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SML2252

Sigma-Aldrich

TP053

≥98% (HPLC)

Synonym(s):

N-Methyl-6-nitro-2-phenylthieno[2,3-d]pyrimidin-4-amine

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5 MG
€55.80
25 MG
€225.00

€55.80

Estimated to ship on28 May 2025

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5 MG
€55.80
25 MG
€225.00

About This Item

Empirical Formula (Hill Notation):
C13H10N4O2S
CAS Number:
1613295-96-7
Molecular Weight:
286.31
UNSPSC Code:
51111800

€55.80

Estimated to ship on28 May 2025

Request a Bulk Order

Assay

≥98% (HPLC)

form

powder

color

yellow to orange

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

CNC1=NC(C2=CC=CC=C2)=NC3=C1C=C(S3)[N+]([O-])=O

InChI

1S/C13H10N4O2S/c1-14-12-9-7-10(17(18)19)20-13(9)16-11(15-12)8-5-3-2-4-6-8/h2-7H,1H3,(H,14,15,16)

InChI key

JHLJMVJTSFLRPS-UHFFFAOYSA-N

Biochem/physiol Actions

TP053 is a potent thienopyrimidine antitubercular agent that kills both replicating and nonreplicating Mycobacterium tuberculosis. It appears that TP053 is a prodrug, which is activated by mycothiol-dependent reductase Rv2466c.
potent thienopyrimidine antitubercular agent that kills both replicating and nonreplicating Mycobacterium tuberculosis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000062065
0000062066

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Leonardo Astolfi Rosado et al.
The Journal of biological chemistry, 292(32), 13097-13110 (2017-06-18)
The Mycobacterium tuberculosis rv2466c gene encodes an oxidoreductase enzyme annotated as DsbA. It has a CPWC active-site motif embedded within its thioredoxin fold domain and mediates the activation of the prodrug TP053, a thienopyrimidine derivative that kills both replicating and
David Albesa-Jové et al.
The Journal of biological chemistry, 290(52), 31077-31089 (2015-11-08)
Rv2466c is a key oxidoreductase that mediates the reductive activation of TP053, a thienopyrimidine derivative that kills replicating and non-replicating Mycobacterium tuberculosis, but whose mode of action remains enigmatic. Rv2466c is a homodimer in which each subunit displays a modular
David Albesa-Jové et al.
ACS chemical biology, 9(7), 1567-1575 (2014-06-01)
The emergence of multidrug- and extensively drug-resistant strains of Mycobacterium tuberculosis highlights the need to discover new antitubercular agents. Here we describe the synthesis and characterization of a new series of thienopyrimidine (TP) compounds that kill both replicating and non-replicating

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