2-(1,3-benzodioxol-5-ylmethyl)isoindole-1,3-dione is a chemical compound that goes by the more common name **N-(1,3-benzodioxol-5-ylmethyl)phthalimide**, also known as **piperonylidene phthalimide** or **PIP**.
**Here's a breakdown of its structure and importance:**
* **Structure:**
* It's a phthalimide derivative with a 1,3-benzodioxol group attached to the nitrogen atom through a methylene bridge.
* The 1,3-benzodioxol group is a ring system found in natural compounds like safrole and piperonal.
* Phthalimide is a cyclic imide derived from phthalic acid, known for its diverse applications.
* **Importance in Research:**
* **Organic Synthesis:** PIP is used as a reagent and building block in organic synthesis. It's particularly useful for:
* **Protecting groups:** The phthalimide group can be used to protect amine groups during reactions and later removed under controlled conditions.
* **Amide Coupling Reactions:** It can be used in the synthesis of amides via reactions with various amines.
* **Ring-Opening Metathesis Polymerization (ROMP):** PIP can be used as a monomer in ROMP to create polymers with unique properties.
* **Medicinal Chemistry:**
* **Antimicrobial Activity:** PIP exhibits antimicrobial activity against certain bacteria and fungi.
* **Anti-cancer Activity:** Some studies suggest that PIP might possess anti-cancer activity, particularly against leukemia cells.
* **Neurological Effects:** It has been investigated for its potential impact on the nervous system, including modulation of neurotransmitter activity.
* **Materials Science:**
* **Polymers and Coatings:** PIP can be incorporated into polymer structures to impart specific properties like improved thermal stability, enhanced mechanical strength, and flame retardancy.
* **Agricultural Chemistry:**
* **Pesticide and Herbicide Development:** PIP is used as a starting material in the synthesis of some agricultural chemicals, such as insecticides and herbicides.
**Important Note:** While PIP has diverse applications in research, further research is needed to understand its full potential and safety profile. Its applications in pharmaceutical and agricultural fields require careful evaluation and regulation.
ID Source | ID |
---|---|
PubMed CID | 714424 |
CHEMBL ID | 1353231 |
CHEBI ID | 108927 |
SCHEMBL ID | 19500873 |
Synonym |
---|
2-(1,3-benzodioxol-5-ylmethyl)-1h-isoindole-1,3(2h)-dione |
smr000077982 |
MLS000064944 , |
STK152841 |
CHEBI:108927 |
AKOS003334866 |
HMS1625C02 |
2-(1,3-benzodioxol-5-ylmethyl)isoindole-1,3-dione |
HMS2451B06 |
CHEMBL1353231 |
bdbm32251 |
2-piperonylisoindoline-1,3-quinone |
cid_714424 |
HMS3440B11 |
Q27187899 |
2-[(2h-1,3-benzodioxol-5-yl)methyl]-2,3-dihydro-1h-isoindole-1,3-dione |
SCHEMBL19500873 |
way-330598 |
Class | Description |
---|---|
phthalimides | A dicarboximide that is phthalimide or derivatives obtained from it by the formal replacement of one or more hydrogens. |
[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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 39.8107 | 0.0013 | 18.0743 | 39.8107 | AID926; AID938 |
pyruvate kinase PKM isoform a | Homo sapiens (human) | Potency | 31.6228 | 0.0401 | 7.4590 | 31.6228 | AID1631; AID1634 |
histone-lysine N-methyltransferase 2A isoform 2 precursor | Homo sapiens (human) | Potency | 14.1254 | 0.0103 | 23.8567 | 63.0957 | AID2662 |
survival motor neuron protein isoform d | Homo sapiens (human) | Potency | 0.7943 | 0.1259 | 12.2344 | 35.4813 | AID1458 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
90-kda heat shock protein beta HSP90 beta, partial | Homo sapiens (human) | IC50 (µMol) | 50.0000 | 0.1736 | 9.8032 | 29.2701 | AID712 |
heat shock protein HSP 90-alpha isoform 2 | Homo sapiens (human) | IC50 (µMol) | 50.0000 | 0.1736 | 9.8032 | 29.2701 | AID712 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
LANA | Human gammaherpesvirus 8 | AC50 | 42.5010 | 0.0420 | 32.4569 | 312.0010 | AID504726 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. 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. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. 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. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. 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. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
AID540299 | A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis | 2010 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21 | Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. |
AID588519 | A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities | 2011 | Antiviral research, Sep, Volume: 91, Issue:3 | High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 1 (14.29) | 29.6817 |
2010's | 5 (71.43) | 24.3611 |
2020's | 1 (14.29) | 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 (12.20) 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 | 7 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |