Page last updated: 2024-11-11

styrylquinoline

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

Description

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

Cross-References

ID SourceID
PubMed CID5357469
CHEMBL ID127579
CHEBI ID51072
CHEBI ID51071
SCHEMBL ID659665
MeSH IDM0460953

Synonyms (42)

Synonym
BIDD:GT0572
STL304835
nsc252077
38101-69-8
nsc-252077
2-(2-phenylethenyl)-(e)-quinoline
nsc77968
nsc-77968
4945-26-0
CHEBI:51072 ,
trans-2-styrylquinoline
2-styrylquinoline
CHEBI:51071
2-[(e)-2-phenylethenyl]quinoline
2-(2-phenylethenyl)quinoline
MLS000767320 ,
smr000429651
2-((e)-styryl)-quinoline
2-styryl-quinoline
CHEMBL127579 ,
bdbm50001290
cid_5357469
AKOS001298823
NCGC00184386-01
NCGC00184386-02
HMS2786M03
SCHEMBL659665
styrylquinoline
2-[(e)-2-phenylethenyl]quinoline #
RLGKSXCGHMXELQ-ZRDIBKRKSA-N
quinoline, 2-styryl-
quinoline, 2-(2-phenylethenyl)-
OPERA_ID_1699
Q27122315
Q27122307
(e)-(styryl)quinoline
AS-0355
2-[(1e)-2-phenylethenyl]quinoline
(e)-2-styrylquinoline
DTXSID801318989
Z46024290
quinoline, 2-[(1e)-2-phenylethenyl]-

Research Excerpts

Overview

Styrylquinolines are a novel group of quinoline drugs that are known to have p53-independent antiproliferative activity and antiviral properties.

ExcerptReferenceRelevance
"Styrylquinoline is a quinoline molecule linked to phenyl rings with an unsaturated ethylene linker, resulting in a flat and rigid conformation. "( An Elite Scaffold and a Wonderful Pharmacophore in Drug Discovery: Styrylquinoline.
Das, R; Dhanawat, M; Mehta, DK, 2021
)
2.3
"Styrylquinolines are a novel group of quinoline drugs that are known to have p53-independent antiproliferative activity and antiviral properties. "( Blocking and dislocation of Candida albicans Cdr1p transporter by styrylquinolines.
Cieślik, W; Krasowska, A; Musioł, R; Romanowicz, A; Szczepaniak, J, 2017
)
2.13
"The styrylquinoline E3 is a promising compound against L. "( [Styrylquinolines-type synthetic compounds with leishmanicidal and cytotoxic activities].
Muñoz, DL; Robledo, SM; Sánchez, EL; Santafé, GG; Torres, OL,
)
1.6

Effects

Styrylquinolines (SQs) have been shown to block viral replication at nontoxic concentrations. They inhibit IN 3'-processing activity in vitro by competing with the DNA substrate binding.

ExcerptReferenceRelevance
"Styrylquinoline has proved to be a potential lead molecule in medicinal chemist's toolkit due to the exploration of a variety of avenues of its activity as a drug candidate."( An Elite Scaffold and a Wonderful Pharmacophore in Drug Discovery: Styrylquinoline.
Das, R; Dhanawat, M; Mehta, DK, 2021
)
1.58
"Styrylquinolines (SQs) have been shown to block viral replication at nontoxic concentrations and to inhibit IN 3'-processing activity in vitro by competing with the DNA substrate binding."( Nuclear import of HIV-1 integrase is inhibited in vitro by styrylquinoline derivatives.
Dargemont, C; Leh, H; Mouscadet, JF; Mousnier, A, 2004
)
1.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
2-styrylquinoline
[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 (38)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency56.23410.003245.467312,589.2998AID2517
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency22.33420.140911.194039.8107AID2451
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency79.43280.631035.7641100.0000AID504339
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency35.48130.177814.390939.8107AID2147
LuciferasePhotinus pyralis (common eastern firefly)Potency0.07570.007215.758889.3584AID588342
glp-1 receptor, partialHomo sapiens (human)Potency10.00000.01846.806014.1254AID624417
thioredoxin reductaseRattus norvegicus (Norway rat)Potency79.43280.100020.879379.4328AID588453; AID588456
BRCA1Homo sapiens (human)Potency0.50120.89137.722525.1189AID624202
phosphopantetheinyl transferaseBacillus subtilisPotency50.11870.141337.9142100.0000AID1490
ATAD5 protein, partialHomo sapiens (human)Potency0.41970.004110.890331.5287AID504466; AID504467
TDP1 proteinHomo sapiens (human)Potency29.09290.000811.382244.6684AID686978; AID686979
Smad3Homo sapiens (human)Potency7.07950.00527.809829.0929AID588855
apical membrane antigen 1, AMA1Plasmodium falciparum 3D7Potency39.81070.707912.194339.8107AID720542
nonstructural protein 1Influenza A virus (A/WSN/1933(H1N1))Potency3.54810.28189.721235.4813AID2326
67.9K proteinVaccinia virusPotency4.73940.00018.4406100.0000AID720579; AID720580
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency50.11870.707936.904389.1251AID504333
pyruvate kinaseLeishmania mexicana mexicanaPotency12.58930.398113.744731.6228AID1721; AID1722
IDH1Homo sapiens (human)Potency18.35640.005210.865235.4813AID686970
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency25.11890.035520.977089.1251AID504332
NPC intracellular cholesterol transporter 1 precursorHomo sapiens (human)Potency2.81840.01262.451825.0177AID485313
chromobox protein homolog 1Homo sapiens (human)Potency79.43280.006026.168889.1251AID540317
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency4.17000.00419.984825.9290AID504444; AID720524
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency112.20203.548119.542744.6684AID743266
pyruvate kinase PKM isoform aHomo sapiens (human)Potency14.12540.04017.459031.6228AID1631; AID1634
ras-related protein Rab-9AHomo sapiens (human)Potency0.50120.00022.621531.4954AID485297
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency89.12510.050127.073689.1251AID588590
urokinase-type plasminogen activator precursorMus musculus (house mouse)Potency5.62340.15855.287912.5893AID540303
plasminogen precursorMus musculus (house mouse)Potency5.62340.15855.287912.5893AID540303
urokinase plasminogen activator surface receptor precursorMus musculus (house mouse)Potency5.62340.15855.287912.5893AID540303
gemininHomo sapiens (human)Potency18.35640.004611.374133.4983AID624297
VprHuman immunodeficiency virus 1Potency39.81071.584919.626463.0957AID651644
muscleblind-like protein 1 isoform 1Homo sapiens (human)Potency15.84890.00419.962528.1838AID2675
DNA dC->dU-editing enzyme APOBEC-3G isoform 1Homo sapiens (human)Potency22.38720.058010.694926.6086AID602310
lamin isoform A-delta10Homo sapiens (human)Potency35.48130.891312.067628.1838AID1487
Endothelin receptor type BRattus norvegicus (Norway rat)Potency12.58930.562315.160931.6228AID1721
Endothelin-1 receptorRattus norvegicus (Norway rat)Potency12.58930.562315.160931.6228AID1721
phosphoglycerate kinaseTrypanosoma brucei brucei TREU927Potency22.38720.07578.474229.0628AID602233
[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)
Protein skinhead-1Caenorhabditis elegansIC50 (µMol)62.40007.390021.523843.9000AID624474; AID651563
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (29)

Assay IDTitleYearJournalArticle
AID84649Inhibitory activity against human T-lymphotropic virus type 1 (HTLV-1) infected HUT-102 cells at 10 uM2003Bioorganic & medicinal chemistry letters, Mar-10, Volume: 13, Issue:5
Substituted quinolines induce inhibition of proliferation of HTLV-1 infected cells.
AID1550485Antileishmanial activity against Leishmania pifanoi MHOM-ET-67/L82 axenic amastigotes incubated for 96 hrs by MTT assay2019European journal of medicinal chemistry, Jun-01, Volume: 171Structure-activity relationships and mechanistic studies of novel mitochondria-targeted, leishmanicidal derivatives of the 4-aminostyrylquinoline scaffold.
AID1550487Cytotoxicity against mouse J774 cells incubated for 48 hrs by MTT assay2019European journal of medicinal chemistry, Jun-01, Volume: 171Structure-activity relationships and mechanistic studies of novel mitochondria-targeted, leishmanicidal derivatives of the 4-aminostyrylquinoline scaffold.
AID1550503Induction of morphological damage in Leishmania donovani MHOM/SD/00/1S-2D promastigotes assessed as increase in intracellular acidic pH at 5 uM pretreated with acridine orange followed by compound addition and measured at 1 hr by acridine orange based con2019European journal of medicinal chemistry, Jun-01, Volume: 171Structure-activity relationships and mechanistic studies of novel mitochondria-targeted, leishmanicidal derivatives of the 4-aminostyrylquinoline scaffold.
AID54900In vitro inhibition of [3H]LTD4 binding to guinea pig lung membranes1992Journal of medicinal chemistry, Oct-16, Volume: 35, Issue:21
Development of a novel series of styrylquinoline compounds as high-affinity leukotriene D4 receptor antagonists: synthetic and structure-activity studies leading to the discovery of (+-)-3-[[[3-[2-(7-chloro-2-quinolinyl)-(E)-ethenyl]phenyl][[3- (dimethyla
AID1550486Antileishmanial activity against Leishmania donovani MHOM/SD/00/1S-2D promastigotes incubated for 72 hrs by MTT assay2019European journal of medicinal chemistry, Jun-01, Volume: 171Structure-activity relationships and mechanistic studies of novel mitochondria-targeted, leishmanicidal derivatives of the 4-aminostyrylquinoline scaffold.
AID1550504Induction of morphological damage in Leishmania donovani MHOM/SD/00/1S-2D promastigotes assessed as increase in intracellular acidic pH at 5 uM pretreated with acridine orange followed by compound addition by acridine orange based fluorescence assay2019European journal of medicinal chemistry, Jun-01, Volume: 171Structure-activity relationships and mechanistic studies of novel mitochondria-targeted, leishmanicidal derivatives of the 4-aminostyrylquinoline scaffold.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation 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.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation 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.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation 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.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation 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
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation 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.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation 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.
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.
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.
AID1224864HCS microscopy assay (F508del-CFTR)2016PloS one, , Volume: 11, Issue:10
Increasing the Endoplasmic Reticulum Pool of the F508del Allele of the Cystic Fibrosis Transmembrane Conductance Regulator Leads to Greater Folding Correction by Small Molecule Therapeutics.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (58)

TimeframeStudies, This Drug (%)All Drugs %
pre-199011 (18.97)18.7374
1990's1 (1.72)18.2507
2000's14 (24.14)29.6817
2010's22 (37.93)24.3611
2020's10 (17.24)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.86

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

MetricThis Compound (vs All)
Research Demand Index11.86 (24.57)
Research Supply Index4.11 (2.92)
Research Growth Index5.97 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.86)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (6.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other56 (93.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]