Mitomycin F

Base Information

• Chemical Name: Mitomycin F
• CAS No.: 18209-14-8
• Molecular Formula: C17H21 N3 O6
• Molecular Weight: 363.37
• UNII: GOQ83S599K
• DSSTox Substance ID: DTXSID40939522
• Nikkaji Number: J361.080B
• Wikidata: Q27279211
• ChEMBL ID: CHEMBL102817
• Mol file: 18209-14-8.mol

Synonyms:mitomycin F;N-methylmitomycin A

Chemical Property of Mitomycin F

Chemical Property:

• Vapor Pressure: 6.46E-13mmHg at 25°C
• Boiling Point: 568°Cat760mmHg
• Flash Point: 297.3°C
• PSA: 112.16000
• Density: 1.46g/cm³
• LogP: -0.23170
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 363.14303540
• Heavy Atom Count: 26
• Complexity: 802

Purity/Quality:

≥95% ^*data from raw suppliers

N-MethylMitomycinA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)C2=C(C1=O)N3CC4C(C3(C2COC(=O)N)OC)N4C)OC
• Isomeric SMILES: CC1=C(C(=O)C2=C(C1=O)N3C[C@H]4[C@@H]([C@@]3([C@@H]2COC(=O)N)OC)N4C)OC
• Uses: 6-O-Methyl Mycophenolic Acid Methyl Ester-d9 is used as an intermediate in the formation of mitomycin B (M371895), an antitumor antibiotic that is also used as an antineoplastic.

Technology Process of Mitomycin F

There total 13 articles about Mitomycin F 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: 30.0%

leucomitomycin (102831-59-4) → N-methylmitomycin A (18209-14-8) + 9-epimitomycin B (13164-90-4) + 7-methoxy-1,2-(N-methylaziridino)mitosene (15973-07-6)

Guidance literature:

With oxygen; silica gel; triethylamine; In chloroform;

DOI:10.1021/jo00228a063

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + C16H19N3O6 (10104-18-4) → N-methylmitomycin A (18209-14-8)

Guidance literature:

In diethyl ether;

Reference yield:

C14H17N3O4 (78879-23-9,78962-35-3) → N-methylmitomycin A (18209-14-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 67.9 percent / pyridine / 4 h / 0 °C

2: 94.2 percent / ammonia / CHCl₃ / 1.5 h

3: 1.) 0.1 N aq. NaOH / 1.) RT, 6 h, 2.) ethyl ether, 0 deg C, 10 min

4: 1.) NaH / 1.) DMF, benzene, -10 deg C, 2.) 15 min

With pyridine; sodium hydroxide; ammonia; sodium hydride; In chloroform;

DOI:10.1021/jo00286a021

upstream raw materials:

leucomitomycin

9-epimitomycin B

dimethyl sulfate

mitomycin A

Downstream raw materials:

C₂₂H₂₄N₄O₆

porfiromycin

7-methoxy-1,2-(N-methylaziridino)mitosene

C₂₂H₃₀N₄O₆

Refernces

Mitomycin C and porfiromycin analogues with substituted ethylamines at position 7

10.1021/jm00355a004

The research focuses on the development and evaluation of analogues of mitomycin C and porfiromycin with substituted ethylamines at position 7. These analogues were synthesized and tested for their antitumor activities against various mouse tumors, including P-388 leukemia, L-1210 leukemia, and B-16 melanoma. The study aimed to identify compounds that are at least as potent as mitomycin C but with reduced leukopenic effects. Key chemicals involved in the research include mitomycin C, porfiromycin, and a variety of ethylamine derivatives such as 2-phenylethylamine, 2-chloroethylamine, 2-hydroxyethylamine, and others with different functional groups at the 2-position of the ethylamine. The analogues were prepared using mitomycin A or N-methyl-mitomycin A as starting materials and various amines for substitution. The synthesized compounds were then purified, characterized, and tested for their biological activities. The results showed that some analogues exhibited better antitumor activity and reduced leukopenia compared to mitomycin C, with notable examples being the mercaptoethylamine analogue (8) and the fluoroethylamine analogue (4). The study also explored structure-activity relationships, finding a limited correlation between the potency of the analogues and their hydrophilicity.