Stallimycin

Base Information

• Chemical Name: Stallimycin
• CAS No.: 636-47-5
• Molecular Formula: C22H27 N9 O4
• Molecular Weight: 481.514
• NSC Number: 82150
• UNII: 80O63P88IS
• DSSTox Substance ID: DTXSID9045637
• Nikkaji Number: J9.449H
• Wikipedia: Distamycin
• Wikidata: Q27269162
• NCI Thesaurus Code: C1517
• Pharos Ligand ID: 6STYFP4JSHCR
• Metabolomics Workbench ID: 122306
• ChEMBL ID: CHEMBL11252
• Mol file: 636-47-5.mol

Synonyms:distamycin;distamycin A;stallimycin;stallimycin hydrochloride;stallimycin monohydrochloride

Chemical Property of Stallimycin

Chemical Property:

• Melting Point: 154-156°
• Refractive Index: 1.6910 (estimate)
• Boiling Point: 579.2°C (rough estimate)
• PSA: 181.06000
• Density: 1.45g/cm³
• LogP: 2.87670
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 481.21860038
• Heavy Atom Count: 35
• Complexity: 825

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C=C1C(=O)NC2=CN(C(=C2)C(=O)NC3=CN(C(=C3)C(=O)NCCC(=N)N)C)C)NC=O
• Therapeutic Function: Antibiotic

Technology Process of Stallimycin

There total 1 articles about Stallimycin 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:

4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid (77716-11-1) → distamycin A (636-47-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 4.3 mg / EDCI; DMAP / dimethylformamide / 16 h / 25 °C

2: 98 percent / aq. LiOH / tetrahydrofuran; methanol / 8 h / 60 °C

3: EDCI; DMAP / dimethylformamide / 14 h / 25 °C

4: HCl / ethanol / 2.5 h / 0 - 25 °C

5: NH₃ / ethanol / 1 h / 25 °C

6: methanol; tetrahydrofuran / 1 h / -40 °C

With hydrogenchloride; dmap; lithium hydroxide; ammonia; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/ja994192d

Reference yield:

distamycin A (636-47-5) → N,N'-Bis-(5-{5-[5-(2-carbamimidoyl-ethylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-1-methyl-1H-pyrrol-3-ylcarbamoyl}-1-methyl-1H-pyrrol-3-yl)-isophthalamide; hydrochloride

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / conc. HCl / methanol / 760 Torr

2: 68 percent / tetrahydrofuran

With hydrogenchloride; In tetrahydrofuran; methanol;

DOI:10.1021/jm00093a023

Reference yield:

distamycin A (636-47-5) → N,N'-Bis-(5-{5-[5-(2-carbamimidoyl-ethylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-1-methyl-1H-pyrrol-3-ylcarbamoyl}-1-methyl-1H-pyrrol-3-yl)-terephthalamide; hydrochloride

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / conc. HCl / methanol / 760 Torr

2: 77 percent / tetrahydrofuran

With hydrogenchloride; In tetrahydrofuran; methanol;

DOI:10.1021/jm00093a023

upstream raw materials:

4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid

Downstream raw materials:

C₂₃H₂₉N₉O₄

Refernces