1850-57-3

Usage

Chemical structure

A complex structure containing four methoxy groups and derived from benzo[a]heptalene, a polycyclic aromatic hydrocarbon.

Classification

An organic molecule.

Biological activities

Known for its potential antioxidant, anti-inflammatory, and anticancer properties.

Research interest

The compound's unique structure and potential biological activities make it a subject of interest for further research in the fields of medicinal chemistry and drug development.

Functional groups

Contains four methoxy groups (-OCH3) attached to the aromatic ring.

Aromaticity

Part of the polycyclic aromatic hydrocarbon family, which is known for its aromatic character.

Hydrogenation

The presence of a dihydro (partially hydrogenated) portion in the molecule, which may contribute to its biological activities.

Carbonyl groups

Contains two carbonyl groups (C=O) at positions 7 and 9, which may play a role in its biological activities and reactivity.

Solubility

Likely to be soluble in organic solvents such as ethanol, methanol, or dimethyl sulfoxide (DMSO) due to its nonpolar nature.

Stability

May be sensitive to light, heat, or acidic conditions, as is common with compounds containing aromatic rings and carbonyl groups.

Synthesis

The synthesis of 1,2,3,10-tetramethoxy-5,6-dihydrobenzo[a]heptalene-7,9-dione may involve multiple steps, including the formation of the benzo[a]heptalene core, followed by the introduction of methoxy groups and the dihydro functionality.

Analytical techniques

Techniques such as nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared (IR) spectroscopy can be used to analyze and confirm the structure of 1,2,3,10-tetramethoxy-5,6-dihydrobenzo[a]heptalene-7,9-dione.

Potential applications

Due to its biological activities, 1,2,3,10-tetramethoxy-5,6-dihydrobenzo[a]heptalene-7,9-dione may be explored for use in the development of new drugs targeting oxidative stress, inflammation, and cancer.

Safety and handling

As with any chemical compound, appropriate safety measures should be taken when handling 1,2,3,10-tetramethoxy-5,6-dihydrobenzo[a]heptalene-7,9-dione, including the use of personal protective equipment (PPE) and proper disposal methods.

Upstream product

• 186581-53-3 diazomethane 
• 3482-37-9 trimethylcolchicinic acid 
• 3476-50-4 deacetylcolchicine 
• 3383-21-9 3,5-di-tert-butyl-o-benzoquinone 
• 64-86-8 colchicine 
• 186374-95-8 (S)-tert-butyl N-(1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalene-7-yl)carbamate 
• 7411-12-3 N-deacetyl-N-formylcolchicine 

Relevant academic research and scientific papers

Attempted oxidative deamination of N-deacetylcolchicinoids with 3,5- di(tert-butyl)-1,2-benzoquinone: Synthesis of 2h-1,4-benzoxazine-type adducts

In an attempt to use 3,5-di(tert-butyl)-1,2-benzoquinone for the oxidative deamination of N-deacetylcolchicine (4) and N- deacetylthiocolchicine (= N-deacetyl-10-demethoxy-10-(metbylthio)colchicine; 5) to give the corresponding ketones 2 and 3, the 2H-1,4-benzoxazine-type adducts 8/9 and 11/12, respectively, were formed instead, showing a new and unexpected behavior of Corey's reagent. The adducts were separated and spectroscopically characterized, and a plausible scheme of formation is reported.

Some Surprising Transformations of Colchicone and Other Colchicine-Derived Tropolones

The alkaloid colchicine represents a prominent lead structure for the development of tubulin-binding chemotherapeutics. In the course of explorative research into semi-synthetic colchicinoids we stumbled upon a number of unexpected and mechanistically surprising transformations which reflect the very particular reactivity of the tropolone ether unit and its interplay with adjacent functional groups. Examples are the selective C-8-methylation of colchicone upon reaction with the Wittig reagent triphenylphosphonium methylide, the AlMe3-mediated isomerization of colchicone to a tetracyclic lactone, and the cyanide-induced reaction of the colchicol-derived mesylate to a rearranged and ring B-defunctionalized cyano-allo-colchicinoid. Finally, the fragmenting rearrangement of a tetracyclic colchicinoid with BF3?OEt2 in the presence of vinyl-MgBr afforded a tropolonyl difluoroborate under concomitant transfer of an O-methyl group from ring C to ring A.

Semisyntheses, X-Ray Crystal Structures and Tubulin-Binding Properties of 7-Oxodeacetamidocolchicine and 7-Oxodeacetamidoisocolchicine

Commercially available (-)-colchicine (1) has been converted, via deacetylcolchiceine (4), into a mixture of 7-oxodeacetamidocolchicine (2) and 7-oxodeacetamidoisocolchicine (3).The X-ray structures and tubulin-binding properties of these title ketones are described.