4-benzyl-N-[(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)methylidene]piperazin-1-amine

• ChemBase ID: 154073
• Molecular Formular: C23H27N5
• Molecular Mass: 373.49398
• Monoisotopic Mass: 373.22664589
• SMILES: Cc1c(c(n(n1)c1ccccc1)C)/C=N/N1CCN(CC1)Cc1ccccc1
• Canonical SMILES: Cc1nn(c(c1/C=N/N1CCN(CC1)Cc1ccccc1)C)c1ccccc1
• InChI: InChI=1S/C23H27N5/c1-19-23(20(2)28(25-19)22-11-7-4-8-12-22)17-24-27-15-13-26(14-16-27)18-21-9-5-3-6-10-21/h3-12,17H,13-16,18H2,1-2H3
• InChIKey: FOORCIAZMIWALX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-benzyl-N-[(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)methylidene]piperazin-1-amine; (1E)-N-(4-benzylpiperazin-1-yl)-1-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)methanimine; (NE)-4-benzyl-N-[(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)methylidene]piperazin-1-amine
• IUPAC Traditional name: 4-benzyl-N-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methylidene]piperazin-1-amine; (1E)-N-(4-benzylpiperazin-1-yl)-1-(3,5-dimethyl-1-phenylpyrazol-4-yl)methanimine; (NE)-4-benzyl-N-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methylidene]piperazin-1-amine
• Synonyms: (4-Benzyl-piperazin-1-yl)-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-ylmethylene)-amine; SANT-1; N-[(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methylene]-4-(phenylmethyl)-1-piperazinamine; SANT-1

Database IDs

• CAS Number: 304909-07-7
• MDL Number: MFCD01827306
• PubChem SID: 162248212
• PubChem CID: 6878030

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.5723802
• LogD (pH = 7.4): 3.2072685
• Log P: 3.5560467
• Molar Refractivity: 116.5581 cm^3
• Polarizability: 44.574654 Å^3
• Polar Surface Area: 36.66 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: >10 mg/mL; H2O: <2 mg/mL; Methanol
• Apperance: Pale Yellow Solid; powder
• Melting Point: 109-111°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Target: Smoothened

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C23H27N5

DETAILS

Sigma Aldrich - S4572

Biochem/physiol Actions
SANT-1 is a potent sonic hedgehog pathway (Shh) antagonist that directly inhibits by binding to the smoothened (Smo) receptor. SANT-1 inhibits wild type and oncogenic Smo with equal potency.

Toronto Research Chemicals - S115000

A potent antagonist of the sonic hedgehog (Shh) signaling pathway (IC50=20nm inShh-LIGHT2 assay an d in Ptch1-/- cells) that acts by binding to smoothened (Smo: KD=1.2 nM), a distant relative of G protein-coupled receptors. In contrast to cyclopamine, SN

REFERENCES

• Chen, J.K., et al.: Proc. Natl. Acad. Sci. USA, 99, 14071 (2002)
• Frank-Kamenetsky, M., et al.: J. Biol. 1, 10 (2002)