14080-59-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Chlorothieno[2,3-d]pyrimidine is used as an intermediate compound for the development of various pharmaceutical products. Its chemical properties make it a suitable candidate for the synthesis of new drugs, particularly those targeting specific biological pathways or receptors.
Used in Chemical Research:
In the field of chemical research, 4-Chlorothieno[2,3-d]pyrimidine is utilized as a key component in the study of novel chemical reactions and the development of new synthetic methods. Its unique structure allows researchers to explore its reactivity and potential applications in creating new molecules with desired properties.
Used in Material Science:
4-Chlorothieno[2,3-d]pyrimidine is also used as a building block in the development of new materials with specific properties, such as optoelectronic materials or advanced polymers. Its incorporation into these materials can lead to enhanced performance or novel functionalities.

InChI:InChI=1/C6H3ClN2S/c7-5-4-1-2-10-6(4)9-3-8-5/h1-3H

Upstream product

• 14080-50-3 thieno[2,3-d]pyrimidin-4(3H)one 
• 75-09-2 dichloromethane 
• 56387-08-7 2-aminothiophene-3-carboxylic acid 
• 4651-81-4 Methyl 2-aminothiophene-3-carboxylate 
• 79-37-8 oxalyl dichloride 
• 14080-50-3 4-hydroxythieno[2,3-d]pyrimidine 
• 4651-82-5 2-amino-3-cyanothiophene 
• 55654-21-2 methyl 2-formylaminothiophene-3-carboxylate 
• 14080-50-3 thieno[2,3-d]pyrimidin-4(1H)-one 

Downstream Products

• 14080-52-5 4-methoxythieno[2,3-d]pyrimidine 
• 14080-54-7 4-phenoxythieno[2,3-d]pyrimidine 
• 18740-24-4 4-phenylsulfanyl-thieno[2,3-d]pyrimidine 
• 272-24-2 Thieno<2,3-d>pyrimidine 
• 14080-56-9 thieno[2,3-d]pyrimidin-4-amine 
• 14080-55-8 4-Thioxo-3,4-dihydro-thieno<2,3-d>pyrimidin 
• 18740-21-1 N-phenylthieno[2,3-d]pyrimidin-4-amine 
• 86825-96-9 4-chlorothieno[2,3-d]pyrimidine-6-carboxylic acid 
• 781616-96-4 4-(4-methoxyphenoxy)thieno[2,3-d]pyrimidine 
• 1174498-41-9 4-(4-methoxyphenyl)thiophene[2,3-d]pyrimidine 
• 1174498-43-1 1-(3-thieno[2,3-d]pyrimidin-4-ylphenyl)ethanone 

Relevant academic research and scientific papers

Design, synthesis, docking, molecular dynamics and bioevaluation studies on novel N-methylpicolinamide and thienopyrimidine derivatives with inhibiting NF-κB and TAK1 activities: Cheminformatics tools RDKit applied in drug design

Using cheminformatics tools RDKit and literature investigation, four series of 24 thienopyrimidine/N-methylpicolinamide derivatives substituted with pyrimidine were designed, synthesized and evaluated for activities against three cancer cell lines (MDA-MB-231, HCT116 and A549), TAK1 kinase and NF-κB signaling pathway. Almost all compounds showed selectivity toward the A549 cell lines and the most promising compound 38 could inhibit TAK1 kinase and NF-κB signaling pathway with the IC50 values of 0.58 and 0.84 μM. Moreover, 38 can induce cell cycle arrest of A549 cells at the G2/M checkpoint with 30.57% and induce apoptosis (34.94%) in a concentration-dependent manner. And western blot showed that compound 38 could inhibit TNF-α-induced IκBα phosphorylation, IκBα degradation, p65 phosphorylation and TAK1 phosphorylation, and reduce the expression of p65. What's more, the studies of docking, molecular dynamics, MM/PBSA and frequency analysis theoretically supported the conclusions of the bioevaluation.

Synthesis and antimicrobial activity of novel thienopyrimidine linked rhodanine derivatives

This work presents the preparation of a new series of N-(substituted phenyl)-2-(4-oxo-5-(4-(thieno[2,3-d]-pyrimidin-4-yloxy)benzylidene)-2-thioxothiazolidin-3-yl)acetamide derivatives (8a-8l). A condensation reaction of thienopyrimidin-2-thioxothiazolidin

Subtle modifications to a thieno[2,3-d]pyrimidine scaffold yield negative allosteric modulators and agonists of the dopamine D2 receptor

We recently described a structurally novel series of negative allosteric modulators (NAMs) of the dopamine D2 receptor (D2R) based on thieno[2,3-d]pyrimidine 1, showing it can be structurally simplified to reveal low molecular weight, fragment-like NAMs that retain robust negative cooperativity, such as 3. Herein, we report the synthesis and functional profiling of analogues of 3, placing specific emphasis on examining secondary and tertiary amino substituents at the 4-position, combined with a range of substituents at the 5/6-positions (e.g. aromatic/aliphatic carbocycles). We identify analogues with diverse pharmacology at the D2R including NAMs with sub-μM affinity (9h) and, surprisingly, low efficacy partial agonists (9d and 9i).

Design, Synthesis, and Biological Evaluation of 6-Substituted Thieno[3,2- d]pyrimidine Analogues as Dual Epidermal Growth Factor Receptor Kinase and Microtubule Inhibitors

The clinical evidence for the success of tyrosine kinase inhibitors in combination with microtubule-targeting agents prompted us to design and develop single agents that possess both epidermal growth factor receptor (EGFR) kinase and tubulin polymerization inhibitory properties. A series of 6-aryl/heteroaryl-4-(3′,4′,5′-trimethoxyanilino)thieno[3,2-d]pyrimidine derivatives were discovered as novel dual tubulin polymerization and EGFR kinase inhibitors. The 4-(3′,4′,5′-trimethoxyanilino)-6-(p-tolyl)thieno[3,2-d]pyrimidine derivative 6g was the most potent compound of the series as an antiproliferative agent, with half-maximal inhibitory concentration (IC50) values in the single- or double-digit nanomolar range. Compound 6g bound to tubulin in the colchicine site and inhibited tubulin assembly with an IC50 value of 0.71 μM, and 6g inhibited EGFR activity with an IC50 value of 30 nM. Our data suggested that the excellent in vitro and in vivo profile of 6g may be derived from its dual inhibition of tubulin polymerization and EGFR kinase.

Synthesis and bioevaluation study of novel N-methylpicolinamide and thienopyrimidine derivatives as selectivity c-Met kinase inhibitors

Four series of N-methylpicolinamide moiety and thienopyrimidine moiety bearing pyridazinone were designed and synthesized and evaluated for the IC50 values against three cancer cell lines (A549, HepG2 and MCF-7) and some selected compounds were

Synthesis and antioxidant evaluation of a new class of thienopyrimidinerhodanine hybrids

Background: Antioxidants are proficient of stabilizing agents in the target cells and biological systems. The homeostatic equilibrium between the reactive oxygen species and endogenous antioxidants is important in maintaining healthy tissues. As some antioxidant agent’s show improved resistance, it is necessary to design the new heterocyclic molecules to form potent antioxidant agents with promising pharmacological applications. Moreover, thienopyrimidine derivatives has been the subject of much research due to their significance in different applications and their extensive potential pharmacological and medicinal activities like antibacterial, antifungal, anticancer, anticonvulsant, anti-inflammatory, analgesic, anti-viral, anti-oxidant, anti-diabetic and antimalarial properties. Although, recently rhodanine was reported as privileged hybrid in drug discovery and exhibited pharmacological activities such as anti-malarial, antibacterial, antiviral, antidiabetic agents. Hence, the development of new molecules within the scope of synthetic procedure of thienopyrimidine scaffold for heterocyclic synthesis would be worthy and well desired. Methods: All the target thienopyrimidine-rhodanine derivatives (5a-l) prepared from the Knoevenagel condensation with different substituted benzaldehydes in the presence of glacial acetic acid and 3-(thieno[2,3-d]pyrimidin-4-yl)-2-thioxothiazolidin-4-one (4). Although, all the synthesized compounds tested for their anti-oxidant activity investigated using DPPH radical scavenging, nitric oxide (NO) and ABTS activity. Results: All the thienopyrimidine-rhodanine derivatives (5a-l) were evaluated for their in vitro anti-oxidant activity. In fact, (Z)-5-(4-methylbenzylidene)-3-(thieno[2,3-d]pyrimidin-4-yl)-2-thioxothiazolidin-4-one (5c) with IC50 value 17.64 ± 0.06 μg/mL and (Z)-5-(2-nitrobenzylidene)-3-(thieno[2,3-d]pyrimidin-4-yl)-2-thioxothiazolidin-4-one (5j) with IC50 value 17.54 ± 0.23μg/mL showed excellent antioxidant activity nearly similar to the standard drug as an ascorbic acid (IC50 = 17.45 ± 0.03μg/mL). Conclusion: The objective of the present work was to design, synthesis and screened for their antioxidant activities of novel thienopyrimidine containing rhodanine derivatives with the hope of discovering new structure leads as the most potent antioxidant agents. Our aim has been achieved by the synthesis of thienopyrimidines with diver functionalities by exploiting 2-thioxothiazolidin-4-one chemistry and tested for antioxidant activity. The compounds 5c and 5j were found most potent activity compare to the standard ascorbic acid. Furthermore, the electron withdrawing groups at position-4 in benzene ring enhanced the activity, whereas the compounds 5d, 5f, 5i and 5l showed good activity all the three radical scavenging methods.

Iridium complex containing thieno-[2,3-d] pyrimidine group and application in electroluminescence device

The invention disclose an iridium complex containing a thieno-[2,3-d] pyrimidine group and application of the iridium complex as a phosphorescence object material in an electroluminescence device. Main ligands in the series of iridium complex molecules are derivatives containing thieno-[2,3-d] pyrimidine heterocyclic rings. Auxiliary ligands are diacetone, tetramethyl-3,5-heptanedione or 2-pyridine carboxylic acid. The iridium complex has the characteristics of high luminous efficiency, stable chemical property, easy purification and the like, and the application of the iridium complex as thephosphorescence object material in an electroluminescence device has excellent luminous efficiency, electron mobility and stability. Through the modification of the main ligands, the luminous wavelength and efficiency of the complex can be adjusted in a visible light band.

A JAK/STAT3 phosphorylation inhibitor and its preparation method and use thereof

The invention provides a JAK/STAT3 phosphorylation inhibitor as well as a preparation method and application thereof. The structural formula of the JAK/STAT3 phosphorylation inhibitor is as shown in a formula I, wherein X is selected from S or O; Y and Z

Preparation and application of thiophene pyrimindine compound containing heteroaryl amide structure

The invention relates to a thiophene pyrimindine compound containing a heteroaryl amide structure shown in the general formula I, and a pharmaceutically acceptable salt, an aquo-complex, a solvate and a predrug of the thiophene pyrimindine compound containing the heteroaryl amide structure, wherein the implications of the substituent group R1, X, Y, D and Z are shown in the description. The invention further relates to a strong effect of inhibiting c-Met kinase of the compound shown in the general formula I, and also relates to application of the compound and the pharmaceutically acceptable salt, the aquo-complex, the solvate and the predrug of the thiophene pyrimindine compound to preparing a medicine used for treating diseases caused by abnormal high expression of the c-Met kinase, particularly application to preparing a medicine for treating and/or preventing cancers.

HETEROCYCLIC COMPOUNDS, PROCESS FOR PREPARATION OF THE SAME AND USE THEREOF

The present invention provides a heterocyclic compound represented by the formula (I), its stereoisomers, or a pharmaceutically acceptable salt thereof, pharmaceutical compositions thereof, and their use in preparing a medicament for the prevention and/or treatment of central nervous system disease.