Porfiromycine

Base Information

• Chemical Name: Porfiromycine
• CAS No.: 801-52-5
• Molecular Formula: C₁₆H₂₀N₄O₅
• Molecular Weight: 348.359
• NSC Number: 56410
• Nikkaji Number: J544.405E
• Wikidata: Q105032661
• ChEMBL ID: CHEMBL1983333
• Mol file: 801-52-5.mol

Synonyms:Porfiromycine;Porphyromycin;MLS000766209;Mitomycin C, N-methyl-;CHEMBL1983333;NSC56410;ENT-50825;Profiromycin;Neuro_000023;SCHEMBL5047;CHEBI:182803;HRHKSTOGXBBQCB-UHFFFAOYSA-N;HMS2270B05;Azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-1,5-dimethyl-, carbamate (ester);BDBM50235885;AKOS030254763;NCGC00246835-01;NCI60_004377;SMR000528838;u 14743;FT-0673976;WLN: T D3 B556 BN EN JV MVTTT&J E1 GO1 H1OVZ KZ L1;Methylmitomycin;N-Methylmitomycin C;801-52-5;Methyl mitomycin C;(11-amino-7-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl)methyl carbamate;(6-Amino-8a-methoxy-1,5-dimethyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl)methyl carbamate;(6-Amino-8a-methoxy-1,5-dimethyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl)methyl carbamate #;6-Amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-1,5-dimethylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dionecarbamate (ester);Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-1,5-dimethyl-, carbamate;Azirino[2',3':3,4]pyrrolo[1,2-a]-indole-4,7-dione, 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethyl-, (1aS,8S,8aR,8bS)-;Azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethyl-, [1aS-(1a.alpha.,8.beta.,8a.alpha.,8b.alpha.)]-;Azirino[2',4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a- methoxy-1,5-dimethyl-, carbamate (ester);Azirino[2',4]pyrrolo[1,2-a]indole-4,7-dione, 6-amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b- hexahydro-8a-methoxy-1,5-dimethyl-,[1aR-(1a.alpha.,8.beta.,8a.alpha.,8b.alpha.)]-

Chemical Property of Porfiromycine

Chemical Property:

• Vapor Pressure: 1.31E-12mmHg at 25°C
• Melting Point: 201.25°C (rough estimate)
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 560.9°C at 760 mmHg
• Flash Point: 293°C
• PSA: 127.96000
• Density: 1.52g/cm³
• LogP: -0.03260
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 348.14336975
• Heavy Atom Count: 25
• Complexity: 787

Purity/Quality:

99% ^*data from raw suppliers

Porfiromycin ^*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)N
• General Description: Porfiromycin is an N-methylated analogue of mitomycin C, classified as an antitumor antibiotic. It shares a similar aziridine-indolequinone core structure and functions as a DNA alkylating agent, leading to cross-linking and inhibition of cancer cell proliferation. While the provided abstract primarily discusses derivatives of mitomycin C and porfiromycin modified at position 7 with substituted ethylamines, it highlights porfiromycin's role as a reference compound in evaluating these analogues. Some derivatives, such as those with mercaptoethylamine or fluoroethylamine substitutions, demonstrated improved antitumor activity and reduced leukopenia compared to mitomycin C, suggesting potential therapeutic advantages. However, the study does not focus on porfiromycin itself but rather on its structural modifications to enhance efficacy and safety profiles.

Technology Process of Porfiromycine

There total 6 articles about Porfiromycine 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: 61.0%

mitomycin C (50-07-7) + methyl iodide (74-88-4) → porfiromycin (801-52-5)

Guidance literature:

With potassium carbonate; In acetone; for 18h; Inert atmosphere; Reflux;

DOI:10.1039/c2ob25902h

Reference yield:

→ porfiromycin (801-52-5,74707-94-1)

Guidance literature:

Mitomycin-C, Methyljodid, K2CO3, Acn.;

DOI:10.1021/jm00325a001

Reference yield:

→ Porifiromycin (801-52-5,74707-94-1)

Guidance literature:

Mitomycin C (1c, VII/1), Kaliumcarbonat, Methyljodid, Aceton, Sieden;

DOI:10.1021/jm00284a006

upstream raw materials:

N-methylmitomycin A

mitomycin C

dimethyl sulfate

mitomycin A

Downstream raw materials:

N-methylmitomycin A

trans-1-methoxy-2-(methylamino)-7-aminomitosene

cis-1-methoxy-2-(methylamino)-7-aminomitosene

N-methyl-7-aminoaziridinomitosene

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.

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