14080-50-3

Usage

Uses

Used in Pharmaceutical Industry:
Thieno[2,3-d]pyrimidin-4(3H)one is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique chemical structure allows it to be a versatile component in the synthesis of novel drugs, potentially leading to the discovery of new treatments for a range of medical conditions.
Used in Chemical Research:
In the field of chemical research, Thieno[2,3-d]pyrimidin-4(3H)one is employed as a subject of study to understand its reactivity, stability, and potential applications in creating new chemical entities. Researchers may use Thieno[2,3-d]pyrimidin-4(3H)one to explore new reaction pathways and develop innovative synthetic methods.
Used in Material Science:
Thieno[2,3-d]pyrimidin-4(3H)one may also find applications in material science, particularly in the development of new materials with unique properties. Its incorporation into polymers or other materials could lead to advancements in areas such as electronics, optics, or nanotechnology.

InChI:InChI=1/C6H4N2OS/c9-5-4-1-2-10-6(4)8-3-7-5/h1-3H,(H,7,8,9)

Upstream product

• 55654-21-2 methyl 2-formylaminothiophene-3-carboxylate 
• 4651-82-5 2-amino-3-cyanothiophene 
• 64-18-6 formic acid 
• 43028-71-3 2-formylaminothiophene-3-carboxamide 
• 4651-81-4 Methyl 2-aminothiophene-3-carboxylate 
• 77287-34-4 formamide 
• 18740-32-4 3-benzyl-3H-thieno[2,3-d]pyrimidin-4-one 
• 14080-51-4 2-aminothiophene-3-carboxamide 
• 122-51-0 orthoformic acid triethyl ester 
• 215928-52-2 2-formylaminothiophene-3-carboxylic acid ethyl ester 
• 3473-63-0 formamidine acetic acid 
• 463-52-5 formamidine 
• 31891-06-2 ethyl 2-aminothiophene-3-carboxylate 
• 56387-08-7 2-aminothiophene-3-carboxylic acid 

Downstream Products

• 18740-32-4 3-benzyl-3H-thieno[2,3-d]pyrimidin-4-one 
• 18740-31-3 3-Methyl-4-oxo-3,4-dihydro-thieno<2,3-d>pyrimidin 
• 14080-59-2 4-chlorothieno[2,3-d]pyrimidine 
• 56844-40-7 6-bromothieno[2,3-d]pyrimidin-4(3H)-one 
• 56844-41-8 6-Nitro-thieno<2,3-d>pyrimid-4-on 
• 94644-73-2 3-β-D-ribofuranosylthieno<2,3-d>pyrimidin-4-one 
• 94620-73-2 C₃₂H₂₄N₂O₈S 
• 14080-56-9 thieno[2,3-d]pyrimidin-4-amine 
• 14080-52-5 4-methoxythieno[2,3-d]pyrimidine 
• 18740-21-1 N-phenylthieno[2,3-d]pyrimidin-4-amine 
• 14080-54-7 4-phenoxythieno[2,3-d]pyrimidine 
• 18740-24-4 4-phenylsulfanyl-thieno[2,3-d]pyrimidine 
• 56844-12-3 6-bromo-4-chlorothieno[2,3-d]pyrimidine 
• 1048007-28-8 4-(4-methylphenyl)thiophene[2,3-d]pyrimidine 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of 4-anilinothieno[2,3-d]pyrimidine-based hydroxamic acid derivatives as novel histone deacetylase inhibitors

A series of 4-anilinothieno[2,3-d]pyrimidine-based hydroxamic acid derivatives as novel HDACs inhibitors were designed, synthesized and evaluated. Most of these compounds displayed good to excellent inhibitory activities against HDAC1, 3, 6. The IC50 values of compound 10r against HDAC1, HDAC3, HDAC6 was 1.14 ± 0.03 nM, 3.56 ± 0.08 nM, 11.43 ± 0.12 nM. Compound 10r noticeably up-regulated the level of histone H3 acetylation compared to the SAHA. Most of the compounds showed the strong anti-proliferative activity against human cancer cell lines including RMPI8226 and HCT-116. The IC50 values of Compounds 10r and 10t against RPMI8226 was 2.39 ± 0.20 μM, 1.41 ± 0.44 μM, respectively, and the HCT-116 was sensitive to the compounds 10h, 10m, 10r, 10w with the IC50 values 1.9 μM.

Evaluation of aromatic 6-substituted thienopyrimidines as scaffolds against parasites that cause trypanosomiasis, leishmaniasis, and malaria

Target repurposing is a proven method for finding new lead compounds that target Trypanosoma brucei, the causative agent of human African trypanosomiasis. Due to the recent discovery of a lapatinib-derived analog 2 with excellent potency against T. brucei (EC50 = 42 nM) and selectivity over human host cells, we have explored other classes of human tyrosine kinase inhibitor scaffolds in order to expand the range of chemotypes for pursuit. Following library expansion, we found compound 11e to have an EC50 of 84 nM against T. brucei cells while maintaining selectivity over human hepatocytes. In addition, the library was tested against causative agents of Chagas' disease, leishmaniasis, and malaria. Two analogs with sub-micromolar potencies for T. cruzi (4j) and Plasmodium falciparum (11j) were discovered, along with an analog with considerable potency against Leishmania major amastigotes (4e). Besides identifying new and potent protozoan growth inhibitors, these data highlight the value of concurrent screening of a chemical library against different protozoan parasites. This journal is

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.

6-Cinnamoyl-4-arylaminothienopyrimidines as highly potent cytotoxic agents: Design, synthesis and structure-activity relationship studies

In this paper, we described the synthesis and cytotoxic activities of two new series of thieno[2,3-d]pyrimidine and thieno[3,2-d] pyrimidine derivatives. Most of the synthesized compounds had significant antiproliferative activities against PC3, MDA-MB-23

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

MACROCYCLIC MCL-1 INHIBITORS AND METHODS OF USE

The present disclosure provides for compounds of Formula (I) wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of Formula (I).

Macrocyclic MCL-1 inhibitors and methods of use

The present disclosure provides for compounds of Formula (I) wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents for the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of Formula (I).

MACROCYCLIC MCL-1 INHIBITORS AND METHODS OF USE

The present disclosure provides for compounds of formula (I), wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of formula (I).

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.