4-bromo-3-chloro-1H-indazole
Names and Identifiers of 4-bromo-3-chloro-1H-indazole
CAS Number |
1000343-46-3 |
|---|---|
MDL Number |
MFCD09026985 |
IUPAC Name |
4-bromo-3-chloro-2H-indazole |
InChI |
InChI=1S/C7H4BrClN2/c8-4-2-1-3-5-6(4)7(9)11-10-5/h1-3H,(H,10,11) |
InChIKey |
VEZIBLSUFZJVBD-UHFFFAOYSA-N |
Canonical SMILES |
C1=CC2=NNC(=C2C(=C1)Br)Cl |
UNSPSC Code |
12352100 |
Physical and chemical properties of 4-bromo-3-chloro-1H-indazole
Acidity coefficient |
10.71±0.40(Predicted) |
|---|---|
Boiling Point |
368.5±22.0 °C at 760 mmHg |
Density |
1.9±0.1 g/cm3 |
Exact Mass |
229.924637 |
Flash Point |
176.6±22.3 °C |
Index of Refraction |
1.730 |
LogP |
3.49 |
Molecular Formula |
C7H4BrClN2 |
Molecular Weight |
231.477 |
PSA |
28.68000 |
Storage condition |
2-8°C |
Vapour Pressure |
0.0±0.8 mmHg at 25°C |
Safety Information of 4-bromo-3-chloro-1H-indazole
Applications of 4-bromo-3-chloro-1H-indazole
4-Bromo-3-chloro-1H-indazole has several applications across various fields:
- Medicinal Chemistry: It serves as a building block for synthesizing pharmaceutical compounds with potential anticancer, anti-inflammatory, and antimicrobial properties.
- Material Science: This compound is utilized in developing novel materials with unique electronic and optical properties due to its structural characteristics.
- Biological Studies: It acts as a probe in biological studies to understand the interaction of indazole derivatives with various biological targets.
Interaction Studies of 4-bromo-3-chloro-1H-indazole
Research indicates that 4-bromo-3-chloro-1H-indazole interacts with multiple cellular targets, affecting various biochemical pathways. Its ability to inhibit kinases and modulate enzyme activity underscores its potential as a therapeutic agent in cancer treatment and inflammation management. The modulation of signaling pathways by this compound may lead to significant changes in gene expression and cellular metabolism.
Similar Compounds: ComparisonSeveral compounds share structural similarities with 4-bromo-3-chloro-1H-indazole, each exhibiting unique properties:
| Compound Name | Key Features |
|---|---|
| 4-Bromo-3-chloro-5-methoxy-1H-indazole | Contains a methoxy group; potential for different reactivity |
| 4-Bromo-3-chloro-1H-indazole-6-carbonitrile | Contains a carbonitrile group; used in medicinal chemistry |
| 3-Bromo-4-chloro-1H-indazole | Different halogen positioning; varies biological activity |
| 5-Methoxy-1H-indazole | Lacks halogens; different pharmacological profile |
| 5-Bromo-4-methoxy-1H-indazole | Unique properties due to different halogen positioning |
Biological Activity of 4-bromo-3-chloro-1H-indazole
The biological activity of 4-bromo-3-chloro-1H-indazole is notable, particularly in the context of medicinal applications. This compound has been shown to interact with various enzymes and proteins, influencing their activity. For instance:
- Kinase Inhibition: It has been observed to inhibit specific kinases involved in cell signaling pathways, which can lead to alterations in cellular processes such as proliferation and apoptosis.
- Apoptosis Induction: In cancer cells, this compound can induce apoptosis by activating pro-apoptotic pathways while inhibiting survival signals, thereby influencing cell growth and survival.
- Inflammation Modulation: It interacts with cyclooxygenase-2 (COX-2), an enzyme critical for the inflammatory response, suggesting potential anti-inflammatory properties.
Physical sample testing spectrum (NMR) of 4-bromo-3-chloro-1H-indazole
