878699-59-3

Usage

Uses

Used in Pharmaceutical Industry:
2-(Chloromethyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one (SALTDATA: FREE) is used as a key intermediate in the synthesis of chalcone analogs containing a thieno[2,3-d]pyrimidin-2-yl group. These chalcone analogs exhibit cytotoxic activity against cultured human lung cancer A549 and colorectal HCT-116 cells, making them promising candidates for the development of novel anticancer drugs.
In the synthesis process, 2-(chloromethyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one serves as a building block, allowing chemists to create a variety of chalcone analogs with different functional groups and properties. This versatility enables the exploration of new therapeutic agents with improved efficacy and selectivity against cancer cells.
Furthermore, the presence of the chloromethyl group in the compound allows for further chemical modifications, such as the introduction of different functional groups or the formation of new bonds with other molecules. This feature expands the range of potential applications and opens up new avenues for research in drug discovery and development.

InChI:InChI=1/C8H7ClN2OS/c1-4-2-5-7(12)10-6(3-9)11-8(5)13-4/h2H,3H2,1H3,(H,10,11,12)

Upstream product

• 4815-32-1 ethyl 2-amino-5-methylthiophene-3-carboxylate 
• 107-14-2 chloroacetonitrile 

Relevant academic research and scientific papers

Synthesis and cytotoxic activity of chalcone analogues containing a thieno[2,3-d]pyrimidin-2-yl group as the A-ring or B-ring

Many natural or synthetic chalcones have potential anti-tumor activity. Here, we synthesized two series of chalcone analogues containing a thieno[2,3-d]pyrimidin-2-yl group and evaluated for their cytotoxic activity towards cultured human lung cancer A549 and colorectal HCT-116 cells. Among them, compound 8d was the most cytotoxic against HCT-116 cells, with an IC50 value of 2.65 μM. Analyses of the phenotypic changes induced by this compound found a dose-dependent accumulation of HCT-116 cells in sub-G1 phase, indicating that compound 8d might induce apoptosis. Furthermore, we found that 8d triggered mitochondrial membrane potential depolarization, promoted reactive oxygen species formation in HCT-116 cells, and increased the percentage of early and late apoptotic cells. Finally, immunoblotting indicated that 8d increased PARP-1 and caspases 3, 7 and 9 cleavage. These data suggest that compound 8d induces apoptosis via the mitochondrial death pathway.

Chalcone analogue containing thieno[2,3-d]pyrimidine-2-yl, preparation method and uses thereof

The invention discloses a chalcone analogue containing thieno[2,3-d]pyrimidine-2-yl, wherein the chalcone analogue is represented by a general formula (I), and various substituents are defined in thespecification. The invention further discloses a preparation method of the compound. According to the present invention, the compound represented by the general formula (I) has inhibiting effects on the proliferation of human breast cancer cell lines (MFC-7 and MDA-MB-231), human cervical cancer cell lines (HeLa), human colon cancer cell lines (HCT-116 and HT-29) and human lung cancer cell lines (A549), has inhibiting effect on the proliferation of human hepatoma cell lines (HepG2), and can be used as an antitumor drug.

Synthesis, cytotoxic evaluation and target identification of thieno[2,3-d]pyrimidine derivatives with a dithiocarbamate side chain at C2 position

Two series of thieno[2,3-d]pyrimidine derivatives bearing a dithiocarbamate side chain at the C2 position were synthesized and evaluated for cytotoxic activity in human lung cancer A549 and colon cancer HCT-116 cell lines. Compound 3n exhibited the most cytotoxic effect on A549 cells with an IC50 value of 4.87 μM, inducing a cell cycle arrest at G2/M phase and activating the spindle assembly checkpoint (SAC). To identify the target protein(s) of 3n, we incorporated biotin with 3n through a three-carbon chain and an amide bond to synthesize probe 10. The targeted proteins were pulled down from the A549 total cell lysate by biotin-streptavidin affinity purification and analyzed by mass spectrometry. Tubulin was the only protein identified, which is related to the SAC and directly binds to probe 10 both in vivo and in vitro. Furthermore, compound 3n inhibited tubulin polymerization in vitro in a dose-dependent manner, competed with taxol in binding to tubulin, exerting cytotoxic activity toward taxol-resistant A549 cells. These results demonstrate that thieno[2,3-d]pyrimidine derivative 3n exhibits cytotoxicity in cancer cells by targeting tubulin to activate the SAC and potentially acts as a therapeutic lead compound for taxol-resistant cancers.

HETEROCYCLIC DERIVATIVES

The present invention relates to a heterocyclic derivative according to formula I wherein the variables are defined as in the specification, or to a pharmaceutically acceptable salt or solvate thereof. The present invention also relates to a pharmaceutica