43088-52-4

Basic information

• Product Name: 3-AMINO-2-METHYL-5,6,7,8-TETRAHYDRO-3H-BENZO[4,5]THIENO[2,3-D]PYRIMIDIN-4-ONE
• Synonyms: 3-amino-2-methyl-5,6,7,8-tetrahydro-[1]benzothiolo[3,2-e]pyrimidin-4-one;3-amino-2-methyl-5,6,7,8-tetrahydrobenzothiopheno[3,2-e]pyrimidin-4-one;5,6,7,8-Tetrahydro-3-amino-2-methylbenzothieno(2,3-d)pyrimidin-4(3H)-one;Benzothieno(2,3-d)pyrimidin-4(3H)-one, 5,6,7,8-tetrahydro-3-amino-2-methyl-
• CAS NO: 43088-52-4
• Molecular Formula: C₁₁H₁₃N₃OS
• Molecular Weight: 235.31
• Mol File: 43088-52-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 472.8°C at 760 mmHg
• Flash Point: 239.7°C
• Appearance: /
• Density: 1.59g/cm³
• Vapor Pressure: 4.15E-09mmHg at 25°C
• Refractive Index: 1.799
• CAS DataBase Reference: 3-AMINO-2-METHYL-5,6,7,8-TETRAHYDRO-3H-BENZO[4,5]THIENO[2,3-D]PYRIMIDIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-2-METHYL-5,6,7,8-TETRAHYDRO-3H-BENZO[4,5]THIENO[2,3-D]PYRIMIDIN-4-ONE(43088-52-4)
• EPA Substance Registry System: 3-AMINO-2-METHYL-5,6,7,8-TETRAHYDRO-3H-BENZO[4,5]THIENO[2,3-D]PYRIMIDIN-4-ONE(43088-52-4)

Safety Data

• Hazardous Substances Data: 43088-52-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H13N3OS/c1-6-13-10-9(11(15)14(6)12)7-4-2-3-5-8(7)16-10/h2-5,12H2,1H3

Upstream product

• 5919-29-9 ethyl 2-acetylamino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 4506-71-2 ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 108-94-1 cyclohexanone 

Downstream Products

• 144846-37-7 N¹-(2-methyl-4-oxo-5,6,7,8-tetrahydrobenzothieno<2,3-d>pyrimidin-3-yl)-N²-tolylthiourea 
• 144846-36-6 N¹-(2-methyl-4-oxo-5,6,7,8-tetrahydrobenzothieno<2,3-d>pyrimidin-3-yl)-N²-phenylthiourea 
• 144846-40-2 N¹-(2-methyl-4-oxo-5,6,7,8-tetrahydrobenzothieno<2,3-d>pyrimidin-3-yl)-N²-4-chlorophenylthiourea 
• 144846-38-8 N¹-(2-methyl-4-oxo-5,6,7,8-tetrahydrobenzothieno<2,3-d>pyrimidin-3-yl)-N²-4-methoxyphenylthiourea 
• 80381-73-3 2-Methyl-3-(4-oxo-cyclohexa-2,5-dienylideneamino)-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one; compound with acetic acid 
• 144846-39-9 N¹-(2-methyl-4-oxo-5,6,7,8-tetrahydrobenzothieno<2,3-d>pyrimidin-3-yl)-N²-4-bromophenylthiourea 
• 300571-95-3 3-[(2-hydroxy-benzylidene)-amino]-2-methyl-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 144846-41-3 3-[3,4-Diphenyl-3H-thiazol-(2Z)-ylideneamino]-2-methyl-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 144846-44-6 2-Methyl-3-[4-phenyl-3-p-tolyl-3H-thiazol-(2Z)-ylideneamino]-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 144846-53-7 3-[3-(4-Chloro-phenyl)-4-phenyl-3H-thiazol-(2Z)-ylideneamino]-2-methyl-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 144846-50-4 3-[3-(4-Bromo-phenyl)-4-phenyl-3H-thiazol-(2Z)-ylideneamino]-2-methyl-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 144846-47-9 3-[3-(4-Methoxy-phenyl)-4-phenyl-3H-thiazol-(2Z)-ylideneamino]-2-methyl-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 144846-42-4 2-Methyl-3-[4-(4-nitro-phenyl)-3-phenyl-3H-thiazol-(2Z)-ylideneamino]-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 144846-45-7 2-Methyl-3-[4-(4-nitro-phenyl)-3-p-tolyl-3H-thiazol-(2Z)-ylideneamino]-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 

Relevant articles and documents

In-Silico Screening of Novel Synthesized Thienopyrimidines Targeting Fms Related Receptor Tyrosine Kinase-3 and Their In-Vitro Biological Evaluation

The present investigation describes the design strategy and synthesis of novel thienopyrimidine compounds in addition to their anticancer activity targeting tyrosine kinase FLT3 en-zyme. The synthesized compounds were subjected to a cytotoxic study where compounds 9a and 9b showed the most potent cytotoxicity against HT-29, HepG-2, and MCF-7 cell lines reflected by their IC50 values for 9a (1.21 ± 0.34, 6.62 ± 0.7 and 7.2 ± 1.9 μM), for 9b (0.85 ± 0.16, 9.11 ± 0.3 and 16.26 ± 2.3 μM) and better than that of reference standard which recorded (1.4 ± 1.16, 13.915 ± 2.2, and 8.43 ± 0.5 μM), respectively. Compounds’ selectivity to malignant cells was determined using selectivity assay, interestingly, all the tested compounds demonstrated an excellent selectivity index (SI) range from 20.2 to 99.7. Target in-silico prediction revealed the FLT3 kinase enzyme was the kinase enzyme of highest probability. Molecular docking studies were performed on the pre-pared compounds which showed promising binding affinity for FLT3 kinase enzyme and the main interactions between the synthesized ligands and kinase active site were similar to those between the co-crystallized ligand and the receptor. Further biological exploration was performed using in-vitro FLT3 kinase enzyme inhibition assay. The results showed that the 2-morpholinoacetamido derivative 10a exhibited highest FLT3 inhibitory activity among the tested compounds followed by compound 9a then 12. Pharmacokinetic assessment disclosed that all the investigated compounds were considered as “drug-like” molecules with promising bioavailabil-ity.

Synthesis and Pharmacological activities of some substituted thienoprymidine-4-ones

-