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SML1120

Sigma-Aldrich

Thiophene-2

≥98% (HPLC)

Synonym(s):

Methyl 2-(perfluorobenzamido)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate, TP2

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5 MG
$103.00
25 MG
$332.00

About This Item

Empirical Formula (Hill Notation):
C18H14F5NO3S
CAS Number:
Molecular Weight:
419.37
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

$103.00


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Quality Level

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.
Thiophene-2 (TP2) is an inhibitor of polyketide synthase 13 (Pks13).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Bihong T Chen et al.
Breast cancer research and treatment, 176(1), 181-189 (2019-04-17)
Older cancer patients are at increased risk of cancer-related cognitive impairment. The purpose of this study was to assess the alterations in intrinsic brain activity associated with adjuvant chemotherapy in older women with breast cancer. Chemotherapy treatment (CT) group included
Maja Schlittler et al.
The Journal of physiology, 599(4), 1083-1096 (2020-10-31)
Acclimatization to hypoxia leads to a reduction in plasma volume (PV) that restores arterial O2 content. Findings from studies investigating the mechanisms underlying this PV contraction have been controversial, possibly as experimental conditions were inadequately controlled. We examined the mechanisms
Richard E Morton et al.
Journal of lipid research, 61(8), 1168-1179 (2020-06-28)
Cholesteryl ester transfer protein (CETP) facilitates the net transfer of cholesteryl esters (CEs) and TGs between lipoproteins, impacting the metabolic fate of these lipoproteins. Previous studies have shown that a CETP antibody can alter CETP's preference for CE versus TG
Yu-Xin Cui et al.
PloS one, 7(1), e30389-e30389 (2012-01-25)
The number and functional activity of circulating progenitor cells (CPCs) is altered in diabetic patients. Furthermore, reduced CPC count has been shown to independently predict cardiovascular events. Validation of CPCs as a biomarker for cardiovascular risk stratification requires rigorous methodology.
"
Valentina Serra et al.
Frontiers in microbiology, 7, 1704-1704 (2016-11-22)

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