2-(3,5-dichlorophenyl)-1,3-benzoxazole-6-carboxylic acid

• ChemBase ID: 177977
• Molecular Formular: C14H7Cl2NO3
• Molecular Mass: 308.11628
• Monoisotopic Mass: 306.98029845
• SMILES: c1(ccc2c(c1)oc(n2)c1cc(cc(c1)Cl)Cl)C(=O)O
• Canonical SMILES: Clc1cc(Cl)cc(c1)c1nc2c(o1)cc(cc2)C(=O)O
• InChI: InChI=1S/C14H7Cl2NO3/c15-9-3-8(4-10(16)6-9)13-17-11-2-1-7(14(18)19)5-12(11)20-13/h1-6H,(H,18,19)
• InChIKey: TXEIIPDJKFWEEC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,5-dichlorophenyl)-1,3-benzoxazole-6-carboxylic acid
• IUPAC Traditional name: tafamidis
• Synonyms: 2-(3,5-Dichlorophenyl)-6-benzoxazolecarboxylic Acid; Fx 1006; Tafamidis

Database IDs

• CAS Number: 594839-88-0
• PubChem SID: 164233887
• PubChem CID: 11001318

CALCULATED PROPERTIES

• Acid pKa: 3.731895
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.4422796
• LogD (pH = 7.4): 0.9179511
• Log P: 4.210308
• Molar Refractivity: 84.6905 cm^3
• Polarizability: 30.196976 Å^3
• Polar Surface Area: 63.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T004750

A benzoxole derivative that is a transthyretin (TTR) amyloid fibril inhibitors. It is a new drug candidate in the treatment of TTR amyloidosis (caused my misfolding of proteins).

REFERENCES

• Razavi, H. et al.: Ange. Chem. Int. Ed., 42, 2758 (2003)