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867164-40-7

867164-40-7 Structure

867164-40-7 Structure
IdentificationBack Directory
[Name]

TRC051384
[CAS]

867164-40-7
[Synonyms]

TRC051384
TRC 051384; TRC-051384
N-[2-(4-Morpholinyl)ethyl]-N'-[4-[3-[6-(4-morpholinyl)-2-pyridinyl]-1-oxo-2-propen-1-yl]phenyl]urea
Urea, N-[2-(4-morpholinyl)ethyl]-N'-[4-[3-[6-(4-morpholinyl)-2-pyridinyl]-1-oxo-2-propen-1-yl]phenyl]-
[Molecular Formula]

C25H31N5O4
[MDL Number]

MFCD28133369
[MOL File]

867164-40-7.mol
[Molecular Weight]

465.54
Chemical PropertiesBack Directory
[Boiling point ]

685.7±55.0 °C(Predicted)
[density ]

1.260±0.06 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[solubility ]

insoluble in EtOH; insoluble in H2O; ≥109 mg/mL in DMSO
[form ]

solid
[pka]

13.47±0.46(Predicted)
[color ]

Yellow
[SMILES]

O=C(C1=CC=C(NC(NCCN2CCOCC2)=O)C=C1)/C=C/C3=CC=CC(N4CCOCC4)=N3
Hazard InformationBack Directory
[Uses]

N-[2-(4-Morpholinyl)ethyl]-N''-[4-[3-[6-(4-morpholinyl)-2-pyridinyl]-1-oxo-2-propen-1-yl]phenyl]urea is a key reactant in the synthesis of TRC051384, which is a small molecule HSP70 inducer.
[Biological Activity]

trc 051384, belonging to substituted 2-propen-1-one class, is a potent inducer of heat shock protein 70 (hsp70) [1]. induction of hsp70 is a natural response of stressed cells that protects neuronal cells from a variety of insults including acute ischemia. therefore, induction of hsp70 provides a potential target for the treatment of stroke [1].
[in vitro]

induction of hsp70 by trc 051384 (6.25, and 12.5 μm) involved heat shock factor-1 (hsf1) activation in hela cells and led to increasing chaperone and anti-inflammatory activity [1]. moreover, trc 051384 (10-50 μm) dose-dependently induced hspa1b overexpression in endothelial cells as well as leucocyte origin [2].
[in vivo]

trc 051384 (9 mg/kg, intra-peritoneal administration) treatment significantly decreased stroke-associated neuronal injury, disability, and increased survival in a rat model of transient ischemic stroke [1]. in addition, trc 051384 (9 mg/kg, intra-peritoneal administration) delayed thrombus formation without increasing bleeding risk in wt mice [2].
[target]

hsp70
[IC 50]

HSP70
[References]

1. mohanan a, deshpande s, jamadarkhana pg, kumar p, gupta rc, chauthaiwale v, et al. delayed intervention in experimental stroke with trc 051384--a small molecule hsp70 inducer. neuropharmacology. 2011;60(6):991-9. 2. allende m, molina e, guruceaga e, tamayo i, gonzalez-porras jr, gonzalez-lopez tj, et al. hsp70 protects from stroke in atrial fibrillation patients by preventing thrombosis without increased bleeding risk. cardiovasc res. 2016;110(3):309-18.
Spectrum DetailBack Directory
[Spectrum Detail]

TRC051384(867164-40-7)1HNMR
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