Page last updated: 2024-12-06

n,n'-bis(salicyl)hydrazine

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

Description

n,n'-bis(salicyl)hydrazine, also known as bis(salicylidene)hydrazine, is a Schiff base compound derived from the condensation of salicylaldehyde and hydrazine. It is a versatile ligand that forms complexes with various transition metals. The compound has been extensively studied due to its potential applications in diverse fields, including:
- **Coordination chemistry:** It forms stable complexes with transition metals, exhibiting interesting magnetic and catalytic properties.
- **Analytical chemistry:** It is used as a chelating agent for the detection and determination of metal ions.
- **Biochemistry:** It has shown potential as an antioxidant and anti-inflammatory agent, inhibiting the formation of reactive oxygen species.
- **Materials science:** It has been explored for the development of new materials with specific optical and electronic properties.
- **Pharmacology:** Its complexes have been investigated for their anticancer, antimicrobial, and antiviral activities.
The synthesis of n,n'-bis(salicyl)hydrazine typically involves the condensation reaction of salicylaldehyde and hydrazine hydrate in an alcoholic solution under reflux conditions. The resulting product is a yellow crystalline solid that is sparingly soluble in water but soluble in most organic solvents.
Its importance in research stems from its ability to act as a bidentate ligand, coordinating to metal ions through the nitrogen and oxygen atoms of the Schiff base moiety. The complexation of n,n'-bis(salicyl)hydrazine with different metal ions leads to the formation of complexes with varying properties and applications.'

N,N'-bis(salicyl)hydrazine: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65303
CHEMBL ID36303
SCHEMBL ID77381
MeSH IDM0274811

Synonyms (37)

Synonym
smr001565325
nsc-691999
NCI60_003912
AE-848/32079025
nsc691999
2-hydroxybenzoic acid 2-(2-hydroxybenzoyl)hydrazide
2-hydroxy-n'-(2-hydroxybenzoyl)benzohydrazide
nsc408200
1,2-bis(2-hydroxybenzoyl)hydrazine
di-2ohphco hydr
mls002701729 ,
nsc-408200
23647-78-1
CHEMBL36303 ,
bdbm50056891
2-hydroxy-benzoic acid n''-(2-hydroxy-benzoyl)-hydrazide
cid_65303
nsc 408200
n,n'-bis-salicylhydrazine
n,n'-disalicylhydrazine
einecs 245-804-4
n,n'-bis(salicyl)hydrazine
AKOS008764352
SCHEMBL77381
n,n'-bis(salicyloyl)hydrazine
n,n'-bis-salicyloyl-hydrazine
bis(salicyloyl)hydrazine
2-hydroxy-n'-(2-hydroxybenzoyl)benzohydrazide #
benzoic acid, 2-hydroxy-, 2-(2-hydroxybenzoyl)hydrazide
n,n'-bis(2-hydroxybenzoyl)hydrazin
DTXSID80178317
sr-01000389107
SR-01000389107-1
n,n'-disalicyloylhydrazine
n'-(2-hydroxybenzoyl)-2-hydroxybenzoic hydrazide
D9R89W89CJ
1,2-disalicyloylhydrazine
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (20)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
glp-1 receptor, partialHomo sapiens (human)Potency5.01190.01846.806014.1254AID624417
GLS proteinHomo sapiens (human)Potency10.00000.35487.935539.8107AID624170
TDP1 proteinHomo sapiens (human)Potency4.04140.000811.382244.6684AID686978; AID686979
Smad3Homo sapiens (human)Potency3.16230.00527.809829.0929AID588855
67.9K proteinVaccinia virusPotency19.11800.00018.4406100.0000AID720579; AID720580
IDH1Homo sapiens (human)Potency7.30780.005210.865235.4813AID686970
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency56.23413.548119.542744.6684AID743266
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency7.07950.050127.073689.1251AID588590
gemininHomo sapiens (human)Potency2.27270.004611.374133.4983AID624296; AID624297
Glycoprotein hormones alpha chainHomo sapiens (human)Potency0.50124.46688.344810.0000AID624291
Guanine nucleotide-binding protein GHomo sapiens (human)Potency8.91251.995325.532750.1187AID624287
[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)
Glutamate receptor ionotropic, kainate 1Rattus norvegicus (Norway rat)IC50 (µMol)1,000.00000.00700.98217.0000AID93546
Glutamate receptor ionotropic, kainate 2Rattus norvegicus (Norway rat)IC50 (µMol)1,000.00000.00701.01327.0000AID93546
Glutamate receptor ionotropic, kainate 3Rattus norvegicus (Norway rat)IC50 (µMol)1,000.00000.00701.01327.0000AID93546
Glutamate receptor ionotropic, kainate 4Rattus norvegicus (Norway rat)IC50 (µMol)1,000.00000.00701.01327.0000AID93546
Glutamate receptor ionotropic, kainate 5Rattus norvegicus (Norway rat)IC50 (µMol)1,000.00000.00701.01327.0000AID93546
Integrase Human immunodeficiency virus 1IC50 (µMol)276.61180.00051.544310.0000AID312515; AID312516; AID312517; AID312518; AID91409; AID91412; AID93517; AID93520; AID93544; AID93545; AID93546; AID93547; AID93671; AID93672; AID93673; AID93674; AID93680
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1CC500.10000.10000.10000.1000AID199986
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell population proliferationGlycoprotein hormones alpha chainHomo sapiens (human)
hormone-mediated signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
regulation of signaling receptor activityGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of steroid biosynthetic processGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell migrationGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid gland developmentGlycoprotein hormones alpha chainHomo sapiens (human)
luteinizing hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIGlycoprotein hormones alpha chainHomo sapiens (human)
negative regulation of organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid hormone generationGlycoprotein hormones alpha chainHomo sapiens (human)
negative regulation of inflammatory response to antigenic stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
renal water homeostasisGuanine nucleotide-binding protein GHomo sapiens (human)
G protein-coupled receptor signaling pathwayGuanine nucleotide-binding protein GHomo sapiens (human)
regulation of insulin secretionGuanine nucleotide-binding protein GHomo sapiens (human)
cellular response to glucagon stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
protein bindingGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
G protein activityGuanine nucleotide-binding protein GHomo sapiens (human)
adenylate cyclase activator activityGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
extracellular regionGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
Golgi lumenGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone complexGlycoprotein hormones alpha chainHomo sapiens (human)
pituitary gonadotropin complexGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
plasma membraneGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay IDTitleYearJournalArticle
AID1745845Primary qHTS for Inhibitors of ATXN expression
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.
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.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
AID91409Inhibition of HIV-1 integrase enzyme at 3`- processing stage of DNA integration1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Salicylhydrazine-containing inhibitors of HIV-1 integrase: implication for a selective chelation in the integrase active site.
AID312518Inhibition of recombinant HIV1 integrase strand transfer activity in presence of manganese2008Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2
2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one-based HIV-1 integrase inhibitors.
AID47145Effective concentration was evaluated on HIV-1 infected CEM cells.(NR-not reached due to cytotoxicity.)1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Salicylhydrazine-containing inhibitors of HIV-1 integrase: implication for a selective chelation in the integrase active site.
AID93671Inhibitory activity against HIV-1 integrase (pre-incubated with Mn+2, and DNA on ice for 15 min followed by drug for 1h) in 3'' processing of postassembly2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Metal-dependent inhibition of HIV-1 integrase.
AID93672Inhibitory activity against HIV-1 integrase (pre-incubated with Mn+2, and DNA on ice for 15 min followed by drug for 1h) in strand transfer of postassembly2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Metal-dependent inhibition of HIV-1 integrase.
AID91412Inhibitory concentration as 50% inhibition of HIV-1 integrase enzyme at strand transfer stage of DNA integration.1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Salicylhydrazine-containing inhibitors of HIV-1 integrase: implication for a selective chelation in the integrase active site.
AID93673Inhibitory activity against HIV-1 integrase (pre-incubated with Mn+2, and drug for 30 min followed by DNA for 1h) in 3''-processing of preassemble2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Metal-dependent inhibition of HIV-1 integrase.
AID312519Antiviral activity against HIV1 in cell based assay2008Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2
2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one-based HIV-1 integrase inhibitors.
AID93547Inhibitory activity against HIV-1 integrase (pre-incubated with Mg+2, and drug for 30 min followed by DNA for 1h) in strand transfer of preassemble2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Metal-dependent inhibition of HIV-1 integrase.
AID312517Inhibition of recombinant HIV1 integrase strand transfer activity in presence of magnesium2008Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2
2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one-based HIV-1 integrase inhibitors.
AID47438Tested for HIV-1 replication in CEM cells.1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Salicylhydrazine-containing inhibitors of HIV-1 integrase: implication for a selective chelation in the integrase active site.
AID93546Inhibitory activity against HIV-1 integrase (preincubated with Mg+2, and drug for 30 min followed by DNA for 1h) in 3''-processing of preassemble2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Metal-dependent inhibition of HIV-1 integrase.
AID93544Inhibitory activity against HIV-1 integrase (pre-incubated with Mg+2, and DNA on ice for 15 min followed by drug for 1h) in 3'' processing of postassembly2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Metal-dependent inhibition of HIV-1 integrase.
AID93517Inhibition of HIV-1 integrase enzyme by 3'-processing method1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Hydrazide-containing inhibitors of HIV-1 integrase.
AID93680Inhibitory activity against HIV-1 integrase2004Bioorganic & medicinal chemistry letters, Mar-22, Volume: 14, Issue:6
HIV-1 integrase pharmacophore model derived from diverse classes of inhibitors.
AID93545Inhibitory activity against HIV-1 integrase (pre-incubated with Mg+2, and DNA on ice for 15 min followed by drug for 1h) in strand transfer of postassembly2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Metal-dependent inhibition of HIV-1 integrase.
AID93674Inhibitory activity against HIV-1 integrase (pre-incubated with Mn+2, and drug for 30 min followed by DNA for 1h) in strand transfer of preassemble2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Metal-dependent inhibition of HIV-1 integrase.
AID93520Inhibition of HIV-1 integrase enzyme1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Hydrazide-containing inhibitors of HIV-1 integrase.
AID199986Cytotoxic concentration against viral replication by Reverse transcriptase2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Metal-dependent inhibition of HIV-1 integrase.
AID312515Inhibition of recombinant HIV1 integrase-mediated 3'-processing activity in presence of magnesium2008Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2
2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one-based HIV-1 integrase inhibitors.
AID312516Inhibition of recombinant HIV1 integrase-mediated 3'-processing activity in presence of manganese2008Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2
2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one-based HIV-1 integrase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (22.22)18.2507
2000's4 (44.44)29.6817
2010's2 (22.22)24.3611
2020's1 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.39

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 Index12.39 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.69 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.39)

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]