1235481-90-9

Basic information

• Product Name: P7C3-A20
• Synonyms: P7C3-A20;3,6-Dibromo-beta-fluoro-N-(3-methoxyphenyl)-9H-carbazole-9-propanamine;P7C3-A20 3,6-Dibromo-beta-fluoro-N-(3-methoxyphenyl)-9H-carbazole-9-propanamine;P7C3-A20, >=98%
• CAS NO: 1235481-90-9
• Molecular Formula: C₂₂H₁₉Br₂FN₂O
• Molecular Weight: 506.2054632
• EINECS: -0
• Product Categories: Inhibitors
• Mol File: 1235481-90-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 641.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.57±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility: Soluble in DMSO (40 mg/ml)
• PKA: 3.25±0.50(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: P7C3-A20(CAS DataBase Reference)
• NIST Chemistry Reference: P7C3-A20(1235481-90-9)
• EPA Substance Registry System: P7C3-A20(1235481-90-9)

Safety Data

• Hazardous Substances Data: 1235481-90-9(Hazardous Substances Data)

Usage

Description

P7C3-A20 is a derivative of P7C3 that possesses proneurogenic and neuroprotective properties. It is known to enhance the proliferation in the subgranular zone (SGZ) of the adult mouse dentate gyrus in a dose-dependent manner and protect U2OS cells from calcium-induced mitochondrial dissolution. Furthermore, it has been shown to decrease contusion volume, increase proliferation in the SGZ, and improve cognitive function in a rat model of traumatic brain injury. Additionally, P7C3-A20 can prevent or reverse dopaminergic cell death and motor deficits in a 6-OHDA rat model of Parkinson's disease.

Uses

Used in Pharmaceutical Industry:
P7C3-A20 is used as a proneurogenic and neuroprotective agent for promoting neuronal growth and protecting against cell death in various neurological conditions.
Used in Neurological Research:
P7C3-A20 is used as a research tool for studying the mechanisms underlying neuronal proliferation, neuroprotection, and the treatment of neurological disorders such as traumatic brain injury and Parkinson's disease.
Used in Drug Development:
P7C3-A20 is used as a potential therapeutic agent for the development of drugs targeting neurological conditions, including traumatic brain injury and neurodegenerative diseases like Parkinson's disease.

References

LoCoco et al. (2017), Pharmacological augmentation of nicotinamide phosphoribosyltransferase (NAMPT) protects against paclitaxel-induced peripheral neuropathy; Elife, 6 e29626 Blaya et al. (2014), Neuroprotective efficacy of a proneurigenic compound after traumatic brain injury; Neurotrauma, 31 476 Vázquez-Rosa et al. (2020), P7C3-A20 treatment one year after TBI in mice repairs the blood-brain barrier, arrests chronic neurodegeneration, and restores cognition; Proc. Natl. Acad. Sci. USA, 117 27667 Bai et al. (2020), The Small Molecule P7C3-A20 Exerts Neuroprotective Effects in a Hypoxic-ischemic Encephalopathy Model via Activation of PI3K/AKT/GSK3? Signaling; Neuroscience, 441 197 Oku et al. (2017), P7C3 Suppresses Neuroinflammation and Protects Retinal Ganglion Cells of Rats from Optic Nerve Crush; Invest. Ophthamol. Vis. Sci., 58 4877

Upstream product

• 1260172-04-0 N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide 
• 1260172-05-1 N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide 
• 6825-20-3 3,6-dibromo-9H-carbazole 
• 16936-99-5 N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide 
• 85446-05-5 3,6-dibromo-9-(oxiran-2-ylmethyl)-9H-carbazole 
• 313268-18-7 1-(3,6-dibromo-9H-carbazol-9-yl)-3-((3-methoxyphenyl)amino)propan-2-ol 
• 1421622-48-1 N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-1,1,1-trifluoro-N-(3-methoxyphenyl)methanesulfonamide 
• 1421622-86-7 N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)-1,1,1-trifluoro-N-(3-methoxyphenyl)methanesulfonamide 
• 23384-33-0 1,1,1-trifluoro-N-(3-methoxyphenyl)methanesulfonamide 
• 536-90-3 m-Anisidine 

Relevant articles and documents

Pro-neurogenic compounds

This invention relates generally to stimulating neurogenesis (e.g., post-natal neurogenesis, e.g., post-natal hippocampal neurogenesis) and protecting from neuron cell death.

Development of proneurogenic, neuroprotective small molecules

Degeneration of the hippocampus is associated with Alzheimer's disease and occurs very early in the progression of the disease. Current options for treating the cognitive symptoms associated with Alzheimer's are inadequate, giving urgency to the search for novel therapeutic strategies. Pharmacologic agents that safely enhance hippocampal neurogenesis may provide new therapeutic approaches. We discovered the first synthetic molecule, named P7C3, which protects newborn neurons from apopotic cell death, and thus promotes neurogenesis in mice and rats in the subgranular zone of the hippocampal dentate gyrus, the site of normal neurogenesis in adult mammals. We describe the results of a medicinal chemistry campaign to optimize the potency, toxicity profile, and stability of P7C3. Systematic variation of nearly every position of the lead compound revealed elements conducive toward increases in activity and regions subject to modification. We have discovered compounds that are orally available, nontoxic, stable in mice, rats, and cell culture, and capable of penetrating the blood-brain barrier. The most potent compounds are active at nanomolar concentrations. Finally, we have identified derivatives that may facilitate mode-of-action studies through affinity chromatography or photo-cross-linking.