thieno[2,3-d]pyrimidin-4(3H)-one

Base Information

• Chemical Name: thieno[2,3-d]pyrimidin-4(3H)-one
• CAS No.: 14080-50-3
• Molecular Formula: C6H4N2OS
• Molecular Weight: 152.177
• Hs Code.: 2934999090
• European Community (EC) Number: 802-694-8
• DSSTox Substance ID: DTXSID00384579
• Nikkaji Number: J2.322.923D
• Wikidata: Q72508429
• ChEMBL ID: CHEMBL2432028
• Mol file: 14080-50-3.mol

Synonyms:thieno(2,3-d)pyrimidin-4(3H)-one

Chemical Property of thieno[2,3-d]pyrimidin-4(3H)-one

Chemical Property:

• Appearance/Colour: Brown solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 262-265 °C
• Refractive Index: 1.801
• Boiling Point: 391.056 °C at 760 mmHg
• PKA: 10.84±0.20(Predicted)
• Flash Point: 190.304 °C
• PSA: 73.99000
• Density: 1.634 g/cm³
• LogP: 0.98460
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 152.00443393
• Heavy Atom Count: 10
• Complexity: 192

Purity/Quality:

97% ^*data from raw suppliers

4-Hydroxythieno[2,3-d]pyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC2=C1C(=O)NC=N2
• General Description: Thieno[2,3-d]pyrimidin-4(3H)-one derivatives exhibit significant antimicrobial and antifungal activity, with some compounds outperforming standard drugs like streptomycin and ampicillin. Notably, derivatives such as compound **22** (with a m-methoxyphenyl group and ethylenediamine side chain) display broad-spectrum antibacterial effects, while compound **15** (with a m-methoxyphenyl group and 2-(2-mercaptoethoxy)ethan-1-ol side chain) shows potent antifungal properties. These compounds also demonstrate low toxicity in both human cells (HFL-1) and in vivo models (C. elegans), highlighting their potential as safe and effective therapeutic agents.

Technology Process of thieno[2,3-d]pyrimidin-4(3H)-one

There total 24 articles about thieno[2,3-d]pyrimidin-4(3H)-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

2-amino-3-cyanothiophene (4651-82-5) + formic acid (64-18-6) → thieno[2,3-d]pyrimidin-4(3H)one (14080-50-3)

Guidance literature:

at 120 ℃; for 4h;

DOI:10.1139/cjc-2018-0220

Reference yield: 94.0%

Methyl 2-aminothiophene-3-carboxylate (4651-81-4) + formamidine acetic acid (3473-63-0) → 4-hydroxythieno[2,3-d]pyrimidine (14080-50-3)

Guidance literature:

In 2-methoxy-ethanol; at 120 ℃; for 3h;

Reference yield: 89.0%

Methyl 2-aminothiophene-3-carboxylate (4651-81-4) + formamidine (463-52-5) → 4-hydroxythieno[2,3-d]pyrimidine (14080-50-3)

Guidance literature:

Microwave irradiation;

DOI:10.1016/j.bmc.2014.01.035

upstream raw materials:

methyl 2-formylaminothiophene-3-carboxylate

2-amino-3-cyanothiophene

formic acid

2-formylaminothiophene-3-carboxamide

Downstream raw materials:

3-benzyl-3H-thieno[2,3-d]pyrimidin-4-one

3-Methyl-4-oxo-3,4-dihydro-thieno<2,3-d>pyrimidin

4-chlorothieno[2,3-d]pyrimidine

6-bromothieno[2,3-d]pyrimidin-4(3H)-one

Refernces

Synthesis, biological evaluation and QSAR studies of new thieno[2,3-d]pyrimidin-4(3H)-one derivatives as antimicrobial and antifungal agents

10.1016/j.bioorg.2020.104509

The research focuses on the synthesis, biological evaluation, and QSAR studies of new thieno[2,3-d]pyrimidin-4(3H)-one derivatives as potential antimicrobial and antifungal agents. The purpose of the study was to develop new compounds that exhibit excellent activity against gram-positive and gram-negative bacteria, as well as fungal species, and to understand their structure-activity relationships. The majority of the synthesized compounds showed promising antimicrobial and antifungal activity, surpassing the potency of control compounds like streptomycin and ampicillin. Particularly, compound 22, with a m-methoxyphenyl group and an ethylenediamine side chain, demonstrated broad-spectrum antibacterial activity, while compound 15, with a m-methoxyphenyl group and a 2-(2-mercaptoethoxy)ethan-1-ol side chain, showed the best antifungal activity. Both compounds 15 and 22 showed no toxic effects in vitro on HFL-1 human embryonic primary cells and in vivo in the nematode C. elegans at their respective MIC concentrations.