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N-(2-Chloroethyl)-N′-[2,3-O-(1-methylethylidene)-5-O-(4-nitrobenzoyl)-D-ribofuranosyl]-N-nitrosourea, also known as Methyl-Methyl-D-ribofuranoside Nitrosourea or simply MMR-Nu, is a synthetic compound that has gained significant attention in the chemical industry due to its unique properties and versatile applications.
The synthetic route to MMR-Nu typically involves several steps, starting with the synthesis of the D-ribofuranosyl chloride.
This intermediate can be synthesized by treating D-ribofuranose with chloroacetic acid and sodium hydroxide, followed by hydrolysis of the resulting chloride salt.
Next, the D-ribofuranosyl chloride is treated with 2,3-O-(1-methylethylidene)-5-O-(4-nitrobenzoyl) anhydride, a compound that can be synthesized by a multi-step reaction sequence using commercially available starting materials.
The reaction between the D-ribofuranosyl chloride and the anhydride forms the ring-closed metabolite, which can be isolated and purified by conventional techniques.
Finally, the ring-closed metabolite is treated with nitrosating agents, such as nitric acid or nitrosonium salt, to introduce the nitrosourea functional group.
The reaction conditions and the choice of nitrosating agent can have a significant impact on the yield and purity of the final product.
Once synthesized, MMR-Nu can be used in a variety of applications in the chemical industry.
One of the most promising applications is as a building block for the synthesis of novel antibiotics.
The unique structure of MMR-Nu, with its combined nitrosourea and ribofuranoside moieties, makes it an attractive scaffold for the development of new antibiotics that can target bacterial metabolism in innovative ways.
MMR-Nu has also been explored as a potential anti-cancer agent, due to its ability to induce oxidative stress in cancer cells.
It has been shown to induce apoptosis in cancer cells in vitro, and to inhibit the growth of cancer cells in animal models.
However, more research is needed to fully understand the mechanisms by which MMR-Nu exerts its anti-cancer effects, and to determine its safety and efficacy in humans.
In addition to its potential medical applications, MMR-Nu has also been explored for its use as a chemical catalyst.
Studies have shown that MMR-Nu can act as a successful catalyst for a variety of organic reactions, such as the Diels-Alder reaction and the Heck reaction.
The unique structure of MMR-Nu is believed to play an important role in its catalytic activity, and further research is needed to fully understand its mechanisms and to develop new applications for this versatile compound.
Overall, MMR-Nu is a synthetic compound with a wide range of potential applications in the chemical industry.
Its unique structure and properties make it an attractive building block for the development of new antibiotics and anti-cancer agents, and its use as a chemical catalyst also holds promise for new applications in the chemical industry.
As research continues to advance our understanding of this compound, it is likely that new applications and uses will be discovered, expanding the potential impact of MMR-Nu in the chemical industry.