Product Introduction of N-(2-dimethylamino-ethyl)-2-methoxy-n-methyl-n-[4-(1-methyl-1h-indol-3-yl)-pyrimidin-2-yl]-5-nitro-benzene-1,4-diamine (CAS 1421372-67-9)
N-(2-dimethylamino-ethyl)-2-methoxy-n-methyl-n-[4-(1-methyl-1h-indol-3-yl)-pyrimidin-2-yl]-5-nitro-benzene-1,4-diamine, with the CAS number 1421372-67-9, is a highly significant chemical compound in the field of organic chemistry and pharmaceutical research. This compound has attracted considerable attention due to its unique chemical structure and potential biological activities. In this article, we will delve into a comprehensive introduction of this product, including its properties, uses, applications in various fields, and preparation methods.
Properties
The chemical formula of N-(2-dimethylamino-ethyl)-2-methoxy-n-methyl-n-[4-(1-methyl-1h-indol-3-yl)-pyrimidin-2-yl]-5-nitro-benzene-1,4-diamine is C₂₄H₂₇N₇O₃. It is a complex organic molecule composed of multiple functional groups. The presence of the dimethylamino-ethyl group, methoxy group, indolyl-pyrimidinyl moiety, and nitro group on the benzene ring endows it with specific physical and chemical properties.
Physically, the compound is expected to have a certain solubility in organic solvents. The nitrogen-containing groups and polar functional groups such as the nitro and methoxy groups contribute to its relatively high polarity compared to some simple hydrocarbons. This polarity can affect its solubility behavior, making it more soluble in polar organic solvents like dimethyl sulfoxide (DMSO) and methanol. However, its solubility in non – polar solvents such as hexane is likely to be limited.
Chemically, the nitro group on the benzene ring is an electron – withdrawing group, which can influence the reactivity of the benzene ring and adjacent functional groups. It can participate in various chemical reactions, such as reduction reactions to form amino groups. The indolyl – pyrimidinyl part of the molecule may also exhibit specific reactivity due to the aromatic and heterocyclic nature of these rings. For example, it may undergo substitution reactions under appropriate conditions.
Uses
One of the primary uses of N-(2-dimethylamino-ethyl)-2-methoxy-n-methyl-n-[4-(1-methyl-1h-indol-3-yl)-pyrimidin-2-yl]-5-nitro-benzene-1,4-diamine is in the field of drug discovery. The unique chemical structure of this compound makes it a potential lead compound for the development of new drugs. The indolyl – pyrimidinyl moiety is often found in many biologically active molecules, and the addition of other functional groups such as the dimethylamino – ethyl and nitro groups may enhance its biological activity and selectivity.
It may act as an inhibitor of specific enzymes or receptors in the body. For example, it could potentially target kinases, which are important enzymes involved in cell signaling pathways. By inhibiting kinases, the compound may be able to regulate abnormal cell growth and proliferation, making it a candidate for the treatment of cancer and other diseases related to abnormal cell signaling.
In addition to its potential in drug development, this compound can also be used as a research tool in chemical and biological studies. It can be used to study the structure – activity relationships of similar compounds. Researchers can modify the structure of N-(2-dimethylamino-ethyl)-2-methoxy-n-methyl-n-[4-(1-methyl-1h-indol-3-yl)-pyrimidin-2-yl]-5-nitro-benzene-1,4-diamine and observe the changes in its biological activity, which helps to understand the key structural features required for a particular biological effect.
Applications in Various Fields
Pharmaceutical Industry
In the pharmaceutical industry, N-(2-dimethylamino-ethyl)-2-methoxy-n-methyl-n-[4-(1-methyl-1h-indol-3-yl)-pyrimidin-2-yl]-5-nitro-benzene-1,4-diamine has great potential for the development of new drugs. As mentioned before, it can be used as a lead compound for the design and synthesis of novel anti – cancer drugs. Many anti – cancer drugs target specific kinases to block the abnormal signaling pathways in cancer cells. The unique structure of this compound may allow it to interact with kinases in a specific way, leading to the inhibition of cancer cell growth.
It can also be explored for the treatment of other diseases such as autoimmune diseases. Autoimmune diseases are caused by an overactive immune system, and some kinases are involved in the regulation of the immune response. By targeting these kinases, the compound may be able to modulate the immune system and provide a new approach for the treatment of autoimmune diseases.
Chemical Research
In chemical research, this compound can be used as a starting material for the synthesis of more complex organic molecules. The functional groups on the molecule can be used for various chemical transformations, such as coupling reactions, substitution reactions, and reduction reactions. For example, the nitro group can be reduced to an amino group, which can then be used for further derivatization. The indolyl – pyrimidinyl moiety can also participate in ring – forming reactions to create new heterocyclic compounds.
Biological Research
In biological research, N-(2-dimethylamino-ethyl)-2-methoxy-n-methyl-n-[4-(1-methyl-1h-indol-3-yl)-pyrimidin-2-yl]-5-nitro-benzene-1,4-diamine can be used to study the function of specific proteins and enzymes. By using this compound as a probe, researchers can determine the binding sites and mechanism of action of kinases and other target proteins. This information is crucial for understanding the biological processes in cells and for the development of more effective drugs.
Preparation Methods
The preparation of N-(2-dimethylamino-ethyl)-2-methoxy-n-methyl-n-[4-(1-methyl-1h-indol-3-yl)-pyrimidin-2-yl]-5-nitro-benzene-1,4-diamine typically involves a multi – step synthesis process. Here is a possible synthetic route:
Step 1: Synthesis of the Indolyl – Pyrimidine Intermediate
The indolyl – pyrimidine part of the molecule can be synthesized first. This may involve the reaction of an appropriate indole derivative with a pyrimidine precursor. For example, 1 – methyl – 1H – indole – 3 – carbaldehyde can react with a pyrimidine derivative in the presence of a base and a catalyst. The reaction conditions may include heating in an appropriate solvent such as ethanol or dimethylformamide (DMF). The product of this reaction is an indolyl – pyrimidine intermediate.
Step 2: Introduction of the Nitro – Benzene Moiety
A nitro – benzene derivative with appropriate functional groups is then reacted with the indolyl – pyrimidine intermediate. This reaction may be a nucleophilic substitution reaction. The reaction conditions need to be carefully controlled to ensure the selectivity of the reaction. For example, the reaction may be carried out in the presence of a base to facilitate the nucleophilic attack of the amino group on the nitro – benzene ring.
Step 3: Introduction of the Dimethylamino – Ethyl and Methyl Groups
The dimethylamino – ethyl and methyl groups can be introduced in subsequent steps. This may involve the reaction of the intermediate with appropriate alkylating agents. For example, a dimethylamino – ethyl halide can be used to introduce the dimethylamino – ethyl group, and a methyl halide can be used to introduce the methyl group. These reactions are usually carried out in the presence of a base and an appropriate solvent.
References
Since there is limited public information specifically about N-(2-dimethylamino-ethyl)-2-methoxy-n-methyl-n-[4-(1-methyl-1h-indol-3-yl)-pyrimidin-2-yl]-5-nitro-benzene-1,4-diamine, general references on organic synthesis and drug discovery can be considered:
- ScienceDirect – A platform for scientific research articles on various fields including organic chemistry and pharmacology.
- American Chemical Society Publications – Offers high – quality research papers on chemical sciences.