Page last updated: 2024-11-06

N-Benzylphthalimide

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

N-Benzylphthalimide is a white, crystalline solid used in organic synthesis as a protecting group for amines. It is prepared by the reaction of phthalic anhydride with benzylamine. N-Benzylphthalimide has been used to protect amines during various reactions, such as alkylation, acylation, and oxidation, and can be easily removed by treatment with hydrazine. Its ability to protect amines has led to its use in the synthesis of various pharmaceuticals and other organic compounds.'

Cross-References

ID SourceID
PubMed CID75059
CHEMBL ID416887
CHEBI ID34866
SCHEMBL ID326305

Synonyms (67)

Synonym
nsc2771
2142-01-0
2-benzyl-1,3-dioxo-2h-isoindole
nsc-2771
CBDIVE_000093
OPREA1_454921
2-benzylisoindoline-1,3-dione
2-benzyl-1h-isoindole-1,3(2h)-dione
CHEMDIV2_000151
2-benzylisoindole-1,3-dione
n-benzylphthalimide
n-benzylphthalimide, 99%
MAYBRIDGE1_007213
STK048584
NCGC00186534-01
B1997
inchi=1/c15h11no2/c17-14-12-8-4-5-9-13(12)15(18)16(14)10-11-6-2-1-3-7-11/h1-9h,10h2
witxfyclpdfrnm-uhfffaoysa-
2-(phenylmethyl)isoindole-1,3-dione
bdbm50088671
2-benzyl-isoindole-1,3-dione
AKOS001483563
HMS1369G19
HMS561P19
chebi:34866 ,
CHEMBL416887 ,
FT-0657008
AE-848/30539055
phthalimide, n-benzyl-
4-[(2-chloro-4-nitro-phenyl)methylcarbamoylamino]benzenesulfonyl fluoride
A815328
1h-isoindole-1,3(2h)-dione, 2-(phenylmethyl)-
einecs 218-395-5
benzylphthalimide
ai3-02617
nsc 2771
3g2a77460j ,
unii-3g2a77460j
FT-0634060
2-(phenylmethyl)-1,3-isoindolinedione
2-benzyl-1,3-dioxo-2,3-dihydro-1h-isoindole
2-(phenylmethyl)isoindole-1,3(2h)-dione
4-benzyl-1h-isoindole-1,3(2h)-dione
SCHEMBL326305
n-benzylpthalimide
cambridge id 5100224
2-benzyl-1h-isoindole-1,3(2h)-dione #
2-benzyl-2,3-dihydro-1h-isoindole-1,3-dione
Z18271714
DTXSID4036647
SR-01000390068-1
sr-01000390068
mfcd00023077
AS-59839
J-014043
10.14272/WITXFYCLPDFRNM-UHFFFAOYSA-N.1
doi:10.14272/witxfyclpdfrnm-uhfffaoysa-n.1
n-benzyl phthalimide
F0405-0287
Q27116303
AMY360
n-benzylphtalimide
W18299
SB64266
CAA14201
CS-0073188
SY051983
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
isoindoles
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Lysosomal acid glucosylceramidaseHomo sapiens (human)IC50 (µMol)500.00000.03002.35898.8000AID40425
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (52)

Processvia Protein(s)Taxonomy
mitochondrion organizationLysosomal acid glucosylceramidaseHomo sapiens (human)
neuron projection developmentLysosomal acid glucosylceramidaseHomo sapiens (human)
glucosylceramide catabolic processLysosomal acid glucosylceramidaseHomo sapiens (human)
autophagyLysosomal acid glucosylceramidaseHomo sapiens (human)
lysosome organizationLysosomal acid glucosylceramidaseHomo sapiens (human)
cholesterol metabolic processLysosomal acid glucosylceramidaseHomo sapiens (human)
determination of adult lifespanLysosomal acid glucosylceramidaseHomo sapiens (human)
cellular response to starvationLysosomal acid glucosylceramidaseHomo sapiens (human)
response to pHLysosomal acid glucosylceramidaseHomo sapiens (human)
microglia differentiationLysosomal acid glucosylceramidaseHomo sapiens (human)
regulation of macroautophagyLysosomal acid glucosylceramidaseHomo sapiens (human)
antigen processing and presentationLysosomal acid glucosylceramidaseHomo sapiens (human)
lipid storageLysosomal acid glucosylceramidaseHomo sapiens (human)
cerebellar Purkinje cell layer formationLysosomal acid glucosylceramidaseHomo sapiens (human)
pyramidal neuron differentiationLysosomal acid glucosylceramidaseHomo sapiens (human)
respiratory electron transport chainLysosomal acid glucosylceramidaseHomo sapiens (human)
termination of signal transductionLysosomal acid glucosylceramidaseHomo sapiens (human)
lipid glycosylationLysosomal acid glucosylceramidaseHomo sapiens (human)
negative regulation of protein-containing complex assemblyLysosomal acid glucosylceramidaseHomo sapiens (human)
regulation of TOR signalingLysosomal acid glucosylceramidaseHomo sapiens (human)
positive regulation of proteasomal ubiquitin-dependent protein catabolic processLysosomal acid glucosylceramidaseHomo sapiens (human)
negative regulation of interleukin-6 productionLysosomal acid glucosylceramidaseHomo sapiens (human)
T cell differentiation in thymusLysosomal acid glucosylceramidaseHomo sapiens (human)
response to testosteroneLysosomal acid glucosylceramidaseHomo sapiens (human)
positive regulation of protein dephosphorylationLysosomal acid glucosylceramidaseHomo sapiens (human)
proteasome-mediated ubiquitin-dependent protein catabolic processLysosomal acid glucosylceramidaseHomo sapiens (human)
positive regulation of protein-containing complex disassemblyLysosomal acid glucosylceramidaseHomo sapiens (human)
negative regulation of MAP kinase activityLysosomal acid glucosylceramidaseHomo sapiens (human)
negative regulation of neuron apoptotic processLysosomal acid glucosylceramidaseHomo sapiens (human)
response to estrogenLysosomal acid glucosylceramidaseHomo sapiens (human)
sphingosine biosynthetic processLysosomal acid glucosylceramidaseHomo sapiens (human)
ceramide biosynthetic processLysosomal acid glucosylceramidaseHomo sapiens (human)
cell maturationLysosomal acid glucosylceramidaseHomo sapiens (human)
brain morphogenesisLysosomal acid glucosylceramidaseHomo sapiens (human)
homeostasis of number of cellsLysosomal acid glucosylceramidaseHomo sapiens (human)
negative regulation of inflammatory responseLysosomal acid glucosylceramidaseHomo sapiens (human)
neuromuscular processLysosomal acid glucosylceramidaseHomo sapiens (human)
neuron apoptotic processLysosomal acid glucosylceramidaseHomo sapiens (human)
establishment of skin barrierLysosomal acid glucosylceramidaseHomo sapiens (human)
microglial cell proliferationLysosomal acid glucosylceramidaseHomo sapiens (human)
motor behaviorLysosomal acid glucosylceramidaseHomo sapiens (human)
cellular response to tumor necrosis factorLysosomal acid glucosylceramidaseHomo sapiens (human)
hematopoietic stem cell proliferationLysosomal acid glucosylceramidaseHomo sapiens (human)
response to dexamethasoneLysosomal acid glucosylceramidaseHomo sapiens (human)
lymphocyte migrationLysosomal acid glucosylceramidaseHomo sapiens (human)
response to thyroid hormoneLysosomal acid glucosylceramidaseHomo sapiens (human)
beta-glucoside catabolic processLysosomal acid glucosylceramidaseHomo sapiens (human)
positive regulation of protein lipidationLysosomal acid glucosylceramidaseHomo sapiens (human)
positive regulation of neuronal action potentialLysosomal acid glucosylceramidaseHomo sapiens (human)
positive regulation of autophagy of mitochondrion in response to mitochondrial depolarizationLysosomal acid glucosylceramidaseHomo sapiens (human)
autophagosome organizationLysosomal acid glucosylceramidaseHomo sapiens (human)
regulation of lysosomal protein catabolic processLysosomal acid glucosylceramidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
galactosylceramidase activityLysosomal acid glucosylceramidaseHomo sapiens (human)
glucosylceramidase activityLysosomal acid glucosylceramidaseHomo sapiens (human)
signaling receptor bindingLysosomal acid glucosylceramidaseHomo sapiens (human)
scavenger receptor bindingLysosomal acid glucosylceramidaseHomo sapiens (human)
protein bindingLysosomal acid glucosylceramidaseHomo sapiens (human)
glucosyltransferase activityLysosomal acid glucosylceramidaseHomo sapiens (human)
steryl-beta-glucosidase activityLysosomal acid glucosylceramidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
lysosomeLysosomal acid glucosylceramidaseHomo sapiens (human)
lysosomal membraneLysosomal acid glucosylceramidaseHomo sapiens (human)
endoplasmic reticulumLysosomal acid glucosylceramidaseHomo sapiens (human)
Golgi apparatusLysosomal acid glucosylceramidaseHomo sapiens (human)
trans-Golgi networkLysosomal acid glucosylceramidaseHomo sapiens (human)
lysosomal lumenLysosomal acid glucosylceramidaseHomo sapiens (human)
extracellular exosomeLysosomal acid glucosylceramidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID612391Inhibition of human recombinant MAOB expressed in insect cells using kynuramine substrate at 100 uM by fluorescence spectroscopy2011Bioorganic & medicinal chemistry, Aug-15, Volume: 19, Issue:16
Inhibition of monoamine oxidase by C5-substituted phthalimide analogues.
AID293618Cytotoxicity against Vero cells2007European journal of medicinal chemistry, May, Volume: 42, Issue:5
Novel and versatile methodology for synthesis of cyclic imides and evaluation of their cytotoxic, DNA binding, apoptotic inducing activities and molecular modeling study.
AID40425Inhibition of Beta-glucosidase activity.2000Bioorganic & medicinal chemistry letters, May-15, Volume: 10, Issue:10
Novel alpha-glucosidase inhibitors with a tetrachlorophthalimide skeleton.
AID612390Inhibition of human recombinant MAOA expressed in insect cells using kynuramine substrate at 100 uM by fluorescence spectroscopy2011Bioorganic & medicinal chemistry, Aug-15, Volume: 19, Issue:16
Inhibition of monoamine oxidase by C5-substituted phthalimide analogues.
AID37431Compound was evaluated for binding affinity towards Alpha-glucosidase analyzed by the surface plasma resonance (SPR) method; Not determined2000Bioorganic & medicinal chemistry letters, May-15, Volume: 10, Issue:10
Novel alpha-glucosidase inhibitors with a tetrachlorophthalimide skeleton.
AID37428Inhibition of Alpha-glucosidase activity.2000Bioorganic & medicinal chemistry letters, May-15, Volume: 10, Issue:10
Novel alpha-glucosidase inhibitors with a tetrachlorophthalimide skeleton.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
AID1159537qHTS screening for TAG (triacylglycerol) accumulators in algae2017Plant physiology, Aug, Volume: 174, Issue:4
Identification and Metabolite Profiling of Chemical Activators of Lipid Accumulation in Green Algae.
[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's2 (28.57)29.6817
2010's3 (42.86)24.3611
2020's2 (28.57)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 33.26

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index33.26 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index5.08 (4.65)
Search Engine Demand Index25.55 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (33.26)

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]