SML1151

Thiophene-4

≥98% (HPLC)

• Synonym(s): 5-(Aminocarbonyl)-4-methyl-2-[(pentafluorobenzoyl)amino]-3-thiophenecarboxylic acid ethyl ester, TP4
• Empirical Formula (Hill Notation): C₁₆H₁₁F₅N₂O₄S
• CAS Number: 551907-64-3
• Molecular Weight: 422.33
• MDL number: MFCD01353700
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825684
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 20 mg/mL, clear
• storage temp.: 2-8°C
• SMILES string: NC(C1=C(C)C(C(OCC)=O)=C(NC(C2=C(F)C(F)=C(F)C(F)=C2F)=O)S1)=O
• InChI: 1S/C16H11F5N2O4S/c1-3-27-16(26)5-4(2)12(13(22)24)28-15(5)23-14(25)6-7(17)9(19)11(21)10(20)8(6)18/h3H2,1-2H3,(H2,22,24)(H,23,25)
• InChI key: ANCBHJKEYPZCTE-UHFFFAOYSA-N

Description

Biochem/physiol Actions

Thiophene-4 (TP4) is an inhibitor of polyketide synthase 13 (Pks13), which plays a critical role in the biosynthesis of mycolic acid, an essential component of the cell wall in M. tuberculosis, and is a potential new target for tuberculosis treatment. TP4 inhibits FadD32-dependent loading of the mycolic acid precursor meromycoloyl chain onto acyl carrier protein (ACP) domains located at the N terminus of Pks13, preventing synthesis of mycolic acid and resulting in mycobacterial cell death. TP4 bacteriosidal activity is equivalent to treatment with the first-line drug isoniazid, and enhances its activity, but is less likely to cause resistance. The minimal inhibitory concentration (MIC) values of TP4 against drug-susceptible multidrug-resistant M. tuberculosis strains is approximately 500 nM.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable