67565-48-4

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-NITROBENZYLOXY)BENZALDEHYDE is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs and improve existing ones.
Used in Organic Synthesis:
In the field of organic synthesis, 4-(4-NITROBENZYLOXY)BENZALDEHYDE is used as a reagent in various chemical reactions, facilitating the creation of a wide range of organic compounds.
Used as a Building Block:
4-(4-NITROBENZYLOXY)BENZALDEHYDE is utilized as a building block in the production of more complex organic compounds, leveraging its strong aromatic properties to enhance the characteristics of the final products.

InChI:InChI=1/C14H11NO4/c16-9-11-3-7-14(8-4-11)19-10-12-1-5-13(6-2-12)15(17)18/h1-9H,10H2

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 100-14-1 4-nitrobenzyl chloride 
• 100-11-8 1-bromomethyl-4-nitro-benzene 

Relevant academic research and scientific papers

ON THE FIRST EXAMPLE OF AN INVERTED SEQUENCE SA N SC IN A PURE POLAR COMPOUND.

Six homologues of the new series 4- left bracket 4 prime -nitrobenzyloxy right bracket benzylidene-4 double prime -alkoxyaniline are presented. The reentrant sequence I N S//A N//r//e S//C was found for the first time in the pure compound: 4- left bracket 4 prime -nitrobenzyloxy right bracket benzylidene-4 double prime -undecyloxaniline, while the dodecyloxy derivative presents the inverted sequence IS//A N S//C S//1.

SP1-independent inhibition of FOXM1 by modified thiazolidinediones

This research article describes an approach to modify the thiazolidinedione scaffold to produce test drugs capable of binding to, and inhibit, the in vitro transcriptional activity of the oncogenic protein FOXM1. This approach allowed us to obtain FOXM1 i

NTR-1 response type fluorescent probe based on benzoindole as well as preparation method and application thereof

The invention discloses an NTR-1 response type fluorescent probe based on benzoindole as well as a preparation method and application of the NTR-1 response type fluorescent probe. The structure of the NTR-1 response type fluorescent probe is as defined in the specification. The method comprises the following steps: subjecting p-hydroxybenzaldehyde to reacting with p-nitrobenzyl bromide to synthesize a stable intermediate NFP-1-M connected through ether bonds, and condensing 1-ethyl-2-methylbenzo[cd]indole-1-chloride with the intermediate NFP-1-M to generate the probe NFP-1. The probe can be used for measuring the hypoxia degree of a cell, and is beneficial to early diagnosis of tumors and the like.

A Cofactor-Substrate-Based Supramolecular Fluorescent Probe for the Ultrafast Detection of Nitroreductase under Hypoxic Conditions

Identifying the location and expression levels of enzymes under hypoxic conditions in cancer cells is vital in early-stage cancer diagnosis and monitoring. By encapsulating a fluorescent substrate, L-NO2, within the NADH mimic-containing metal–organic capsule Zn-MPB, we developed a cofactor-substrate-based supramolecular luminescent probe for ultrafast detection of hypoxia-related enzymes in solution in vitro and in vivo. The host–guest structure fuses the coenzyme and substrate into one supramolecular probe to avoid control by NADH, switching the catalytic process of nitroreductase from a double-substrate mechanism to a single-substrate one. This probe promotes enzyme efficiency by altering the substrate catalytic process and enhances the electron transfer efficiency through an intra-molecular pathway with increased activity. The enzyme content and fluorescence intensity showed a linear relationship and equilibrium was obtained in seconds, showing potential for early tumor diagnosis, biomimetic catalysis, and prodrug activation.

Design, synthesis and biological evaluation of tetrahydroquinoline-based reversible LSD1 inhibitors

The targeted regulation of LSD1, which is highly expressed in a variety of tumor cells, is a promising cancer therapy strategy. Several LSD1 inhibitors are currently under clinical evaluation, and most of these inhibitors are irreversible. Here, we report the design, synthesis and biochemical evaluation of novel tetrahydroquinoline-based reversible LSD1 inhibitors. Compounds 18s and 18x, which are selective to LSD1 over MAO-A/B, exhibit excellent LSD1 inhibition at the molecular levels with IC50 = 55 nM and 540 nM, respectively. The classic Lineweaver–Burk plots revealed that compound 18s could reversibly bind the LSD1 enzyme in a noncompetitive manner. Molecular docking was used to reveal the potential binding-mode of the compounds and interpret the structure-activity relationships. Furthermore, compounds 18s and 18x significantly inhibited proliferation (IC50 = 1.13 μM and 1.15 μM, respectively) and induced apoptosis in MGC-803 cells with high expression of LSD1. Compound 18x showed acceptable liver microsomal stability. Meanwhile, 18x did not appear to inhibit CYPs at 10 μM in vitro. Remarkably, the oral administration of compound 18x can inhibit the growth of MGC-803 xenograft tumors without significant side effects. Our findings suggest that tetrahydroquinoline-based LSD1 inhibitors deserve further investigation for the treatment of LSD1 overexpressing cancer.

Structure-guided evolution of a 2-phenyl-4-carboxyquinoline chemotype into PPARα selective agonists: New leads for oculovascular conditions

Small molecule agonism of PPARα represents a promising new avenue for the development of non-invasive treatments for oculovascular diseases like diabetic retinopathy and age-related macular degeneration. Herein we report initial structure–activity relatio

Novel cinnamic acid–tryptamine hybrids as potent butyrylcholinesterase inhibitors: Synthesis, biological evaluation, and docking study

A novel series of cinnamic acid–tryptamine hybrids was designed, synthesized, and evaluated as cholinesterase inhibitors. Anticholinesterase assays showed that all of the synthesized compounds displayed a clearly selective inhibition of butyrylcholinesterase (BChE), but only a moderate inhibitory effect toward acetylcholinesterase (AChE) was detected. Among these cinnamic acid–tryptamine hybrids, compound 7d was found to be the most potent inhibitor of BChE with an IC50 value of 0.55 ± 0.04 μM. This compound showed a 14-fold higher inhibitory potency than the standard drug donepezil (IC50 = 7.79 ± 0.81 μM) and inhibited BChE through a mixed-type inhibition mode. Moreover, a docking study revealed that compound 7d binds to both the catalytic anionic site (CAS) and the peripheral anionic site (PAS) of BChE. Also, compound 7d was evaluated against β-secretase, which exhibited low activity (inhibition percentage: 38%).

Three including animal pen oxygen radical porphyrin the synthetic method of the compound of

The invention discloses a synthesis method of benzyloxy-containing porphyrin compounds. A propanoic acid-glacial acetic acid-nitrobenzene mixed solvent conventional heating process is utilized to synthesize two novel porphyrin compounds at high yield, namely meso-tetra(3-methoxy-4-benzyloxyphenyl)porphyrin and meso-tetra[4-(4-nitrobenzyloxy)phenyl]porphyrin; and the synthesis of meso-tetra(4-benzyloxyphenyl)porphyrin is improved. The invention also discloses a synthesis technique of benzyloxy-substituted aromatic aldehydes, namely 4-benzyloxybenzaldehyde, 3-methoxy-4-benzyloxybenzaldehyde and 4-(4-nitrobenzyloxy)benzaldehyde; and the synthesis technique is simple to operate, has the advantages of high yield, low cost and high purity, and is suitable for industrial production.

Isoxazol-5(4H)one derivatives as PTP1B inhibitors showing an anti-obesity effect

In developing inhibitors of therapeutic target enzymes, significant time and effort are committed to the preparation of large numbers of compounds. In an effort to develop a potent inhibitor of protein tyrosine phosphatase (PTP) 1B as an anti-obesity and/or anti-diabetic agent, we constructed an isoxazolone chemical library by using a simplified procedure that circumvents tedious workup and purification steps. The 10× 7 isoxazolone derivatives were synthesized by coupling the two halves of the target compounds. When mixed and heated in test tubes, the precursors produced the reaction products as precipitates. After brief washing, the products were pure enough to be used for enzymatic experiments. With the precursors for the coupling reactions prepared, the 10× 7 library compounds could be prepared in a day by using the present protocol. The library compounds thus obtained were examined for their inhibitory activities against PTP1B. Among them, compound C3 was the most potent inhibitor of PTP1B with an IC50 of 2.3 μM. The in vivo effect of C3 was also examined in an obesity-prone mouse strain. Diet-induced obese (DIO)/diabetic mice were divided into two groups and each group was fed a high-fat diet (HFD) or HFD+C3 for four weeks. The group of C3-fed mice gained significantly less weight relative to the HFD-fed control group during the four weeks of the drug feeding period. In contrast to the anti-obesity effect of C3, no difference was observed in the glycemic control of the HFD and HFD+C3 mice groups.

INHIBITORS OF HIV REPLICATION

Compounds of formula (I) wherein R1, R2, n and R3 are defined herein, are useful as inhibitors of HIV replication.