89567-04-4

Basic information

• Product Name: 2-(CHLOROMETHYL)-5,6,7,8-TETRAHYDRO[1]BENZOTHIENO[2,3-D]PYRIMIDIN-4-AMINE
• Synonyms: 2-(CHLOROMETHYL)-5,6,7,8-TETRAHYDRO[1]BENZOTHIENO[2,3-D]PYRIMIDIN-4-AMINE;CHEMBRDG-BB 5107403;2-(chloromethyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-amine(SALTDATA: 2HCl);2-(ChloroMethyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyriMidin-4-aMine;2-(Chloromethyl)-5,6,7,8-tetrahydro-benzothieno[2,3-d]pyrimidin-4-amine
• CAS NO: 89567-04-4
• Molecular Formula: C₁₁H₁₂ClN₃S
• Molecular Weight: 253.75
• Mol File: 89567-04-4.mol

Chemical Properties

• Appearance: /
• Density: 1.439g/cm³
• Refractive Index: 1.717
• CAS DataBase Reference: 2-(CHLOROMETHYL)-5,6,7,8-TETRAHYDRO[1]BENZOTHIENO[2,3-D]PYRIMIDIN-4-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(CHLOROMETHYL)-5,6,7,8-TETRAHYDRO[1]BENZOTHIENO[2,3-D]PYRIMIDIN-4-AMINE(89567-04-4)
• EPA Substance Registry System: 2-(CHLOROMETHYL)-5,6,7,8-TETRAHYDRO[1]BENZOTHIENO[2,3-D]PYRIMIDIN-4-AMINE(89567-04-4)

Safety Data

• Hazardous Substances Data: 89567-04-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(CHLOROMETHYL)-5,6,7,8-TETRAHYDRO[1]BENZOTHIENO[2,3-D]PYRIMIDIN-4-AMINE is used as a potential pharmaceutical compound for its unique structure, which may offer novel therapeutic properties. Further research is needed to explore its potential uses and properties in drug development.
Used in Chemical Research:
2-(CHLOROMETHYL)-5,6,7,8-TETRAHYDRO[1]BENZOTHIENO[2,3-D]PYRIMIDIN-4-AMINE is used as a building block for the synthesis of other chemical compounds in research settings. Its unique structure may contribute to the development of new materials or compounds with specific properties and applications.

InChI:InChI=1/C11H12ClN3S/c12-5-8-14-10(13)9-6-3-1-2-4-7(6)16-11(9)15-8/h1-5H2,(H2,13,14,15)

Upstream product

• 4651-91-6 3-cyano-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene 
• 107-14-2 chloroacetonitrile 
• 108-94-1 cyclohexanone 

Downstream Products

• 1443221-52-0 N-[5-(4-amino-5,6,7,8-tetrahydrobenzo[4,5]-thieno[2,3-d]pyrimidin-2-yl)-4-phenylthiazol-2-yl]benzamide 
• 1443221-51-9 N-[5-(4-amino-5,6,7,8-tetrahydrobenzo[4,5]-thieno[2,3-d]pyrimidin-2-yl)-4-phenylthiazol-2-yl]-4-methylbenzamide 
• 1443221-50-8 N-[5-(4-amino-5,6,7,8-tetrahydro-benzo[4,5]-thieno[2,3-d]pyrimidin-2-yl)-4-phenylthiazol-2-yl]-4-methoxybenzamide 
• 1443221-57-5 furan-2-carboxylic acid [5-(4-amino-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-yl)-4-phenylthiazol-2-yl]amide 
• 77373-45-6 4-amino-2-methyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine 
• 333786-73-5 4-amino-2-(4-methoxyphenyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine 

Relevant articles and documents

For FGFR1 tetrahydroben-and thieno [2, 3 - d] amino pyrimidine derivative and its preparation method and application

The invention relates to tetrahydrobenzothieno[2,3-d]aminopyrimidine derivatives acting on FGFR1, and a preparation method and application thereof. The structure of the tetrahydrobenzothieno[2,3-d]aminopyrimidine derivatives is disclosed as Formula (I). The anti-apoptosis experiment research on the three cells H460 (human lung cancer cell), A549 (human lung adenocarcinoma cell) and U251 (glioma cell) indicates that all the detected compounds have certain inhibition activity, and the inhibition activity increases as the concentration increases. Meanwhile, the FGFR1 kinase inhibition activity experiment indicates that the compounds have certain antitumor activity.

Synthesis and Evaluation of Biological and Antitumor Activities of Tetrahydrobenzothieno[2,3-d]Pyrimidine Derivatives as Novel Inhibitors of FGFR1

A series of tetrahydrobenzothieno[2,3-d]pyrimidine derivatives were designed, synthesized, and evaluated as inhibitors of FGFR1. These analogs were synthesized via Gewald's reaction under mild conditions. The structures of the synthesized compounds were characterized by spectroscopic data (IR, 1H NMR and MS). Their antitumor activities were evaluated against H460, A549 and U251 cell lines in vitro. Results revealed that the tested compounds showed moderate antitumor activities. Structure-activity relationship analyses indicated that compounds with an aromatic ring substituted in the C-2 position or with larger molecules such as 3g, 4c, and 7 were more effective than others. The compound, 3g (78.8% FGFR1 inhibition at 10 μm), was identified to have the most potent antitumor activities, with IC50 values of 7.7, 18.9, and 13.3 μm against the H460, A549, and U251 cell lines, respectively. Together, the results suggested that tetrahydrobenzothieno[2,3-d]pyrimidine derivatives may serve as a potential agent for the treatment of FGFR1-mediated cancers.

New insight into adenosine receptors selectivity derived from a novel series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamides and furamides

A series of [5-substituted-4-phenyl-1,3-thiazol-2-yl] benzamide and furamide analogues were investigated in radioligand binding studies at adenosine receptor subtypes with an aim to obtain potent and selective adenosine receptor ligands. Benzamide and furamide linked to thiazole was found to be crucial for high adenosine receptor affinity. The most potent compound indentified in this study was 5d with low nanomolar affinity for all four adenosine receptor subtypes. Compounds 5a and 5g showed moderate selectivity for A2A adenosine receptors. Molecular docking versus all four human adenosine receptors combined with membrane molecular dynamics studies were performed to rationalise the peculiar selectivity profile of 5d antagonist.