384351-45-5

Basic information

• Product Name: 4-CHLORO-5-(4-FLUOROPHENYL)THIENO[2,3-D]PYRIMIDINE
• Synonyms: THIENO[2,3-D]PYRIMIDINE, 4-CHLORO-5-(4-FLUOROPHENYL)-;OTAVA-BB BB7410330246;4-CHLORO-5-(4-FLUOROPHENYL)THIENO[2,3-D]PYRIMIDINE;AKOS BBS-00006938;BUTTPARK 47\15-15
• CAS NO: 384351-45-5
• Molecular Formula: C₁₂H₆ClFN₂S
• Molecular Weight: 264.71
• Mol File: 384351-45-5.mol

Chemical Properties

• Melting Point: 137-139°C
• Appearance: /
• CAS DataBase Reference: 4-CHLORO-5-(4-FLUOROPHENYL)THIENO[2,3-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-5-(4-FLUOROPHENYL)THIENO[2,3-D]PYRIMIDINE(384351-45-5)
• EPA Substance Registry System: 4-CHLORO-5-(4-FLUOROPHENYL)THIENO[2,3-D]PYRIMIDINE(384351-45-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 384351-45-5(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
4-Chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine is used as a potential pharmaceutical drug candidate due to its unique molecular structure and possible biological activities. Its heterocyclic nature allows it to be a versatile building block in the design and synthesis of new therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, 4-chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine can be used as a key intermediate or reactant in the synthesis of more complex organic molecules, contributing to the development of novel chemical entities with specific applications.
Used in Material Science:
4-Chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine may also have applications in material science, where its unique properties could be harnessed to create new materials with specialized functions, such as in sensors, optoelectronics, or other advanced technologies.

Upstream product

• 519016-84-3 2-amino-4-(4-fluorophenyl)thiophene-3-carbonitrile 
• 579-48-6 2-(1-(4-fluorophenyl)ethylidene)malononitrile 
• 35978-37-1 5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one 
• 35978-33-7 ethyl 2-amino-4-(4-fluorophenyl)-thiophene-3-carboxylate 
• 403-42-9 1-(4-fluorophenyl)ethanone 

Downstream Products

• 1321618-77-2 3-fluoro-4-(5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yloxy)aniline 
• 1321618-87-4 N-(3-fluoro-4-(5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yloxy)phenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide 
• 1181227-94-0 3-{[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]thio}propanoic acid 
• 866207-47-8 4,6-dichloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine 

Relevant articles and documents

Design and synthesis of novel protein kinase CK2 inhibitors on the base of 4-aminothieno[2,3-d]pyrimidines

An extension of our previous research work has resulted in a number of new ATP-competitive CK2 inhibitors that have been identified among 4-aminothieno[2,3-d]pyrimidine derivatives. The most active compounds obtained in the course of the research are 3-(5-p-tolyl-thieno[2,3-d]pyrimidin-4-ylamino)-benzoic acid, 5e (NHTP23, IC50 = 0.01 μM), 3-(5-phenyl-thieno[2,3-d]pyrimidin-4-ylamino)-benzoic acid, 5g (NHTP25, IC50 = 0.065 μM) and 3-(6-methyl-5-phenyl-thieno[2,3-d]pyrimidin-4-ylamino)-benzoic acid, 5n (NHTP33, IC50 = 0.008 μM). Structure-activity relationships of the tested 4-aminothieno[2,3-d]pyrimidine derivatives have been studied and their binding mode with ATP-acceptor site of CK2 has been proposed. A negative effect of intramolecular hydrogen bonding in the compounds' structure is discussed.

Discovery of novel c-Met kinase inhibitors bearing a thieno[2,3-d] pyrimidine or furo[2,3-d]pyrimidine scaffold

A series of thieno[2,3-d]pyrimidines and furo[2,3-d]pyrimidines were synthesized and evaluated for the c-Met inhibition. Thieno[2,3-d]pyrimidine 6b stood out as the most potent showing an IC50 of 35.7 nM. This compound displayed high inhibitory effect on cell proliferation in BaF3-TPR-Met cells and showed high selectivity for c-Met family against other 14 tested kinases. However, compound 6b was found ineffective in the c-Met-dependent U-87MG human gliobastoma xenograft model that may be relevant to its poor PK profile.

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.

THIENOPYRIMIDINE DERIVATIVES AS POTASSIUM CHANNEL INHIBITORS

The present invention provides thienopyrimidine compounds which are potasium channels inhibitors. Pharmaceutical compositions comprising the compounds and their use in the treatment of arrhythmia are also provided.