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Sigma-Aldrich

Thiophene-2

≥98% (HPLC)

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Synonym(s):
Methyl 2-(perfluorobenzamido)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate, TP2
Empirical Formula (Hill Notation):
C18H14F5NO3S
CAS Number:
420089-51-6
Molecular Weight:
419.37
MDL number:
MFCD01337175
PubChem Substance ID:
329825660

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(OC)C1=C(NC(C2=C(F)C(F)=C(F)C(F)=C2F)=O)SC3=C1CCCCC3

InChI

1S/C18H14F5NO3S/c1-27-18(26)9-7-5-3-2-4-6-8(7)28-17(9)24-16(25)10-11(19)13(21)15(23)14(22)12(10)20/h2-6H2,1H3,(H,24,25)

InChI key

AVRWEULSKHQETA-UHFFFAOYSA-N

Biochem/physiol Actions

Thiophene-2 (TP2) 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. TP2 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. TP2 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 TP2 against drug-susceptible multidrug-resistant M. tuberculosis strains is approximately 1 μM.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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