Compounds > n,n'-bis(salicyl)hydrazine

Page last updated: 2024-12-06

n,n'-bis(salicyl)hydrazine

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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 Source	ID
PubMed CID	65303
CHEMBL ID	36303
SCHEMBL ID	77381
MeSH ID	M0274811

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

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
glp-1 receptor, partial	Homo sapiens (human)	Potency	5.0119	0.0184	6.8060	14.1254	AID624417
GLS protein	Homo sapiens (human)	Potency	10.0000	0.3548	7.9355	39.8107	AID624170
TDP1 protein	Homo sapiens (human)	Potency	4.0414	0.0008	11.3822	44.6684	AID686978; AID686979
Smad3	Homo sapiens (human)	Potency	3.1623	0.0052	7.8098	29.0929	AID588855
67.9K protein	Vaccinia virus	Potency	19.1180	0.0001	8.4406	100.0000	AID720579; AID720580
IDH1	Homo sapiens (human)	Potency	7.3078	0.0052	10.8652	35.4813	AID686970
parathyroid hormone/parathyroid hormone-related peptide receptor precursor	Homo sapiens (human)	Potency	56.2341	3.5481	19.5427	44.6684	AID743266
DNA polymerase iota isoform a (long)	Homo sapiens (human)	Potency	7.0795	0.0501	27.0736	89.1251	AID588590
geminin	Homo sapiens (human)	Potency	2.2727	0.0046	11.3741	33.4983	AID624296; AID624297
Glycoprotein hormones alpha chain	Homo sapiens (human)	Potency	0.5012	4.4668	8.3448	10.0000	AID624291
Guanine nucleotide-binding protein G	Homo sapiens (human)	Potency	8.9125	1.9953	25.5327	50.1187	AID624287
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Glutamate receptor ionotropic, kainate 1	Rattus norvegicus (Norway rat)	IC50 (µMol)	1,000.0000	0.0070	0.9821	7.0000	AID93546
Glutamate receptor ionotropic, kainate 2	Rattus norvegicus (Norway rat)	IC50 (µMol)	1,000.0000	0.0070	1.0132	7.0000	AID93546
Glutamate receptor ionotropic, kainate 3	Rattus norvegicus (Norway rat)	IC50 (µMol)	1,000.0000	0.0070	1.0132	7.0000	AID93546
Glutamate receptor ionotropic, kainate 4	Rattus norvegicus (Norway rat)	IC50 (µMol)	1,000.0000	0.0070	1.0132	7.0000	AID93546
Glutamate receptor ionotropic, kainate 5	Rattus norvegicus (Norway rat)	IC50 (µMol)	1,000.0000	0.0070	1.0132	7.0000	AID93546
Integrase	Human immunodeficiency virus 1	IC50 (µMol)	276.6118	0.0005	1.5443	10.0000	AID312515; 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

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Reverse transcriptase/RNaseH	Human immunodeficiency virus 1	CC50	0.1000	0.1000	0.1000	0.1000	AID199986
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Process	via Protein(s)	Taxonomy
G protein-coupled receptor signaling pathway	Glycoprotein hormones alpha chain	Homo sapiens (human)
positive regulation of cell population proliferation	Glycoprotein hormones alpha chain	Homo sapiens (human)
hormone-mediated signaling pathway	Glycoprotein hormones alpha chain	Homo sapiens (human)
regulation of signaling receptor activity	Glycoprotein hormones alpha chain	Homo sapiens (human)
positive regulation of steroid biosynthetic process	Glycoprotein hormones alpha chain	Homo sapiens (human)
positive regulation of cell migration	Glycoprotein hormones alpha chain	Homo sapiens (human)
thyroid gland development	Glycoprotein hormones alpha chain	Homo sapiens (human)
luteinizing hormone secretion	Glycoprotein hormones alpha chain	Homo sapiens (human)
organ growth	Glycoprotein hormones alpha chain	Homo sapiens (human)
follicle-stimulating hormone signaling pathway	Glycoprotein hormones alpha chain	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Glycoprotein hormones alpha chain	Homo sapiens (human)
negative regulation of organ growth	Glycoprotein hormones alpha chain	Homo sapiens (human)
follicle-stimulating hormone secretion	Glycoprotein hormones alpha chain	Homo sapiens (human)
thyroid hormone generation	Glycoprotein hormones alpha chain	Homo sapiens (human)
negative regulation of inflammatory response to antigenic stimulus	Guanine nucleotide-binding protein G	Homo sapiens (human)
renal water homeostasis	Guanine nucleotide-binding protein G	Homo sapiens (human)
G protein-coupled receptor signaling pathway	Guanine nucleotide-binding protein G	Homo sapiens (human)
regulation of insulin secretion	Guanine nucleotide-binding protein G	Homo sapiens (human)
cellular response to glucagon stimulus	Guanine nucleotide-binding protein G	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Process	via Protein(s)	Taxonomy
hormone activity	Glycoprotein hormones alpha chain	Homo sapiens (human)
protein binding	Glycoprotein hormones alpha chain	Homo sapiens (human)
follicle-stimulating hormone activity	Glycoprotein hormones alpha chain	Homo sapiens (human)
G protein activity	Guanine nucleotide-binding protein G	Homo sapiens (human)
adenylate cyclase activator activity	Guanine nucleotide-binding protein G	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Process	via Protein(s)	Taxonomy
extracellular region	Glycoprotein hormones alpha chain	Homo sapiens (human)
extracellular space	Glycoprotein hormones alpha chain	Homo sapiens (human)
Golgi lumen	Glycoprotein hormones alpha chain	Homo sapiens (human)
follicle-stimulating hormone complex	Glycoprotein hormones alpha chain	Homo sapiens (human)
pituitary gonadotropin complex	Glycoprotein hormones alpha chain	Homo sapiens (human)
extracellular space	Glycoprotein hormones alpha chain	Homo sapiens (human)
plasma membrane	Guanine nucleotide-binding protein G	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay ID	Title	Year	Journal	Article
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2006	Cytometry. 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.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. 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.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. 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.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID91409	Inhibition of HIV-1 integrase enzyme at 3`- processing stage of DNA integration	1998	Journal 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.
AID312518	Inhibition of recombinant HIV1 integrase strand transfer activity in presence of manganese	2008	Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2	2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one-based HIV-1 integrase inhibitors.
AID47145	Effective concentration was evaluated on HIV-1 infected CEM cells.(NR-not reached due to cytotoxicity.)	1998	Journal 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.
AID93671	Inhibitory 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 postassembly	2002	Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26	Metal-dependent inhibition of HIV-1 integrase.
AID93672	Inhibitory 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 postassembly	2002	Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26	Metal-dependent inhibition of HIV-1 integrase.
AID91412	Inhibitory concentration as 50% inhibition of HIV-1 integrase enzyme at strand transfer stage of DNA integration.	1998	Journal 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.
AID93673	Inhibitory activity against HIV-1 integrase (pre-incubated with Mn+2, and drug for 30 min followed by DNA for 1h) in 3''-processing of preassemble	2002	Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26	Metal-dependent inhibition of HIV-1 integrase.
AID312519	Antiviral activity against HIV1 in cell based assay	2008	Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2	2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one-based HIV-1 integrase inhibitors.
AID93547	Inhibitory activity against HIV-1 integrase (pre-incubated with Mg+2, and drug for 30 min followed by DNA for 1h) in strand transfer of preassemble	2002	Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26	Metal-dependent inhibition of HIV-1 integrase.
AID312517	Inhibition of recombinant HIV1 integrase strand transfer activity in presence of magnesium	2008	Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2	2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one-based HIV-1 integrase inhibitors.
AID47438	Tested for HIV-1 replication in CEM cells.	1998	Journal 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.
AID93546	Inhibitory activity against HIV-1 integrase (preincubated with Mg+2, and drug for 30 min followed by DNA for 1h) in 3''-processing of preassemble	2002	Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26	Metal-dependent inhibition of HIV-1 integrase.
AID93544	Inhibitory 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 postassembly	2002	Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26	Metal-dependent inhibition of HIV-1 integrase.
AID93517	Inhibition of HIV-1 integrase enzyme by 3'-processing method	1997	Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6	Hydrazide-containing inhibitors of HIV-1 integrase.
AID93680	Inhibitory activity against HIV-1 integrase	2004	Bioorganic & medicinal chemistry letters, Mar-22, Volume: 14, Issue:6	HIV-1 integrase pharmacophore model derived from diverse classes of inhibitors.
AID93545	Inhibitory 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 postassembly	2002	Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26	Metal-dependent inhibition of HIV-1 integrase.
AID93674	Inhibitory activity against HIV-1 integrase (pre-incubated with Mn+2, and drug for 30 min followed by DNA for 1h) in strand transfer of preassemble	2002	Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26	Metal-dependent inhibition of HIV-1 integrase.
AID93520	Inhibition of HIV-1 integrase enzyme	1997	Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6	Hydrazide-containing inhibitors of HIV-1 integrase.
AID199986	Cytotoxic concentration against viral replication by Reverse transcriptase	2002	Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26	Metal-dependent inhibition of HIV-1 integrase.
AID312515	Inhibition of recombinant HIV1 integrase-mediated 3'-processing activity in presence of magnesium	2008	Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2	2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one-based HIV-1 integrase inhibitors.
AID312516	Inhibition of recombinant HIV1 integrase-mediated 3'-processing activity in presence of manganese	2008	Journal 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)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	2 (22.22)	18.2507
2000's	4 (44.44)	29.6817
2010's	2 (22.22)	24.3611
2020's	1 (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.

Metric	This Compound (vs All)
Research Demand Index	12.39 (24.57)
Research Supply Index	2.30 (2.92)
Research Growth Index	4.69 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (12.39)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	9 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
digallic acid digallic acid: structure given in first source	2.02	1	benzoate ester; gallate ester
salicylamide salamide: a major impurity of hydrochlorothiazide; structure in first source	1.99	1	phenols; salicylamides	antirheumatic drug; non-narcotic analgesic
hydrazine diamine : Any polyamine that contains two amino groups.	1.99	1	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
salicyl hydrazide 2-hydroxybenzohydrazide: structure in first source	1.99	1
1,4,5,8-naphthalenetetracarboxylic acid 1,4,5,8-naphthalenetetracarboxylic acid: structure given in first source	2.02	1
pannarin pannarin: photoirradiation of above cpd leads to its decomposition which is reduced by oxygen. pannarin : A member of the class of depsidones that is 11H-dibenzo[b,e][1,4]dioxepine substituted by methyl groups at positions 1,6 and 9, chloro group at position 2, hydroxy group at position 3, formyl group at position 4, methoxy group at position 8 and an oxo group at position 11. It is a lichen metabolite isolated from several Psoroma species.	2.02	1	aldehyde; aromatic ether; depsidones; organic heterotricyclic compound; organochlorine compound; phenols	antimicrobial agent; antineoplastic agent; apoptosis inducer; lichen metabolite
4,7-Dihydroxy-2H-1-benzopyran-2-one [no description available]	2.02	1	hydroxycoumarin

Condition	Indicated	Relationship Strength	Studies	Trials
Innate Inflammatory Response [description not available]	0	2.05	1	0
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	0	2.05	1	0

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