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N-benzyl-4-chloro-N-cyclohexylbenzaMide is a high-affinity RAGE (Receptor for Advanced Glycation End products) receptor antagonist with an IC50 of 0.6 μM. It is a blood-brain-barrier permeant blocker of RAGE V domain-mediated ligand binding, with Ki values of 25, 148, and 230 nM against Aβ40, HMGB1, and S100B, respectively. It can lower levels of Aβ via binding to the V domain of RAGE and block multiple mechanisms of Aβ40and Aβ42-induced cellular stress in RAGE-expressing brain endothelium, neurons, and microglia in vitro and in vivo.

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  • 945714-67-0 Structure
  • Basic information

    1. Product Name: N-benzyl-4-chloro-N-cyclohexylbenzaMide
    2. Synonyms: N-benzyl-4-chloro-N-cyclohexylbenzaMide;4-Chloro-N-cyclohexyl-N-(phenylmethyl)benzamide
    3. CAS NO:945714-67-0
    4. Molecular Formula: C20H22ClNO
    5. Molecular Weight: 327.84778
    6. EINECS: N/A
    7. Product Categories: API
    8. Mol File: 945714-67-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 497.6±38.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.18±0.1 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: 2-8°C
    8. Solubility: Soluble in DMSO (up to 35 mg/ml) or in Ethanol (up to 20 mg/ml)
    9. PKA: -1.54±0.20(Predicted)
    10. Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
    11. CAS DataBase Reference: N-benzyl-4-chloro-N-cyclohexylbenzaMide(CAS DataBase Reference)
    12. NIST Chemistry Reference: N-benzyl-4-chloro-N-cyclohexylbenzaMide(945714-67-0)
    13. EPA Substance Registry System: N-benzyl-4-chloro-N-cyclohexylbenzaMide(945714-67-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 945714-67-0(Hazardous Substances Data)

945714-67-0 Usage

Uses

Used in Pharmaceutical Industry:
N-benzyl-4-chloro-N-cyclohexylbenzaMide is used as a RAGE receptor antagonist for lowering levels of Aβ and blocking multiple mechanisms of Aβ40and Aβ42-induced cellular stress in RAGE-expressing brain endothelium, neurons, and microglia. It can cross the blood-brain barrier and has been shown to attenuate blood-brain barrier and white matter fiber damage in a rat model of intracerebral hemorrhage.
Used in Oncology:
N-benzyl-4-chloro-N-cyclohexylbenzaMide is used as an inhibitor of breast cancer cell invasion and metastasis. It has been shown to impair breast cancer cell invasion and metastasis by antagonizing RAGE.

in vitro

fps-zm1 was identified as a high-affinity inhibitor of the receptor for advanced glycation end products. fps-zm1 could block the binding of amyloid β (aβ) protein to rage and inhibit aβ40- and aβ42-induced cellular stress in rage-expressing cells [1].

in vivo

animal study found that fps-zm1 was nontoxic to mice and readily crossed the blood-brain barrier (bbb). in aged appsw/0 mice overexpressing human aβ-precursor protein, fps-zm1 could inhibit rage-mediated influx of circulating aβ40 and aβ42 into the brain. fps-zm1 bound exclusively to rage in brain, which inhibited β-secretase activity and aβ production and suppressed microglia activation and the neuroinflammatory response. moreover, the blockade of rage actions at the bbb and in the brain could reduce aβ40 and aβ42 levels in brain in aged appsw/0 mice [1].

References

1) Deane?et al.?(2012),?A multimodal RAGE-specific inhibitor reduces amyloid β-mediated brain disorder in a mouse model of Alzheimer disease; J. Clin. Invest.?122?1377 2) Hong?et al.?(2016),?Effects of RAGE-Specific Inhibitor FPS-ZM1 on Amyloid-β Metabolism and AGEs-Induced Inflammation and Oxidative Stress in Rat Hippocampus?; Neurochem. Res.?41?1192 3) Yang?et al.?(2015),?Receptor for advanced glycation end-product antagonist reduces blood-brain barrier damage after intracerebral hemorrhage; Stroke?46?1328 4) Li?et al. (2015),?Blockade of high mobility box-1 signaling via the receptor for advanced end-products ameliorates inflammatory damage after acute intracerebral hemorrhage; Neurosci. Lett.?609?109 5) Kwak?et al.?(2017),?Targeting of RAGE-ligand signaling impairs breast cancer cell invasion and metastasis;?Oncogene?36?155

Check Digit Verification of cas no

The CAS Registry Mumber 945714-67-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 9,4,5,7,1 and 4 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 945714-67:
(8*9)+(7*4)+(6*5)+(5*7)+(4*1)+(3*4)+(2*6)+(1*7)=200
200 % 10 = 0
So 945714-67-0 is a valid CAS Registry Number.

945714-67-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name N-benzyl-4-chloro-N-cyclohexylbenzamide

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:945714-67-0 SDS

945714-67-0Downstream Products

945714-67-0Relevant articles and documents

Structure-activity relationships of small molecule inhibitors of RAGE-Aβ binding

Ross, Nathan T.,Deane, Rashid,Perry, Sheldon,Miller, Benjamin L.

, p. 7653 - 7658 (2013/08/23)

The Receptor for Advanced Glycation Endproducts ('RAGE') mediates transport of amyloid-β peptide (Aβ) into the brain, and is therefore an important target for the development of therapeutic agents for Alzheimer's disease. We describe structure-activity relationships for inhibition of RAGE-Aβ binding, derived from the analysis of a library of tertiary amides.

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