Page last updated: 2024-12-06

n-phenylphthalimide

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Description

N-phenylphthalimide is a white solid that is commonly used as a reagent in organic synthesis. It can be synthesized through the reaction of phthalic anhydride with aniline. The compound has been shown to exhibit antifungal and antibacterial activity, making it a potential candidate for the development of new antimicrobial agents. Research on N-phenylphthalimide often focuses on its potential applications in drug discovery, materials science, and catalysis.'

N-phenylphthalimide: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID68215
CHEMBL ID9020
SCHEMBL ID123618
MeSH IDM0113306

Synonyms (56)

Synonym
HMS1578O16
smr001547169
n-phenylphthalimide
phthalanil
520-03-6
1h-isoindole-1, 2-phenyl-
phthalimide, n-phenyl-
nsc-2769
nsc2769
n-phenyl-4-nitrophthalimide
mls002637643 ,
1h-isoindole-1,3(2h)-dione, 2-phenyl-
2-phenyl-isoindole-1,3-dione
OPREA1_380408
OPREA1_603933
brn 0010683
einecs 208-282-9
ai3-03744
nsc 2769
phthalimidobenzene
n-phenylphthalimide, 98%
STK174445
2-phenyl-1h-isoindole-1,3(2h)-dione
bdbm50088679
2-phenylisoindoline-1,3-dione
CHEMBL9020 ,
n-phenylphtalimide
2-phenylisoindole-1,3-dione
AKOS001268564
A7652
NCGC00246780-01
EN300-56140
unii-la29qa196m
5-21-10-00292 (beilstein handbook reference)
la29qa196m ,
2-phenyl-2,3-dihydro-1h-isoindole-1,3-dione
FT-0632274
SCHEMBL123618
n-phenyl phthalimide
n-(phenyl) phthalimide
DTXSID3060166
2-phenyl-1h-isoindole-1,3(2h)-dione #
n-phenylphthalic acid imide
AC-26721
sr-01000197336
SR-01000197336-1
AS-59263
BCP14277
2-phenyl-1h-isoindole-1,3(2h)dione
2-phenyl-1,3-isoindolinedione
mfcd00023044
AMY582
D70889
CS-0156128
SY042993
Z57398053
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Lysosomal acid glucosylceramidaseHomo sapiens (human)IC50 (µMol)500.00000.03002.35898.8000AID40425
Prostaglandin G/H synthase 1Ovis aries (sheep)IC50 (µMol)0.00100.00032.177410.0000AID162144
Prostaglandin G/H synthase 2Ovis aries (sheep)IC50 (µMol)0.00100.00101.453910.0000AID160735
[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 (42)

Assay IDTitleYearJournalArticle
AID257636Inhibitory activity in HUVEC tube formation assay at 100 uM2005Bioorganic & medicinal chemistry letters, Dec-15, Volume: 15, Issue:24
Angiogenesis inhibitors derived from thalidomide.
AID281484Inhibition of rabbit liver carboxylesterase expressed in sf21 cells up to 100 uM2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
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.
AID162144Inhibitory activity (RA1) against Prostaglandin G/H synthase 1 was calculated relative to aspirin2002Bioorganic & medicinal chemistry letters, Apr-08, Volume: 12, Issue:7
Thalidomide and its analogues as cyclooxygenase inhibitors.
AID281483Inhibition of human liver CE1 expressed in sf21 cells up to 100 uM2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
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.
AID218272In vitro cytotoxicity against human embryonic lung fibroblast WI-38 cells.1997Journal of medicinal chemistry, Aug-29, Volume: 40, Issue:18
Novel biological response modifiers: phthalimides with tumor necrosis factor-alpha production-regulating activity.
AID257637Inhibitory activity in HUVEC tube formation assay at 30 uM2005Bioorganic & medicinal chemistry letters, Dec-15, Volume: 15, Issue:24
Angiogenesis inhibitors derived from thalidomide.
AID1266445Induction of bovine LPL stabilization using intralipid as substrate at 25 uM preincubated for 10 mins with human recombinant ANGPTL4 followed by substrate addition measured after 45 mins relative to control2015European journal of medicinal chemistry, Oct-20, Volume: 103Structure-activity relationships for lipoprotein lipase agonists that lower plasma triglycerides in vivo.
AID1266444Induction of bovine LPL stabilization using intralipid as substrate at 12.5 uM preincubated for 10 mins with human recombinant ANGPTL4 followed by substrate addition measured after 45 mins relative to control2015European journal of medicinal chemistry, Oct-20, Volume: 103Structure-activity relationships for lipoprotein lipase agonists that lower plasma triglycerides in vivo.
AID128449Effect on Serum cholesterol levels on CF1 male mice at a dose of 20 (mg/kg)/day after 9 days1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Hypolipidemic activity of phthalimide derivatives. 2. N-phenylphthalimide and derivatives.
AID439754Inhibition of [3H]2-OG binding to human MGL at 1 mM by liquid scintillation counting2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors.
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.
AID40425Inhibition of Beta-glucosidase activity.2000Bioorganic & medicinal chemistry letters, May-15, Volume: 10, Issue:10
Novel alpha-glucosidase inhibitors with a tetrachlorophthalimide skeleton.
AID160735Inhibitory activity (RA2) against Prostaglandin G/H synthase 2 was calculated relative to aspirin2002Bioorganic & medicinal chemistry letters, Apr-08, Volume: 12, Issue:7
Thalidomide and its analogues as cyclooxygenase inhibitors.
AID251886Cell growth-inhibitory activity toward human leukemia cell line HL60 at 10 uM concentration2005Bioorganic & medicinal chemistry letters, Jan-17, Volume: 15, Issue:2
Tubulin-polymerization inhibitors derived from thalidomide.
AID281482Inhibition of human intestinal carboxylesterase expressed in sf21 cells up to 100 uM2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID439746Inhibition of [3H]ethanolamine binding to human recombinant FAAH at 1 mM by liquid scintillation counting2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors.
AID1266443Induction of bovine LPL stabilization using intralipid as substrate at 6.25 uM preincubated for 10 mins with human recombinant ANGPTL4 followed by substrate addition measured after 45 mins relative to control2015European journal of medicinal chemistry, Oct-20, Volume: 103Structure-activity relationships for lipoprotein lipase agonists that lower plasma triglycerides in vivo.
AID128448Effect on Serum cholesterol levels on CF1 male mice at a dose of 20 (mg/kg)/day after 16 days1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Hypolipidemic activity of phthalimide derivatives. 2. N-phenylphthalimide and derivatives.
AID257638Inhibitory activity in HUVEC tube formation assay at 10 uM2005Bioorganic & medicinal chemistry letters, Dec-15, Volume: 15, Issue:24
Angiogenesis inhibitors derived from thalidomide.
AID251887Cell growth-inhibitory activity toward human leukemia cell line HL60 at 3 uM concentration2005Bioorganic & medicinal chemistry letters, Jan-17, Volume: 15, Issue:2
Tubulin-polymerization inhibitors derived from thalidomide.
AID1266442Induction of bovine LPL stabilization using intralipid as substrate at 3.12 uM preincubated for 10 mins with human recombinant ANGPTL4 followed by substrate addition measured after 45 mins relative to control2015European journal of medicinal chemistry, Oct-20, Volume: 103Structure-activity relationships for lipoprotein lipase agonists that lower plasma triglycerides in vivo.
AID128463Effect on Serum triglyceride levels on CF1 male mice at a dose of 20 (mg/kg)/day after 14 days1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Hypolipidemic activity of phthalimide derivatives. 2. N-phenylphthalimide and derivatives.
AID81272Tumor necrosis factor-alpha production in human leukemia cell line (HL-60) stimulated with 50 nM okadaic acid (OA), at 30 uMolar.1997Journal of medicinal chemistry, Aug-29, Volume: 40, Issue:18
Novel biological response modifiers: phthalimides with tumor necrosis factor-alpha production-regulating activity.
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.
AID37428Inhibition of Alpha-glucosidase activity.2000Bioorganic & medicinal chemistry letters, May-15, Volume: 10, Issue:10
Novel alpha-glucosidase inhibitors with a tetrachlorophthalimide skeleton.
AID251888Cell growth-inhibitory activity toward human leukemia cell line HL60 at 6 uM concentration2005Bioorganic & medicinal chemistry letters, Jan-17, Volume: 15, Issue:2
Tubulin-polymerization inhibitors derived from thalidomide.
AID81275Tumor necrosis factor-alpha production in human leukemia cell line (HL-60) stimulated with 10 nM 12-O-tetradecanoylphorbol 13-acetate (TPA) at 30 uMolar.1997Journal of medicinal chemistry, Aug-29, Volume: 40, Issue:18
Novel biological response modifiers: phthalimides with tumor necrosis factor-alpha production-regulating activity.
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.
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.
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
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 (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (3.85)18.7374
1990's3 (11.54)18.2507
2000's11 (42.31)29.6817
2010's10 (38.46)24.3611
2020's1 (3.85)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.86

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 Index29.86 (24.57)
Research Supply Index3.30 (2.92)
Research Growth Index5.10 (4.65)
Search Engine Demand Index27.14 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.86)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (3.85%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other25 (96.15%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]