25412-75-3

Usage

Uses

Used in Pharmaceutical Industry:
4-nitrobenzamidine is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form complex molecular structures that can target specific biological pathways. Its incorporation into drug molecules can enhance their efficacy and selectivity, contributing to the development of novel therapeutic agents.
Used in Dye Industry:
In the dye industry, 4-nitrobenzamidine is utilized as a precursor for the production of dyes with specific color properties. Its chemical structure allows for the creation of dyes with unique hues and stability, which are essential for various applications such as textiles, printing, and plastics.
Used in Organic Chemistry Research:
4-nitrobenzamidine is employed as a reagent in organic chemistry reactions, particularly in the synthesis of heterocyclic compounds. Its reactivity and functional groups enable the formation of diverse chemical structures, facilitating the exploration of new synthetic routes and the discovery of novel compounds with potential applications.
Used in Anti-cancer Research:
4-nitrobenzamidine has been researched for its potential as an anti-cancer agent due to its ability to inhibit the growth of certain cancer cells. Its unique chemical properties allow it to interact with cellular targets, disrupting essential processes within cancer cells and potentially leading to their death. Further research is needed to fully understand its mechanism of action and optimize its therapeutic potential.

InChI:InChI=1/C7H7N3O2/c8-7(9)5-1-3-6(4-2-5)10(11)12/h1-4H,(H3,8,9)

Upstream product

• 57-13-6 urea 
• 619-72-7 4-nitrobenzonitrile 
• 19402-64-3 ammonium benzenesulfonate 
• 115127-49-6 3-bromo-3-(4-nitrophenyl)diazirine 
• 930-69-8 sodium thiophenolate 
• 39184-67-3 3-chloro-3-(p-nitrophenyl)diazirine 
• 7647-01-0 hydrogenchloride 
• 902-47-6 p-nitrobenzoic anhydride 
• 62-23-7 4-nitro-benzoic acid 
• 3858-83-1 p-aminobenzamidine 
• 39739-52-1 methyl imini ester hydrochloride of 4-nitrobenzoic acid 
• 192332-48-2 N'-hydroxy-4-nitrobenzimidamide 
• 555-16-8 4-nitrobenzaldehdye 
• 52708-02-8 4-nitrobenzimidic acid methyl ester 

Downstream Products

• 51769-82-5 N-acetyl-4-nitrobenzamide 
• 92577-32-7 5,6-dimethyl-2-(4-nitro-phenyl)-3H-pyrimidin-4-one 
• 91397-16-9 4,6-dimethyl-2-(4-nitrophenyl)pyrimidine 
• 3858-83-1 p-aminobenzamidine 
• 55978-27-3 N-(4-Nitrostyrylsulfonyl)-4-nitro-benzamidin 
• 108444-62-8 2-(4-Nitro-phenyl)-5-vinyl-pyrimidine 
• 118543-30-9 4-[1-(4-Methoxy-phenyl)-6-(4-methoxy-phenylamino)-4-(4-nitro-phenyl)-1H-[1,3,5]triazin-(2Z)-ylideneamino]-6-methyl-3-methylsulfanyl-4H-[1,2,4]triazin-5-one 
• 18826-96-5 4-amino-6-methyl-3-methylthio-1,2,4-triazin-5-one 
• 118543-29-6 4-[1-(3-Chloro-phenyl)-6-(3-chloro-phenylamino)-4-(4-nitro-phenyl)-1H-[1,3,5]triazin-(2Z)-ylideneamino]-6-methyl-3-methylsulfanyl-4H-[1,2,4]triazin-5-one 
• 118543-31-0 4-[1-(3-Methoxy-phenyl)-6-(3-methoxy-phenylamino)-4-(4-nitro-phenyl)-1H-[1,3,5]triazin-(2Z)-ylideneamino]-6-methyl-3-methylsulfanyl-4H-[1,2,4]triazin-5-one 
• 118543-27-4 6-Methyl-3-methylsulfanyl-4-[4-(4-nitro-phenyl)-1-phenyl-6-phenylamino-1H-[1,3,5]triazin-(2Z)-ylideneamino]-4H-[1,2,4]triazin-5-one 
• 118543-28-5 4-[1-(4-Chloro-phenyl)-6-(4-chloro-phenylamino)-4-(4-nitro-phenyl)-1H-[1,3,5]triazin-(2Z)-ylideneamino]-6-methyl-3-methylsulfanyl-4H-[1,2,4]triazin-5-one 
• 95674-92-3 N,N'-bis(phenylthio)-4-nitrobenzenecarboximidoamide 
• 118377-77-8 1-Chloro-3,5-bis-(4-nitro-phenyl)-1λ⁴-[1,2,4,6]thiatriazine 

Relevant academic research and scientific papers

Preparation method for p-aminobenzamidine hydrochloride

The invention discloses a preparation method for p-aminobenzamidine hydrochloride, and belongs to the field of drug synthesis. The preparation method comprises the following steps: taking p-aminobenzamidine as a starting raw material, and enabling the p-aminobenzamidine and hydroxylamine hydrochloride to generate nitrobenzonitrile; then, enabling the nitrobenzonitrile to react with ammonium salt to generate p-aminobenzamidine; carrying out acylation and reduction on the p-aminobenzamidine to obtain p-aminobenzamidine imidogen n-hexyl formate; finally, performing salifying on the p-aminobenzamidine imidogen n-hexyl formate and hydrogen chloride to obtain the p-aminobenzamidine hydrochloride. Compared with the prior art, the preparation method for the p-aminobenzamidine hydrochloride disclosed by the invention has the characteristics of being simple to operate, easy to control in reaction, low in production cost and the like, and has a very good popularization and application value.

A to prepare to aminobenzoic amidine hydrochloride method

The invention relates to the technical field of pharmaceutical chemistry and provides a method for preparing p-amino-benzamidine hydrochloride. The method comprises the following steps: (1) p-nitrobenzonitfile II undergoes an amidining reaction in an amidining reagent I to obtain an intermediate p-nitrobenzene methylenimine III; (2) the intermediate p-nitrobenzene methylenimine III undergoes an amidining reaction in an amidining reagent II to obtain p-nitrobenzamidine IV; and (3) under an acidic condition, p-nitrobenzamidine IV undergoes a reduction reaction in a reaction solvent II by the use of a reducing agent to obtain p-amino-benzamidine hydrochloride. In the step (1), the amidining reagent I is thionyl chloride, phosphorus trichloride or phosphorus pentachloride; in the step (2), the amidining reagent II is ammonium carbonate, ammonium bicarbonate or ammonium chloride; and in the step (3), the reaction solvent II is a mixed solvent of water and alcohols. The synthetic method provided by the invention is safe and simple and has advantages of high yield and good product quality. The preparation method of p-amino-benzamidine hydrochloride is suitable for industrial production.

Electrochemical and mARC-catalyzed enzymatic reduction of para-substituted benzamidoximes: Consequences for the prodrug concept "amidoximes instead of amidines"

The mitochondrial amidoxime reducing component (mARC) activates amidoxime prodrugs by reduction to the corresponding amidine drugs. This study analyzes relationships between the chemical structure of the prodrug and its metabolic activation and compares its enzyme-mediated vs. electrochemical reduction. The enzyme kinetic parameters KM and Vmax for the N-reduction of ten para-substituted derivatives of the model compound benzamidoxime were determined by incubation with recombinant proteins and subcellular fractions from pig liver followed by quantification of the metabolites by HPLC. A clear influence of the substituents at position 4 on the chemical properties of the amidoxime function was confirmed by correlation analyses of 1H NMR chemical shifts and the redox potentials of the 4-substituted benzamidoximes with Hammett's σ. However, no clear relationship between the kinetic parameters for the enzymatic reduction and Hammett's σ or the lipophilicity could be found. It is thus concluded that these properties as well as the redox potential of the amidoxime can be largely ignored during the development of new amidoxime prodrugs, at least regarding prodrug activation.

One-pot synthesis of 2,5-disubstituted pyrimidines from nitriles

A practical, one-step process for the synthesis of 2,5-disubstituted pyrimidines is presented. The protocol proved to be general for the synthesis of a variety of pyrimidine-containing compounds bearing an assortment of functional groups.

Structural and biochemical basis for the firm chemo- and regioselectivity of the nitro-forming N-oxygenase AurF

Site-directed mutagenesis based on the crystal structure of AurF, a nitro group forming monooxygenase from Streptomyces thioluteus, revealed that AurF variants are capable of selectively transforming guanidyl- and amidinyl-substituted anilines into the corresponding nitro compounds. Our results provide new insights into the biochemical basis of regioselective N-oxygenation. The Royal Society of Chemistry.

Reaction of arylhalodiazirines with thiophenoxide: A redox process

Phenylbromodiazirine reacts with thiophenoxide ion in methanol to give benzonitrile, benzamidine, ammonia, and diphenyl disulfide. The reaction is general for arylhalodiazirines, with electron-withdrawing groups on the aromatic ring exerting a small rate-enhancing effect. Three potential mechanisms are suggested for this redox process. These mechanisms include an N-sulfenylated diazirine, a diazirinyl radical, and a diazirinyl anion. Ring opening of these intermediates and subsequent transformations would lead to benzonitriles, benzamidine, and ammonia. A key intermediate in these transformations is PhSNH2, 32. This intermediate has been independently generated and found to rapidly convert to ammonia and diphenyl disulfide under the reaction conditions. Another proposed intermediate, N-(phenylthio)benzamidine, 38, has also been independently generated and subjected to the reaction conditions, where benzamidine and more diphenyl disulfide result. Theoretical calculations suggest the existence of isomeric diazirinyl anions. In addition to a diazirinyl ion with charge essentially on carbon, there is also an allylic-type ion with charge on the two nitrogen atoms. Single-electron reduction of a diazirinyl radical necessarily leads to a nitrogen-centered diazirinyl anion. Conversion of this anion to the carbon-centered diazirinyl anion is a forbidden process. These theoretical studies suggest that the diazirinyl anion may be a viable intermediate in solution.