Page last updated: 2024-12-09

3-chloro-1-(3,4-dichlorophenyl)-4-(4-morpholinyl)-1h-pyrrole-2,5-dione

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

Description

3-chloro-1-(3,4-dichlorophenyl)-4-(4-morpholinyl)-1H-pyrrole-2,5-dione: an inhibitor of RAD51 that disrupts homologous recombination in human cells; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1074953
CHEMBL ID1271993
SCHEMBL ID13186471
MeSH IDM0578781

Synonyms (49)

Synonym
HY-15317
ri-1
MLS-0067124.0002
MLS-0067124.0001 ,
3-chloro-1-(3,4-dichlorophenyl)-4-morpholin-4-ylpyrrole-2,5-dione
CHEMBL1271993
AKOS015997897
415713-60-9
CS-0726
S8077
AB00082114-01
3-chloro-1-(3,4-dichlorophenyl)-4-morpholin-4-yl-1h-pyrrole-2,5-dione
3-chloro-1-(3,4-dichlorophenyl)-4-morpholino-1h-pyrrole-2,5-dione
cid_1074953
3-chloro-1-(3,4-dichlorophenyl)-4-(4-morpholinyl)pyrrole-2,5-dione
3-chloro-1-(3,4-dichlorophenyl)-4-morpholino-3-pyrroline-2,5-quinone
3-chloranyl-1-(3,4-dichlorophenyl)-4-morpholin-4-yl-pyrrole-2,5-dione
bdbm39120
SCHEMBL13186471
STL503566
3-chloro-1-(3,4-dichlorophenyl)-4-(morpholin-4-yl)-1h-pyrrole-2,5-dione
3-chloro-1-(3,4-dichlorophenyl)-4-(4-morpholinyl)-1h-pyrrole-2,5-dione
rad51 inhibitor(ri-1)
J-690294
n-(4-hydroxy-3-methoxybenzyl)octadecanamide
rad51 inhibitor ri-1
EX-A207
1h-pyrrole-2,5-dione, 3-chloro-1-(3,4-dichlorophenyl)-4-(4-morpholinyl)-
rad51 inhibitor 1
ri1
ri 1
DTXSID30360083
mfcd00814248
HMS3653B10
MWSUIZKGNWELRF-UHFFFAOYSA-N
1-(3,4-dichlorophenyl)-3-chloro-4-morpholino-1h-pyrrole-2,5-dione
ri-1, >=98% (hplc)
NCGC00371132-01
3-chloro-1-(3,4-dichlorophenyl)-4-(morpholin-4-yl)pyrrole-2,5-dione
SW219349-1
(3-chloro-1-(3,4-dichlorophenyl)-4-(4-morpholinyl)-1h-pyrrole-2,5-dione)
BCP08293
FT-0700305
AS-16752
Q18392915
CCG-268183
ri-1 (chemical)
unii-s8wg8zrq99
s8wg8zrq99 ,

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Replicase polyprotein 1abBetacoronavirus England 1IC50 (µMol)10.00000.00403.43889.5100AID1640022
bcl-2-related protein A1Mus musculus (house mouse)IC50 (µMol)1.40330.41907.756335.1000AID1070; AID1231; AID621
Replicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2IC50 (µMol)2.83500.00022.45859.9600AID1640021
DNA repair protein RAD51 homolog 1Homo sapiens (human)IC50 (µMol)6.82006.82006.82006.8200AID724821
Bcl-2-related protein A1Homo sapiens (human)IC50 (µMol)0.62500.00441.65144.3000AID528201; AID528202
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cell cycle checkpoint protein RAD1Homo sapiens (human)EC50 (µMol)5.00005.00005.00005.0000AID1178404
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (35)

Processvia Protein(s)Taxonomy
DNA damage checkpoint signalingCell cycle checkpoint protein RAD1Homo sapiens (human)
DNA damage responseCell cycle checkpoint protein RAD1Homo sapiens (human)
substantia nigra developmentCell cycle checkpoint protein RAD1Homo sapiens (human)
meiotic recombination checkpoint signalingCell cycle checkpoint protein RAD1Homo sapiens (human)
cellular response to ionizing radiationCell cycle checkpoint protein RAD1Homo sapiens (human)
DNA repairCell cycle checkpoint protein RAD1Homo sapiens (human)
double-strand break repair via homologous recombinationDNA repair protein RAD51 homolog 1Homo sapiens (human)
telomere maintenance via recombinationDNA repair protein RAD51 homolog 1Homo sapiens (human)
double-strand break repair via homologous recombinationDNA repair protein RAD51 homolog 1Homo sapiens (human)
DNA recombinase assemblyDNA repair protein RAD51 homolog 1Homo sapiens (human)
regulation of protein phosphorylationDNA repair protein RAD51 homolog 1Homo sapiens (human)
DNA unwinding involved in DNA replicationDNA repair protein RAD51 homolog 1Homo sapiens (human)
DNA repairDNA repair protein RAD51 homolog 1Homo sapiens (human)
DNA recombinationDNA repair protein RAD51 homolog 1Homo sapiens (human)
DNA damage responseDNA repair protein RAD51 homolog 1Homo sapiens (human)
regulation of double-strand break repair via homologous recombinationDNA repair protein RAD51 homolog 1Homo sapiens (human)
telomere maintenance via telomere lengtheningDNA repair protein RAD51 homolog 1Homo sapiens (human)
replication fork processingDNA repair protein RAD51 homolog 1Homo sapiens (human)
interstrand cross-link repairDNA repair protein RAD51 homolog 1Homo sapiens (human)
positive regulation of DNA ligationDNA repair protein RAD51 homolog 1Homo sapiens (human)
meiotic cell cycleDNA repair protein RAD51 homolog 1Homo sapiens (human)
cellular response to ionizing radiationDNA repair protein RAD51 homolog 1Homo sapiens (human)
cellular response to hydroxyureaDNA repair protein RAD51 homolog 1Homo sapiens (human)
cellular response to camptothecinDNA repair protein RAD51 homolog 1Homo sapiens (human)
replication-born double-strand break repair via sister chromatid exchangeDNA repair protein RAD51 homolog 1Homo sapiens (human)
mitotic recombination-dependent replication fork processingDNA repair protein RAD51 homolog 1Homo sapiens (human)
double-strand break repair involved in meiotic recombinationDNA repair protein RAD51 homolog 1Homo sapiens (human)
regulation of DNA damage checkpointDNA repair protein RAD51 homolog 1Homo sapiens (human)
chromosome organization involved in meiotic cell cycleDNA repair protein RAD51 homolog 1Homo sapiens (human)
reciprocal meiotic recombinationDNA repair protein RAD51 homolog 1Homo sapiens (human)
mitotic recombinationDNA repair protein RAD51 homolog 1Homo sapiens (human)
DNA strand invasionDNA repair protein RAD51 homolog 1Homo sapiens (human)
negative regulation of apoptotic processBcl-2-related protein A1Homo sapiens (human)
transmembrane transportBcl-2-related protein A1Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damageBcl-2-related protein A1Homo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic processBcl-2-related protein A1Homo sapiens (human)
extrinsic apoptotic signaling pathway in absence of ligandBcl-2-related protein A1Homo sapiens (human)
release of cytochrome c from mitochondriaBcl-2-related protein A1Homo sapiens (human)
mitochondrial fusionBcl-2-related protein A1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (27)

Processvia Protein(s)Taxonomy
damaged DNA bindingCell cycle checkpoint protein RAD1Homo sapiens (human)
protein bindingCell cycle checkpoint protein RAD1Homo sapiens (human)
double-stranded DNA 3'-5' DNA exonuclease activityCell cycle checkpoint protein RAD1Homo sapiens (human)
3'-5'-RNA exonuclease activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
RNA-dependent RNA polymerase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
cysteine-type endopeptidase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA 5'-cap (guanine-N7-)-methyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA (nucleoside-2'-O-)-methyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA guanylyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
RNA endonuclease activity, producing 3'-phosphomonoestersReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
ISG15-specific peptidase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
5'-3' RNA helicase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
protein guanylyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
DNA strand exchange activityDNA repair protein RAD51 homolog 1Homo sapiens (human)
chromatin bindingDNA repair protein RAD51 homolog 1Homo sapiens (human)
double-stranded DNA bindingDNA repair protein RAD51 homolog 1Homo sapiens (human)
single-stranded DNA bindingDNA repair protein RAD51 homolog 1Homo sapiens (human)
protein bindingDNA repair protein RAD51 homolog 1Homo sapiens (human)
ATP bindingDNA repair protein RAD51 homolog 1Homo sapiens (human)
ATP hydrolysis activityDNA repair protein RAD51 homolog 1Homo sapiens (human)
single-stranded DNA helicase activityDNA repair protein RAD51 homolog 1Homo sapiens (human)
enzyme bindingDNA repair protein RAD51 homolog 1Homo sapiens (human)
identical protein bindingDNA repair protein RAD51 homolog 1Homo sapiens (human)
DNA polymerase bindingDNA repair protein RAD51 homolog 1Homo sapiens (human)
ATP-dependent DNA damage sensor activityDNA repair protein RAD51 homolog 1Homo sapiens (human)
ATP-dependent activity, acting on DNADNA repair protein RAD51 homolog 1Homo sapiens (human)
protein bindingBcl-2-related protein A1Homo sapiens (human)
channel activityBcl-2-related protein A1Homo sapiens (human)
BH domain bindingBcl-2-related protein A1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (26)

Processvia Protein(s)Taxonomy
nucleusCell cycle checkpoint protein RAD1Homo sapiens (human)
nucleoplasmCell cycle checkpoint protein RAD1Homo sapiens (human)
chromosomeCell cycle checkpoint protein RAD1Homo sapiens (human)
intracellular membrane-bounded organelleCell cycle checkpoint protein RAD1Homo sapiens (human)
checkpoint clamp complexCell cycle checkpoint protein RAD1Homo sapiens (human)
double membrane vesicle viral factory outer membraneReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
site of double-strand breakDNA repair protein RAD51 homolog 1Homo sapiens (human)
presynaptic intermediate filament cytoskeletonDNA repair protein RAD51 homolog 1Homo sapiens (human)
nuclear ubiquitin ligase complexDNA repair protein RAD51 homolog 1Homo sapiens (human)
nuclear chromosomeDNA repair protein RAD51 homolog 1Homo sapiens (human)
chromosome, telomeric regionDNA repair protein RAD51 homolog 1Homo sapiens (human)
condensed chromosomeDNA repair protein RAD51 homolog 1Homo sapiens (human)
condensed nuclear chromosomeDNA repair protein RAD51 homolog 1Homo sapiens (human)
lateral elementDNA repair protein RAD51 homolog 1Homo sapiens (human)
male germ cell nucleusDNA repair protein RAD51 homolog 1Homo sapiens (human)
nucleusDNA repair protein RAD51 homolog 1Homo sapiens (human)
nucleoplasmDNA repair protein RAD51 homolog 1Homo sapiens (human)
nucleolusDNA repair protein RAD51 homolog 1Homo sapiens (human)
cytoplasmDNA repair protein RAD51 homolog 1Homo sapiens (human)
mitochondrionDNA repair protein RAD51 homolog 1Homo sapiens (human)
mitochondrial matrixDNA repair protein RAD51 homolog 1Homo sapiens (human)
centrosomeDNA repair protein RAD51 homolog 1Homo sapiens (human)
cytosolDNA repair protein RAD51 homolog 1Homo sapiens (human)
PML bodyDNA repair protein RAD51 homolog 1Homo sapiens (human)
site of double-strand breakDNA repair protein RAD51 homolog 1Homo sapiens (human)
perinuclear region of cytoplasmDNA repair protein RAD51 homolog 1Homo sapiens (human)
chromatinDNA repair protein RAD51 homolog 1Homo sapiens (human)
protein-containing complexDNA repair protein RAD51 homolog 1Homo sapiens (human)
condensed nuclear chromosomeDNA repair protein RAD51 homolog 1Homo sapiens (human)
cytoplasmBcl-2-related protein A1Homo sapiens (human)
cytosolBcl-2-related protein A1Homo sapiens (human)
mitochondrial outer membraneBcl-2-related protein A1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (18)

Assay IDTitleYearJournalArticle
AID1178404Inhibition of RAD1 (unknown origin) binding to ssDNA2014Bioorganic & medicinal chemistry letters, Jul-15, Volume: 24, Issue:14
Targeting the homologous recombination pathway by small molecule modulators.
AID724821Inhibition of human RAD51 binding to single stranded DNA by fluorescence polarization assay2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
An optimized RAD51 inhibitor that disrupts homologous recombination without requiring Michael acceptor reactivity.
AID528201Inhibition of N-terminal FITC BH3 peptide binding to GST-tagged Bfl1 by fluorescence polarization assay2010Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22
Inhibition of Bfl-1 with N-aryl maleimides.
AID1309743Inhibition of Escherichia coli BL21(DE3) expressing human N-terminal 6-histidine/Avi-tagged RAD51 binding to circular pRS306 virion ssDNA preincubated for 40 mins followed by ssDNA addition measured after 5 mins by agarose gel electrophoresis2016Journal of medicinal chemistry, 05-26, Volume: 59, Issue:10
Development of Small Molecules that Specifically Inhibit the D-loop Activity of RAD51.
AID724820Cytotoxicity against HEK293 cells after 24 hrs2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
An optimized RAD51 inhibitor that disrupts homologous recombination without requiring Michael acceptor reactivity.
AID724818Half life of the compound in DMSO at 10 mg by HPLC analysis in the presence of glutathione2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
An optimized RAD51 inhibitor that disrupts homologous recombination without requiring Michael acceptor reactivity.
AID724819Induction of sensitization to Mitomycin C in HEK293 cells after 24 hrs2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
An optimized RAD51 inhibitor that disrupts homologous recombination without requiring Michael acceptor reactivity.
AID1309744Effect on stabilization of Escherichia coli BL21(DE3) expressing human N-terminal 6-histidine/Avi-tagged RAD51-circular pRS306 virion ssDNA nucleoprotein filament at 30 uM after 40 mins in presence of NaCl by SYBR gold staining based agarose gel electroph2016Journal of medicinal chemistry, 05-26, Volume: 59, Issue:10
Development of Small Molecules that Specifically Inhibit the D-loop Activity of RAD51.
AID528202Inhibition of N-terminal FITC BH3 peptide binding to GST-tagged Bfl1 by time resolved-FRET assay2010Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22
Inhibition of Bfl-1 with N-aryl maleimides.
AID724822Inhibition of human RAD51 binding to single stranded DNA at 59 uM by fluorescence polarization based assay2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
An optimized RAD51 inhibitor that disrupts homologous recombination without requiring Michael acceptor reactivity.
AID724817Irreversible inhibition of human RAD51 binding to single stranded DNA at 10 uM after 30 mins by fluorescence polarization based assay2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
An optimized RAD51 inhibitor that disrupts homologous recombination without requiring Michael acceptor reactivity.
AID724814Inhibition of RAD51-mediated homologous recombination in HEK293 cells at 20 uM after 24 hrs by reporter gene assay based FACS analysis2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
An optimized RAD51 inhibitor that disrupts homologous recombination without requiring Michael acceptor reactivity.
AID724813Inhibition of RAD51 in HEK293 cells assessed as stimulation of single strand annealing at 20 uM after 24 hrs by reporter gene assay based FACS analysis2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
An optimized RAD51 inhibitor that disrupts homologous recombination without requiring Michael acceptor reactivity.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's10 (83.33)24.3611
2020's2 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.21

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 Index13.21 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index5.77 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.21)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (8.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (91.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]