4-({4-oxo-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-5-ylidene}methyl)benzoic acid

• ChemBase ID: 16041
• Molecular Formular: C18H10F3NO3S2
• Molecular Mass: 409.4021096
• Monoisotopic Mass: 409.00541985
• SMILES: N1(C(=S)S/C(=C\c2ccc(C(=O)O)cc2)/C1=O)c1cc(C(F)(F)F)ccc1
• Canonical SMILES: S=C1S/C(=C\c2ccc(cc2)C(=O)O)/C(=O)N1c1cccc(c1)C(F)(F)F
• InChI: InChI=1S/C18H10F3NO3S2/c19-18(20,21)12-2-1-3-13(9-12)22-15(23)14(27-17(22)26)8-10-4-6-11(7-5-10)16(24)25/h1-9H,(H,24,25)/b14-8-
• InChIKey: JIMHYXZZCWVCMI-ZSOIEALJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-({4-oxo-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-5-ylidene}methyl)benzoic acid; 4-{[(5Z)-4-oxo-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-5-ylidene]methyl}benzoic acid
• IUPAC Traditional name: 4-({4-oxo-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-5-ylidene}methyl)benzoic acid; 4-{[(5Z)-4-oxo-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-5-ylidene]methyl}benzoic acid
• Synonyms: 5-[(4-Carboxyphenyl)methylene]-2-thioxo-3-[(3-trifluoromethyl)phenyl-4-thiazolidinone; CFTR(inh)-172; 4-[4-Oxo-2-thioxo-3-(3-trifluoromethyl-phenyl)-thiazolidin-(5Z)-ylidenemethyl]-benzoic acid

Database IDs

• CAS Number: 307510-92-5
• MDL Number: MFCD06411408; MFCD01164609
• PubChem SID: 160979348; 24724436
• PubChem CID: 1554208

CALCULATED PROPERTIES

• Acid pKa: 4.0682955
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.7128618
• LogD (pH = 7.4): 2.0382972
• Log P: 5.1568947
• Molar Refractivity: 102.1161 cm^3
• Polarizability: 37.526173 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL; H2O: insoluble
• Apperance: yellow powder

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 36/37/38-43-50/53
• Safety Statements: 26-36/37-60-61
• TSCA Listed: false
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H317-H319-H335-H410
• GHS Precautionary statements: P261-P273-P280-P305 + P351 + P338-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H10F3NO3S2

DETAILS

Sigma Aldrich - C2992

Biochem/physiol Actions
CFTR(inh)-172 is an inhibitor of the cystic fibrosis transmembrane conductance regulator (CFTR). With a Ki = 300 nM,. CFTR(inh)-172 leads to rapid, reversible and voltage-independent inhibition; it is an antidiarrheal agent in animals. CTFR(inh)-172 may be a useful tool to study animal models of cystic fibrosis and intestinal fluid loss in cholera and other secretory diarrheas. CTFR(inh)-172 is structurally-unrelated to known, but non-specific CFTR inhibitors DPC, NPPB (Cat. No. N4779) and Glibenclamide.