93033-58-0

Basic information

• Product Name: 3-(BENZYLOXY)BENZALDEHYDE OXIME
• Synonyms: 3-(BENZYLOXY)BENZALDEHYDE OXIME
• CAS NO: 93033-58-0
• Molecular Formula: C₁₄H₁₃NO₂
• Molecular Weight: 227.26
• Mol File: 93033-58-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(BENZYLOXY)BENZALDEHYDE OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(BENZYLOXY)BENZALDEHYDE OXIME(93033-58-0)
• EPA Substance Registry System: 3-(BENZYLOXY)BENZALDEHYDE OXIME(93033-58-0)

Safety Data

• Hazardous Substances Data: 93033-58-0(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 100-83-4 meta-hydroxybenzaldehyde 
• 1700-37-4 3-Benzyloxybenzaldehyde 

Downstream Products

• 1062547-93-6 3-(benzyloxy)-N-hydroxybenzene carboximidoyl chloride 
• 188295-22-9 3-[N-(3-benzyloxyphenyl)methyl]amino-5-ethoxypyrrolidin-2-one 
• 188295-15-0 3-N-[(3-benzyloxyphenyl)methyl]aminopyrrolidine-2,5-dione 
• 61147-43-1 4-cyano-2-benzyloxypyridine 
• 1700-37-4 3-Benzyloxybenzaldehyde 
• 104566-43-0 [3-(benzyloxy)phenyl]methanamine 

Relevant articles and documents

Dibenzazepine-linked isoxazoles: New and potent class of α-glucosidase inhibitors

α-Glucosidase inhibition is a valid approach for controlling hyperglycemia in diabetes. In the current study, new molecules as a hybrid of isoxazole and dibenzazepine scaffolds were designed, based on their literature as antidiabetic agents. For this, a series of dibenzazepine-linked isoxazoles (33–54) was prepared using Nitrile oxide-Alkyne cycloaddition (NOAC) reaction, and evaluated for their α-glucosidase inhibitory activities to explore new hits for treatment of diabetes. Most of the compounds showed potent inhibitory potency against α-glucosidase (EC 3.2.1.20) enzyme (IC50 = 35.62 ± 1.48 to 333.30 ± 1.67 μM) using acarbose as a reference drug (IC50 = 875.75 ± 2.08 μM). Structure-activity relationship, kinetics and molecular docking studies of active isoxazoles were also determined to study enzyme-inhibitor interactions. Compounds 33, 40, 41, 46, 48–50, and 54 showed binding interactions with critical amino acid residues of α-glucosidase enzyme, such as Lys156, Ser157, Asp242, and Gln353.

Synthesis and anticancer activity of benzyloxybenzaldehyde derivatives against HL-60 cells

A series of benzyloxybenzaldehyde derivatives were prepared and tested against the HL-60 cell line for anticancer activity. Preliminary structure-activity relationships were established. It was discovered that 2-(benzyloxy)benzaldehyde (17), 2-(benzyloxy)-4-methoxybenzaldehyde (26), 2-(benzyloxy)-5-methoxybenzaldehyde (27), 2-(benzyloxy)-5-chlorobenzaldehyde (28), 2-[(3-methoxybenzyl)oxy]benzaldehyde (29), 2-[(2-chlorobenzyl)oxy] benzaldehyde (30), and 2-[(4-chlorobenzyl)oxy]benzaldehyde (31) exhibited significant activity at 1-10 μM. Among them, compound 29 was the most potent one. The morphological assessment and DNA fragmentation analysis indicated that these compounds arrested cell cycle progression at G2/M phase and induced cell apoptosis. They resulted in the loss of mitochondrial membrane potential after 12 h of treatment.

Regioselective reductions of various 3-aminosuccinimides; application to the synthesis of two heterocyclic systems

The synthesis of novel pyrrolo[3,2-c]isoquinolines is investigated starting from 3-aminosuccinimides. Various known routes leading to 3-aminosuccinimides were tested but a new approach via nucleophilic addition of arylalkylamines on maleimide gave better results. The regioselectivity of the reduction of these compounds was shown to depend on the degree of substitution of the concerned 3-aminosuccinimide. The hydroxylactams are formed in-situ, then converted into the ethoxylactams. The latter, after generation of an iminium salt, afforded the target pyrroloisoquinolines and two further derivatives of another new heterocyclic system: the 3,6-methano-2,5-benzodiazocine.