4656-86-4

Basic information

• Product Name: 1,5-dihydro-4H-imidazo[4,5-d]-1,2,3-triazin-4-one
• Synonyms: 1,5-dihydro-4H-imidazo[4,5-d]-1,2,3-triazin-4-one;4,5-Dihydro-1H-imidazo[4,5-d]-1,2,3-triazin-4-one;7H-Imidazo[4,5-d]-1,2,3-triazine-4(3H)-one;3,7-Dihydro-4H-iMidazo[4,5-d]-1,2,3-triazin-4-one;3,7-Dihydro-4H-IMidazo[4,5-d]-v-triazin-4-one;NSC 22419;Dacarbazine IMpurity A (3,7-Dihidro-4H-IMidazo[4,5-d][1,2,3]triazin-4-One);Dacarbazine Related Compound B (50 mg) (2-azahypoxanthine monohydrate)
• CAS NO: 4656-86-4
• Molecular Formula: C₄H₃N₅O
• Molecular Weight: 137.09952
• EINECS: 225-096-3
• Mol File: 4656-86-4.mol

Chemical Properties

• Boiling Point: 512.9°C at 760 mmHg
• Flash Point: 264°C
• Appearance: /
• Density: 2.263g/cm³
• Vapor Pressure: 1.25E-10mmHg at 25°C
• Refractive Index: 2.088
• PKA: 8.66±0.20(Predicted)
• CAS DataBase Reference: 1,5-dihydro-4H-imidazo[4,5-d]-1,2,3-triazin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-dihydro-4H-imidazo[4,5-d]-1,2,3-triazin-4-one(4656-86-4)
• EPA Substance Registry System: 1,5-dihydro-4H-imidazo[4,5-d]-1,2,3-triazin-4-one(4656-86-4)

Safety Data

• Hazardous Substances Data: 4656-86-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,5-dihydro-4H-imidazo[4,5-d]-1,2,3-triazin-4-one is used as a degradation product of Dacarbazine for understanding the adverse effects associated with Dacarbazine treatment. This knowledge can help in the development of safer and more effective cancer therapies.

InChI:InChI=1/C4H3N5O/c10-4-2-3(6-1-5-2)7-9-8-4/h1H,(H2,5,6,7,8,10)

Upstream product

• 91026-74-3 5-Acetamidoimidazole-4-carboxamide 
• 360-97-4 5-Aminoimidazole-4-carboxamide 
• 7008-85-7 5-diazoimidazole-4-carboxamide 
• 188612-55-7 5-amino-N 1-ethyl-1H-imidazole-1,4-dicarboxamide 
• 4342-03-4 5-(3,3-dimethyl-1-triazeno)imidazone-4-carboxamide 
• 88795-61-3 4-ethoxyimidazo<4,5-d>-1,2,3-triazine 
• 88795-60-2 4-methoxyimidazo<4,5-d>-1,2,3-triazine 
• 64-17-5 ethanol 
• 49850-59-1 6-(Methylthio)-2-azapurine 
• 67-56-1 methanol 
• 188612-53-5 5-amino-N₁-methyl-1H-imidazole-1,4-dicarboxamide 
• 72-40-2 5-amino-1H-imidazole-4-carboxamide monohydrochloride 
• 97378-14-8 5-(2-hydroxy-naphthalen-1-ylazo)-1⁽³⁾H-imidazole-4-carboxylic acid amide 
• 308321-34-8 5-(2-hydroxy-5-methyl-phenylazo)-1H-imidazole-4-carboxylic acid amide 

Downstream Products

• 36519-17-2 7-(2,3,5,-tri-O-acetyl-β-D-ribofuranosyl)imidazo[4,5-d][1,2,3]triazin-4-one 
• 1643356-24-4 C₁₅H₁₇N₅O₈ 

Relevant articles and documents

Validated spectral manipulations for determination of an anti-neoplastic drug and its related impurities including its hazardous degradation product

Innovative and specific double dual wavelength, dual ratio subtraction spectrophotometric methods were carried out along with a successive ratio subtraction spectrophotometric method for determination of dacarbazine and its related impurities including toxic and hazardous ones. For determination of dacarbazine by the double dual wavelength method, the absorbance differences between 323 and 350 nm of the zero order absorption spectra of dacarbazine were used. The values of absorbance difference between 267.2 and 286.2 nm of the zero order spectra of 5-amino-imidazole-4 carboxamide were used for its determination by the dual ratio subtraction method. The zero order absorption spectrum of 2-azahypoxanthine at 235 nm was used for its determination after applying the successive ratio subtraction method. ICH guidelines were followed for validation of the developed methods, where linear relationships were obtained in the range of 4-20, 1-16, and 2-20 μg mL?1for dacarbazine, 5-amino imidazole-4-carboxamide and 2-azahypoxanthine, respectively. Accurate, precise, and specific results were obtained upon applying the proposed methods according to ICH guidelines. Furthermore, the developed methods were successfully applied for determination of dacarbazine in its pharmaceutical formulation. Comparing the results of the developed methods with those of the official USP spectrophotometric method statistically showed no significant difference. The developed methods don't need any sophisticated techniques so they are considered cost effective methods. Moreover, the introduced methods have the advantages of being green where water was used as a solvent. The methods proved to be more economic, fast and simple than other reported HPLC methods.

Triazines and Related Products. Part 23. New Photo-products from 5-Diazoimidazole-4-carboxamide (Diazo-IC)

Photolysis of Diazo-IC in dilute aqueous solution affords products which differ according to the pH of the medium.At pH 1, or pH 7.4 - 12 the product is 2-azahypoxanthine (2): in the intervening pH range the product is 4-carbamoylimidazolium-5-olate (3).In the dark only 2-azahypoxanthine is formed.Photolysis of Diazo-IC in concentrated solution containing citric acid (1 mol equiv.) at pH 2.5 affords a marroon imidazolylazoimidazolium olate (8) and 2-azahypoxanthine.

PASE synthesis of 1-azolyl-1H-1,2,4-triazoles by the reaction of diazoazoles with ethyl isocyanoacetate

PASE (pot, atom and step economic) synthesis of 1-azolyl-1H-1,2,4-triazole derivatives in up to 91% yield has been accomplished by addition of 5-diazoazoles to ethyl isocyanoacetate.

Acid-base characteristics of 5-diazoimidazole derivatives

The transformation of 5-diazoimidazoles containing a carboxamide, ethoxycarbonyl, or nitro group at position 4 into diazonium salts was studied by UV and IR spectroscopy. It was shown by means of model compounds and chemical transformations that nitrosamines are involved in the transformation. 1998 Plenum Publishing Corporation.

Biosynthesis of the Fairy Chemicals, 2-Azahypoxanthine and Imidazole-4-carboxamide, in the Fairy Ring-Forming Fungus Lepista sordida

Fairy rings resulting from a fungus-plant interaction appear worldwide. 2-Azahypoxanthine (AHX) and imidazole-4-carboxamide (ICA) were first isolated from the culture broth of one of the fairy ring-forming fungi, Lepista sordida. Afterward, a common metabolite of AHX in plants, 2-aza-8-oxohypoxanthine (AOH), was found in AHX-treated rice. The biosynthetic pathway of the three compounds that are named as fairy chemicals (FCs) in plants has been partially elucidated; however, that in mushrooms remains unknown. In this study, it was revealed that the carbon skeletons of AHX and ICA were constructed from Gly in L. sordida mycelia and the fungus metabolized 5-aminoimidazole-4-carboxamide (AICA) to both of the compounds. These results indicated that FCs were biosynthesized by a diversion of the purine metabolic pathway in L. sordida mycelia, similar to that in plants. Furthermore, we showed that recombinant adenine phosphoribosyltransferase (APRT) catalyzed reversible interconversion not only between 5-aminoimidazole-4-carboxamide-1-β-d-ribofuranosyl 5′-monophosphate (AICAR) and AICA but also between ICA-ribotide (ICAR) and ICA. Furthermore, the presence of ICAR in L. sordida mycelia was proven for the first time by LC-MS/MS detection, and this study provided the first report that there was a novel metabolic pathway of ICA in which its ribotide was an intermediate in the fungus.

Practical synthesis of natural plant-growth regulator 2-azahypoxanthine, its derivatives, and biotin-labeled probes

We describe a practical, large-scale synthesis of the "fairy- ring" plant-growth regulator 2-azahypoxanthine (AHX), and its biologically active hydroxyl metabolite (AOH) and riboside derivative (AHXr). AHXr, a biosynthetic intermediate, was synthesized from inosine via a biomimetic route. Biotinylated derivatives of AHX and AHXr were also synthesized as probes for mechanistic studies. This journal is the Partner Organisations 2014.

Reactions of 5-diazoimidazoles with steroid hydrazones

The reaction of 5-diazoimidazoles with steroid hydrazones was studied. The structure of the steroid derivative was found to have a significant effect on the direction of the nitrogen transfer in the unstable intermediate tetrazene. The presence of a labile proton in the reaction mixture permits stabilization of one of the tetrazene forms such that only direction was found for the nitrogen transfer in all the reactions studied, leading to imidazole azides and iminosteroid derivatives.

Structural studies on bioactive compounds. Part 38.1 Reactions of 5-aminoimidazole-4-carboxamide: Synthesis of imidazo[1,5-a]quinazoline-3-carboxamides

5-Aminoimidazole-4-carboxamide reacts with aromatic aldehydes to afford Schiff bases which can be cyclised to imidazo[1,5-a]quinazoline-3-carboxamides in DMF/sodium hydride. The potassium salt of imidazo[1,5-a]quinazoline-3-carboxylic acid undergoes deuterium exchange in D2O at the 1-position.

A 15N NMR investigation of a series of benzotriazinones and related antitumour heterocycles

A series of 3-substituted 1,2,3-benzotriazin-4-ones, 1 and 2, were synthesized by standard methods and the 15N NMR spectra were recorded. All spectra were obtained using the natural abundance of the nitrogen-15 isotope. The chemical shifts appear in the normal range for N-1, N-2 and N-3 of the triazine ring, and also correlate with the chemical shifts in the spectra of the imidazolotriazinone, 4, and the imidazolotetrazinone, 5. Significantly, the spectra of 1a, 2 and 4, recorded with full NOE, show inversion of the singlet assigned to N-3, demonstrating that these compounds exist in the tautomeric form shown. The structure of the 4-iminobenzotriazinone (3) was confirmed by this 15N NMR analysis. The spectrum shows a signal for the NH-bearing imino-nitrogen atom, which is an inverted singlet in the NOE spectrum, whereas the signal from the N-3 atom of 3 is not inverted in the NOE spectrum. Copyright

Synthesis of new heteroaromatic systems: Naphth[2,1-e] imidazo[5,1-c]-1,2,4-triazines and benz[e]imidazo-[5,1-c]-1,2,4-triazines

Cyclization of azo compounds, synthesized 5-diazoimidazoles and 2-naphthol or p-substituted phenols, into naphth[2,1-e]imidazo[5,1-c]-1,2,4-triazines and benz[e]imidazo[5,1-c]-1,2,4-triazines occurs only in the presence of p-toluenesulfonic acid. Imidazo[4,5-d]-1,2,3-triazines are also formed in this reaction when an amide substituent is present in the imidazole ring.