Page last updated: 2024-10-15

2-hydroxy-1-naphthylaldehyde isonicotinoyl hydrazone

Description

2-hydroxy-1-naphthylaldehyde isonicotinoyl hydrazone: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID135400486
CHEMBL ID390195
SCHEMBL ID800974
MeSH IDM0332305

Synonyms (22)

Synonym
2-hydroxy-1-naphthylaldehyde isonicotinoyl hydrazone
n'-[(e)-(2-hydroxynaphthalen-1-yl)methylidene]pyridine-4-carbohydrazide
CHEMBL390195 ,
2-hydroxy-1 naphthylaldehydeisonicotinoyl hydrazone
AKOS001279162
n'-[(2-hydroxynaphthalen-1-yl)methylidene]pyridine-4-carbohydrazide
EN300-55000
isonicotinic acid, [(2-hydroxy-1-naphthalenyl)methylene]hydrazide
n-[(e)-(2-hydroxy-1-naphthyl)methyleneamino]pyridine-4-carboxamide
S5772
SCHEMBL800974
bdbm50484830
as8351, >=98% (hplc)
n'-[(2-hydroxy-1-naphthyl)methylene]isonicotinohydrazide
(e)-n'-((2-hydroxynaphthalen-1-yl)methylene)isonicotinohydrazide
Z49547268
329183-01-9
HY-100744
CS-7838
n-[(e)-(2-hydroxynaphthalen-1-yl)methylideneamino]pyridine-4-carboxamide
n'-((2-hydroxynaphthalen-1-yl)methylene)isonicotinohydrazide
mfcd00033110
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1IC50 (µMol)100.00000.00011.076810.0000AID649483
Integrase Human immunodeficiency virus 1IC50 (µMol)100.00000.00051.544310.0000AID725310; AID725311
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID725313Inhibition of human Flag-tagged LEDGF interaction to His6-tagged HIV1 integrase expressed in Escherichia coli BL21 (DE3) preincubated for 20 mins measured after 1 hr by AlphaScreen proximity luminescent assay2013Bioorganic & medicinal chemistry, Feb-15, Volume: 21, Issue:4
Discovery of novel inhibitors of LEDGF/p75-IN protein-protein interactions.
AID619952Toxicity in human SK-N-MC cells assessed as cell viability after 3 hrs by trypan blue staining2011Journal of medicinal chemistry, Oct-13, Volume: 54, Issue:19
Halogenated 2'-benzoylpyridine thiosemicarbazone (XBpT) chelators with potent and selective anti-neoplastic activity: relationship to intracellular redox activity.
AID1317567Selectivity index, ratio of IC50 for rat L8 cells to IC50 for human SK-N-MC cells2016European journal of medicinal chemistry, Sep-14, Volume: 120Aroylhydrazone iron chelators: Tuning antioxidant and antiproliferative properties by hydrazide modifications.
AID303517Inhibition of cellular iron uptake from 59Fe]transferrin in human SK-N-MC cells at 50 uM relative to control2007Journal of medicinal chemistry, Nov-29, Volume: 50, Issue:24
Design, synthesis, and characterization of new iron chelators with anti-proliferative activity: structure-activity relationships of novel thiohydrazone analogues.
AID716228Inhibition to 59Fe uptake from 59Fe-transferrin in human SK-N-MC cells at 25 uM after 3 hrs2012Journal of medicinal chemistry, Aug-23, Volume: 55, Issue:16
Novel second-generation di-2-pyridylketone thiosemicarbazones show synergism with standard chemotherapeutics and demonstrate potent activity against lung cancer xenografts after oral and intravenous administration in vivo.
AID292409Inhibition of iron uptake from transferrin in SK-N-MC cells at 50 uM relative to control2007Journal of medicinal chemistry, Jul-26, Volume: 50, Issue:15
Design, synthesis, and characterization of novel iron chelators: structure-activity relationships of the 2-benzoylpyridine thiosemicarbazone series and their 3-nitrobenzoyl analogues as potent antitumor agents.
AID1317563Antiproliferative activity against rat L8 cells after 22 to 72 hrs by MTT assay2016European journal of medicinal chemistry, Sep-14, Volume: 120Aroylhydrazone iron chelators: Tuning antioxidant and antiproliferative properties by hydrazide modifications.
AID312542Induction of intracellular iron mobilization in human SK-MN-C cells relative to control2008Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2
Structure-activity relationships of novel iron chelators for the treatment of iron overload disease: the methyl pyrazinylketone isonicotinoyl hydrazone series.
AID619948Induction of Fe efflux in human SK-N-MC cells assessed as release of intracellular 59Fe up to 25 uM after 3 hrs by gamma-scintillation counting2011Journal of medicinal chemistry, Oct-13, Volume: 54, Issue:19
Halogenated 2'-benzoylpyridine thiosemicarbazone (XBpT) chelators with potent and selective anti-neoplastic activity: relationship to intracellular redox activity.
AID725311Inhibition of wild type HIV1 integrase 3'-processing activity using 5'-end 32P-labeled linear oligonucleotide as substrate preincubated for 30 mins2013Bioorganic & medicinal chemistry, Feb-15, Volume: 21, Issue:4
Discovery of novel inhibitors of LEDGF/p75-IN protein-protein interactions.
AID1317566Selectivity index, ratio of IC50 for HUVEC to IC50 for human SK-N-MC cells2016European journal of medicinal chemistry, Sep-14, Volume: 120Aroylhydrazone iron chelators: Tuning antioxidant and antiproliferative properties by hydrazide modifications.
AID649483Inhibition of ribonuclease H activity of HIV1 reverse transcriptase using as poly(dC)-[3H]poly(rG) as substrate2012European journal of medicinal chemistry, Apr, Volume: 50Identification of HIV-1 reverse transcriptase dual inhibitors by a combined shape-, 2D-fingerprint- and pharmacophore-based virtual screening approach.
AID439759Antiproliferative activity against human SK-N-MC cells after 96 hrs by MTT assay2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
Thiosemicarbazones from the old to new: iron chelators that are more than just ribonucleotide reductase inhibitors.
AID292406Antiproliferative activity against human SK-N-MC cells after 72 hrs by MTT assay2007Journal of medicinal chemistry, Jul-26, Volume: 50, Issue:15
Design, synthesis, and characterization of novel iron chelators: structure-activity relationships of the 2-benzoylpyridine thiosemicarbazone series and their 3-nitrobenzoyl analogues as potent antitumor agents.
AID312543Inhibition of [59Fe]uptake from human transferrin in SK-MN-C cells relative to control2008Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2
Structure-activity relationships of novel iron chelators for the treatment of iron overload disease: the methyl pyrazinylketone isonicotinoyl hydrazone series.
AID312544Antiproliferative activity against human SK-MN-C cells by MTT assay2008Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2
Structure-activity relationships of novel iron chelators for the treatment of iron overload disease: the methyl pyrazinylketone isonicotinoyl hydrazone series.
AID303516Effect on iron efflux in human SK-N-MC cells assessed as cellular iron release2007Journal of medicinal chemistry, Nov-29, Volume: 50, Issue:24
Design, synthesis, and characterization of new iron chelators with anti-proliferative activity: structure-activity relationships of novel thiohydrazone analogues.
AID677905Antiproliferative activity against human SK-N-MC cells after 72 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Sep-01, Volume: 22, Issue:17
Synthesis and characterization of quinoline-based thiosemicarbazones and correlation of cellular iron-binding efficacy to anti-tumor efficacy.
AID619949Inhibition of 59Fe uptake from transferrin in human SK-N-MC cells at 25 uM after 3 hrs relative to control2011Journal of medicinal chemistry, Oct-13, Volume: 54, Issue:19
Halogenated 2'-benzoylpyridine thiosemicarbazone (XBpT) chelators with potent and selective anti-neoplastic activity: relationship to intracellular redox activity.
AID716220Antiproliferative activity at human A549 cells after 72 hrs by MTT assay2012Journal of medicinal chemistry, Aug-23, Volume: 55, Issue:16
Novel second-generation di-2-pyridylketone thiosemicarbazones show synergism with standard chemotherapeutics and demonstrate potent activity against lung cancer xenografts after oral and intravenous administration in vivo.
AID1317562Antiproliferative activity against human SK-N-MC cells after 22 to 72 hrs by MTT assay2016European journal of medicinal chemistry, Sep-14, Volume: 120Aroylhydrazone iron chelators: Tuning antioxidant and antiproliferative properties by hydrazide modifications.
AID725310Inhibition of wild type HIV1 integrase strand transfer activity using 5'-end 32P-labeled linear oligonucleotide as substrate preincubated for 30 mins2013Bioorganic & medicinal chemistry, Feb-15, Volume: 21, Issue:4
Discovery of novel inhibitors of LEDGF/p75-IN protein-protein interactions.
AID716219Antiproliferative activity at human MRC5 cells after 72 hrs by MTT assay2012Journal of medicinal chemistry, Aug-23, Volume: 55, Issue:16
Novel second-generation di-2-pyridylketone thiosemicarbazones show synergism with standard chemotherapeutics and demonstrate potent activity against lung cancer xenografts after oral and intravenous administration in vivo.
AID1763360Antimalarial activity against Plasmodium falciparum 7G82021Bioorganic & medicinal chemistry, 06-01, Volume: 39A trio of quinoline-isoniazid-phthalimide with promising antiplasmodial potential: Synthesis, in-vitro evaluation and heme-polymerization inhibition studies.
AID716221Antiproliferative activity at human DMS53 cells after 72 hrs by MTT assay2012Journal of medicinal chemistry, Aug-23, Volume: 55, Issue:16
Novel second-generation di-2-pyridylketone thiosemicarbazones show synergism with standard chemotherapeutics and demonstrate potent activity against lung cancer xenografts after oral and intravenous administration in vivo.
AID1317564Antiproliferative activity against HUVEC after 22 to 72 hrs by MTT assay2016European journal of medicinal chemistry, Sep-14, Volume: 120Aroylhydrazone iron chelators: Tuning antioxidant and antiproliferative properties by hydrazide modifications.
AID439762Antiproliferative activity against human SK-N-MC cells after 72 hrs by MTT assay2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
Thiosemicarbazones from the old to new: iron chelators that are more than just ribonucleotide reductase inhibitors.
AID722575Cytotoxicity against human SK-N-MC cells assessed as growth inhibition after 72 hrs by MTT assay2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
Alkyl substituted 2'-benzoylpyridine thiosemicarbazone chelators with potent and selective anti-neoplastic activity: novel ligands that limit methemoglobin formation.
AID303514Antiproliferative activity against human SK-N-MC cells by MTT assay2007Journal of medicinal chemistry, Nov-29, Volume: 50, Issue:24
Design, synthesis, and characterization of new iron chelators with anti-proliferative activity: structure-activity relationships of novel thiohydrazone analogues.
AID716222Induction of 59Fe mobilization in human SK-N-MC cells at 25 uM after 3 hrs by gamma-scintillation counter2012Journal of medicinal chemistry, Aug-23, Volume: 55, Issue:16
Novel second-generation di-2-pyridylketone thiosemicarbazones show synergism with standard chemotherapeutics and demonstrate potent activity against lung cancer xenografts after oral and intravenous administration in vivo.
AID619945Antiproliferative activity against human SK-N-MC cells after 72 hrs by MTS assay2011Journal of medicinal chemistry, Oct-13, Volume: 54, Issue:19
Halogenated 2'-benzoylpyridine thiosemicarbazone (XBpT) chelators with potent and selective anti-neoplastic activity: relationship to intracellular redox activity.
AID370485Antiproliferative activity against human SK-N-MC cells after 72 hrs by MTT assay2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
2-Acetylpyridine thiosemicarbazones are potent iron chelators and antiproliferative agents: redox activity, iron complexation and characterization of their antitumor activity.
AID439761Antiproliferative activity against human SK-N-MC cells2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
Thiosemicarbazones from the old to new: iron chelators that are more than just ribonucleotide reductase inhibitors.
AID716225Antiproliferative activity at human SK-N-MC cells after 72 hrs by MTT assay2012Journal of medicinal chemistry, Aug-23, Volume: 55, Issue:16
Novel second-generation di-2-pyridylketone thiosemicarbazones show synergism with standard chemotherapeutics and demonstrate potent activity against lung cancer xenografts after oral and intravenous administration in vivo.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (8.70)18.2507
2000's11 (47.83)29.6817
2010's9 (39.13)24.3611
2020's1 (4.35)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (4.35%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other22 (95.65%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]