Compounds > 3-(5-methoxy-2-methyl-1h-indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one
Page last updated: 2024-11-13

3-(5-methoxy-2-methyl-1h-indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one

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Cross-References

ID SourceID
PubMed CID51039247
CHEMBL ID2032358
SCHEMBL ID13723990
SCHEMBL ID13723992
MeSH IDM0575049

Synonyms (12)

Synonym
CHEMBL2032358
SCHEMBL13723990
SCHEMBL13723992
1363421-46-8
momipp
BS-46755
(e)-3-(5-methoxy-2-methyl-1h-indol-3-yl)-1-(pyridin-4-yl)prop-2-en-1-one
nsc-781549
nsc781549
HY-119624
CS-0077056
AKOS040753122
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (57)

Assay IDTitleYearJournalArticle
AID1202838Inhibition of tubulin polymerization in in human U251 cells at 0.1 uM after 4 hrs by immunoblot analysis2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity.
AID1065050Induction of methuosis in human U251 cells assessed as detachment of vacuolated cells at 10 uM after 2 days by phase-contrast microscopic analysis2014ACS medicinal chemistry letters, Jan-09, Volume: 5, Issue:1
Differential Induction of Cytoplasmic Vacuolization and Methuosis by Novel 2-Indolyl-Substituted Pyridinylpropenones.
AID662460Induction of methuosis in human U251 cells assessed as induction of cellular vacuolization at 2.5 to 10 uM after 3 days by phase contrast microscopic analysis2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID1498014Antiproliferative activity against human MCF7 cells after 48 hrs by MTS assay2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Discovery and Identification of Small Molecules as Methuosis Inducers with in Vivo Antitumor Activities.
AID1202833Cell cycle arrest in human U251 cells assessed as accumulation at S phase at 0.1 uM after 24 hrs by DNA histogram based flow cytometry2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity.
AID662463Cytotoxicity against human U251 cells assessed as inhibition of colony formation at 2 to 10 uM treated for 48 hrs followed by washout measured after 2 weeks relative to control2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID662465Induction of methuosis in human temozolomide-resistant U251 cells assessed as induction of cellular vacuolization at 2.5 to 10 uM after 3 days by phase contrast microscopic analysis2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID662471Cytotoxicity against HMEC assessed as reduction of cell viability at 10 uM after 24 hrs by MTT assay relative to control2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID1202821Induction of methuosis in human U251 cells assessed as cytoplasmic vacuolization measured as nonviable cell at 2.5 uM after 48 hrs by phase contrast microscopy2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity.
AID1498008Antiproliferative activity against human A375 cells after 48 hrs by MTS assay2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Discovery and Identification of Small Molecules as Methuosis Inducers with in Vivo Antitumor Activities.
AID1202835Disruption of microtubule organization in human U251 cells at 3 uM after 24 hrs by DAPI staining-based immunofluorescence microscopy2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity.
AID1202823Growth inhibition of human U251 cells at 2.5 uM after 24 hrs sulphorhodomine B colorimetric assay2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity.
AID1498007Induction of methuosis in human MDA-MB-231 cells assessed as increase in vacuole formation at 10 uM after 24 hrs by phase contrast microscopic analysis relative to control2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Discovery and Identification of Small Molecules as Methuosis Inducers with in Vivo Antitumor Activities.
AID1498006Induction of methuosis in human MDA-MB-231 cells assessed as increase in vacuole formation at 1 uM after 24 hrs by phase contrast microscopic analysis relative to control2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Discovery and Identification of Small Molecules as Methuosis Inducers with in Vivo Antitumor Activities.
AID662456Cytotoxicity against human U251 cells assessed as inhibition of colony formation at 10 uM treated for 48 hrs followed by washout measured after 2 weeks relative to control2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID662464Cytotoxicity against human U251 cells assessed as inhibition of colony formation at 5 to 20 uM treated for 48 hrs followed by washout measured after 2 weeks relative to control2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID662468Cytotoxicity against human doxorubicin-resistant MCF7 cells assessed as inhibition of colony formation at 2.5 to 10 uM treated for 48 hrs followed by washout measured after 2 weeks2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID1065054Growth inhibition of human U251 cells preincubated for 24 hrs followed by compound-washout measured at 48 hrs by sulforhodamine assay2014ACS medicinal chemistry letters, Jan-09, Volume: 5, Issue:1
Differential Induction of Cytoplasmic Vacuolization and Methuosis by Novel 2-Indolyl-Substituted Pyridinylpropenones.
AID662470Induction of methuosis in human doxorubicin-resistant MCF7 cells assessed as induction of cellular vacuolization at 2.5 to 10 uM after 3 days by phase contrast microscopic analysis2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID662466Cytotoxicity against human temozolomide-resistant U251 cells assessed as reduction of cell viability at 2.5 to 10 uM after 24 hrs by MTT assay2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID1202829Cell cycle arrest in human U251 cells assessed as accumulation at G2/M phase at 3 uM after 24 hrs by DNA histogram based flow cytometry2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity.
AID662467Cytotoxicity against human MCF7 cells assessed as inhibition of colony formation at 2.5 to 10 uM treated for 48 hrs followed by washout measured after 2 weeks2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID1326506Induction of microtubule disruption in human U251 cells at 5 uM by DAPI staining based immunofluorescence microscopy2016European journal of medicinal chemistry, Oct-21, Volume: 122Synthesis and biological evaluation of isomeric methoxy substitutions on anti-cancer indolyl-pyridinyl-propenones: Effects on potency and mode of activity.
AID1202822Cytotoxicity against human U251 cells at 10 uM after 48 hrs by phase contrast microscopy2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity.
AID1498015Antiproliferative activity against human HCT116 cells after 48 hrs by MTS assay2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Discovery and Identification of Small Molecules as Methuosis Inducers with in Vivo Antitumor Activities.
AID1065051Induction of methuosis in human U251 cells assessed as heavily vacuolated cells at 10 uM after 1 day by phase-contrast microscopic analysis2014ACS medicinal chemistry letters, Jan-09, Volume: 5, Issue:1
Differential Induction of Cytoplasmic Vacuolization and Methuosis by Novel 2-Indolyl-Substituted Pyridinylpropenones.
AID662469Induction of methuosis in human MCF7 cells assessed as induction of cellular vacuolization at 2.5 to 10 uM after 3 days by phase contrast microscopic analysis2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID1498018Cytotoxicity against human MCF10A cells assessed as reduction in cell viability after 48 hrs by MTS assay2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Discovery and Identification of Small Molecules as Methuosis Inducers with in Vivo Antitumor Activities.
AID1065052Induction of methuosis in human U251 cells assessed as sparse cells at 10 uM after 1 day by phase-contrast microscopic analysis2014ACS medicinal chemistry letters, Jan-09, Volume: 5, Issue:1
Differential Induction of Cytoplasmic Vacuolization and Methuosis by Novel 2-Indolyl-Substituted Pyridinylpropenones.
AID662475Cytotoxicity against human fibroblasts cells assessed as reduction of cell viability at 10 uM after 24 hrs by MTT assay relative to control2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID1202820Induction of methuosis in human U251 cells assessed as cytoplasmic vacuolization at 2.5 uM up to 48 hrs by phase contrast microscopy2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity.
AID1065049Induction of methuosis in human U251 cells assessed as loss of membrane integrity at 10 uM after 2 days by phase-contrast microscopic analysis2014ACS medicinal chemistry letters, Jan-09, Volume: 5, Issue:1
Differential Induction of Cytoplasmic Vacuolization and Methuosis by Novel 2-Indolyl-Substituted Pyridinylpropenones.
AID1326497Induction of methuosis in human U251 cells assessed as loss of membrane integrity at >=2.5 uM after 48 hrs by phase contrast microscopic analysis2016European journal of medicinal chemistry, Oct-21, Volume: 122Synthesis and biological evaluation of isomeric methoxy substitutions on anti-cancer indolyl-pyridinyl-propenones: Effects on potency and mode of activity.
AID1326499Mitotic arrest in human U251 cells assessed as accumulation at G1/G0 phase at 3 uM after 24 hrs by propidium iodide staining based flow cytometric analysis2016European journal of medicinal chemistry, Oct-21, Volume: 122Synthesis and biological evaluation of isomeric methoxy substitutions on anti-cancer indolyl-pyridinyl-propenones: Effects on potency and mode of activity.
AID1202817Growth inhibition of human U251 cells after 24 hrs sulphorhodomine B colorimetric assay2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity.
AID1326493Growth inhibition of human U251 cells after 48 hrs by sulforhodamine B colorimetric assay2016European journal of medicinal chemistry, Oct-21, Volume: 122Synthesis and biological evaluation of isomeric methoxy substitutions on anti-cancer indolyl-pyridinyl-propenones: Effects on potency and mode of activity.
AID1498017Antiproliferative activity against human HepG2 cells after 48 hrs by MTS assay2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Discovery and Identification of Small Molecules as Methuosis Inducers with in Vivo Antitumor Activities.
AID1202832Cell cycle arrest in human U251 cells assessed as accumulation at G2/M phase at 0.1 uM after 24 hrs by DNA histogram based flow cytometry2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity.
AID1065053Cytotoxicity against human U251 cells assessed as cell viability at 10 uM after 2 days by trypan blue dye-exclusion assay relative to control2014ACS medicinal chemistry letters, Jan-09, Volume: 5, Issue:1
Differential Induction of Cytoplasmic Vacuolization and Methuosis by Novel 2-Indolyl-Substituted Pyridinylpropenones.
AID1498013Antiproliferative activity against human MDA-MB-435S cells after 48 hrs by MTS assay2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Discovery and Identification of Small Molecules as Methuosis Inducers with in Vivo Antitumor Activities.
AID1326496Induction of methuosis in human U251 cells assessed as cell detachment from dish at >=2.5 uM after 48 hrs by phase contrast microscopic analysis2016European journal of medicinal chemistry, Oct-21, Volume: 122Synthesis and biological evaluation of isomeric methoxy substitutions on anti-cancer indolyl-pyridinyl-propenones: Effects on potency and mode of activity.
AID1498011Antiproliferative activity against human A549 cells after 48 hrs by MTS assay2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Discovery and Identification of Small Molecules as Methuosis Inducers with in Vivo Antitumor Activities.
AID1498009Antiproliferative activity against human SK-MEL-28 cells after 48 hrs by MTS assay2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Discovery and Identification of Small Molecules as Methuosis Inducers with in Vivo Antitumor Activities.
AID662474Cytotoxicity against human fibroblasts assessed as induction of cytoplasmic vacuolization at 1 to 10 uM after 24 hrs by phase contrast microscopic analysis2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID662476Cytotoxicity against human fibroblasts cells at stationary growth phase assessed as reduction of cell viability at 10 uM after 24 hrs by MTT assay2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID1498012Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTS assay2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Discovery and Identification of Small Molecules as Methuosis Inducers with in Vivo Antitumor Activities.
AID1202819Induction of methuosis in human U251 cells assessed as cytoplasmic vacuolization at 2.5 uM within 4 hrs by phase contrast microscopy2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity.
AID662457Induction of methuosis in human U251 cells assessed as induction of cellular vacuolization at 10 uM after 24 to 48 hrs by phase contrast microscopic analysis2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID1202834Cell cycle arrest in human U251 cells assessed as accumulation at S phase at 3 uM after 24 hrs by DNA histogram based flow cytometry2015Journal of medicinal chemistry, Mar-12, Volume: 58, Issue:5
Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity.
AID1326495Induction of methuosis in human U251 cells after 4 to 48 hrs by phase contrast microscopic analysis2016European journal of medicinal chemistry, Oct-21, Volume: 122Synthesis and biological evaluation of isomeric methoxy substitutions on anti-cancer indolyl-pyridinyl-propenones: Effects on potency and mode of activity.
AID662455Cytotoxicity against human U251 cells assessed as reduction of cell viability at 10 uM after 24 hrs by MTT assay relative to control2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID662458Cytotoxicity against human U251 cells after 24 hrs by MTT assay2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID1498016Antiproliferative activity against human BGC823 cells after 48 hrs by MTS assay2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Discovery and Identification of Small Molecules as Methuosis Inducers with in Vivo Antitumor Activities.
AID1498010Antiproliferative activity against human SK-MEL-30 cells after 48 hrs by MTS assay2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Discovery and Identification of Small Molecules as Methuosis Inducers with in Vivo Antitumor Activities.
AID662473Cytotoxicity against HMEC assessed as induction of cytoplasmic vacuolization at 1 to 10 uM after 24 hrs by phase contrast microscopic analysis2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID662472Cytotoxicity against human MCF7 cells assessed as reduction of cell viability at 10 uM after 24 hrs by MTT assay relative to control2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
AID662459Cytotoxicity against human U251 cells assessed as reduction of cell growth and viability at 2.5 to 10 uM after 3 days by MTT assay2012Journal of medicinal chemistry, Mar-08, Volume: 55, Issue:5
Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's5 (100.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.72

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 Index12.72 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.72)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
staurosporine
[no description available]		2.1710indolocarbazole alkaloid;
organic heterooctacyclic compound		apoptosis inducer;
bacterial metabolite;
EC 2.7.11.13 (protein kinase C) inhibitor;
geroprotector
demecolcine
Demecolcine: An alkaloid isolated from Colchicum autumnale L. and used as an antineoplastic.. (-)-demecolcine : A secondary amino compound that is (S)-colchicine in which the N-acetyl group is replaced by an N-methyl group. Isolable from the autumn crocus, Colchicum autumnale, it is less toxic than colchicine and is used as an antineoplastic.		2.1110alkaloid;
secondary amino compound		antineoplastic agent;
microtubule-destabilising agent
ConditionIndicatedRelationship StrengthStudiesTrials
Astrocytoma, Grade IV
[description not available]		02.1110
Glioblastoma
A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.		02.1110