Page last updated: 2024-12-09

2-acetylpyridine thiosemicarbazone

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

Description

2-acetylpyridine thiosemicarbazone: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5480198
CHEMBL ID416771
SCHEMBL ID941092
MeSH IDM0104716

Synonyms (22)

Synonym
2-(1-(pyridin-2-yl)ethylidene)hydrazinecarbothioamide
(1e)-1-pyridin-2-ylethan-1-one thiosemicarbazone
4-(1-pyridin-2-yl ethylene) thiosemicarbazone
bdbm50148056
(e)-2-(1-(2-pyridinyl)ethylidene)hydrazinecarbothioamide
hydrazinecarbothioamide, 2-(1-(2-pyridinyl)ethylidene)-, (e)-
[(e)-1-(2-pyridyl)ethylideneamino]thiourea
2-acetylpyridine thiosemicarbazone
haptsc
SR-01000636717-1
2-acetylpyridinethiosemicarbazone
CHEMBL416771 ,
[(e)-1-pyridin-2-ylethylideneamino]thiourea
142564-62-3
AKOS006242415
CCG-47070
2-acetylpyridine thiosemi-carbazone
SCHEMBL941092
RIFVPOHZBSIFRL-IZZDOVSWSA-N
(e)-2-(1-(pyridin-2-yl)ethylidene)hydrazinecarbothioamide
DTXSID101197659
(2e)-2-[1-(2-pyridinyl)ethylidene]hydrazinecarbothioamide

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
" Rifampin, amikacin, and clofazimine were active when tested singly or in combination with Compounds L and 3I."( Activity of 2-acetylpyridine and 2-acetylquinoline thiosemicarbazones tested in vitro in combination with other antituberculous drugs.
Collins, FM; Klayman, DL; Morrison, NE, 1982
)
0.26

Bioavailability

ExcerptReferenceRelevance
" (l)-Tyr-NH-i-Bu cHPMPA (11) was converted in rat or mouse plasma solely to two active metabolites and had significantly enhanced oral bioavailability vs parent drug 1 in a mouse model (39% vs <5%)."( Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: synthesis, stability, antiviral activity, and in vivo transport studies.
Borysko, KZ; Breitenbach, JM; Collins, M; Drach, JC; Hilfinger, JM; Kashemirov, BA; Krylov, IS; McKenna, CE; Peterson, LW; Serpi, M; Zakharova, VM, 2011
)
0.37

Dosage Studied

2-acetylpyridine thiosemicarbazones were tested in mice against Mycobacterium leprae by the kinetic method and found to be nearly inactive in a dosage of 0.

ExcerptRelevanceReference
" A comparison of the inhibitory effects of 2-acetylpyridine thiosemicarbazone itself on viral reductase and on virus replication in vitro demonstrated a similarity in the dose-response relationships for the two parameters."( Selective inhibition of herpes simplex virus ribonucleoside diphosphate reductase by derivatives of 2-acetylpyridine thiosemicarbazone.
Drach, JC; Shipman, C; Turk, SR, 1986
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
CruzipainTrypanosoma cruziIC50 (µMol)20.00000.00022.04508.0000AID54705
Cysteine protease Trypanosoma brucei rhodesienseIC50 (µMol)20.00000.00313.87667.7500AID197812
Cysteine proteinase falcipain 2a Plasmodium falciparum (malaria parasite P. falciparum)IC50 (µMol)20.00000.00580.44035.0000AID72524
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (38)

Assay IDTitleYearJournalArticle
AID478785Antimycobacterial activity against Mycobacterium tuberculosis H37Rv after 7 days by resazurine microtiter assay2010European journal of medicinal chemistry, May, Volume: 45, Issue:5
Thiosemicarbazones, semicarbazones, dithiocarbazates and hydrazide/hydrazones: anti-Mycobacterium tuberculosis activity and cytotoxicity.
AID1136827Toxicity in ICR/HA Swiss mouse infected with Plasmodium berghei KBG 173 assessed as mortality at 160 mg/kg, sc administered 72 hrs post infection measured for 6 days1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
2-Acetylpyridine thiosemicarbazones. 1. A new class of potential antimalarial agents.
AID1640018Luciferase/luciferin-expressing antifolate-resistant parasites were used to infect a culture of HepG2 cells that were pre-incubated with compounds. Infected hepatocytes emit light due to the luciferase reaction. Assay results are presented as the percent 2018Science (New York, N.Y.), 12-07, Volume: 362, Issue:6419
Open-source discovery of chemical leads for next-generation chemoprotective antimalarials.
AID38490anti-filarial Activity was measured against Brugia pahangi in jirds at 12.5 mg/kg/day(5 days) dose1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
2-acetylpyridine thiosemicarbazones. 13. Derivatives with antifilarial activity.
AID1136826Toxicity in ICR/HA Swiss mouse infected with Plasmodium berghei KBG 173 assessed as mortality at 40 mg/kg, sc administered 72 hrs post infection measured for 6 days1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
2-Acetylpyridine thiosemicarbazones. 1. A new class of potential antimalarial agents.
AID370486Octanol-water partition coefficient, log P of the compound2009Journal 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.
AID478786Cytotoxicity against mouse J774 cells after 24 hrs by resazurin assay2010European journal of medicinal chemistry, May, Volume: 45, Issue:5
Thiosemicarbazones, semicarbazones, dithiocarbazates and hydrazide/hydrazones: anti-Mycobacterium tuberculosis activity and cytotoxicity.
AID1188736Inhibition of recombinant Trypanosoma cruzi cruzain using Z-Phe-Argaminomethylcoumarin as fluorogenic substrate preincubated at 100 uM for 10 mins before substrate addition by fluorimetry2014European journal of medicinal chemistry, Oct-30, Volume: 862-Pyridyl thiazoles as novel anti-Trypanosoma cruzi agents: structural design, synthesis and pharmacological evaluation.
AID636699Cytotoxicity against human KB cells after 48 hrs by crystal violet staining based spectrophotometric analysis2011Journal of medicinal chemistry, Aug-25, Volume: 54, Issue:16
Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: synthesis, stability, antiviral activity, and in vivo transport studies.
AID490968Cytotoxicity against human K562 cells after 48 hrs by MTT assay2010European journal of medicinal chemistry, Jul, Volume: 45, Issue:7
Mn(II), Co(II) and Zn(II) complexes with heterocyclic substituted thiosemicarbazones: synthesis, characterization, X-ray crystal structures and antitumor comparison.
AID478787Selectivity index, ratio of IC50 for mouse J774 cells to MIC for Mycobacterium tuberculosis H37Rv2010European journal of medicinal chemistry, May, Volume: 45, Issue:5
Thiosemicarbazones, semicarbazones, dithiocarbazates and hydrazide/hydrazones: anti-Mycobacterium tuberculosis activity and cytotoxicity.
AID9441anti-filarial Activity was measured against Acanthocheilonema viteae in jirds at 1.56 mg/kg/day(5 days) dose1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
2-acetylpyridine thiosemicarbazones. 13. Derivatives with antifilarial activity.
AID72524Inhibition of falcipain2 from Plasmodium falciparum2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Synthesis and structure-activity relationships of parasiticidal thiosemicarbazone cysteine protease inhibitors against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi.
AID1640019Luciferase/luciferin-expressing antifolate-resistant parasites were used to infect a culture of HepG2 cells that were pre-incubated with compounds. Infected hepatocytes emit light due to the luciferase reaction. Assay results are presented as the percent 2018Science (New York, N.Y.), 12-07, Volume: 362, Issue:6419
Open-source discovery of chemical leads for next-generation chemoprotective antimalarials.
AID38487anti-filarial Activity was measured against Brugia pahangi in jirds at 1.56 mg/kg/day(5 days) dose1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
2-acetylpyridine thiosemicarbazones. 13. Derivatives with antifilarial activity.
AID1188733Cytotoxicity against human HepG2 cells after 48 hrs by2014European journal of medicinal chemistry, Oct-30, Volume: 862-Pyridyl thiazoles as novel anti-Trypanosoma cruzi agents: structural design, synthesis and pharmacological evaluation.
AID41385Survival of infected bovine embryo skeletal muscle (BESM) cells against Trypanosoma cruzi in days at a dose of 5 uM; Toxicity = None2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Synthesis and structure-activity relationships of parasiticidal thiosemicarbazone cysteine protease inhibitors against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi.
AID38489anti-filarial Activity was measured against Brugia pahangi in jirds at 100 mg/kg/day(5 days) dose;toxic1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
2-acetylpyridine thiosemicarbazones. 13. Derivatives with antifilarial activity.
AID54705Inhibition of cruzain from Trypanosoma cruzi2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Synthesis and structure-activity relationships of parasiticidal thiosemicarbazone cysteine protease inhibitors against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi.
AID9443anti-filarial Activity was measured against Acanthocheilonema viteae in jirds at 12.5 mg/kg/day(5 days) dose1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
2-acetylpyridine thiosemicarbazones. 13. Derivatives with antifilarial activity.
AID1188735Trypanocidal activity against epimastigote forms of Trypanosoma cruzi Y assessed as reduction in viable parasites after 11 days by Neubauer chamber counting method2014European journal of medicinal chemistry, Oct-30, Volume: 862-Pyridyl thiazoles as novel anti-Trypanosoma cruzi agents: structural design, synthesis and pharmacological evaluation.
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.
AID370487Induction of iron mobilization in 59Fe]transferrin labeled human SK-N-MC cells assessed as iron release at 25 uM after 3 hrs by gamma scintillation counter2009Journal 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.
AID1188734Antitrypanosomal activity against trypomastigote forms of Trypanosoma cruzi Y infected in LLC-MK2 cells assessed as reduction in viable parasites after 24 hrs by Neubauer chamber counting method2014European journal of medicinal chemistry, Oct-30, Volume: 862-Pyridyl thiazoles as novel anti-Trypanosoma cruzi agents: structural design, synthesis and pharmacological evaluation.
AID1136829Toxicity in ICR/HA Swiss mouse infected with Plasmodium berghei KBG 173 assessed as mortality at 640 mg/kg, sc administered 72 hrs post infection measured for 6 days1979Journal of medicinal chemistry, Jul, Volume: 22, Issue:7
2-Acetylpyridine thiosemicarbazones. 1. A new class of potential antimalarial agents.
AID370489Reduction of cellular iron uptake from 59Fe]transferrin in human SK-N-MC cells at 25 uM after 3 hrs relative to control2009Journal 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.
AID1332977Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 after 7 days by microplate alamar blue assay2016European journal of medicinal chemistry, Nov-10, Volume: 123Synthesis and biological activity of furoxan derivatives against Mycobacterium tuberculosis.
AID67528Tested for antiamnesic activity against HK-9 strain of Entamoeba histolytica2000Bioorganic & medicinal chemistry letters, Oct-16, Volume: 10, Issue:20
Synthesis and antiamoebic activity of new cyclooctadiene ruthenium(II) complexes with 2-acetylpyridine and benzimidazole derivatives.
AID84795Compound was evaluated for inhibition of Herpes simplex virus -1 (HSV-1) - induced cytopathic effect in HUT78 cells (in vitro)1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Novel thiosemicarbazones derived from formyl- and acyldiazines: synthesis, effects on cell proliferation, and synergism with antiviral agents.
AID370490Induction of iron removal from 59Fe]transferrin assessed as iron release after 3 hrs relative to control2009Journal 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.
AID215879Effective dose required to inhibit Trypanosoma brucei rhodesiense in culture2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Synthesis and structure-activity relationships of parasiticidal thiosemicarbazone cysteine protease inhibitors against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi.
AID157677Effective inhibition of Plasmodium falciparum2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Synthesis and structure-activity relationships of parasiticidal thiosemicarbazone cysteine protease inhibitors against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi.
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.
AID105576Compound was evaluated for inhibition of HIV-1- induced cytopathic effect in MT-4 cells(in vitro)1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Novel thiosemicarbazones derived from formyl- and acyldiazines: synthesis, effects on cell proliferation, and synergism with antiviral agents.
AID1188739Inhibition of recombinant Trypanosoma cruzi cruzain using Z-Phe-Argaminomethylcoumarin as fluorogenic substrate preincubated for 10 mins before substrate addition by fluorimetry2014European journal of medicinal chemistry, Oct-30, Volume: 862-Pyridyl thiazoles as novel anti-Trypanosoma cruzi agents: structural design, synthesis and pharmacological evaluation.
AID1377531Inhibition of baker's yeast alpha-glucosidase preincubated for 10 mins followed by PNPG addition measured after 30 mins2017European journal of medicinal chemistry, Sep-29, Volume: 138Hydrazinyl arylthiazole based pyridine scaffolds: Synthesis, structural characterization, in vitro α-glucosidase inhibitory activity, and in silico studies.
AID197812Inhibition of rhodesain from Trypanosoma brucei rhodesiense2004Journal of medicinal chemistry, Jun-03, Volume: 47, Issue:12
Synthesis and structure-activity relationships of parasiticidal thiosemicarbazone cysteine protease inhibitors against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi.
AID636700Cytotoxicity against HFF cells after 48 hrs by visual cytotoxicity observation assay2011Journal of medicinal chemistry, Aug-25, Volume: 54, Issue:16
Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: synthesis, stability, antiviral activity, and in vivo transport studies.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (40)

TimeframeStudies, This Drug (%)All Drugs %
pre-199013 (32.50)18.7374
1990's5 (12.50)18.2507
2000's8 (20.00)29.6817
2010's14 (35.00)24.3611
2020's0 (0.00)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%
Reviews2 (5.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other38 (95.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]