Cas no 1806839-88-2 (2,3-Dibromo-4-(difluoromethyl)-5-nitropyridine)
2,3-Dibromo-4-(difluoromethyl)-5-nitropyridine Chemical and Physical Properties
Names and Identifiers
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- 2,3-Dibromo-4-(difluoromethyl)-5-nitropyridine
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- Inchi: 1S/C6H2Br2F2N2O2/c7-4-3(6(9)10)2(12(13)14)1-11-5(4)8/h1,6H
- InChI Key: RTUZVCZKVKHTCL-UHFFFAOYSA-N
- SMILES: BrC1=C(N=CC(=C1C(F)F)[N+](=O)[O-])Br
Computed Properties
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 5
- Heavy Atom Count: 14
- Rotatable Bond Count: 1
- Complexity: 226
- XLogP3: 3
- Topological Polar Surface Area: 58.7
2,3-Dibromo-4-(difluoromethyl)-5-nitropyridine Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| Alichem | A029073811-250mg |
2,3-Dibromo-4-(difluoromethyl)-5-nitropyridine |
1806839-88-2 | 97% | 250mg |
$940.80 | 2022-03-31 | |
| Alichem | A029073811-500mg |
2,3-Dibromo-4-(difluoromethyl)-5-nitropyridine |
1806839-88-2 | 97% | 500mg |
$1,581.10 | 2022-03-31 | |
| Alichem | A029073811-1g |
2,3-Dibromo-4-(difluoromethyl)-5-nitropyridine |
1806839-88-2 | 97% | 1g |
$2,920.40 | 2022-03-31 |
2,3-Dibromo-4-(difluoromethyl)-5-nitropyridine Related Literature
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Aloke Das,K. K. Mahato,Chayan K. Nandi,Tapas Chakraborty,Shridhar R. Gadre,Nikhil A. Gokhale Phys. Chem. Chem. Phys., 2002,4, 2162-2168
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Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755
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Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
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Nan Fu,Naphaporn Chiewchan,Xiao Dong Chen Food Funct., 2020,11, 211-220
Additional information on 2,3-Dibromo-4-(difluoromethyl)-5-nitropyridine
Introduction to 2,3-Dibromo-4-(difluoromethyl)-5-nitropyridine (CAS No. 1806839-88-2)
2,3-Dibromo-4-(difluoromethyl)-5-nitropyridine, identified by the Chemical Abstracts Service Number (CAS No.) 1806839-88-2, is a specialized organic compound that has garnered significant attention in the field of medicinal chemistry and pharmaceutical research. This compound belongs to the nitropyridine class, a group of heterocyclic compounds known for their diverse biological activities and utility in drug development. The structural features of 2,3-dibromo-4-(difluoromethyl)-5-nitropyridine, particularly the presence of bromine and fluorine substituents, make it a promising candidate for further exploration in synthetic chemistry and bioactivity studies.
The molecular structure of this compound consists of a pyridine ring substituted with two bromine atoms at the 2- and 3-positions, a difluoromethyl group at the 4-position, and a nitro group at the 5-position. This specific arrangement of functional groups imparts unique electronic and steric properties to the molecule, which can be exploited in designing novel pharmacophores. The bromine atoms, for instance, can serve as versatile handles for further chemical modifications via cross-coupling reactions, while the difluoromethyl group is often incorporated into drug molecules to enhance metabolic stability and binding affinity.
In recent years, there has been a growing interest in nitropyridines as scaffolds for developing new therapeutic agents. The nitro group not only contributes to the lipophilicity of the molecule but also serves as a site for bioconversion into pharmacologically relevant species. For example, nitroaromatic compounds have been extensively studied for their potential applications in treating inflammation, cancer, and infectious diseases. The halogenated pyridines, including 2,3-dibromo-4-(difluoromethyl)-5-nitropyridine, are particularly intriguing due to their ability to modulate enzyme activity and receptor binding through steric and electronic effects.
One of the most compelling aspects of 2,3-dibromo-4-(difluoromethyl)-5-nitropyridine is its potential utility in the synthesis of kinase inhibitors. Kinases are enzymes that play critical roles in cell signaling pathways and are frequently targeted in anticancer therapies. The presence of both bromine and fluorine substituents makes this compound an attractive intermediate for constructing kinase inhibitors via palladium-catalyzed cross-coupling reactions. Such reactions allow for the introduction of aryl or heteroaryl groups at various positions on the pyridine ring, thereby diversifying the chemical space for kinase inhibition.
Recent advancements in computational chemistry have also highlighted the importance of halogenated pyridines in drug design. Molecular modeling studies suggest that compounds like 2,3-dibromo-4-(difluoromethyl)-5-nitropyridine can exhibit high binding affinity to protein targets due to favorable interactions between halogen atoms and amino acid residues in binding pockets. These interactions can be both electrostatic and hydrophobic in nature, contributing to improved drug-like properties such as solubility and bioavailability.
The pharmaceutical industry has been particularly interested in developing small-molecule inhibitors that target protein-protein interactions (PPIs). PPIs are involved in numerous biological processes and are considered attractive drug targets due to their critical roles in disease pathogenesis. The structural complexity of 2,3-dibromo-4-(difluoromethyl)-5-nitropyridine makes it a promising candidate for designing molecules that can disrupt PPIs through allosteric modulation or competitive inhibition. Preliminary studies have shown that derivatives of this compound can interact with specific PPIs with high selectivity.
In addition to its potential applications in oncology, 2,3-dibromo-4-(difluoromethyl)-5-nitropyridine has shown promise in other therapeutic areas. For instance, it has been investigated as a lead compound for developing antiviral agents. The ability of nitroaromatic compounds to interfere with viral replication cycles makes them valuable candidates for antiviral drug discovery. The unique structural features of this compound may allow it to inhibit viral enzymes or disrupt viral-protein interactions effectively.
The synthesis of 2,3-dibromo-4-(difluoromethyl)-5-nitropyridine presents an interesting challenge due to the need for precise functionalization at multiple positions on the pyridine ring. Traditional synthetic routes often involve multi-step sequences with careful control over reaction conditions to avoid unwanted side products. Advances in synthetic methodology have enabled more efficient access to halogenated pyridines through one-pot reactions or catalytic processes that minimize purification steps.
The role of fluorinated compounds in medicinal chemistry cannot be overstated. Fluoroatoms are known to enhance metabolic stability, improve pharmacokinetic properties, and increase binding affinity towards biological targets. The presence of a difluoromethyl group at the 4-position of 2,3-dibromo-4-(difluoromethyl)-5-nitropyridine contributes significantly to these desirable properties. This substitution pattern has been successfully employed in numerous drug candidates that have advanced into clinical development.
In conclusion,2,3-Dibromo-4-(difluoromethyl)-5-nitropyridine (CAS No. 1806839-88-2) represents a structurally intriguing compound with broad applications in pharmaceutical research. Its unique combination of functional groups makes it a versatile scaffold for developing novel therapeutics targeting various diseases. As research continues to uncover new biological activities and synthetic methodologies for halogenated pyridines,2,3-dibromo-4-(difluoromethyl)-5-nitropyridine is likely to remain at the forefront of medicinal chemistry innovation.
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