| Identification | Back Directory | [Name]
TP2 | [CAS]
420089-51-6 | [Synonyms]
Thiophene-2
Thiophene-2 >=98% (HPLC)
Methyl 2-(perfluorobenzamido)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate | [Molecular Formula]
C18H14F5NO3S | [MDL Number]
MFCD01337175 | [MOL File]
420089-51-6.mol | [Molecular Weight]
419.37 |
| Chemical Properties | Back Directory | [Boiling point ]
463.5±45.0 °C(Predicted) | [density ]
1.490±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble10mg/mL, clear | [form ]
powder | [pka]
10.33±0.20(Predicted) | [color ]
white to beige | [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) | [InChIKey]
AVRWEULSKHQETA-UHFFFAOYSA-N | [SMILES]
O=C(OC)C1=C(NC(C2=C(F)C(F)=C(F)C(F)=C2F)=O)SC3=C1CCCCC3 |
| Hazard Information | Back Directory | [Uses]
Thiophene-2 (TP2) is a specific polyketide synthase 13 (Pks13) inhibitor. Thiophene-2 inhibits mycolic acid biosynthesis and rapidly leads to mycobacterial cell death. Thiophene-2 is active against Mycobacterium tuberculosis with a MIC value of 1 μM, and has potent anti-tuberculosis activity[1]. | [Definition]
ChEBI: Thiophene-2 is an organosulfur heterocyclic compound. | [Biological Activity]
Thiophene-2 (TP2) is an inhibitor of polyketide synthase 13 (Pks13)which plays a critical role in the biosynthesis of mycolic acidan essential component of the cell wall in M. tuberculosisand 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 Pks13preventing synthesis of mycolic acid and resulting in mycobacterial cell death. TP2 bacteriosidal activity is equivalent to treatment with the first-line drug isoniazidand enhances its activitybut 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. | [References]
[1] Regina Wilson, et al. Antituberculosis Thiophenes Define a Requirement for Pks13 in Mycolic Acid Biosynthesis. Nat Chem Biol. 2013 Aug;9(8):499-506. DOI:10.1038/nchembio.1277 |
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