56844-40-7

Usage

Uses

Used in Pharmaceutical Industry:
6-BROMO-1H-THIENO[2,3-D]PYRIMIDIN-4-ONE is used as a key intermediate in the synthesis of various biologically active compounds, contributing to the development of new pharmaceuticals. Its unique structure allows for the creation of diverse drug candidates with potential therapeutic applications.
Used in Agricultural Industry:
In the agricultural sector, 6-BROMO-1H-THIENO[2,3-D]PYRIMIDIN-4-ONE serves as a building block for the synthesis of agrochemicals, including pesticides and herbicides. Its reactivity and structural features enable the development of effective compounds for crop protection and enhancement of agricultural productivity.
Used in Organic Synthesis:
6-BROMO-1H-THIENO[2,3-D]PYRIMIDIN-4-ONE is utilized as a valuable intermediate in organic synthesis, providing a platform for the creation of a wide range of chemical compounds. Its unique reactivity and structural attributes make it an essential component in the synthesis of complex organic molecules for various applications.

InChI:InChI=1/C6H3BrN2OS/c7-4-1-3-5(10)8-2-9-6(3)11-4/h1-2H,(H,8,9,10)

Upstream product

• 14080-50-3 thieno[2,3-d]pyrimidin-4(3H)one 
• 4651-81-4 Methyl 2-aminothiophene-3-carboxylate 
• 77287-34-4 formamide 
• 14080-50-3 4-hydroxythieno[2,3-d]pyrimidine 
• 43028-71-3 2-formylaminothiophene-3-carboxamide 
• 4651-82-5 2-amino-3-cyanothiophene 

Downstream Products

• 56844-12-3 6-bromo-4-chlorothieno[2,3-d]pyrimidine 
• 1428537-29-4 C₁₇H₁₅N₃O₃S 
• 1428537-30-7 C₁₄H₁₂N₂O₃S 

Relevant academic research and scientific papers

Discovery of S64315, a Potent and Selective Mcl-1 Inhibitor

Myeloid cell leukemia 1 (Mcl-1) has emerged as an attractive target for cancer therapy. It is an antiapoptotic member of the Bcl-2 family of proteins, whose upregulation in human cancers is associated with high tumor grade, poor survival, and resistance to chemotherapy. Here we report the discovery of our clinical candidate S64315, a selective small molecule inhibitor of Mcl-1. Starting from a fragment derived lead compound, we have conducted structure guided optimization that has led to a significant (3 log) improvement of target affinity as well as cellular potency. The presence of hindered rotation along a biaryl axis has conferred high selectivity to the compounds against other members of the Bcl-2 family. During optimization, we have also established predictive PD markers of Mcl-1 inhibition and achieved both efficient in vitro cell killing and tumor regression in Mcl-1 dependent cancer models. The preclinical candidate has drug-like properties that have enabled its development and entry into clinical trials.

Discovery of thieno[2,3-d]pyrimidin-4(3H)-one derivatives as a new class of ROCK inhibitors

Herein, we report the discovery of a series of thieno[2,3-d]pyrimidin-4(3H)-one derivatives as a new class of ROCK inhibitors. Structure-activity relationship studies of these compounds led to the identification of the most potent compound, 3-(3-methoxybenzyl)-6-(1H-pyrrolo[2,3-b]pyridin-4-yl)thieno[2,3-d]pyrimidin-4(3H)-one (8k), which showed IC50 values of 0.004 μM and 0.001 μM against ROCK Ⅰ and ROCK Ⅱ, respectively. In vitro, 8k significantly reduced the phosphorylation level of ROCK downstream signaling protein and induce changes in cell morphology and migration. Overall, this study provides a promising lead compound for drug discovery targeting ROCKs.

NOVEL PYRIMIDINE DERIVATIVE AND ANTIBACTERIAL AGENT CONTAINING THE SAME

PROBLEM TO BE SOLVED: To provide a novel compound that has a dihydrofolic acid reductase inhibitory activity with improved efficacy, and can extend the range of choices of drug therapy for infections caused by resistant bacteria; an antibacterial agent containing the compound or a salt thereof; and a dihydrofolic acid reductase inhibitor with improved efficacy. SOLUTION: The present invention provides a compound having a 2, 4-diaminopyrimidine skeleton, represented by the formula (I), or a salt thereof, and an antibacterial agent containing the compound or a salt thereof as an active ingredient. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

One-pot synthesis of α-aminophosphonates via a cascade sequence of allylamine isomerization/hydrophosphonylation

A Rh/Ni-catalyzed cascade sequence of allylamine isomerization and hydrophosphonylation to synthesize α-aminophosphonates has been disclosed. The reaction, which not only allows the generation of widespread valuable α-aminophosphonates under simple system

THIENOPYRIMIDINONE NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed herein, in part, are heteroaromatic compounds and methods of use in treating neuropsychiatric disorders, e.g., schizophrenia and major depressive disorder. Pharmaceutical compositions and methods of making heteroaromatic compounds are provided.

Pharmacophore Mapping of Thienopyrimidine-Based Monophosphonate (ThP-MP) Inhibitors of the Human Farnesyl Pyrophosphate Synthase

The human farnesyl pyrophosphate synthase (hFPPS), a key regulatory enzyme in the mevalonate pathway, catalyzes the biosynthesis of the C-15 isoprenoid farnesyl pyrophosphate (FPP). FPP plays a crucial role in the post-translational prenylation of small GTPases that perform a plethora of cellular functions. Although hFPPS is a well-established therapeutic target for lytic bone diseases, the currently available bisphosphonate drugs exhibit poor cellular uptake and distribution into nonskeletal tissues. Recent drug discovery efforts have focused primarily on allosteric inhibition of hFPPS and the discovery of non-bisphosphonate drugs for potentially treating nonskeletal diseases. Hit-to-lead optimization of a new series of thienopyrimidine-based monosphosphonates (ThP-MPs) led to the identification of analogs with nanomolar potency in inhibiting hFPPS. Their interactions with the allosteric pocket of the enzyme were characterized by crystallography, and the results provide further insight into the pharmacophore requirements for allosteric inhibition.

Discovery of a novel series of thienopyrimidine as highly potent and selective PI3K inhibitors

Inhibition of the phosphoinositide 3-kinase (PI3K)/AKT/mammalian target of rapamycin (mTOR) signaling pathway provides a promising new approach for cancer therapy. Through a rational design, a novel series of thienopyrimidine was discovered as highly pote

Protozoan Parasite Growth Inhibitors Discovered by Cross-Screening Yield Potent Scaffolds for Lead Discovery

Tropical protozoal infections are a significant cause of morbidity and mortality worldwide; four in particular (human African trypanosomiasis (HAT), Chagas disease, cutaneous leishmaniasis, and malaria) have an estimated combined burden of over 87 million disability-adjusted life years. New drugs are needed for each of these diseases. Building on the previous identification of NEU-617 (1) as a potent and nontoxic inhibitor of proliferation for the HAT pathogen (Trypanosoma brucei), we have now tested this class of analogs against other protozoal species: T. cruzi (Chagas disease), Leishmania major (cutaneous leishmaniasis), and Plasmodium falciparum (malaria). Based on hits identified in this screening campaign, we describe the preparation of several replacements for the quinazoline scaffold and report these inhibitors' biological activities against these parasites. In doing this, we have identified several potent proliferation inhibitors for each pathogen, such as 4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-(4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)phenyl)quinoline-3-carbonitrile (NEU-924, 83) for T. cruzi and N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-7-(4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)phenyl)cinnolin-4-amine (NEU-1017, 68) for L. major and P. falciparum.

4-AMINO-6-ARYL[2,3-D]PYRIMIDINES FOR THE INHIBITION OF EGFR TYROSINE KINASE

This invention relates to certain new pyrrolo-, thieno-, and furo-[2,3- d]pyrimidine compounds, such as of general formula (I) These compounds are epidermal growth factor receptor tyrosine kinase inhibitors and therefore offer potential in the treatment of cancer.

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