring structure (C ring) and (b) a second substituent/functional group that comes off the B ring. The aromatic ring structure is typically a six membered ring phenolic or aniline structure, or may also be a fused ring structure such as a substituted or unsubstituted naphthalene. The second substituent on the B ring may for example be a substituent which has been found to provide enhanced tubulin binding activity (for example a carbonyl group), or may be a substituent that facilitates functionalisation of the B ring (for example an hydroxyl or amine group), or it may be a binding agent for a target that is preferentially expressed on vasculature undergoing angiogenesis, and not expressed on quiescent vasculature.