296262-16-3

Basic information

• Product Name: (5,6-DIMETHYL-THIENO[2,3-D]PYRIMIDIN-4-YLSULFANYL)-ACETIC ACID
• Synonyms: AURORA 20736;(5,6-DIMETHYL-THIENO[2,3-D]PYRIMIDIN-4-YLSULFANYL)-ACETIC ACID;OTAVA-BB BB7013460024;[(5,6-Dimethylthieno[2,3-d]pyrimidin-4-yl)thio]acetic acid;2-(5,6-dimethylthieno[2,3-d]pyrimidin-4-yl)sulfanylacetic acid
• CAS NO: 296262-16-3
• Molecular Formula: C10H10N2O2S2
• Molecular Weight: 254.33
• Mol File: 296262-16-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5,6-DIMETHYL-THIENO[2,3-D]PYRIMIDIN-4-YLSULFANYL)-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (5,6-DIMETHYL-THIENO[2,3-D]PYRIMIDIN-4-YLSULFANYL)-ACETIC ACID(296262-16-3)
• EPA Substance Registry System: (5,6-DIMETHYL-THIENO[2,3-D]PYRIMIDIN-4-YLSULFANYL)-ACETIC ACID(296262-16-3)

Safety Data

• Hazardous Substances Data: 296262-16-3(Hazardous Substances Data)

Upstream product

• 18593-44-7 5,6-dimethylthieno<2,3-d>pyrimidin-4(3H)-one 
• 4815-24-1 2-amino-4,5-dimethyl-3-thiophenecarboxylic acid ethyl ester 
• 108831-68-1 4-chloro-5,6-dimethyl-thieno[2,3-d]pyrimidine 
• 18593-44-7 5,6-dimethyl-3H-thieno[2,3-d]pyrimidin-4-one 
• 457640-91-4 methyl 2-((5,6-dimethylthieno[2,3-d]pyrimidin-4-yl)thio)acetate 
• 338425-01-7 C₁₂H₁₄N₂O₂S₂ 
• 307512-33-0 5,6-dimethyl-3H-thieno[2,3-d]pyrimidine-4-thione 

Relevant articles and documents

Scaffold-hopping identifies furano[2,3-d]pyrimidine amides as potent Notum inhibitors

The carboxylesterase Notum is a key negative regulator of the Wnt signaling pathway by mediating the depalmitoleoylation of Wnt proteins. Our objective was to discover potent small molecule inhibitors of Notum suitable for exploring the regulation of Wnt signaling in the central nervous system. Scaffold-hopping from thienopyrimidine acids 1 and 2, supported by X-ray structure determination, identified 3-methylimidazolin-4-one amides 20–24 as potent inhibitors of Notum with activity across three orthogonal assay formats (biochemical, extra-cellular, occupancy). A preferred example 24 demonstrated good stability in mouse microsomes and plasma, and cell permeability in the MDCK-MDR1 assay albeit with modest P-gp mediated efflux. Pharmacokinetic studies with 24 were performed in vivo in mouse with single oral administration of 24 showing good plasma exposure and reasonable CNS penetration. We propose that 24 is a new chemical tool suitable for cellular studies to explore the fundamental biology of Notum.

Stimulation of cortical bone formation with thienopyrimidine based inhibitors of Notum Pectinacetylesterase

A group of small molecule thienopyrimidine inhibitors of Notum Pectinacetylesterase are described. We explored both 2-((5,6-thieno[2,3-d]pyrimidin-4-yl)thio)acetic acids and 2-((6,7-thieno[3,2-d]pyrimidin-4-yl)thio)acetic acids. In both series, highly potent, orally active Notum Pectinacetylesterase inhibitors were identified.

Synthesis and biological evaluation of substituted (thieno[2,3-d]pyrimidin- 4-ylthio)carboxylic acids as inhibitors of human protein kinase CK2

A novel series of substituted (thieno[2,3-d]pyrimidin-4-ylthio)carboxylic acids has been synthesized and tested in vitro towards human protein kinase CK2. It was revealed that the most active compounds inhibiting CK2 are 3-{[5-(4-methylphenyl)thieno[2,3-d]pyrimidin-4-yl]thio}propanoic acid and 3-{[5-(4-ethoxyphenyl)thieno[2,3-d]pyrimidin-4-yl]thio}propanoic acid (IC 50 values are 0.1 μM and 0.125 μM, respectively). Structure-activity relationships of 28 tested thienopyrimidine derivatives have been studied and binding mode of this chemical class has been predicted. Evaluation of the inhibitors on seven protein kinases revealed considerable selectivity towards CK2.