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Imatinib (Pyridine)-N-oxide, also known as STI571, is a cancer drug used to treat chronic myeloid leukemia (CML) and gastrointestinal stromal tumors (GISTs).
The drug is a tyrosine kinase inhibitor, which works by blocking the activity of abnormal proteins in the body that can cause cancer.
There are several synthetic routes to prepare imatinib (Pyridine)-N-oxide, which can be broadly classified into two categories: chemical synthesis and biological synthesis.
In chemical synthesis, the drug is prepared by chemical reactions in a laboratory, while in biological synthesis, the drug is produced by biological systems such as bacteria or yeast.
Chemical Synthesis of Imatinib (Pyridine)-N-oxide:
The chemical synthesis of imatinib (Pyridine)-N-oxide involves several steps, including the preparation of the starting materials and the subsequent reaction steps to form the final product.
One of the most common chemical synthesis routes to imatinib (Pyridine)-N-oxide involves the following steps:
- Preparation of the starting material: 2-chloro-4-(ethylamino)-6-(methylthio) pyridine.
This compound is prepared by reacting 2-chloropyridine with ethylamine and methylthioaniline in the presence of a solvent such as acetonitrile. - Condensation reaction: The product from step 1 is then reacted with methyl iodide in the presence of a Lewis acid catalyst such as zinc chloride to form a intermediate that undergoes a condensation reaction.
- Nitration: The intermediate is then treated with nitric acid to introduce a nitro group.
- Sullfonation: The product from step 3 is then treated with a sulfuric acid in the presence of a solvent such as water to introduce a sulfonate group.
- oxidation: The product from step 4 is then treated with oxalic acid in the presence of a solvent such as dimethylformamide to introduce an oxide group.
- Deprotection: The final step involves deprotecting the intermediate compound by treating it with a base such as sodium hydroxide.
The entire process of chemical synthesis of imatinib (Pyridine)-N-oxide involves several steps, each with its own set of challenges and complexities.
The final product must also be purified and characterized to ensure its purity and identity.
Biological Synthesis of Imatinib (Pyridine)-N-oxide:
The biological synthesis of imatinib (Pyridine)-N-oxide involves the use of biological systems such as bacteria or yeast to produce the drug.
This process is also known as biotechnology.
In this process, genetically modified bacteria or yeast are used to produce the drug in a controlled environment.
The biological synthesis of imatinib (Pyridine)-N-oxide involves several steps, including:
- Construction of the gene: The first step involves constructing the gene for imatinib (Pyridine)-N-oxide in the biological system.
This is done by using a plasmid vector that contains the gene for imatinib (Pyridine)-N-oxide. - Transformation: The next step involves transforming the biological system with the plasmid vector.
This is done by introducing the plasmid into the bacteria or yeast cells. - Cultivation: The next step involves cultivating the biological system under conditions that promote the production of imatinib (Pyridine)-N-oxide.
The cells are grown in a medium that contains the necessary nutrients and chemicals for the cells to survive and produce the drug. - Isolation and purification: The final step involves isolating and purifying the imatinib (Pyridine)-N-oxide from the biological system.
The purified product is then characterized to ensure its purity and identity.
Advantages of Biological Synthesis:
The biological synthesis of imatinib (Pyridine)-N-oxide has several advantages over chemical synthesis.
Some of these