59898-60-1

Basic information

• Product Name: 3-ETHYL-2-MERCAPTO-5,6-DIMETHYLTHIENO[2,3-D]PYRIMIDIN-4(3H)-ONE
• Synonyms: 3-ethyl-5,6-dimethyl-2-thioxo-2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-one
• CAS NO: 59898-60-1
• Molecular Formula: C10H12N2OS2
• Molecular Weight: 240.35
• Mol File: 59898-60-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 399.8°C at 760 mmHg
• Flash Point: 195.6°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 1.34E-06mmHg at 25°C
• Refractive Index: 1.668
• CAS DataBase Reference: 3-ETHYL-2-MERCAPTO-5,6-DIMETHYLTHIENO[2,3-D]PYRIMIDIN-4(3H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ETHYL-2-MERCAPTO-5,6-DIMETHYLTHIENO[2,3-D]PYRIMIDIN-4(3H)-ONE(59898-60-1)
• EPA Substance Registry System: 3-ETHYL-2-MERCAPTO-5,6-DIMETHYLTHIENO[2,3-D]PYRIMIDIN-4(3H)-ONE(59898-60-1)

Safety Data

• Hazardous Substances Data: 59898-60-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H12N2OS2/c1-4-12-9(13)7-5(2)6(3)15-8(7)11-10(12)14/h4H2,1-3H3,(H,11,14)

Upstream product

• 59898-40-7 2-(3-ethyl-thioureido)-4,5-dimethyl-thiophene-3-carboxylic acid ethyl ester 
• 126105-84-8 3-Ethyl-4-imino-5,6-dimethyl-3,4-dihydro-1H-thieno[2,3-d]pyrimidine-2-thione 
• 542-85-8 Ethyl isothiocyanate 
• 4815-24-1 2-amino-4,5-dimethyl-3-thiophenecarboxylic acid ethyl ester 
• 4651-94-9 2-amino-4,5-dimethylthiophene-3-carbonitrile 

Relevant articles and documents

Synthesis, anticancer activity and photostability of novel 3-ethyl-2-mercapto-thieno[2,3-d]pyrimidin-4(3H)-ones

Some derivatives of 3-ethyl-2-mercapto-thieno[2,3-d]pyrimidin-4(3H)-ones were synthesized using ethyl 2-aminothiophene-3-carboxylates as precursors in order to estimate their cytotoxicity, respectively proliferative activity. Thienopyrimidinones containing thiosemicarbazide as well as 1,3,4-thiadiazole moieties were evaluated for their cytotoxical effect on four cancer cell lines: HT-29, breast cancer cells MDA-MB-231, HeLa, HepG2 as well as human diploid cell line Lep-3. Compounds 5b, 6a and 6b revealed cytotoxicity to the four studied cancer cell lines. The highst cytotoxicity against MDA-MB-31 exhibited the thiosemicarbazide 5b with IC502.31.10?4?μM, but most active towards HT-29?cell lines was thienopyrimidine 6c with IC500.001?μM. Compound 6a showed the highest inhibitory activity with IC50- 0.99?μM to human liver carcinoma HepG2 cells and low cytotoxicity towards Lep3 (IC50?=?191?μM). The thienopyrimidine derivative linked to thiadiazole 6b was toxic to the four studied cancer cell lines, especially to HeLa (IC50–0.83?μM), and besides that the compound demonstrated toxicity to Lep 3?cells at very high concentration 89?×?103?μM. The solid-state photostability of the derivatives 5a-c and 6a-c was tested by irradiation with UV light. All of the studied compounds show solid-state photostability in 240?min of irradiation. Using MOE software molecular docking of the three ligands 5b, 6b and 7 was accomplished into an internal pocket formed by the activation segment and the P-loop ofV599EB-Raf. It was established that the binding of the ligands toV599EB-Raf promotes an inactive conformation of the enzyme.

Synthesis of 3 substituted thieno[2,3 d]pyrimidin 4(3H) one 2 mercaptoacetic acids and their ethyl esters for pharmacological screening

3 Substituted thieno[2,3 d]pyrimidin 4(3H) one 2 mercaptoacetic acids and their ethyl esters were synthesized from 2 mercaptothieno[2,3 d]pyrimidin 4 (3H) ones, which were obtained by cyclization of thienylthioureas in acidic medium. Analgesic, anti inflammatory, and anticonvulsant activities were found in some of these compounds. Significant antimicrobial activity was exhibited by thienylthioureas.