Page last updated: 2024-11-12

n-cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide

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Description

N-cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide: has antineoplastic activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID19582717
CHEMBL ID1222381
CHEBI ID95020
SCHEMBL ID509365
MeSH IDM0559868

Synonyms (45)

Synonym
CHEMBL1222381
n-cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide
AKOS004090583
NCGC00182348-01
neuronal differentiation inducer iii
S7914
c11h10n2o2s
BRD-K53903639-001-01-3
SYENTKHGMVKGAQ-UHFFFAOYSA-N
832115-62-5
n-cyclopropyl-5-(thiophen-2-yl)-1,2-oxazole-3-carboxamide
SCHEMBL509365
CS-5072
isx 9
n-cyclopropyl-5-(2-thienyl)-3-isoxazolecarboxamide
HB3401
n-cyclopropyl-5-(2-thienyl)-3-isoxa zolecarboxamide
isx-9
HY-12323
AC-30932
isoxazole 9 (isx-9)
n-cyclopropyl-5-thiophen-2-yl-1,2-oxazole-3-carboxamide
EX-A937
isoxazole 9
FT-0699834
CHEBI:95020
n-cyclopropyl-5-(thiophen-2-yl)-isoxazole-3-carboxamide
F17380
isoxazole 9(isx9)
BCP16038
isx9
DTXSID50880071
Q27166781
n-cyclopropyl-5-thiophen-2-yl-3-isoxazolecarboxamide
neuronal differentiation inducer iii - cas 832115-62-5
Z220650400
mfcd04133937
AS-16612
EN300-141479
HMS3886J19
CCG-266818
BI162774
isx-9 (gmp)
HY-12323G
CS-0622784
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
heteroareneA heterocyclic compound formally derived from an arene by replacement of one or more methine (-C=) and/or vinylene (-CH=CH-) groups by trivalent or divalent heteroatoms, respectively, in such a way as to maintain the continuous pi-electron system characteristic of aromatic systems and a number of out-of-plane pi-electrons corresponding to the Hueckel rule (4n+2).
aromatic amideAn amide in which the amide linkage is bonded directly to an aromatic system.
[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 (1)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LuciferasePhotinus pyralis (common eastern firefly)Potency10.69100.007215.758889.3584AID588342
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (69)

Assay IDTitleYearJournalArticle
AID500522Induction of C57BL/6 mouse P19CL6 cell differentiation at 50 uM after 4 days2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500558Induction of NMDA receptor-mediated neuroD gene expression in rat HCN cells at 50 uM after 24 hrs by RT-PCR analysis in presence of NMDA receptor antagonist MK8012008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500557Induction of L-type calcium channel/NMDA receptor-mediated neuroD gene expression in rat HCN cells at 50 uM after 24 hrs by RT-PCR analysis in presence of multiple inhibitors2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500527Induction of rat HCN cell differentiation assessed as increase in GluR2 gene expression after 3 hrs by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500578Induction of CAMK-mediated MREx3 activity in rat HCN cells by luciferase reporter gene assay in presence of 200 nM PKC inhibitor Go69762008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500537Induction of rat HCN cell differentiation assessed as increase in NR1 gene expression after 3 days by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500532Induction of rat HCN cell differentiation assessed as increase in Tuj1 gene expression after 1 day by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500582Induction of rat HCN cell proliferation at 20 uM after 20 days by BrdU incorporation assay2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500555Induction of NMDA receptor-mediated neuroD gene expression in rat HCN cells at 50 uM after 3 hrs by RT-PCR analysis in presence of NMDA receptor antagonist MK8012008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500551Induction of L-type calcium channel-mediated neuroD gene expression in rat HCN cells after 24 hrs by luciferase reporter gene assay in presence of NMDA receptor antagonist MK8012008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500571Induction of HDAC5 translocation in cytoplasm of rat HCN cells assessed as phosphorylated HDAC5 accumulation2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500577Induction of CAMK-mediated MREx3 activity in rat HCN cells by luciferase reporter gene assay in presence of 2.5 uM CAMK inhibitor KN932008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500549Induction of NMDA receptor-mediated Ca2+ influx in rat HCN cells at 5 uM by Fura-2 imaging analysis in presence of NMDA receptor antagonist MK8012008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500519Inhibition of LIF/BMP2-mediated rat HCN cell differentiation into astrocytes at 25 uM2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500560Induction of rat HCN cell differentiation assessed as induction of induction of MREx3 gene expression by luciferase reporter gene assay2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500575Induction of HDAC5 translocation in nucleus of rat HCN cells assessed as GFP-HDAC5 fusion protein accumulation at 20 uM by fluorescence assay2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500548Induction of L-type calcium channel/NMDA receptor-mediated Ca2+ influx in rat HCN cells at 5 uM by Fura-2 imaging analysis in presence of multiple of inhibitors2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500570Induction of HDAC5 translocation in nucleus of rat HCN cells assessed as phosphorylated HDAC5 accumulation2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500517Induction of rat HCN cell differentiation assessed as induction of neuronal reporter neuroD activity by luciferase reporter gene assay2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500546Induction of NMDA receptor-mediated Ca2+ influx in rat HCN cells in presence of NMDA receptor antagonist MK8012008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500574Effect on subcellular distribution of CREB protein in rat HCN cells after 5 days2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500525Induction of rat HCN differentiation into Tuj1 neurons at 25 uM after 4 days2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500524Inhibition of gliogenesis differentiation in rat HCN cells at 25 uM after 4 days2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500535Induction of rat HCN cell differentiation assessed as increase in GluR2 gene expression after 3 days by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500583Induction of rat HCN cell differentiation into Tuj1 neurons at 20 uM after 4 days in presence of caspase inhibitor Q-VD-Oph2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500533Induction of rat HCN cell differentiation assessed as increase in NR1 gene expression after 1 day by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500545Induction of L-type calcium channel/NMDA receptor-mediated Ca2+ influx in rat HCN cells in presence multiple inhibitors2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500526Induction of rat HCN cell differentiation assessed as increase in neuroD gene expression after 3 hrs by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500779Induction of HDAC5 translocation in nucleus of rat HCN cells assessed as GFP-HDAC5 S258A S498A mutant fusion protein accumulation at 5 uM by fluorescence assay2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500544Induction of L-type calcium channel/NMDA receptor-mediated Ca2+ influx in rat HCN cells2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500541Induction of rat HCN cell differentiation assessed as increase in p27Kip1 gene expression after 9 days by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500563Induction of rat HCN cell differentiation assessed as upregulation of MEF2D expression after 2 to 4 days by protein blotting analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500528Induction of rat HCN cell differentiation assessed as increase in Tuj1 gene expression after 3 hrs by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500581Induction of CAMK-mediated MREx3 activity in rat HCN cells by luciferase reporter gene assay in presence of 2.5 uM potassium channel inhibitor KN922008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500543Induction of LIF/BMP2-mediated rat HCN cell differentiation into Tuj1 neurons after 4 days2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500580Induction of CAMK2 phosphorylation in rat HCN cells by Western blot analysis in presence of 2.5 uM CAMK inhibitor KN932008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500540Induction of rat HCN cell differentiation assessed as increase in MAP2AB gene expression after 9 days by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500531Induction of rat HCN cell differentiation assessed as increase in GluR2 gene expression after 1 day by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500520Induction of mouse neuronal progenitor cell differentiation at 25 uM after 4 days2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500569Induction of HDAC5 phosphorylation in rat HCN cells after 24 hrs2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500539Induction of rat HCN cell differentiation assessed as increase in DCX gene expression after 9 days by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500536Induction of rat HCN cell differentiation assessed as increase in Tuj1 gene expression after 3 days by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500523Induction of mouse progenitor cell differentiation into Tuj1 neurons at 20 uM after 4 days2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500568Induction of HDAC5 phosphorylation in rat HCN cells after 6 hrs2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500564Induction of neurogenesis in undifferentiated rat HCN cells assessed as MEF2A protein level at 8 to 64 uM after 9 hrs by protein blotting analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500538Induction of rat HCN cell differentiation assessed as increase in beta-TUB3 gene expression after 9 days by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500572Effect on subcellular distribution of MEF2A protein in rat HCN cells after 5 days2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500566Induction of neurogenesis in undifferentiated rat HCN cells assessed as MAP2AB protein level at 8 to 64 uM after 9 hrs by protein blotting analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500550Induction of L-type calcium channel-mediated neuroD gene expression in rat HCN cells after 24 hrs by luciferase reporter gene assay in presence of multiple inhibitors2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500534Induction of rat HCN cell differentiation assessed as increase in neuroD gene expression after 3 days by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500562Induction of rat HCN cell differentiation assessed as upregulation of MEF2A expression after 2 to 4 days by protein blotting analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500565Induction of neurogenesis in undifferentiated rat HCN cells assessed as MEF2C protein level at 8 to 64 uM after 9 hrs by protein blotting analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500552Induction of L-type calcium channel-mediated neuroD gene expression in rat HCN cells after 24 hrs by luciferase reporter gene assay in presence of NMDA receptor antagonist nifedipine2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500554Induction of L-type calcium channel/NMDA receptor-mediated neuroD gene expression in rat HCN cells at 50 uM after 3 hrs by RT-PCR analysis in presence of multiple inhibitors2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500567Induction of neurogenesis in undifferentiated rat HCN cells assessed as GlR2/3 protein level at 8 to 64 uM after 9 hrs by protein blotting analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500584Cytotoxicity in rat HCN cells at 20 uM after 4 days2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500521Induction of mouse C57BL/6 P19CL6 cell differentiation assessed as induction of neuronal reporter gluR2 expression by luciferase reporter gene assay2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500547Induction of L-type calcium channel/NMDA receptor-mediated Ca2+ influx in rat HCN cells at 5 uM by Fura-2 imaging analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500561Induction of rat HCN cell differentiation assessed as upregulation of MEF2C expression after 2 to 4 days by protein blotting analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500529Induction of rat HCN cell differentiation assessed as increase in NR1 gene expression after 3 hrs by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500556Induction of NMDA receptor-mediated neuroD gene expression in rat HCN cells at 50 uM after 3 hrs by RT-PCR analysis in presence of NMDA receptor antagonist nifedipine2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500553Induction of rat HCN cell differentiation assessed as increase in neuroD gene expression at 10 uM after 3 hrs by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500518Induction of rat HCN cell differentiation assessed as induction of neuronal reporter neuroD activity at 20 uM after 24 hrs by luciferase reporter gene assay2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500573Effect on subcellular distribution of MEF2C protein in rat HCN cells after 5 days2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500530Induction of rat HCN cell differentiation assessed as increase in neuroD gene expression after 1 day by RT-PCR analysis2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500585Induction of mouse progenitor cell differentiation into Map2ab-positive neurons at 20 uM after 4 days2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500559Induction of NMDA receptor-mediated neuroD gene expression in rat HCN cells at 50 uM after 24 hrs by RT-PCR analysis in presence of NMDA receptor antagonist nifedipine2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500542Induction of LIF/BMP2-mediated rat HCN cell differentiation into GFAP-positive astrocytes after 4 days2008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
AID500579Induction of CAMK-mediated HDAC5 phosphorylation in rat HCN cells by Western blot analysis in presence of 2.5 uM CAMK inhibitor KN932008Nature chemical biology, Jul, Volume: 4, Issue:7
Small-molecule activation of neuronal cell fate.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (7.69)29.6817
2010's9 (69.23)24.3611
2020's3 (23.08)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.08

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 Index13.08 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index5.72 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.08)

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%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]