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Instruction of N-(2-Chloroethyl)-N′-[2,3-O-(1-methylethylidene)-5-O-(4-nitrobenzoyl)-D-ribofuranosyl]-N-nitrosourea: A Comprehensive Overview
N-(2-Chloroethyl)-N′-[2,3-O-(1-methylethylidene)-5-O-(4-nitrobenzoyl)-D-ribofuranosyl]-N-nitrosourea (CM0581) is an antineoplastic agent that belongs to the class of nitrosoureas.
In recent years, there has been a significant amount of research conducted on CM0581 due to its potential therapeutic applications in the treatment of various types of cancer.
This article provides an instruction on the chemical structure, synthesis, and properties of CM0581, as well as its potential therapeutic applications and its use in the chemical industry.
Chemical Structure of CM0581
CM0581 is a member of the nitrosourea class of compounds, which are characterized by the presence of a nitroso (-NO) group attached to a carbon atom in a nitrogen mustard or urea group.
CM0581 contains a 2-chloroethyl group as the alkylating agent, which is attached to an ethylene glycol linker through an N-methylene bridge.
The 2,3-O-(1-methylethylidene) group is linked to the C-5 position of the ribofuranosyl ring, while the 4-nitrobenzoyl group is attached to the N-5 position of the ribofuranosyl ring through a carbamoyl moiety.
Synthesis of CM0581
The synthesis of CM0581 can be achieved through various methods, depending on the starting materials and the desired product.
One common synthesis method involves the condensation of 2-chloroethanol with 1,2,3-trioxane in the presence of a strong acid catalyst, such as sulfuric acid.
This reaction involves the formation of a carbonate intermediate, which is then treated with a base, such as sodium hydroxide, to produce the corresponding sodium salt.
The sodium salt is then treated with a mixture of pyridine and bromotrimethylsilane to form the desired N-bromo urea derivative.
The N-bromo urea derivative is then treated with a nitrating reagent, such as nitric acid, to introduce the nitroso (-NO) group at the C-2 position.
The nitroso derivative is then treated with an aqueous solution of sodium carbonate and sodium bicarbonate to remove the bromide ion, followed by treatment with an aqueous solution of sodium hydroxide to produce the corresponding sodium hydroxide complex.
The sodium hydroxide complex is then treated with an amine, such as trimethylamine, to form the corresponding amide.
The amide is then treated with an aqueous solution of sodium azide to introduce the azide ion, followed by treatment with an aqueous solution of sodium hydroxide to cyclize the product and form the desired nitrosourea derivative.
Properties of CM0581
CM0581 exhibits a number of unique properties that make it an attractive candidate for therapeutic applications.
One of its most notable properties is its ability to inhibit cell proliferation and induce cell death in a variety of cancer cell lines, including those of the breast, ovarian, and lung cancers.
CM0581 is also relatively specific to cancer cells, as it has little effect on normal cells, making it a potentially safer and more effective treatment option compared to traditional chemotherapy agents.
Another unique property of CM0581 is its ability to cross the blood-brain barrier, allowing it to target cancer cells in the central