3-amino-N-[(4-chlorophenyl)methyl]-4,6-dimethylthieno[2,3-b]pyridine-2-carboxamide

• ChemBase ID: 154502
• Molecular Formular: C17H16ClN3OS
• Molecular Mass: 345.84644
• Monoisotopic Mass: 345.07026083
• SMILES: Cc1cc(nc2c1c(c(s2)C(=O)NCc1ccc(cc1)Cl)N)C
• Canonical SMILES: Clc1ccc(cc1)CNC(=O)c1sc2c(c1N)c(C)cc(n2)C
• InChI: InChI=1S/C17H16ClN3OS/c1-9-7-10(2)21-17-13(9)14(19)15(23-17)16(22)20-8-11-3-5-12(18)6-4-11/h3-7H,8,19H2,1-2H3,(H,20,22)
• InChIKey: FPRULFHDSFKYBV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-amino-N-[(4-chlorophenyl)methyl]-4,6-dimethylthieno[2,3-b]pyridine-2-carboxamide
• IUPAC Traditional name: 3-amino-N-[(4-chlorophenyl)methyl]-4,6-dimethylthieno[2,3-b]pyridine-2-carboxamide
• Synonyms: 2-Furoyl-Leu-Ile-Gly-Arg-Leu-Orn-NH2 trifluoroacetate salt; 2-Fly; 2-f-LIGRLO-NH2; 2-fAP; 2fLI; f-LIGRLO-NH2; 2-Furoyl-LIGRLO-amide trifluoroacetate salt

Database IDs

• CAS Number: 729589-58-6(freebase)
• MDL Number: MFCD03821022
• PubChem SID: 162248641
• PubChem CID: 714286

CALCULATED PROPERTIES

• Acid pKa: 15.655625
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.00014
• LogD (pH = 7.4): 4.000199
• Log P: 4.0001993
• Molar Refractivity: 94.7035 cm^3
• Polarizability: 35.73852 Å^3
• Polar Surface Area: 68.01 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >2 mg/mL
• Apperance: white powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C36H63N11O8 · xC2HF3O2

DETAILS

Sigma Aldrich - F3681

Biochem/physiol Actions
2-Furoyl-LIGRLO-amide is a potent and selective protease-activated receptor 2 (PAR2) agonist. PAR-2 activation is associated with increases in cAMP and intracellular Ca(2+). Immunoblot analysis revealed increases in phosphorylation of epidermal growth factor (EGF) receptor (EGFR) tyrosine kinase, Src, Pyk2, cRaf, and ERK1/2 in response to PAR-2 activation. 2-Furoyl-LIGRLO-amide is nearly 100-fold more potent than SLIGRL-NH2 (Cat. No. S9317). 2-Furoyl-LIGRLO-amide caused both an endothelium-dependent relaxation and an endothelium-independent contraction. It produced delayed (6 hours later) facilitation of capsaicin-evoked visceral nociception, an effect being much more potent than SLIGRL-NH2. Such effects were mimicked by i.col. trypsin. 2-f-LIGRL-NH2, coadministered repeatedly with caerulein six times in total, abolished the caerulein-evoked abdominal hyperalgesia/allodynia in WT, but not PAR2-KO, mice. Repeated doses of 2-f-LIGRL-NH2 moderately attenuated the severity of caerulein-induced pancreatitis in WT animals. It induced a similar dose-dependent increase in Ca2 levels in the presence and absence of b-arrestins.