1207-59-6

Usage

Derived from

Benzaldehyde

Substituents

Two methoxy and one nitro group on the benzene ring

Usage

Organic synthesis, medicinal chemistry (building block for synthesis of pharmaceuticals and fine chemicals), reagent in preparation of other compounds, chemical intermediate in production of dyes and pigments

Biological activities

Antioxidant, anticancer agent

Upstream product

• 55669-73-3 1,1-diacetoxy-1-(2,5-dimethoxyphenyl)methane 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 143536-20-3 2,5-dimethoxy-4-nitrobenzaldehyde diacetate 

Downstream Products

• 1568-70-3 4-methoxy-2-nitrophenol 

Relevant academic research and scientific papers

SMALL MOLECULE INDUCERS OF REACTIVE OXYGEN SPECIES AND INHIBITORS OF MITOCHONDRIAL ACTIVITY

This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a quinazolinedione structure which function as reactive oxygen species (ROS) inducers and inhibitors of mitochondrial activity within cancer cells (e.g., pancreatic cancer cells), and their use as therapeutics for the treatment of cancer (e.g., pancreatic cancer) and other diseases.

Targeted Nanoparticles for the Delivery of Novel Bioactive Molecules to Pancreatic Cancer Cells

Pancreatic ductal adenocarcinoma (PDAC) is an aggressive disease with poor prognosis and limited therapeutic options. Therefore, there is an urgent need to identify new, safe, and targeted therapeutics for effective treatment of late as well as early stage disease. Plectin-1 (Plec-1) was recently identified as specific biomarker for detecting PDAC at an early stage. We envisioned that multivalent attachment of nanocarriers incorporating certain drugs to Plec-1-derived peptide would increase specific binding affinity and impart high specificity for PDAC cells. Previously, we discovered a novel class of compounds (e.g., quinazolinediones, QDs) that exert their cytotoxic effects by modulating ROS-mediated cell signaling. Herein, we prepared novel QD242-encapsulated polymeric nanoparticles (NPs) functionalized with a peptide to selectively bind to Plec-1. Similarly, we prepared QD-based NPs densely decorated with an isatoic anhydride derivative. Furthermore, we evaluated their impact on ligand binding and antiproliferative activity against PDAC cells. The targeted NPs were more potent than the nontargeted constructs in PDAC cells warranting further development.

Synthesis and adrenolytic activity of 1-(1H-indol-4-yloxy)-3-(2-(2-methoxy phenoxy)ethylamino)propan-2-ol analogs and its enantiomers. Part 2

The synthesis of (2RS)-1-(5-methoxy-1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol and (2RS)-1-(7-methoxy-1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol and its enantiomers, analogs of 1-(1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol ((RS)-9) is described. Compounds were tested for electrographic, antiarrhythmic, hypotensive and spasmolytic activities as well as for α1-, α2- and β1-adrenoceptors binding affinities. The antagonist potency of the new compounds was compared with carvedilol and (RS)-9.

Efficient synthesis of novel six-member ring-fused quinoline derivatives via the Friedlaender reaction

Novel quinolines fused with a six-member ring 5a-j were prepared in high yields (75-95%) via the Friedlaender reaction of dimethoxy-substituted o-aminobenzaldehydes of 3a or 3b with cyclic ketones 4, respectively. The structures of 5aj were determined by IR, 1H NMR, MS, and elemental analysis.

Synthesis of hipposudoric and norhipposudoric acids: The pigments responsible for the color reaction of the red sweat of Hippopotamus amphibius

Highly unstable pigments, hipposudoric acid and norhipposudoric acid, isolated from the red sweat of hippopotamus were synthesized using the Pschorr reaction for the construction of the fluorene nucleus as the key step and the careful oxidation in the las

Synthesis of novel pentacyclic pyrrolothiazolobenzoquinolinones, analogs of natural marine alkaloids

Multistep synthesis (12 steps) of new pentacyclic compounds, which are structurally very close to natural marine alkaloids, was performed via a Diels-Alder reaction between 4-methylene-5-(bromomethylene)-4,5-dihydrothiazole and a protected dioxotryptamine

Nitration of electron-rich aromatic compounds by cerium ammonium nitrate coated on silica

Treatment of electron-rich aromatic derivatives with cerium (IV) ammonium nitrate coated on silica (CANSio2) affords nitro aromatic compounds. The scope and the limitation of this reaction are discussed.

Incorporation of Quinoline-5,8-quinone Moiety into Polyaza Cavities

Silica gel supported nitric acid treatment of 2,5-dimethoxybenzaldehyde followed by reduction with iron powder provides 3,6-dimethoxy-2-aminobenzaldehyde.Friedlaender condensation of this species with a variety of ketones and diketones leads to 5,8-dimethoxyquinoline derivatives which may be oxidized by ceric ammonium nitrate (CAN) and pyridine-2,6-dicarboxylic acid N-oxide (PDANO) to the corresponding quinones.The quinone functionality can be incorporated into larger cavities by a selective stepwise Friedlaender approach and the CAN/PDANO oxidation appears to work preferentially for 5,8-dimethoxyquinoline.

Re-examination of the synthesis of 3,5-dimethoxy-2-nitrobenzaldehyde

An efficient and reproducible synthetic method is proposed for the preparation of 2-nitro-3,6-dimethoxybenzaldehyde.

Selective synthesis of 2,5-dimethoxy-4-nitrobenzaldehyde

A selective preparation of 2,5-dimethoxy-4-nitrobenzaldehyde is proposed in a procedure involving the transformation of the aldehyde group to a diacetoxymethyl group.