Page last updated: 2024-12-05

2-amino-5-nitrothiazole

Description

2-Amino-5-nitrothiazole (ANT) is a heterocyclic compound with significant biological activity. It is known for its anti-inflammatory, antimicrobial, and anticancer properties. ANT can be synthesized through various methods, including the reaction of 2-aminothiazole with nitric acid or the condensation of 2-aminothiazole with nitroethane. The compound has been studied for its potential as a drug for treating inflammatory diseases, infections, and cancer. Its effectiveness is attributed to its ability to inhibit various enzymes involved in inflammatory pathways and cell proliferation. Research on ANT is ongoing to explore its therapeutic potential and optimize its pharmacological properties.'

2-amino-5-nitrothiazole: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID8486
CHEMBL ID408049
CHEBI ID82386
SCHEMBL ID375929
SCHEMBL ID19435597
MeSH IDM0107208

Synonyms (92)

Synonym
MLS002152868
smr001224487
u7458
aminzol soluble
5-nitrothiazol-2-amine
OPREA1_237935
5-nitro-1,3-thiazol-2-amine
inchi=1/c3h3n3o2s/c4-3-5-1-2(9-3)6(7)8/h1h,(h2,4,5
NCGC00091644-01
enheptyne
enheptin (van)
ccris 37
nitromin ido
5-nitro-2-thiazolamine
5-nitrothiazol-2-ylamine
nsc 4
hsdb 4022
brn 0126797
einecs 204-490-9
aminonitrothiazolum
ai3-50030
5-nitro-2-aminothiazole
enheptin premix
STK317992
121-66-4
usaf ek-6561
enheptin t
wln: t5n csj bz dnw
enheptin-t
amnizol soluble
aminonitrothiazole
nsc4
nci-c03065
2-amino-5-nitrothiazole
thiazole, 2-amino-5-nitro-
2-thiazolamine, 5-nitro-
nsc-4
u 7458
entramin
5-nitro-2-thiazolylamine
nitramin ido
enheptin
2-amino-5-nitrothiazole, 97%
AC-2989
A0381
CHEMBL408049
chebi:82386 ,
AKOS000120496
A804773
NCGC00091644-02
unii-1gr77a37z5
1gr77a37z5 ,
4-27-00-04675 (beilstein handbook reference)
C19324
cas-121-66-4
dtxcid8066
tox21_303575
dtxsid6020066 ,
NCGC00257304-01
NCGC00259926-01
tox21_202377
BP-10109
FT-0611187
PS-3292
AM20080158
S12411
aminonitrothiazol
2-amino-5-nitrothiazole [mi]
2-amino-5-nitrothiazole [hsdb]
2-amino-5-nitrothiazol
2-amino-5-nitrothiazole [iarc]
2-amino 5-nitro thiazole
5-nitro-thiazol-2-ylamine
entramine
2-amino-5-nitro-thiazol
SCHEMBL375929
5-nitro-1,3-thiazol-2-amine #
2-amino-5-nitro-1,3-thiazole
STR02181
W-108451
mfcd00005326
F0001-0347
SCHEMBL19435597
Q27155915
EN300-16819
CS-0030564
SB31744
PD162659
2-amino-5-nitrothiazole (iarc)
2-amino-4-nitrothiazole
hexamor
Z56786623

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" trans-[PtCl2(NH3)-(misonidazole)] is more toxic than the cis isomer."( Platinum complexes with one radiosensitizing ligand [PtCl2(NH3) (sensitizer)]: radiosensitization and toxicity studies in vitro.
Adomat, H; Farrell, NP; Skov, KA, 1987
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
thiazolesAn azole in which the five-membered heterocyclic aromatic skeleton contains a N atom and one S atom.
C-nitro compoundA nitro compound having the nitro group (-NO2) attached to a carbon atom.
[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 (19)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LuciferasePhotinus pyralis (common eastern firefly)Potency39.91490.007215.758889.3584AID1224835
acetylcholinesteraseHomo sapiens (human)Potency67.66830.002541.796015,848.9004AID1347397; AID1347399
15-lipoxygenase, partialHomo sapiens (human)Potency39.81070.012610.691788.5700AID887
AR proteinHomo sapiens (human)Potency30.88730.000221.22318,912.5098AID743054
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency25.11890.011212.4002100.0000AID1030
isocitrate dehydrogenase 1, partialHomo sapiens (human)Potency50.11876.309627.099079.4328AID602179
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency0.00180.000214.376460.0339AID588532
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency34.65610.003041.611522,387.1992AID1159552; AID1159555
estrogen nuclear receptor alphaHomo sapiens (human)Potency44.05350.000229.305416,493.5996AID743075; AID743079
peroxisome proliferator-activated receptor deltaHomo sapiens (human)Potency0.01550.001024.504861.6448AID743215
aryl hydrocarbon receptorHomo sapiens (human)Potency47.66950.000723.06741,258.9301AID743085; AID743122
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency15.84890.001815.663839.8107AID894
serine/threonine-protein kinase PLK1Homo sapiens (human)Potency21.19230.168316.404067.0158AID720504
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency56.77440.000627.21521,122.0200AID651741; AID743219
gemininHomo sapiens (human)Potency2.31090.004611.374133.4983AID624296
Polyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)Potency25.11890.316212.765731.6228AID881
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency25.11890.00638.235039.8107AID881
Nuclear receptor ROR-gammaHomo sapiens (human)Potency21.13170.026622.448266.8242AID651802
[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)
glycogen synthase kinase-3 alphaHomo sapiens (human)AC50300.00000.013529.7434171.7000AID463203
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (34)

Processvia Protein(s)Taxonomy
lipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
phospholipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
apoptotic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell population proliferationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of macrophage derived foam cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell migrationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
prostate gland developmentPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
regulation of epithelial cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of chemokine productionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of peroxisome proliferator activated receptor signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of keratinocyte differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell cyclePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of growthPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
hepoxilin biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
endocannabinoid signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cannabinoid biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxin A4 biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid oxidationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxygenase pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of transcription by RNA polymerase IINuclear receptor ROR-gammaHomo sapiens (human)
xenobiotic metabolic processNuclear receptor ROR-gammaHomo sapiens (human)
regulation of glucose metabolic processNuclear receptor ROR-gammaHomo sapiens (human)
regulation of steroid metabolic processNuclear receptor ROR-gammaHomo sapiens (human)
intracellular receptor signaling pathwayNuclear receptor ROR-gammaHomo sapiens (human)
circadian regulation of gene expressionNuclear receptor ROR-gammaHomo sapiens (human)
cellular response to sterolNuclear receptor ROR-gammaHomo sapiens (human)
positive regulation of circadian rhythmNuclear receptor ROR-gammaHomo sapiens (human)
regulation of fat cell differentiationNuclear receptor ROR-gammaHomo sapiens (human)
positive regulation of DNA-templated transcriptionNuclear receptor ROR-gammaHomo sapiens (human)
adipose tissue developmentNuclear receptor ROR-gammaHomo sapiens (human)
T-helper 17 cell differentiationNuclear receptor ROR-gammaHomo sapiens (human)
regulation of transcription by RNA polymerase IINuclear receptor ROR-gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (17)

Processvia Protein(s)Taxonomy
iron ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
calcium ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
protein bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 13S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 8(S)-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 15-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 9S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingNuclear receptor ROR-gammaHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificNuclear receptor ROR-gammaHomo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specificNuclear receptor ROR-gammaHomo sapiens (human)
DNA-binding transcription factor activityNuclear receptor ROR-gammaHomo sapiens (human)
protein bindingNuclear receptor ROR-gammaHomo sapiens (human)
oxysterol bindingNuclear receptor ROR-gammaHomo sapiens (human)
zinc ion bindingNuclear receptor ROR-gammaHomo sapiens (human)
ligand-activated transcription factor activityNuclear receptor ROR-gammaHomo sapiens (human)
sequence-specific double-stranded DNA bindingNuclear receptor ROR-gammaHomo sapiens (human)
nuclear receptor activityNuclear receptor ROR-gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
nucleusPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytosolPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytoskeletonPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
plasma membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
adherens junctionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
focal adhesionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
extracellular exosomePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
nucleusNuclear receptor ROR-gammaHomo sapiens (human)
nucleoplasmNuclear receptor ROR-gammaHomo sapiens (human)
nuclear bodyNuclear receptor ROR-gammaHomo sapiens (human)
chromatinNuclear receptor ROR-gammaHomo sapiens (human)
nucleusNuclear receptor ROR-gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
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.
AID1745845Primary 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.
AID651635Viability Counterscreen for Primary 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.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1067348Antimicrobial activity against promastigote stage of Leishmania amazonensis IFLA/BR/67/PH-8 clinical isolate after 72 hrs by Neubauer chamber analysis2014Bioorganic & medicinal chemistry, Mar-01, Volume: 22, Issue:5
2-acylamino-5-nitro-1,3-thiazoles: preparation and in vitro bioevaluation against four neglected protozoan parasites.
AID1067349Antimicrobial activity against Trichomonas vaginalis GT3 incubated for 48 hrs followed by compound washout measured after 48 hrs2014Bioorganic & medicinal chemistry, Mar-01, Volume: 22, Issue:5
2-acylamino-5-nitro-1,3-thiazoles: preparation and in vitro bioevaluation against four neglected protozoan parasites.
AID1067350Antimicrobial activity against Giardia intestinalis IMSS:0696:1 incubated for 48 hrs followed by compound washout measured after 48 hrs2014Bioorganic & medicinal chemistry, Mar-01, Volume: 22, Issue:5
2-acylamino-5-nitro-1,3-thiazoles: preparation and in vitro bioevaluation against four neglected protozoan parasites.
AID1194390Giardicidal activity against Giardia intestinalis IMSS:0696:1 compound treated for 48 hrs followed by incubation for 48 hrs in compound-free medium by cell counting2015Bioorganic & medicinal chemistry, May-01, Volume: 23, Issue:9
Synthesis of nitro(benzo)thiazole acetamides and in vitro antiprotozoal effect against amitochondriate parasites Giardia intestinalis and Trichomonas vaginalis.
AID1194392Inhibition of Giardia intestinalis fructose 1,6-bisphosphate aldolase at 400 nM after 2 hrs by spectrophotometry2015Bioorganic & medicinal chemistry, May-01, Volume: 23, Issue:9
Synthesis of nitro(benzo)thiazole acetamides and in vitro antiprotozoal effect against amitochondriate parasites Giardia intestinalis and Trichomonas vaginalis.
AID1067358Antimicrobial activity against epimastigote stage of Trypanosoma cruzi MHOM/MX/1994/Ninoa clinical isolate after 72 hrs by Neubauer chamber analysis2014Bioorganic & medicinal chemistry, Mar-01, Volume: 22, Issue:5
2-acylamino-5-nitro-1,3-thiazoles: preparation and in vitro bioevaluation against four neglected protozoan parasites.
AID318681Anticarcinogenic activity in rat assessed as induction of tumors per day2008Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6
QSAR modeling of the rodent carcinogenicity of nitrocompounds.
AID1067357Cytotoxicity against African green monkey Vero cells assessed as cell viability after 48 hrs by SRB assay2014Bioorganic & medicinal chemistry, Mar-01, Volume: 22, Issue:5
2-acylamino-5-nitro-1,3-thiazoles: preparation and in vitro bioevaluation against four neglected protozoan parasites.
AID756681Activation of AMPK in rat L6 cells assessed as increase of [3H]dGlc uptake at 100 uM after 5 hrs in presence of insulin2013Journal of medicinal chemistry, Jul-11, Volume: 56, Issue:13
Synthesis and mechanism of hypoglycemic activity of benzothiazole derivatives.
AID756686Activation of AMPKalpha in rat L6 cells assessed as phosphorylation at Thr172 after 40 mins to 24 hrs by Western blot analysis2013Journal of medicinal chemistry, Jul-11, Volume: 56, Issue:13
Synthesis and mechanism of hypoglycemic activity of benzothiazole derivatives.
AID1194391Cytotoxicity against African green monkey Vero cells after 48 hrs by MTT assay2015Bioorganic & medicinal chemistry, May-01, Volume: 23, Issue:9
Synthesis of nitro(benzo)thiazole acetamides and in vitro antiprotozoal effect against amitochondriate parasites Giardia intestinalis and Trichomonas vaginalis.
AID1194389Trichomonicidal activity against Trichomonas vaginalis GT3 compound treated for 48 hrs followed by incubation for 48 hrs in compound-free medium by cell counting2015Bioorganic & medicinal chemistry, May-01, Volume: 23, Issue:9
Synthesis of nitro(benzo)thiazole acetamides and in vitro antiprotozoal effect against amitochondriate parasites Giardia intestinalis and Trichomonas vaginalis.
AID756690Activation of AMPK in rat L6 cells assessed as increase of [3H]dGlc uptake at 100 uM after 5 hrs relative to control2013Journal of medicinal chemistry, Jul-11, Volume: 56, Issue:13
Synthesis and mechanism of hypoglycemic activity of benzothiazole derivatives.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (24)

TimeframeStudies, This Drug (%)All Drugs %
pre-199014 (58.33)18.7374
1990's0 (0.00)18.2507
2000's2 (8.33)29.6817
2010's7 (29.17)24.3611
2020's1 (4.17)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.58

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index31.58 (24.57)
Research Supply Index3.22 (2.92)
Research Growth Index4.16 (4.65)
Search Engine Demand Index37.86 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.58)

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%
Other24 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
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