Page last updated: 2024-12-09

2-(1,3-benzodioxol-5-ylmethyl)isoindole-1,3-dione

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

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.

Cross-References

ID SourceID
PubMed CID714424
CHEMBL ID1353231
CHEBI ID108927
SCHEMBL ID19500873

Synonyms (18)

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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phthalimidesA 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 Targets (7)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
thyroid stimulating hormone receptorHomo sapiens (human)Potency39.81070.001318.074339.8107AID926; AID938
pyruvate kinase PKM isoform aHomo sapiens (human)Potency31.62280.04017.459031.6228AID1631; AID1634
histone-lysine N-methyltransferase 2A isoform 2 precursorHomo sapiens (human)Potency14.12540.010323.856763.0957AID2662
survival motor neuron protein isoform dHomo sapiens (human)Potency0.79430.125912.234435.4813AID1458
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
90-kda heat shock protein beta HSP90 beta, partialHomo sapiens (human)IC50 (µMol)50.00000.17369.803229.2701AID712
heat shock protein HSP 90-alpha isoform 2Homo sapiens (human)IC50 (µMol)50.00000.17369.803229.2701AID712
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LANAHuman gammaherpesvirus 8AC5042.50100.042032.4569312.0010AID504726
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (15)

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.
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.
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
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & 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.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral 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]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (14.29)29.6817
2010's5 (71.43)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.20

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 Index12.20 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.28 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.20)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]