3'-Aminobenzanilide

Name: 3'-Aminobenzanilide
SKU: ACM16091262
Rating: 5 (1 reviews)

CAS

16091-26-2

Catalog Number

ACM16091262

Category

Main Products

Molecular Weight

212.25

Molecular Formula

C13H12N2O

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Specification

Boiling Point

308.3 °C at 760 mmHg

Melting Point

124-125 °C

Appearance

Light yellow to Yellow Powder or Crystals

3-Aminobenzanilide Can Quench the Photosensitizing Active Substance of Imatinib

Li, Ming-De, et al. Chemistry-A European Journal, 2018, 24(25), 6654-6659.

Imatinib (IMT) is an effective tyrosine kinase inhibitor commonly used to treat Philadelphia chromosome-positive chronic myeloid leukemia and gastrointestinal stromal tumors. However, long-term use of imatinib has been associated with various skin reactions, including heightened photosensitivity, dermatological conditions, psoriasis, pseudoporphyria, and squamous cell carcinoma. The reason for imatinib's photosensitivity and its related skin reactions remains unclear. Given its properties as a photosensitizing agent, understanding its photoreactivity and interactions with biomolecules is crucial.
A recent photophysical and photobiological study of IMT and its major chromophores has shown that neither imatinib nor its anilino-pyrimidine component (2) acts as DNA photosensitizers. In contrast, the pyridyl-pyrimidine substructure (1) exhibits significant phototoxic potential, linked to the formation of a long-lived triplet excited state. Notably, this reactive triplet state can be effectively quenched by 3-aminobenzanilide (5), another part of the imatinib molecule.

Application Examples of 3-Aminobenzanilide in the Synthesis of Amide Compounds

Brooks, Simon J., et al. Chemistry-A European Journal, 2007, 13(12), 3320-3329.

Pyridine-2,6-dicarboxylic acid bis-[(3-phenylcarbamoylphenyl)amide)] (5)
A stirring solution of 3-aminobenzanilide (0.48 g, 2.26 mmol), triethylamine (0.35 mL, 2.49 mmol), and DMAP (0.004 g, catalyst) in dry dichloromethane (50 mL) was prepared in an oven-dried 250 mL three-necked round-bottom flask and allowed to stir for 15 minutes. Afterward, 2,6-pyridinedicarbonyl chloride (0.23 g, 1.13 mmol) was added, and the mixture was stirred at room temperature for 18 hours. The resulting white precipitate was collected by filtration and washed with dichloromethane and water, yielding compound 5 as a white solid (0.32 g, 5.80 mmol, 52%).
N,N'-Bis-(3-phenylcarbamoylphenyl)isophthalamide (6)
A dry 100 mL three-necked flask contained a solution made from 3-aminobenzanilide (1.00 g, 4.7 mmol), triethylamine (0.72 mL, 5.2 mmol), DMAP (0.003 g as catalyst), and dry dichloromethane (30 mL). After stirring the mixture for half an hour portions of isophthaloyl dichloride (0.48 g, 2.3 mmol) were added gradually. The reaction mixture received mechanical stirring for 16 hours after the addition of the reagent. The white precipitate underwent filtration followed by successive washing with dichloromethane and water before drying under high vacuum. The crude product underwent purification through suspension in acidic methanol followed by an 18-hour reflux process. The hot suspension underwent filtration before being washed with methanol twice. The purification process yielded Compound 6 as a white solid (0.65 g, 1.17 mmol, 54%).