ChemicalBook > CAS DataBase List > (S)-A-METHYL-A-[[[(4-NITROPHENYL)AMINO]CARBONYL]AMINO]-N-[[1-(2-PYRIDINYL)CYCLOHEXYL]METHYL]-1H-INDOLE-3-PROPANAMIDE

(S)-A-METHYL-A-[[[(4-NITROPHENYL)AMINO]CARBONYL]AMINO]-N-[[1-(2-PYRIDINYL)CYCLOHEXYL]METHYL]-1H-INDOLE-3-PROPANAMIDE

Product Name
(S)-A-METHYL-A-[[[(4-NITROPHENYL)AMINO]CARBONYL]AMINO]-N-[[1-(2-PYRIDINYL)CYCLOHEXYL]METHYL]-1H-INDOLE-3-PROPANAMIDE
CAS No.
204066-82-0
Chemical Name
(S)-A-METHYL-A-[[[(4-NITROPHENYL)AMINO]CARBONYL]AMINO]-N-[[1-(2-PYRIDINYL)CYCLOHEXYL]METHYL]-1H-INDOLE-3-PROPANAMIDE
Synonyms
PD 168368;(2S)-3-(1H-INDOL-3-YL)-2-METHYL-2-[(4-NITROPHENYL)CARBAMOYLAMINO]-N-[(1-PYRIDIN-2-YLCYCLOHEXYL)METHYL]PROPANAMIDE;(S)-α-Methyl-α-[[[(4-nitrophenyl)amino]carbonyl]amino]-N-[[1-(2-pyridinyl)cyclohexyl]methyl]-1H-indole-3-propanamide;(S)-A-METHYL-A-[[[(4-NITROPHENYL)AMINO]CARBONYL]AMINO]-N-[[1-(2-PYRIDINYL)CYCLOHEXYL]METHYL]-1H-INDOLE-3-PROPANAMIDE;1H-Indole-3-propanamide, α-methyl-α-[[[(4-nitrophenyl)amino]carbonyl]amino]-N-[[1-(2-pyridinyl)cyclohexyl]methyl]-, (αS)-
CBNumber
CB32453427
Molecular Formula
C31H34N6O4
Formula Weight
554.64
MOL File
204066-82-0.mol
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(S)-A-METHYL-A-[[[(4-NITROPHENYL)AMINO]CARBONYL]AMINO]-N-[[1-(2-PYRIDINYL)CYCLOHEXYL]METHYL]-1H-INDOLE-3-PROPANAMIDE Property

Boiling point:
819.7±65.0 °C(Predicted)
Density 
1.300±0.06 g/cm3(Predicted)
storage temp. 
Store at +4°C
solubility 
DMF: 10 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2) (1:2): 0.3 mg/ml
form 
A crystalline solid
pka
11.60±0.46(Predicted)
color 
White to off-white
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical
Product number
17920
Product name
PD 168368
Purity
≥95%
Packaging
500μg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
17920
Product name
PD 168368
Purity
≥95%
Packaging
1mg
Price
$61
Updated
2024/03/01
Cayman Chemical
Product number
17920
Product name
PD 168368
Purity
≥95%
Packaging
5mg
Price
$243
Updated
2024/03/01
Cayman Chemical
Product number
17920
Product name
PD 168368
Purity
≥95%
Packaging
10mg
Price
$347
Updated
2024/03/01
AK Scientific
Product number
4346CR
Product name
CID9937534
Packaging
10mg
Price
$484
Updated
2021/12/16
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(S)-A-METHYL-A-[[[(4-NITROPHENYL)AMINO]CARBONYL]AMINO]-N-[[1-(2-PYRIDINYL)CYCLOHEXYL]METHYL]-1H-INDOLE-3-PROPANAMIDE Chemical Properties,Usage,Production

Uses

PD 168368 is a potent, competitive, and selective neuromedin B receptor (NMB-R) antagonist with the Ki of 15–45 nM[1]. PD 168368 is neuromedin B receptor (NMBR; IC50=96 nM) / gastrin-releasing peptide receptor (GRPR IC50=3500 nM) antagonist[2]. PD 168368 also is a mixed FPR1/FPR2/FPR3 agonist with EC50s of 0.57, 0.24, and 2.7 nM, respectively[3].

Biological Activity

Potent neuromedin B receptor antagonist (NMB-R, BB 1 ) (IC 50 = 40 nM) that displays ~ 40-fold selectivity over the gastrin-releasing peptide receptor (GRP-R, BB 2 ) and > 300-fold selectivity over BRS-R (bb 3 ). Antagonizes neuromedin B-stimulated calcium release and inhibits proliferation of rat glioma cells (IC 50 = 2 μ M).

in vivo

PD 168368 (PD168368) potently inhibits in vivo metastasis of breast cancer. PD 168368 (1.2 mg/kg; intraperitoneal injection for 30 days) inhibits metastasis of breast cancer in mice[4].

Animal Model:Female BALB/c-nude mice (age 8-10 weeks) bearing MDA-MB-231 xenograft model[4]
Dosage:1.2 mg/kg
Administration:Intraperitoneal injection for 30 days
Result:No metastatic tumor nodules were observed in lungs of PD 168368-treated mice compared to PEG-injected mice.

References

[1] R R Ryan, et al. Comparative pharmacology of the nonpeptide neuromedin B receptor antagonist PD 168368. J Pharmacol Exp Ther. 1999 Sep;290(3):1202-11. PMID:10454496
[2] K Tokita, et al. Tyrosine 220 in the 5th transmembrane domain of the neuromedin B receptor is critical for the high selectivity of the peptoid antagonist PD168368. J Biol Chem. 2001 Jan 5;276(1):495-504. DOI:10.1074/jbc.M006059200
[3] Igor A Schepetkin, et al. Gastrin-releasing peptide/neuromedin B receptor antagonists PD176252, PD168368, and related analogs are potent agonists of human formyl-peptide receptors. Mol Pharmacol. 2011 Jan;79(1):77-90. DOI:10.1124/mol.110.068288
[4] Hyun-Joo Park, et al. Neuromedin B receptor antagonism inhibits migration, invasion, and epithelial-mesenchymal transition of breast cancer cells. Int J Oncol. 2016 Sep;49(3):934-42. DOI:10.3892/ijo.2016.3590

(S)-A-METHYL-A-[[[(4-NITROPHENYL)AMINO]CARBONYL]AMINO]-N-[[1-(2-PYRIDINYL)CYCLOHEXYL]METHYL]-1H-INDOLE-3-PROPANAMIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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(S)-A-METHYL-A-[[[(4-NITROPHENYL)AMINO]CARBONYL]AMINO]-N-[[1-(2-PYRIDINYL)CYCLOHEXYL]METHYL]-1H-INDOLE-3-PROPANAMIDE Suppliers

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204066-82-0, (S)-A-METHYL-A-[[[(4-NITROPHENYL)AMINO]CARBONYL]AMINO]-N-[[1-(2-PYRIDINYL)CYCLOHEXYL]METHYL]-1H-INDOLE-3-PROPANAMIDERelated Search:


  • (S)-A-METHYL-A-[[[(4-NITROPHENYL)AMINO]CARBONYL]AMINO]-N-[[1-(2-PYRIDINYL)CYCLOHEXYL]METHYL]-1H-INDOLE-3-PROPANAMIDE
  • PD 168368
  • (S)-α-Methyl-α-[[[(4-nitrophenyl)amino]carbonyl]amino]-N-[[1-(2-pyridinyl)cyclohexyl]methyl]-1H-indole-3-propanamide
  • (2S)-3-(1H-INDOL-3-YL)-2-METHYL-2-[(4-NITROPHENYL)CARBAMOYLAMINO]-N-[(1-PYRIDIN-2-YLCYCLOHEXYL)METHYL]PROPANAMIDE
  • 1H-Indole-3-propanamide, α-methyl-α-[[[(4-nitrophenyl)amino]carbonyl]amino]-N-[[1-(2-pyridinyl)cyclohexyl]methyl]-, (αS)-
  • 204066-82-0
  • C31H34N6O4
  • Neuromedin B antagonist displaying ~40-fold selectivity over GRP-R, BB2 and >300-fold selectivity over BRS-R.