Oglufanide

Base Information

• Chemical Name: Oglufanide
• CAS No.: 38101-59-6
• Deprecated CAS: 122933-59-9
• Molecular Formula: C16H19 N3 O5
• Molecular Weight: 333.344
• UNII: 4RHY598T5U
• DSSTox Substance ID: DTXSID10924324
• Nikkaji Number: J895.715K
• Wikidata: Q4457491
• NCI Thesaurus Code: C76274
• Metabolomics Workbench ID: 78793
• ChEMBL ID: CHEMBL2111029
• Mol file: 38101-59-6.mol

Synonyms:alpha-glutamyltryptophan;Glu-Trp;L-alpha-glutamyl-L-tryptophan

Chemical Property of Oglufanide

Chemical Property:

• Vapor Pressure: 6.29E-23mmHg at 25°C
• Melting Point: 121-122℃
• Refractive Index: 1.659
• Boiling Point: 738.9°Cat760mmHg
• PKA: 3.09±0.10(Predicted)
• Flash Point: 400.7°C
• PSA: 145.51000
• Density: 1.428g/cm³
• LogP: 1.56310
• Storage Temp.: -15°C
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 333.13247072
• Heavy Atom Count: 24
• Complexity: 484

Purity/Quality:

99.0% ^*data from raw suppliers

Thymogen(Oglufanide) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)NC(=O)C(CCC(=O)O)N
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)C[C@@H](C(=O)O)NC(=O)[C@H](CCC(=O)O)N
• Recent ClinicalTrials: IM-862 in Treating Patients With Recurrent Ovarian Cancer
• Uses: Treatment of Kaposi’s sarcoma and solid tumor cancers (angiogenesis inhibitor); immunomodulator.

Technology Process of Oglufanide

There total 2 articles about Oglufanide 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: 87.0%

Nα-Cbz-glutamate-tryptophan benzyl ester (1383158-11-9) → α-glu-trp (38101-59-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; water; at 20 ℃; under 7500.75 Torr;

DOI:10.1002/cbic.201200017

Reference yield:

N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) → α-glu-trp (38101-59-6)

Guidance literature:

Multi-step reaction with 3 steps

1: alcalase-CLEA / tetrahydrofuran / 16 h / 37 °C / Molecular sieve

2: papain / N,N-dimethyl-formamide / 25 °C / pH 8 / aq. buffer

3: palladium 10% on activated carbon; hydrogen / methanol; water / 20 °C / 7500.75 Torr

With palladium 10% on activated carbon; alcalase-CLEA; hydrogen; papain; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1002/cbic.201200017

upstream raw materials:

Nα-Cbz-glutamate-tryptophan benzyl ester

N-benzyloxycarbonyl-L-glutamic acid

Refernces