Page last updated: 2024-12-07

2-(2,6-dioxopiperidin-3-yl)phthalimidine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

## 2-(2,6-Dioxopiperidin-3-yl)phthalimidine: A Molecule with Potential

**2-(2,6-Dioxopiperidin-3-yl)phthalimidine**, also known as **phthalimidine derivative**, is a molecule with a complex structure incorporating a phthalimidine ring system and a 2,6-dioxopiperidine ring. Its importance lies in its potential for various research applications, including:

**1. Anti-cancer activity:**

* **Potential to inhibit cell growth and induce apoptosis:** Studies have shown that 2-(2,6-dioxopiperidin-3-yl)phthalimidine exhibits anti-proliferative effects against various cancer cell lines, potentially by interfering with cell cycle progression and triggering programmed cell death.
* **Targeting specific cancer pathways:** Its specific structure and interactions with biological targets are being explored for targeting cancer pathways, potentially leading to more effective and targeted cancer therapies.

**2. Anti-bacterial activity:**

* **Potential to inhibit bacterial growth:** Some research suggests that this molecule may have antibacterial properties, potentially inhibiting the growth of certain bacteria, including drug-resistant strains.
* **Developing new antibiotic therapies:** Exploring the antibacterial mechanisms of 2-(2,6-dioxopiperidin-3-yl)phthalimidine could lead to the development of novel antibiotic therapies to combat bacterial infections.

**3. Chemical probe for biological studies:**

* **Understanding biological processes:** Its unique structure and potential for biological interactions make it a valuable chemical probe to study various biological processes, such as enzyme activity and protein-protein interactions.
* **Developing new diagnostic tools:** Its ability to bind to specific targets could be utilized in developing new diagnostic tools for detecting diseases and monitoring treatment responses.

**4. Lead compound for drug development:**

* **Structurally modifiable for optimization:** The complex structure of 2-(2,6-dioxopiperidin-3-yl)phthalimidine allows for modifications to enhance its activity, improve its pharmacokinetic properties, and reduce side effects.
* **Developing new therapeutic agents:** Its potential in various biological applications makes it a promising lead compound for developing new therapeutic agents for various diseases, including cancer, bacterial infections, and neurodegenerative disorders.

**However, it's important to note that:**

* The research on 2-(2,6-dioxopiperidin-3-yl)phthalimidine is still ongoing, and further studies are needed to confirm its efficacy and safety in humans.
* Its potential applications and the mechanisms of action are still being investigated and require further research to be fully understood.

Overall, 2-(2,6-dioxopiperidin-3-yl)phthalimidine represents a promising molecule with potential applications in various research fields, especially in the development of new therapeutic agents and diagnostic tools. Its specific structure and potential for biological interactions make it an exciting research target for future investigations.

2-(2,6-dioxopiperidin-3-yl)phthalimidine: thalidomide analog; structure; RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID91585
CHEMBL ID304572
SCHEMBL ID476917
MeSH IDM0041166

Synonyms (39)

Synonym
em 12
3-(1,3-dihydro-1-oxo-2h-isoindol-2-yl)-2,6-piperidinedione
glutarimide, 2-(1-oxo-2-isoindolinyl)-
2,6-piperidinedione, 3-(1,3-dihydro-1-oxo-2h-isoindol-2-yl)-
phthalimidine, 2-(2,6-dioxopiperiden-3-yl)-
2-(2,6-dioxopiperiden-3-yl) phthalimidine
phthalimidinoglutarimide
3-(1,3-dihydro-1-oxo-2h-isoindol-2-yl)-2,6-dioxopiperidine
CHEMBL304572
26581-81-7
3-(3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione
em-12
2-(2,6-dioxopiperidin-3-yl)phthalimidine
2-(1-oxo-2-isoindolinyl)glutarimide
(+-)-em 12
1-oxo-2(2,6-dioxopiperidin-3-yl)-isoindoline
1-oxo-2-(2,6-dioxopiperidin-3-yl)isoindoline
1-oxo-2-(2,6-dioxopiperidin-3-yl)-isoindoline
WENKGSGGXGQHSH-UHFFFAOYSA-N
em12
SCHEMBL476917
3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione
TQR1041
mfcd01748359
Q26840990
phthalimidine, 2-(2,6-dioxopiperiden-3-yl)
AT11987
GS-9752
BBA58181
3-(1-oxo-2,3-dihydro-1h-isoindol-2-yl)piperidine-2,6-dione
CS-0168360
HY-138793
PD163468
STARBLD0036086
BP-27971
DTXSID401034323
EN300-1697928
AKOS040758563
Z3068705955

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" The mean plasma elimination half-life was in the range of 5 h for the enantiomers, as well as for the racemic mixture, although there was a tendency toward slower elimination and higher plasma AUC values of the S-enantiomer: thus, after administration of the (greater than 99%) pure enantiomers, the plasma AUC value of the administered S-enantiomer was found to be more than one-third higher than that of the administered R-enantiomer."( The enantiomers of the teratogenic thalidomide analogue EM 12: 1. Chiral inversion and plasma pharmacokinetics in the marmoset monkey.
Nau, H; Neubert, D; Schmahl, HJ, 1988
)
0.27

Dosage Studied

ExcerptRelevanceReference
"The dose-response of the teratogenic potency of the thalidomide (Thd) derivative EM12 was evaluated in the common marmoset (Callithrix jacchus)."( Embryotoxic effects of thalidomide derivatives in the non-human primate callithrix jacchus. IV. Teratogenicity of micrograms/kg doses of the EM12 enantiomers.
Felies, A; Heger, W; Klug, S; Merker, HJ; Nau, H; Neubert, D; Schmahl, HJ, 1994
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DNA-binding protein IkarosHomo sapiens (human)DC500.19270.02670.10310.1927AID1769486
Protein cereblonHomo sapiens (human)DC500.19270.00800.48352.1000AID1769486
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (13)

Processvia Protein(s)Taxonomy
chromatin organizationDNA-binding protein IkarosHomo sapiens (human)
mesoderm developmentDNA-binding protein IkarosHomo sapiens (human)
lymphocyte differentiationDNA-binding protein IkarosHomo sapiens (human)
erythrocyte differentiationDNA-binding protein IkarosHomo sapiens (human)
negative regulation of DNA-templated transcriptionDNA-binding protein IkarosHomo sapiens (human)
regulation of transcription by RNA polymerase IIDNA-binding protein IkarosHomo sapiens (human)
protein ubiquitinationProtein cereblonHomo sapiens (human)
positive regulation of Wnt signaling pathwayProtein cereblonHomo sapiens (human)
negative regulation of protein-containing complex assemblyProtein cereblonHomo sapiens (human)
positive regulation of protein-containing complex assemblyProtein cereblonHomo sapiens (human)
negative regulation of monoatomic ion transmembrane transportProtein cereblonHomo sapiens (human)
locomotory exploration behaviorProtein cereblonHomo sapiens (human)
proteasome-mediated ubiquitin-dependent protein catabolic processProtein cereblonHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
DNA bindingDNA-binding protein IkarosHomo sapiens (human)
protein bindingDNA-binding protein IkarosHomo sapiens (human)
protein domain specific bindingDNA-binding protein IkarosHomo sapiens (human)
metal ion bindingDNA-binding protein IkarosHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingDNA-binding protein IkarosHomo sapiens (human)
DNA-binding transcription factor activityDNA-binding protein IkarosHomo sapiens (human)
protein bindingProtein cereblonHomo sapiens (human)
transmembrane transporter bindingProtein cereblonHomo sapiens (human)
metal ion bindingProtein cereblonHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
nucleusDNA-binding protein IkarosHomo sapiens (human)
nucleoplasmDNA-binding protein IkarosHomo sapiens (human)
cytosolDNA-binding protein IkarosHomo sapiens (human)
pericentric heterochromatinDNA-binding protein IkarosHomo sapiens (human)
protein-containing complexDNA-binding protein IkarosHomo sapiens (human)
nucleusProtein cereblonHomo sapiens (human)
cytoplasmProtein cereblonHomo sapiens (human)
cytosolProtein cereblonHomo sapiens (human)
membraneProtein cereblonHomo sapiens (human)
perinuclear region of cytoplasmProtein cereblonHomo sapiens (human)
Cul4A-RING E3 ubiquitin ligase complexProtein cereblonHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID194624Inhibition of angiogenesis (new microvessel growth) in rat aortic ring model at 100 uM in Endothelial basal medium (EBM) and Dimethylsulfoxide (DMSO)2003Journal of medicinal chemistry, Aug-28, Volume: 46, Issue:18
Thalidomide metabolites and analogues. 3. Synthesis and antiangiogenic activity of the teratogenic and TNFalpha-modulatory thalidomide analogue 2-(2,6-dioxopiperidine-3-yl)phthalimidine.
AID194625Inhibition of angiogenesis (new microvessel growth) in rat aortic ring model at 200 uM in Endothelial basal medium (EBM) and Dimethylsulfoxide (DMSO)2003Journal of medicinal chemistry, Aug-28, Volume: 46, Issue:18
Thalidomide metabolites and analogues. 3. Synthesis and antiangiogenic activity of the teratogenic and TNFalpha-modulatory thalidomide analogue 2-(2,6-dioxopiperidine-3-yl)phthalimidine.
AID1769477Distribution coefficient, logD of compound at 1 mg/ml measured at pH 7.4 by chromatography based LC-UV analysis2021ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11
Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition.
AID1769482Stability in human plasma assessed as half life at 1 uM by LC-MS/MS analysis2021ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11
Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition.
AID1769479Efflux ratio of apparent permeability of compound across basolateral to apical side over apical to basolateral side in human Caco-2 cells at 10 uM incubated for 90 mins by LC-MS/MS analysis2021ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11
Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition.
AID1769480Kinetic solubility of compound in PBS at 200 uM incubated for 30 mins by LC-MS/MS analysis2021ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11
Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition.
AID1769486Protac activity at CRBN/HiBiT-tagged IKZF1 in human MOLT-4 cells assessed as IKZF1 degradation by measuring luminescence by luminescence based HiBiT assay2021ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11
Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition.
AID185281Inhibition of microvessel outgrowth in the rat aortic ring assay2004Journal of medicinal chemistry, Apr-22, Volume: 47, Issue:9
Comparative molecular field analysis and comparative molecular similarity indices analysis of thalidomide analogues as angiogenesis inhibitors.
AID1769483Drug accumulation in human MOLT-4 cells assessed as intracellular unbound fraction incubated for 4 hrs by LC-MS analysis2021ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11
Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition.
AID1769481Metabolic stability in human liver microsome assessed as half-life at 1 uM in presence of NADPH incubated up to 60 mins by LC-MS/MS analysis2021ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11
Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition.
AID1769484Drug accumulation in human MOLT-4 cells assessed as intracellular drug accumulation incubated for 4 hrs by LC-MS analysis2021ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11
Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition.
AID1769478Apparent permeability in in human Caco-2 cells at 10 uM incubated for 90 mins by LC-MS/MS analysis2021ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11
Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition.
AID1769485Drug accumulation in human MOLT-4 cells assessed as intracellular bioavailability by LC-MS analysis2021ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11
Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (21)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (38.10)18.7374
1990's7 (33.33)18.2507
2000's4 (19.05)29.6817
2010's1 (4.76)24.3611
2020's1 (4.76)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.48

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 Index11.48 (24.57)
Research Supply Index3.09 (2.92)
Research Growth Index4.57 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.48)

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%
Other21 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]