4055-39-4

Basic information

• Product Name: Mitomycin A
• Synonyms: [(1aS,8S,8aR,8bS)-6,8a-Dimethoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2,3,4]pyrrolo[1,2-a]indol-8-yl]methyl Carbamate;[(1aS,8S,8aR,8bS)-6,8a-Dimethoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2,’3’:3,4]pyrrolo[1,2-a]indol-8-yl]methyl Carbamate;(1aS,8S,8aR,8bS)-8-[[(Aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-6,8a-dimethoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione;((1aS,8S,8aR,8bS)-6,8a-dimethoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2,3:3,4]pyrrolo[1,2-a]indol-8-yl)methyl carbamate(WXG00529);Mitomycin EP Impurity B
• CAS NO: 4055-39-4
• Molecular Formula: C₁₆H₁₉N₃O₆
• Molecular Weight: 349.341
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Amines;Chiral Reagents;Heterocycles
• Mol File: 4055-39-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 159-1610C (dec)
• Boiling Point: 483.53°C (rough estimate)
• Flash Point: 309.1 ºC
• Appearance: red-violet crystals
• Density: 1.2205 (rough estimate)
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: -20°C Freezer
• PKA: 13.27±0.50(Predicted)
• CAS DataBase Reference: Mitomycin A(CAS DataBase Reference)
• NIST Chemistry Reference: Mitomycin A(4055-39-4)
• EPA Substance Registry System: Mitomycin A(4055-39-4)

Safety Data

• Hazardous Substances Data: 4055-39-4(Hazardous Substances Data)

Usage

Chemical Properties

Red-Violet Crystals

Uses

The 6-methoxy analog of Mitomycin C. An antitumor antibiotic

Definition

ChEBI: A member of the family of mitomycins that exhibits antibiotic and antitumour properties as well as a high level of toxicity.

Upstream product

• 7041-61-4 7-hydroxy-9a-methoxymitosane 
• 20667-76-9 1-methyl-3-(p-tolyl)triaz-1-ene 
• 132732-87-7 (8aR)-8a-bromoalbomitomycin A 
• 20667-76-9 3-methyl-1-p-tolyltriazene 
• 50-07-7 mitomycin C 
• 132732-87-7 (8aS)-8a-bromoalbomitomycin A 
• 124-41-4 sodium methylate 
• 128583-70-0 7-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-9a-methoxymitosane 
• 67-56-1 methanol 
• 122644-74-0 1a-acetyl-7-demethoxy-6,7-dihydro-7,7-(ethylenedioxy)-6-(phenylselenyl)mitomycin A 
• 186581-53-3 diazomethane 

Downstream Products

• 78327-27-2 C₁₈H₁₉N₅O₅S 
• 84397-45-5 C₁₈H₂₀N₆O₅ 
• 93367-29-4 7-N,7'-N'-bis(2-ethyl)mitomycin C disulfide 
• 134143-14-9 7-N-<4-O-(Sodium 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didedoxy-α-D-glycero-D-galacto-2-nonulopyranosylonate)phenyl>-9a-methoxymitosane 
• 134136-43-9 7-N-<4-O-(Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didedoxy-α-D-glycero-D-galacto-2-nonulopyranosylonate)phenyl>-9a-methoxymitosane 
• 84397-40-0 C₂₂H₂₂N₆O₅ 
• 368450-38-8 1-hydrohy-2-amino-7-methoxymitosene 
• 104641-80-7 1,2-trans-2-amino-1-hydroxy-7-methoxymitosene 
• 104713-11-3 1,2-cis-2-amino-1-hydroxy-7-methoxymitosene 
• 145246-95-3 1a-N-chloromitomycin A 
• 132732-87-7 (8aS)-8a-bromoalbomitomycin A 
• 132732-87-7 (8aR)-8a-bromoalbomitomycin A 
• 5047-66-5 7-methoxy-1,2-aziridinomitosene 
• 155694-37-4 <1aS-(1aα,8δ,8aα,8bα)>-8<<(aminocarbonyl)oxy>methyl>-1,1a,2,8,8a,8b-hexahydro-4-hydroxy-6-(hydroxy)imino-8a-methoxy-5-methylazilidino<2',3':3,4>pyrrolo<1,2-a>indole-7-one 

Relevant articles and documents

Reaction of glycosyl halides with 7-hydroxy-9a-methoxymitosane sodium salt

-

Facile Nucleophilic Cleavage of Selenide with Dimedone. Synthesis of Novel 6-Demethylmitomycins

-

7-(diphenylmethyl)oxy-9a-methoxymitosane

7-(Diphenylmethyl)oxy-9a-methoxymitosane is a novel intermediate for conversion into 7-amino and 7-oxy-9a-methoxymitosanes and is also useful for inhibiting mammalian tumor growth. The compound is prepared by reacting 7-hydroxy-9a-methoxymitosane with diazodiphenylmethane. In a preferred reaction, the compound is prepared from mitomycin C via 7-hydroxy-9a-methoxymitosane without drying (water removal). The intermediate is advantageously converted to the very effective anti-tumor agent 7-[2-(4-nitrophenyldithio)ethylamino]-9a-methoxymitosane in unexpectedly high yields using a two step process where the first step constitutes conversion to 7-[2-(2-pyridyldithio)ethylamino]-9a-methoxymitosane or 7-[2-(3-nitro-2-pyridyldithio)ethylamino]-9a-methoxymitosane.