Page last updated: 2024-12-10

2-(4-chlorophenyl)-5-methyl-4-oxo-2,3-dihydro-1H-thieno[3,4-d]pyrimidine-7-carboxylic acid ethyl ester

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## 2-(4-Chlorophenyl)-5-methyl-4-oxo-2,3-dihydro-1H-thieno[3,4-d]pyrimidine-7-carboxylic acid ethyl ester

This is a long and complex chemical name, but it describes a specific molecule with a particular structure. Here's a breakdown of the name and its significance:

**Structure:** The name describes a molecule containing a **fused ring system** with a **thienopyrimidine core**. This core is a combination of a thiophene ring (a five-membered ring with a sulfur atom) and a pyrimidine ring (a six-membered ring with two nitrogen atoms).

**Substituents:** The name also indicates the presence of several **substituents** attached to this core:

* **2-(4-Chlorophenyl):** A 4-chlorophenyl group is attached at the 2-position of the thienopyrimidine core. This means a benzene ring with a chlorine atom at the 4-position is connected to the thienopyrimidine ring.
* **5-Methyl:** A methyl group (CH3) is attached at the 5-position.
* **4-oxo:** A carbonyl group (C=O) is attached at the 4-position.
* **2,3-dihydro:** The 2 and 3 positions of the pyrimidine ring are saturated, meaning they have two hydrogen atoms attached instead of a double bond.
* **1H:** A hydrogen atom is attached at the 1-position of the pyrimidine ring.
* **7-carboxylic acid ethyl ester:** This indicates a carboxyl group (-COOH) is attached at the 7-position of the thienopyrimidine core, and the carboxyl group is esterified with an ethyl group (-COOC2H5).

**Why is it important for research?**

This molecule, often referred to as a **thienopyrimidine derivative,** is important for research due to its potential **biological activity:**

* **Anti-cancer activity:** Thienopyrimidine derivatives have been shown to possess anti-cancer properties, potentially through various mechanisms such as inhibiting cell growth, inducing apoptosis (programmed cell death), and interfering with DNA replication. This specific compound has been studied for its potential as an anti-cancer drug.
* **Anti-inflammatory activity:** Thienopyrimidines also have shown potential anti-inflammatory effects. They may work by inhibiting the production of inflammatory mediators.
* **Antimicrobial activity:** Some thienopyrimidine derivatives have exhibited antimicrobial activity, which could lead to the development of new antibiotics.
* **Other therapeutic applications:** The specific molecule mentioned has been investigated for its potential in other areas like anti-viral activity.

**Research in progress:** Scientists are actively exploring the biological properties of this and related thienopyrimidine derivatives to understand their mechanisms of action and potential therapeutic applications. Ongoing research aims to:

* **Optimize its activity:** Researchers are working to modify the structure of this molecule to improve its potency, selectivity, and pharmacological properties.
* **Develop new drug candidates:** The goal is to develop new drugs based on this chemical scaffold to treat various diseases.
* **Understand its mechanisms:** Researchers are trying to elucidate the molecular mechanisms by which this molecule exerts its biological activity.

**In conclusion,** 2-(4-Chlorophenyl)-5-methyl-4-oxo-2,3-dihydro-1H-thieno[3,4-d]pyrimidine-7-carboxylic acid ethyl ester is a promising molecule for research due to its potential biological activity and its potential as a lead compound for the development of new drugs.

Cross-References

ID SourceID
PubMed CID3733246
CHEMBL ID1306269
CHEBI ID120053

Synonyms (12)

Synonym
MLS000554087
2-(4-chloro-phenyl)-5-methyl-4-oxo-1,2,3,4-tetrahydro-thieno[3,4-d]pyrimidine-7-carboxylic acid ethyl ester
smr000146404
CHEBI:120053
ethyl 2-(4-chlorophenyl)-5-methyl-4-oxo-2,3-dihydro-1h-thieno[3,4-d]pyrimidine-7-carboxylate
AKOS005465745
ethyl 2-(4-chlorophenyl)-5-methyl-4-oxo-1,2,3,4-tetrahydrothieno[3,4-d]pyrimidine-7-carboxylate
STK533873
CHEMBL1306269
HMS2281K18
Q27207855
2-(4-chlorophenyl)-5-methyl-4-oxo-2,3-dihydro-1h-thieno[3,4-d]pyrimidine-7-carboxylic acid ethyl ester
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
organosulfur heterocyclic compound
organic heterobicyclic compound
organonitrogen heterocyclic compoundAny organonitrogen compound containing a cyclic component with nitrogen and at least one other element as ring member atoms.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (12)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency19.95260.177814.390939.8107AID2147
Chain A, CruzipainTrypanosoma cruziPotency31.62280.002014.677939.8107AID1476
acid sphingomyelinaseHomo sapiens (human)Potency25.118914.125424.061339.8107AID504937
TDP1 proteinHomo sapiens (human)Potency24.84460.000811.382244.6684AID686978; AID686979
IDH1Homo sapiens (human)Potency23.10930.005210.865235.4813AID686970
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency28.18380.001815.663839.8107AID894
huntingtin isoform 2Homo sapiens (human)Potency12.58930.000618.41981,122.0200AID1688
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency35.48130.00798.23321,122.0200AID2546
muscleblind-like protein 1 isoform 1Homo sapiens (human)Potency14.12540.00419.962528.1838AID2675
neuropeptide S receptor isoform AHomo sapiens (human)Potency12.58930.015812.3113615.5000AID1461
Glycoprotein hormones alpha chainHomo sapiens (human)Potency3.54814.46688.344810.0000AID624291
Inositol monophosphatase 1Rattus norvegicus (Norway rat)Potency28.18381.000010.475628.1838AID1457
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (14)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell population proliferationGlycoprotein hormones alpha chainHomo sapiens (human)
hormone-mediated signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
regulation of signaling receptor activityGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of steroid biosynthetic processGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell migrationGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid gland developmentGlycoprotein hormones alpha chainHomo sapiens (human)
luteinizing hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIGlycoprotein hormones alpha chainHomo sapiens (human)
negative regulation of organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid hormone generationGlycoprotein hormones alpha chainHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
protein bindingGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
extracellular regionGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
Golgi lumenGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone complexGlycoprotein hormones alpha chainHomo sapiens (human)
pituitary gonadotropin complexGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's3 (60.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.56

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.56 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]