5649-76-3

Basic information

• Product Name: 2H-Naphth[2,3-d]imidazol-2-one,1,3-dihydro-(8CI,9CI)
• Synonyms: 2H-Naphth[2,3-d]imidazol-2-one,1,3-dihydro-(8CI,9CI);1H-Naphtho[2,3-d]imidazol-2(3H)-one
• CAS NO: 5649-76-3
• Molecular Formula: C₁₁H₈N₂O
• Molecular Weight: 184.19402
• Product Categories: BENZIMIDAZOLE
• Mol File: 5649-76-3.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2H-Naphth[2,3-d]imidazol-2-one,1,3-dihydro-(8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Naphth[2,3-d]imidazol-2-one,1,3-dihydro-(8CI,9CI)(5649-76-3)
• EPA Substance Registry System: 2H-Naphth[2,3-d]imidazol-2-one,1,3-dihydro-(8CI,9CI)(5649-76-3)

Safety Data

• Hazardous Substances Data: 5649-76-3(Hazardous Substances Data)

Upstream product

• 16673-87-3 3-acetylamino-[2]naphthoic acid amide 
• 856211-46-6 3-acetylamino-[2]naphthoyl azide 
• 62-53-3 aniline 
• 771-97-1 2,3-Diaminonaphthalene 
• 57-13-6 urea 
• 530-62-1 1,1'-carbonyldiimidazole 
• 201230-82-2 carbon monoxide 

Relevant articles and documents

Sequence-Specific Quantitation of Mutagenic DNA Damage via Polymerase Amplification with an Artificial Nucleotide

DNA mutations can result from replication errors due to different forms of DNA damage, including low-abundance DNA adducts induced by reactions with electrophiles. The lack of strategies to measure DNA adducts within genomic loci, however, limits our unde

In-Gene Quantification of O6-Methylguanine with Elongated Nucleoside Analogues on Gold Nanoprobes

Exposure of DNA to chemicals can result in the formation of DNA adducts, a molecular initiating event in genotoxin-induced carcinogenesis. O6-Methylguanine (O6-MeG) is a highly mutagenic DNA adduct that forms in human genomic DNA upon reaction with methylating agents of dietary, environmental, or endogenous origin. In this work, we report the design and synthesis of novel non-natural nucleoside analogues 1′-β-[1-naphtho[2,3-d]imidazol-2(3H)-one)]-2′-deoxy-d-ribofuranose and 1′-β-[1-naphtho[2,3-d]imidazole]-2′-deoxy-d-ribofuranose and their use for quantifying O6-MeG within mutational hotspots of the human KRAS gene. The novel nucleoside analogues were incorporated into oligonucleotides conjugated to gold nanoparticles to comprise a DNA hybridization probe system for detecting O6-MeG in a sequence-specific manner on the basis of colorimetric readout of the nanoparticles. The concept described herein is unique in utilizing new nucleoside analogues with elongated hydrophobic surfaces to successfully measure in-gene abundance of O6-MeG in mixtures with competing unmodified DNA.

BASE-MODIFIED-NUCLEOSIDE ANALOGS FOR THE DETECTION OF O6-ALKYL GUANINE

The present disclosure provides novel compounds containing a base- modified nucleoside of formula and methods for detecting the presence of guanine in a nucleic acid and for isolating O6-alkyl guanine comprising nucleic acid. The disclosure is based on base-modified-nucleoside analogs that form stable base pairs with O6-alkyl guanine.

A NEW SYNTHESIS OF HETEROCYCLES VIA CARBONILATION OF AMINES WITH CARBON MONOXIDE IN THE PRESENCE OF SELENIUM

Amines which contain a second functional group in the appropriate position react with carbon monoxide in the presence of selenium to form heterocyclic derivatives in which carbon monoxide is incorporated.For instance, diamines, aminoalcohols, and their related compounds undergo carbonylation to give cyclic ureas, urethanes and the corresponding carbonylated compounds.For diamines and amino alcohols with more than two carbon atoms between the functional groups, intermolecular carbonylative coupling takes place competing with the intramolecular reaction.High selectivity has been attained under specified reaction conditions.Anilines having cyano or acetyl groups on the ortho position afford new classes of selenium-containing heterocycles.In these reactions, carbamoselenoate has been suggested as the common key intermediate.

A New Synthesis of Cyclic Ureas, Cyclic Urethanes, and a Quinazolinedione. Selenium-Assisted Carbonylation of Aromatic Amines with Carbon Monoxide

Five-, six-, and seven-membered cyclic ureas were synthesized in excellent yields from various aromatic diamines by reaction with carbon monoxide and a stoichiometric or excess amount of selenium in the presence of an oxidizing agent such as oxygen or dimethyl sulfoxide producing selectively the five- and six-membered cyclic ureas.In the case of 2-(2-aminoethyl)aniline under the catalytic conditions, intra- and intermolecular carbonylation competed resulting in the formation of a mixture of the seven-membered cyclic urea, 1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-one and the acyclic urea, 1,3-bisurea.The distribution ratio of these two products varied depending on the reaction conditions, but selective formation of the cyclic urea was attained only when a stoichiometric or excess amount of selenium was used.In addition to the above diamino compounds, 2-carbamoylaniline, 2-amino-3-pyridinol, and 2-(hydroxymethyl)-aniline also underwent similar carbonylation to give 2,4(1H,3H)-quinazolinedione, oxazolopyridin-2-(3H)-one, and 1,4-dihydro-2H-3,1-benzoxazin-2-one, respectively.

A NEW SYNTHESIS OF CYCLIC UREAS FROM AROMATIC DIAMINES BY SELENIUM-ASSISTED CARBONYLATION WITH CARBON MONOXIDE

Aromatic cyclic ureas have been synthesized in good yields from o-amino or o-aminoalkyl substituted aromatic amines by the reaction with carbon monoxide using selenium.