15535-98-5

Basic information

• Product Name: 4-HYDROXY-BENZAMIDINE
• Synonyms: 4-hydroxybenziMidaMide;BenzenecarboxiMidaMide,4-hydroxy-;4-hydroxybenzene-1-carboximidamide
• CAS NO: 15535-98-5
• Molecular Formula: C₇H₈N₂O
• Molecular Weight: 136.15
• Mol File: 15535-98-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 4-HYDROXY-BENZAMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-BENZAMIDINE(15535-98-5)
• EPA Substance Registry System: 4-HYDROXY-BENZAMIDINE(15535-98-5)

Safety Data

• Hazardous Substances Data: 15535-98-5(Hazardous Substances Data)

Upstream product

• 767-00-0 4-cyanophenol 
• 49787-00-0 N',4-dihydroxybenzamidine 
• 79416-60-7 4-Hydroxybenzimidsaeureethylester 
• 57943-60-9 4-hydroxybenzimidic acid methyl ester hydrochloride 

Downstream Products

• 64407-57-4 N,N-dicyclohexylurea 
• 84437-20-7 Benzoic acid 4-carbamimidoyl-2-nitro-phenyl ester 
• 95065-32-0 Benzoic acid 2,6-dibromo-4-carbamimidoyl-phenyl ester 
• 84435-43-8 3-Amino-4-hydroxy-benzamidine; compound with methanesulfonic acid 
• 146978-48-5 moxilubant 
• 40761-72-6 p-amidinophenyl benzoate 
• 84436-55-5 4-amidino-2-nitrophenol 
• 112021-85-9 (E)-3-(2-Hydroxy-phenyl)-2-methyl-acrylic acid 4-carbamimidoyl-phenyl ester 
• 2315-75-5 4-hydroxy-3,5-diiodo-benzamidine 
• 84435-79-0 4-amidino-2,6-dibromophenol 

Relevant articles and documents

New quinoline-arylamidine hybrids: Synthesis, DNA/RNA binding and antitumor activity

Four series of new hybrid molecules with 7-chloroquinoline and arylamidine moieties joined through the rigid -O- (groups I (2a-g) and II (5a-g)) or flexible -NH-CH2-CH2-O- (groups III (8a-g) and IV (10a-g)) linker were synthesized, and their DNA/RNA binding properties and cytotoxic activity were tested, against several human cancer lines. The compounds and their interaction with DNA and RNA were studied by UV–Vis and CD spectroscopy. The obtained results showed that the binding affinity of the investigated compounds increases proportionally with the increase of the length and number of groups able to form hydrogen bonds with ds-polynucleotides. Improvement of binding was additionally achieved by reduction of the structural rigidity of the investigated compounds, new hybrid compounds preferentially bind to ctDNA. For most of them the DNA/RNA grooves are dominant binding sites, except for the compounds from group II for which intercalation in polyA-polyU was the dominant binding mode. The antiproliferative effects were tested by the MTT test on normal (MDCK1), carcinoma (HeLa and CaCo2) and leukemia cell lines (Raji and K462). The GI50 values for all investigated compounds ranged from 5 to more than 100 × 10?6 mol dm?3. Carcinoma cells were more resistant to the investigated compounds than leukemia cells. The most effective compounds against leukemia cell lines were from group IV (10a-g), with GI50 values ranging from of 5 and 35 × 10?6 mol dm?3. The cell cycle arrest was investigated by flow cytometry and the obtained results indicate that the selected compounds, 2d, 2e, 8a, 10d, 10e, and 10f, induce changes in the cell cycle of treated cells, but the cycle phase distribution varies between them. A significant decrease in the number of cells in S phase (p 0.001) was observed in all treated cells, but only 10d and 10f induce cell cycle arrest at G0/G1 phase, dominantly.

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.

Atlantic cod trypsin-catalyzed peptide synthesis with inverse substrates as acyl donor components

Atlantic cod trypsin-catalyzed peptide synthesis has been studied by using p-amidino- and p-guanidinophenyl esters of N-(tert-butyloxycarbonyl)amino acid as acyl donor components. The reaction temperature was optimized at 0 °C. The method was shown to be successful as effectively for synthesizing the peptide and useful for preparing dipeptide between D-amino acid with D-amino acid and β-amino acid with β-amino acid, respectively. The enzymatic hydrolysis of the resulting products was negligible.

Antitumor and anti-Pneumocystis carinii activities of novel bisbenzamidines

Among a library of 17 bisbenzamidines connected with various linkers, compounds with a flexible pentanediamide (10) or hexanediamide (12) linker were the most potent derivatives against rat Pneumocystis carinii (IC50 values of 3 and 2 nM, respe