Thieno[2,3-d]pyrimidin-4(3H)-one
[CAS# 14080-50-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Thiophene
• Name: Thieno[2,3-d]pyrimidin-4(3H)-one
• Molecular Formula: C₆H₄N₂OS
• Molecular Weight: 152.17
• CAS Registry Number: 14080-50-3
• EC Number: 802-694-8
• SMILES: C1=CSC2=C1C(=O)NC=N2

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Thieno[2,3-d]pyrimidin-4(3H)-one is a heterocyclic compound that is noteworthy for its presence in a variety of pharmacologically active molecules. The discovery of thieno[2,3-d]pyrimidin-4(3H)-one dates back to the mid-20th century, when researchers began to explore the potential therapeutic benefits of fused heterocyclic systems. The interest in this compound and its derivatives stems from their structural similarities to naturally occurring nucleic acids, making them promising candidates for interacting with biological systems. Early research in the synthesis of thieno[2,3-d]pyrimidin-4(3H)-one focused on developing new methods for the efficient construction of fused ring systems.

The structure of thieno[2,3-d]pyrimidin-4(3H)-one consists of a thiophene ring fused to a pyrimidine ring with a keto functional group at the 4-position. This arrangement provides a rigid and planar structure that enables efficient stacking interactions and hydrogen bonding, which are essential for drug receptor binding.

Thieno[2,3-d]pyrimidin-4(3H)-one is the core structure of a variety of bioactive molecules, and derivatives of thieno[2,3-d]pyrimidin-4(3H)-one have shown potent activity against various cancer cell lines. They act by inhibiting key enzymes involved in cell proliferation and survival, such as tyrosine kinases and topoisomerases. The ability of this compound to interfere with nucleic acid metabolism makes it a valuable scaffold for the development of antiviral agents, including inhibitors targeting viral replication processes. Modification of thieno[2,3-d]pyrimidin-4(3H)-one has led to the development of anti-inflammatory drugs that reduce inflammation by inhibiting specific enzymes involved in inflammatory responses.

In chemical biology, thieno[2,3-d]pyrimidin-4(3H)-one derivatives are used to study biological processes, and researchers use these compounds as probes to study enzyme inhibition and understand the mechanism of action of various enzymes, which aids in drug design and development. These compounds are used to study protein-ligand interactions, providing insights into the binding affinity and specificity of potential drug candidates.

In addition to pharmaceuticals, thieno[2,3-d]pyrimidin-4(3H)-one has applications in materials science, where its derivatives are used as organic semiconductors due to their electronic properties, as organic light-emitting diodes (OLEDs) and organic photovoltaic cells. Thieno[2,3-d]pyrimidin-4(3H)-one is used in the synthesis of conductive polymers, which contribute to the development of flexible and lightweight electronic devices.

In synthetic chemistry, the compound is used as a building block for the following: It is a precursor for the synthesis of various fused heterocyclic systems, expanding the chemical space available for drug discovery. The core structure is used to design ligands for metal complexes used in catalysis and coordination chemistry.

References

2020. Synthesis and Antibacterial and Antifungal Activity of New Thieno[2,3-d]Pyrimidin-4(3H)-One Derivatives. Pharmaceutical Chemistry Journal. B. Kahveci, İ. S. Doğan, E. Menteşe, H. E. Sellitepe, D. Kart.
DOI: 10.1007/s11094-020-02252-5

2022. Recent Advances in the Synthesis of Heterocycles Over Heterogeneous Cerium-Based Nanocatalysts. Emerging Nanomaterials for Advanced Technologies. Cong Chien Truong, Dinesh Kumar Mishra, Hoang Long Ngo.
DOI: 10.1007/978-3-030-80371-1_25

2018. A Convenient One-pot Synthesis of 2,3-Disubstituted Thieno[2,3-d]pyrimidin-4(3H)-ones from 2H-Thieno[2,3-d][1,3]oxazine-2,4(1H)-diones, Aromatic Aldehydes and Amines. SynOpen. Feize Liu, Xueling Hou, Li Nie, Khurshed Bozorov, Michael Decker, Guozheng Huang.
DOI: 10.1055/s-0037-1610157