53990-33-3

Basic information

• Product Name: Z-PHG-OH
• Synonyms: CBZ-PHG-OH;CBZ-L-PHENYLGLYCINE;BENZYLOXYCARBONYL-L-PHENYLGLYCINE;N-ALPHA-CARBOBENZOXY-L-PHENYLGLYCINE;N-ALPHA-CBZ-L-PHENYLGLYCINE;N-CBZ-L-PHENYLGLYCINE;Z-(PHENYL)GLY-OH;Z-PHENYLGLYCINE
• CAS NO: 53990-33-3
• Molecular Formula: C₁₆H₁₅NO₄
• Molecular Weight: 285.29
• EINECS: 1533716-785-6
• Product Categories: Phenylglycine [Phg]
• Mol File: 53990-33-3.mol
• Article Data: 24

Chemical Properties

• Melting Point: 131.0 to 135.0 °C
• Boiling Point: 495.3 °C at 760 mmHg
• Flash Point: 253.4 °C
• Appearance: /
• Density: 1.275 g/cm³
• Vapor Pressure: 1.25E-10mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: Store at RT.
• Solubility: DMSO (Slightly), Ethanol (Slightly)
• PKA: 3.49±0.10(Predicted)
• BRN: 4703006
• CAS DataBase Reference: Z-PHG-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-PHG-OH(53990-33-3)
• EPA Substance Registry System: Z-PHG-OH(53990-33-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 53990-33-3(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

Uses

Z-L-Phenylglycine is an intermediate for the synthesis of Asimadoline Hydrochlorine (A788250), used in the treatment of IBS, a disorder associated with pain and altered bowel function.

InChI:InChI=1/C16H15NO4/c18-15(19)14(13-9-5-2-6-10-13)17-16(20)21-11-12-7-3-1-4-8-12/h1-10,14H,11H2,(H,17,20)(H,18,19)/t14-/m0/s1

Upstream product

• 127862-77-5 Benzyloxycarbonylamino-phenyl-acetic acid 2,2,2-trifluoro-ethyl ester 
• 15962-49-9 (S)-phenylglycine ethyl ester 
• 2935-35-5 (S)-2-phenylglycine 
• 147780-61-8 (S)-methyl 2-(benzyloxycarbonylamino)-2-phenylacetate 
• 501-53-1 benzyl chloroformate 
• 59410-82-1 (S)-α-phenylglycine ethyl ester hydrochloride 
• 621-84-1 O-benzyl carbamate 
• 100-42-5 styrene 
• 2835-06-5 phenylglycin 
• 5840-78-8 4-phenyl-oxazolidine-2,5-dione 
• 394210-43-6 2,5-dioxo-4-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 928765-35-9 (R/S)-N-benzyloxycarbonyl-1,3-diphenylprop-2-en-1-ylamine 
• 591-51-5 phenyllithium 
• 193091-62-2 (E)-(R)-O-(1-phenylbutyl)cinnamaldehyde oxime 

Downstream Products

• 60379-01-3 N-<(phenylmethoxy)carbonyl>-L-phenylalanine phenylmethyl ester 
• 205654-79-1 (2S,4S)-3-benzyloxycarbonyl-2,4-diphenyl-1,3-oxazolidin-5-one 
• 208448-22-0 methyl (2S)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate 
• 208448-13-9 methyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate 
• 208448-27-5 2-(trimethylsilyl)ethyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate 
• 340732-83-4 [1-(benzyloxycarbonylamino-phenyl-acetyl)-4-tert-butoxycarbonylmethyl-3-oxo-piperazin-2-yl]-acetic acid methyl ester 
• 394734-93-1 (S)-benzyl 2-(dimethylamino)-2-oxo-1-phenylethylcarbamate 
• 147780-61-8 (S)-methyl 2-(benzyloxycarbonylamino)-2-phenylacetate 
• 83871-06-1 N-benzyloxycarbonyl-L-phenylalanyl-L-prolinamide 
• 1266229-67-7 benzyl {(1S)-2-[(3S,8aR)-3-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-oxo-1-phenylethyl}carbamate 
• 136401-24-6 benzyl N-(1-methoxy-1-phenylmethyl)carbamate 
• 1431506-16-9 Z-PheGly-Cys(Trt)-OMe 

Relevant articles and documents

Design and synthesis of novel symmetric fluorene-2,7-diamine derivatives as potent hepatitis C virus inhibitors

Hepatitis C virus (HCV) is an international challenge. Since the discovery of NS5A direct-acting antivirals, researchers turned their attention to pursue novel NS5A inhibitors with optimized design and structure. Herein we explore highly potent hepatitis C virus (HCV) NS5A inhibitors; the novel analogs share a common symmetrical prolinamide 2,7-diaminofluorene scaffold. Modification of the 2,7-diaminofluorene backbone included the use of (S)-prolinamide or its isostere (S,R)-piperidine-3-caboxamide, both bearing different amino acid residues with terminal carbamate groups. Compound 26 exhibited potent inhibitory activity against HCV genotype (GT) 1b (effective concentration (EC50) = 36 pM and a selectivity index of >2.78 × 106). Compound 26 showed high selectivity on GT 1b versus GT 4a. Interestingly, it showed a significant antiviral effect against GT 3a (EC50 = 1.2 nM). The structure-activity relationship (SAR) analysis revealed that picomolar inhibitory activity was attained with the use of S-prolinamide capped with R- isoleucine or R-phenylglycine residues bearing a terminal alkyl carbamate group.

THERAPEUTIC USE OF LEVOROTATORY ?-LACTAMS IN HEMATOPOIESIS, IMMUNO-ONCOLOGY THERAPY, AND REGULATION OF LIPOPROTEIN AND APOLIPOPROTEIN LEVELS

A method for increasing the number of CD4+ T-lymphocytes in the serum of a subject in need of such treatment comprising administering to the subject a pharmaceutical composition comprising an amount of an L-isomer of β-lactam effective to increase the number of CD4+ T-lymphocytes in said patient's serum.

COMPOUNDS USEFUL AS CSF1 MODULATORS

This invention relates to novel compounds and to pharmaceutical compositions comprising the novel compounds. More specifically, the invention relates to compounds useful as Colony Stimulating Factor 1 Receptor (cFMS) modulators (e.g. cFMS inhibitors). This invention also relates to processes for preparing the compounds, uses of the compounds in treatment and methods of treatment employing the compounds. Specifically, the invention relates to the use of the compounds for the treatment of cancer and autoimmune diseases.