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4-(2-Chlorophenoxy)-N-[3-[(methylamino)carbonyl]phenyl]-1-Piperidinecarboxamide

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4-(2-Chlorophenoxy)-N-[3-[(methylamino)carbonyl]phenyl]-1-Piperidinecarboxamide Basic information

Product Name:
4-(2-Chlorophenoxy)-N-[3-[(methylamino)carbonyl]phenyl]-1-Piperidinecarboxamide
Synonyms:
  • A939572;A-939572;A 939572
  • SCD inhibitor
  • stearoyl-CoA desaturase (SCD) inhibitor
  • A939572
  • 4-(2-Chlorophenoxy)-N-[3-[(methylamino)carbonyl]phenyl]-1-Piperidinecarboxamide
  • 4-(2-Chlorophenoxy)-N-(3-(methylcarbamoyl)-phenyl)piperidine-1-carboxamide (A939572)
  • SCD1 Inhibitor (DMSO solution)
  • SCD1 Inhibitor (DMSO solution), SCD1(stearoyl-CoA desaturase 1) inhibitor
CAS:
1032229-33-6
MF:
C20H22ClN3O3
MW:
387.86
Mol File:
1032229-33-6.mol
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4-(2-Chlorophenoxy)-N-[3-[(methylamino)carbonyl]phenyl]-1-Piperidinecarboxamide Chemical Properties

Boiling point:
633.5±55.0 °C(Predicted)
Density 
1.302±0.06 g/cm3(Predicted)
storage temp. 
Store at -20°C
solubility 
insoluble in H2O; ≥17.15 mg/mL in DMSO; ≥2.5 mg/mL in EtOH with ultrasonic
form 
solid
pka
13.65±0.70(Predicted)
color 
White to off-white
InChI
InChI=1S/C20H22ClN3O3/c1-22-19(25)14-5-4-6-15(13-14)23-20(26)24-11-9-16(10-12-24)27-18-8-3-2-7-17(18)21/h2-8,13,16H,9-12H2,1H3,(H,22,25)(H,23,26)
InChIKey
DPYTYQFYDLYWHZ-UHFFFAOYSA-N
SMILES
N1(C(NC2=CC=CC(C(NC)=O)=C2)=O)CCC(OC2=CC=CC=C2Cl)CC1
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Safety Information

WGK Germany 
WGK 3
Storage Class
11 - Combustible Solids
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4-(2-Chlorophenoxy)-N-[3-[(methylamino)carbonyl]phenyl]-1-Piperidinecarboxamide Usage And Synthesis

Uses

4-(2-Chlorophenoxy)-N-[3-[(methylamino)carbonyl]phenyl]-1-piperidinecarboxamide is a stearoyl-CoA desaturase 1 (SCD1) inhibitor.

Biological Activity

A 939572 is a potent stearoyl-CoA desaturase 1 (SCD1) inhibitor (IC50 = 0.4 nM). Selective for SCD1 over a range of kinases and hERG channels. Inhibits proliferation of squamous cell carcinoma FaDu cells in vitro. Also induces cell death of undifferentiated human embryonic stem cells (ESCs). Orally bioavailable.

in vivo

Athymic nude (nu/nu) mice bearing A498 ccRCC xenografts are treated with A939572 (30mg/kg, p.o.) and Tem individually or in combination over the course of four weeks, and tumor volume (mm3) is recorded. A939572 and Tem monotherapy generate similar growth responses with approximately 20-30% reductions in tumor volume (vs. placebo control) being observed upon study completion, with values reaching statistical significance only within the last week of treatment. The combination group yields over a 60% decrease in tumor volume (vs. placebo control) by study completion with significant reductions recorded after approximately 1 week of treatment[2].

storage

Store at +4°C

References

[1] xin z, zhao h, serby m d, et al. discovery of piperidine-aryl urea-based stearoyl-coa desaturase 1 inhibitors. bioorganic & medicinal chemistry letters, 2008, 18(15): 4298-4302.
[2] Low glycaemic diets alter lipid metabolism to influence tumour growth Authors: Lien Et al. Nature  2021;599:302.

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