78655-54-6

Basic information

• Product Name: [(1R,2R)-2,7-diamino-1-hydroxy-6-methyl-5,8-dioxo-2,3,5,8-tetrahydro-1H-pyrrolo[1,2-a]indol-9-yl]methyl carbamate
• CAS NO: 78655-54-6
• Molecular Formula: C₁₄H₁₆N₄O₅
• Molecular Weight: 320.3006
• Mol File: 78655-54-6.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 560.8°C at 760 mmHg
• Flash Point: 293°C
• Density: 1.9g/cm³
• Vapor Pressure: 2.06E-13mmHg at 25°C
• Refractive Index: 1.826
• CAS DataBase Reference: [(1R,2R)-2,7-diamino-1-hydroxy-6-methyl-5,8-dioxo-2,3,5,8-tetrahydro-1H-pyrrolo[1,2-a]indol-9-yl]methyl carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: [(1R,2R)-2,7-diamino-1-hydroxy-6-methyl-5,8-dioxo-2,3,5,8-tetrahydro-1H-pyrrolo[1,2-a]indol-9-yl]methyl carbamate(78655-54-6)
• EPA Substance Registry System: [(1R,2R)-2,7-diamino-1-hydroxy-6-methyl-5,8-dioxo-2,3,5,8-tetrahydro-1H-pyrrolo[1,2-a]indol-9-yl]methyl carbamate(78655-54-6)

Safety Data

• Hazardous Substances Data: 78655-54-6(Hazardous Substances Data)

Usage

Description

[(1R,2R)-2,7-diamino-1-hydroxy-6-methyl-5,8-dioxo-2,3,5,8-tetrahydro-1H-pyrrolo[1,2-a]indol-9-yl]methyl carbamate is a complex carbamate derivative featuring a pyrroloindole ring, with a hydroxy group, two amino groups, and a methyl group. Its unique molecular structure suggests potential pharmacological properties, making it a candidate for exploration in medicinal chemistry and drug development.

Uses

Used in Pharmaceutical Industry:
[(1R,2R)-2,7-diamino-1-hydroxy-6-methyl-5,8-dioxo-2,3,5,8-tetrahydro-1H-pyrrolo[1,2-a]indol-9-yl]methyl carbamate is used as a potential pharmaceutical compound for its possible pharmacological properties. [(1R,2R)-2,7-diamino-1-hydroxy-6-methyl-5,8-dioxo-2,3,5,8-tetrahydro-1H-pyrrolo[1,2-a]indol-9-yl]methyl carbamate's unique structure may offer novel therapeutic applications in the treatment of various diseases.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, [(1R,2R)-2,7-diamino-1-hydroxy-6-methyl-5,8-dioxo-2,3,5,8-tetrahydro-1H-pyrrolo[1,2-a]indol-9-yl]methyl carbamate is used as a subject of study to understand its potential interactions with biological targets. This research could lead to the development of new drugs with improved efficacy and safety profiles.
Used in Drug Development:
[(1R,2R)-2,7-diamino-1-hydroxy-6-methyl-5,8-dioxo-2,3,5,8-tetrahydro-1H-pyrrolo[1,2-a]indol-9-yl]methyl carbamate is utilized in drug development as a starting point for the synthesis of new therapeutic agents. Its structural features may be optimized to enhance its pharmacological activity and selectivity towards specific biological targets.

Upstream product

• 114612-47-4 2,7-diamino-1-hydroxymitosene 1-uridilate 
• 170899-74-8 mitomycin C 
• 23405-83-6 2'-deoxyguanylyl-(3'-> 5')-2'-deoxycytidine 
• 50-07-7 mitomycin C 
• 57-14-7 N,N-Dimethylhydrazine 
• 144-55-8 sodium hydrogencarbonate 
• 103422-25-9 7-aminoaziridinomitosene 
• 127-09-3 sodium acetate 
• 148091-11-6 mitomycin C 
• 958-09-8 2'-deoxy-D-adenosine 
• 3471-32-7 4-Methoxyphenylhydrazine 
• 362-76-5 2',3'-isopropylideneguanosine 
• 81990-97-8 Carbamic acid (R)-2,7-diamino-1-[2-amino-9-(4-hydroxy-5-phosphonooxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yloxy]-6-methyl-5,8-dioxo-2,3,5,8-tetrahydro-1H-pyrrolo[1,2-a]indol-9-ylmethyl ester 

Downstream Products

• 1415221-68-9 C₂₂H₂₀N₄O₅ 
• 1415221-69-0 C₂₅H₂₇N₅O₆ 
• 1415221-71-4 trans-N²-phenylacetyl-2,7-diamino-1-azidomitosene 
• 1415221-70-3 cis-N²-phenylacetyl-2,7-diamino-1-azidomitosene 
• 1415221-72-5 trans-N²-phenylacetyl-2,7-diamino-1-aminomitosene 

Relevant articles and documents

Synthesis of Mitomycin C and Decarbamoylmitomycin C N2 deoxyguanosine-adducts

Mitomycin C (MC) and Decarbamoylmitomycin C (DMC) - a derivative of MC lacking the carbamate on C10 - are DNA alkylating agents. Their cytotoxicity is attributed to their ability to generate DNA monoadducts as well as intrastrand and interstrand cross-lin

Synthesis of Mitomycin C and decarbamoylmitomycin C N6 deoxyadenosine-adducts

Mitomycin C (MC), an anti-cancer drug, and its analog, decarbamoylmitomycin C (DMC), are DNA-alkylating agents. MC is currently used in the clinics and its cytotoxicity is mainly due to its ability to form Interstrand Crosslinks (ICLs) which impede DNA replication and, thereby, block cancer cells proliferation. However, both MC and DMC are also able to generate monoadducts with DNA. In particular, we recently discovered that DMC, like MC, can form deoxyadenosine (dA) monoadducts with DNA. The biological role played by these monoadducts is worthy of investigation. To probe the role of these adducts and to detect them in enzymatic digests of DNA extracted from culture cells treated by both drugs, we need access to reference compounds i.e. MC and DMC dA-mononucleoside adducts. Previous biomimetic methods used to generate MC and DMC mononucleoside adducts are cumbersome and very low yielding. Here, we describe the diastereospecific chemical synthesis of both C-1 epimers of MC and DMC deoxyadenosine adducts. The key step of the synthesis involves an aromatic substitution reaction between a 6-fluoropurine 2′-deoxyribonucleoside and appropriately protected stereoisomeric triaminomitosenes to form protected-MC-dA adducts with either an S or R stereochemical configuration at the adenine-mitosene linkage. Fluoride-based deprotection methods generated the final four reference compounds: the two stereoisomeric MC-dA adducts and the two stereoisomeric DMC-dA adducts. The MC and DMC-dA adducts synthesized here will serve as standards for the detection and identification of such adducts formed in the DNA of culture cells treated with both drugs.

Reaction of reductively activated mitomycin C with aqueous bicarbonate: Isolation and characterization of an oxazolidinone derivative of cis-1-hydroxy-2,7-diaminomitosene

The reductive activation of mitomycin C in aqueous bicarbonate buffer resulted in the formation of a previously unknown compound, characterized as an oxazolidinone derivative of cis-1-hydroxy-2,7-diaminomitosene. This compound is the result of a cyclization reaction of bicarbonate with the aziridine ring of aziridinomitosene, and was observed at bicarbonate concentrations close to those present in physiological plasma.