N-Phthalyl-L-tryptophan

Base Information

• Chemical Name: N-Phthalyl-L-tryptophan
• CAS No.: 48208-26-0
• Molecular Formula: C₁₉H₁₄N₂O₄
• Molecular Weight: 334.331
• DSSTox Substance ID: DTXSID801017660
• Nikkaji Number: J1.770.381A
• Wikidata: Q27166807
• Pharos Ligand ID: K143X3H2MCPA
• ChEMBL ID: CHEMBL1564869
• Mol file: 48208-26-0.mol

Synonyms:2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-(1H-indol-3-yl)propanoic acid;N-phthaloyl-L-tryptophan;N-phthaloyltryptophan;RG108

Chemical Property of N-Phthalyl-L-tryptophan

Chemical Property:

• Vapor Pressure: 7E-19mmHg at 25°C
• Melting Point: 192-194℃
• Refractive Index: 1.723
• Boiling Point: 670.3°C at 760 mmHg
• PKA: 3.62±0.10(Predicted)
• Flash Point: 359.2°C
• PSA: 90.47000
• Density: 1.47g/cm³
• LogP: 2.39770
• Storage Temp.: Store at RT
• Sensitive.: Light Sensitive
• Solubility.: DMSO: >10mg/mL
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 334.09535693
• Heavy Atom Count: 25
• Complexity: 554

Purity/Quality:

99% ^*data from raw suppliers

N-Phthalyl-L-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)C(CC3=CNC4=CC=CC=C43)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)[C@@H](CC3=CNC4=CC=CC=C43)C(=O)O
• Description: RG-108 (48208-26-0) is a non-nucleoside DNA methyltransferase inhibitor. IC50=115 nM1 Inhibits DNA methylation in human tumor cell lines without toxicity2. RG-108 enhances the reversion of neural progenitor cells to the pluripotent state.3
• Uses: DNA methylation regulates gene expression in normal and malignant cells. RG-108 is a non-nucleoside DNA methyltransferase inhibitor (IC50 = 115 nM in vitro). It significantly reduces the methylation of genomic DNA in cells at 10 μM without detectable toxicity, distinguishing it from nucleoside-based inhibitors like 5-azacytidine. Further, RG-108 inhibits DNA methyltransferase activity by blocking the enzyme active site. Through these actions, RG-108 demethylates and reactivates epigenetically silenced tumor suppressor genes. RG108 has been used:in reprogramming and increasing cell plasticity of primary multipotent mesenchymal stromal cells (MMSC)as an inhibitor of DNA methyltransferase (DNMTi) in human retinal pigment epithelial ARPE-19 cellsas a DNA methyltransferase inhibitor in C33A2 cells to test its effect on papillomavirus late gene expression (HPV16)

Technology Process of N-Phthalyl-L-tryptophan

There total 5 articles about N-Phthalyl-L-tryptophan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) + methyl 2-(N-succinimidyloxycarbonyl)benzoate (438470-19-0) → N-phthalimide-L-tryptophan (32675-71-1,48208-26-0,62361-30-2)

Guidance literature:

L-Tryptophan; methyl 2-(N-succinimidyloxycarbonyl)benzoate; With sodium carbonate; In water; acetonitrile;

With hydrogenchloride; In water; acetonitrile;

Reference yield: 100.0%

L-tryptophan hydrochloride (6159-33-7) + methyl 2-(N-succinimidyloxycarbonyl)benzoate (438470-19-0) → N-phthalimide-L-tryptophan (32675-71-1,48208-26-0,62361-30-2)

Guidance literature:

With potassium carbonate; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1021/jo016347h

Reference yield: 98.0%

N-ethoxycarbonylphthalimide (22509-74-6) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → N-phthalimide-L-tryptophan (32675-71-1,48208-26-0,62361-30-2)

Guidance literature:

L-Tryptophan; With sodium carbonate; In water;

N-ethoxycarbonylphthalimide; In water; at 20 ℃; for 2h;

DOI:10.1016/j.polymer.2010.03.034

upstream raw materials:

phthalic anhydride

L-Tryptophan

L-tryptophan hydrochloride

methyl 2-(N-succinimidyloxycarbonyl)benzoate

Downstream raw materials:

phthalimide

N-phthalimidotryptamine

N-Phth-Trp-Phe-OMe

N-Phth-Trp-Gly-O-pClPh

Refernces

• 1、 Chen, Zhongxiang,Fan, Hongjun,Yang, Shiwei,Bian, Guangling,Song, Ling. "Chiral sensors for determining the absolute configurations of α-amino acid derivatives". . p. 6933 - 6939. Retrieved 2018/10/02.
• 2、 Asgatay, Saa?dia,Champion, Christine,Marloie, Ga?l,Drujon, Thierry,Senamaud-Beaufort, Catherine,Ceccaldi, Alexandre,Erdmann, Alexandre,Rajavelu, Arumugam,Schambel, Philippe,Jeltsch, Albert,Lequin, Olivier,Karoyan, Philippe,Arimondo, Paola B.,Guianvarc'H, Dominique. "Synthesis and evaluation of analogues of N-phthaloyl-l-tryptophan (RG108) as inhibitors of DNA methyltransferase 1". . p. 421 - 434. Retrieved 2014/02/14.