Cat. No. B7587051
M. Wt: 203.24 g/mol
InChI Key: OYFBMVJQTPBPKQ-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Overview
1. Description
6. Future directions
2. Detailed synthesis method
7. Scientific research applications
3. Mechanism of action
8. Properties
4. Biochemical and physiological effects
9. Disclaimer
5. Advantages and limitations for lab experiments
Description
N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine, also known as DPCPX, is a potent and selective antagonist of the adenosine A1 receptor. This small molecule has gained significant attention in scientific research due to its potential therapeutic applications in various diseases, including cancer, cardiovascular diseases, and neurological disorders.
Detailed Synthesis Method
Design of the Synthesis Pathway
The synthesis pathway for N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine involves the conversion of commercially available starting materials into the target compound through a series of chemical reactions.
Starting Materials
2,2-dimethylcyclopropanecarboxylic acid, ammonium hydroxide, formaldehyde, ammonium formate, sodium nitrite, sodium azide, sodium borohydride, 7H-purin-6-amine
Reaction
Step 1: Conversion of 2,2-dimethylcyclopropanecarboxylic acid to 2,2-dimethylcyclopropylamine, a. React 2,2-dimethylcyclopropanecarboxylic acid with ammonium hydroxide and formaldehyde to form 2,2-dimethylcyclopropylamine, Step 2: Conversion of 2,2-dimethylcyclopropylamine to N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine, a. React 2,2-dimethylcyclopropylamine with ammonium formate and sodium nitrite to form the corresponding diazonium salt, b. React the diazonium salt with sodium azide to form the corresponding azide, c. Reduce the azide with sodium borohydride to form N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine
Mechanism Of Action
N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine acts as a competitive antagonist of the adenosine A1 receptor, which is a G protein-coupled receptor that plays a crucial role in regulating various physiological processes, including neurotransmission, cardiac function, and immune response. By blocking the adenosine A1 receptor, N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine inhibits the downstream signaling pathways that are activated by adenosine, leading to the suppression of various cellular processes.
Biochemical And Physiological Effects
N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine has been shown to have several biochemical and physiological effects, including the inhibition of tumor angiogenesis and metastasis, the regulation of cardiac function, and the protection of neurons against oxidative stress and apoptosis. N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine has also been shown to modulate the immune response by inhibiting the production of pro-inflammatory cytokines.
Advantages And Limitations For Lab Experiments
One of the main advantages of using N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine in lab experiments is its high potency and selectivity for the adenosine A1 receptor, which allows for precise targeting of this receptor. However, one limitation of using N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine is its relatively low solubility in water, which can make it challenging to use in certain experimental conditions.
Future Directions
There are several potential future directions for the use of N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine in scientific research. One area of interest is the development of N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine-based therapies for cancer, cardiovascular diseases, and neurological disorders. Another potential direction is the investigation of the role of the adenosine A1 receptor in other physiological processes, such as inflammation and metabolism. Additionally, the development of new analogs of N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine with improved solubility and pharmaco*kinetic properties could further enhance its potential therapeutic applications.
Scientific Research Applications
N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine has been extensively studied for its potential therapeutic applications in various diseases. In cancer research, N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine has been shown to inhibit the growth of cancer cells by blocking the adenosine A1 receptor, leading to the suppression of tumor angiogenesis and metastasis. In cardiovascular research, N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine has been investigated for its role in regulating cardiac function and reducing ischemic injury. In neurological research, N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine has been studied for its neuroprotective effects and potential use in the treatment of neurodegenerative diseases.
properties
IUPAC Name | N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine | Source |
|---|---|---|
| Details | Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07) | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI | InChI=1S/C10H13N5/c1-10(2)3-6(10)15-9-7-8(12-4-11-7)13-5-14-9/h4-6H,3H2,1-2H3,(H2,11,12,13,14,15) | Source |
| Details | Computed by InChI 1.0.6 (PubChem release 2021.05.07) | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key | OYFBMVJQTPBPKQ-UHFFFAOYSA-N | Source |
| Details | Computed by InChI 1.0.6 (PubChem release 2021.05.07) | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES | CC1(CC1NC2=NC=NC3=C2NC=N3)C | Source |
| Details | Computed by OEChem 2.3.0 (PubChem release 2021.05.07) | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula | C10H13N5 | Source |
| Details | Computed by PubChem 2.1 (PubChem release 2021.05.07) | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Weight | 203.24 g/mol | Source |
| Details | Computed by PubChem 2.1 (PubChem release 2021.05.07) | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Product Name | N-(2,2-dimethylcyclopropyl)-7H-purin-6-amine | |
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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.
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