## 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
ID Source | ID |
---|---|
PubMed CID | 91585 |
CHEMBL ID | 304572 |
SCHEMBL ID | 476917 |
MeSH ID | M0041166 |
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 |
Excerpt | Reference | Relevance |
---|---|---|
" 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 |
Excerpt | Relevance | Reference |
---|---|---|
"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 |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
DNA-binding protein Ikaros | Homo sapiens (human) | DC50 | 0.1927 | 0.0267 | 0.1031 | 0.1927 | AID1769486 |
Protein cereblon | Homo sapiens (human) | DC50 | 0.1927 | 0.0080 | 0.4835 | 2.1000 | AID1769486 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Process | via Protein(s) | Taxonomy |
---|---|---|
DNA binding | DNA-binding protein Ikaros | Homo sapiens (human) |
protein binding | DNA-binding protein Ikaros | Homo sapiens (human) |
protein domain specific binding | DNA-binding protein Ikaros | Homo sapiens (human) |
metal ion binding | DNA-binding protein Ikaros | Homo sapiens (human) |
RNA polymerase II cis-regulatory region sequence-specific DNA binding | DNA-binding protein Ikaros | Homo sapiens (human) |
DNA-binding transcription factor activity | DNA-binding protein Ikaros | Homo sapiens (human) |
protein binding | Protein cereblon | Homo sapiens (human) |
transmembrane transporter binding | Protein cereblon | Homo sapiens (human) |
metal ion binding | Protein cereblon | Homo sapiens (human) |
[Information is prepared from geneontology information from the June-17-2024 release] |
Process | via Protein(s) | Taxonomy |
---|---|---|
nucleus | DNA-binding protein Ikaros | Homo sapiens (human) |
nucleoplasm | DNA-binding protein Ikaros | Homo sapiens (human) |
cytosol | DNA-binding protein Ikaros | Homo sapiens (human) |
pericentric heterochromatin | DNA-binding protein Ikaros | Homo sapiens (human) |
protein-containing complex | DNA-binding protein Ikaros | Homo sapiens (human) |
nucleus | Protein cereblon | Homo sapiens (human) |
cytoplasm | Protein cereblon | Homo sapiens (human) |
cytosol | Protein cereblon | Homo sapiens (human) |
membrane | Protein cereblon | Homo sapiens (human) |
perinuclear region of cytoplasm | Protein cereblon | Homo sapiens (human) |
Cul4A-RING E3 ubiquitin ligase complex | Protein cereblon | Homo sapiens (human) |
[Information is prepared from geneontology information from the June-17-2024 release] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID194624 | Inhibition of angiogenesis (new microvessel growth) in rat aortic ring model at 100 uM in Endothelial basal medium (EBM) and Dimethylsulfoxide (DMSO) | 2003 | Journal 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. |
AID194625 | Inhibition of angiogenesis (new microvessel growth) in rat aortic ring model at 200 uM in Endothelial basal medium (EBM) and Dimethylsulfoxide (DMSO) | 2003 | Journal 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. |
AID1769477 | Distribution coefficient, logD of compound at 1 mg/ml measured at pH 7.4 by chromatography based LC-UV analysis | 2021 | ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11 | Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition. |
AID1769482 | Stability in human plasma assessed as half life at 1 uM by LC-MS/MS analysis | 2021 | ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11 | Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition. |
AID1769479 | Efflux 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 analysis | 2021 | ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11 | Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition. |
AID1769480 | Kinetic solubility of compound in PBS at 200 uM incubated for 30 mins by LC-MS/MS analysis | 2021 | ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11 | Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition. |
AID1769486 | Protac activity at CRBN/HiBiT-tagged IKZF1 in human MOLT-4 cells assessed as IKZF1 degradation by measuring luminescence by luminescence based HiBiT assay | 2021 | ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11 | Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition. |
AID185281 | Inhibition of microvessel outgrowth in the rat aortic ring assay | 2004 | Journal 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. |
AID1769483 | Drug accumulation in human MOLT-4 cells assessed as intracellular unbound fraction incubated for 4 hrs by LC-MS analysis | 2021 | ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11 | Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition. |
AID1769481 | Metabolic 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 analysis | 2021 | ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11 | Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition. |
AID1769484 | Drug accumulation in human MOLT-4 cells assessed as intracellular drug accumulation incubated for 4 hrs by LC-MS analysis | 2021 | ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11 | Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition. |
AID1769478 | Apparent permeability in in human Caco-2 cells at 10 uM incubated for 90 mins by LC-MS/MS analysis | 2021 | ACS medicinal chemistry letters, Nov-11, Volume: 12, Issue:11 | Physicochemistry of Cereblon Modulating Drugs Determines Pharmacokinetics and Disposition. |
AID1769485 | Drug accumulation in human MOLT-4 cells assessed as intracellular bioavailability by LC-MS analysis | 2021 | ACS 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] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 8 (38.10) | 18.7374 |
1990's | 7 (33.33) | 18.2507 |
2000's | 4 (19.05) | 29.6817 |
2010's | 1 (4.76) | 24.3611 |
2020's | 1 (4.76) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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.
| This Compound (11.48) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 21 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |