Compounds > 3-phenylpyridine
Page last updated: 2024-11-05

3-phenylpyridine

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

3-Phenylpyridine is a heterocyclic organic compound with a pyridine ring substituted at the 3-position by a phenyl group. It is a colorless solid with a melting point of 40-42 °C. 3-Phenylpyridine is an important building block in organic synthesis and has a wide range of applications in pharmaceuticals, agrochemicals, and materials science. It is commonly synthesized via the Friedländer synthesis, where a 2-aminopyridine is reacted with a benzaldehyde in the presence of a base. 3-Phenylpyridine has been shown to exhibit biological activity, including anti-inflammatory, antimicrobial, and anticancer properties. It is also used as a ligand in coordination chemistry and as a precursor for the synthesis of other heterocyclic compounds. Its importance in research stems from its versatile nature and its potential for development as a therapeutic agent. It is studied extensively to explore its biological activity, synthetic applications, and potential for the development of new drugs and materials.'

Cross-References

ID SourceID
PubMed CID13886
CHEMBL ID34657
SCHEMBL ID141605
MeSH IDM0162696

Synonyms (40)

Synonym
AC-5100
edz6kb7jvc ,
unii-edz6kb7jvc
einecs 213-762-6
inchi=1/c11h9n/c1-2-5-10(6-3-1)11-7-4-8-12-9-11/h1-9
1008-88-4
3-phenylpyridine ,
pyridine, 3-phenyl-
3-phenylpyridine, 97%
bdbm24680
3-phenylpyridine, 33
CHEMBL34657
3-phenyl-pyridine
P1040
AKOS000121465
m-phenylpyridine;3-azabiphenyl;phenylpyridine
A23542
FT-0616353
SCHEMBL141605
3-(phenyl)pyridine
3-phenyl pyridine
5-phenylpyridine
ss-phenylpyridine
DTXSID0061404
3-phenyipyridine
m-phenylpyridine
W-200635
J-640105
mfcd00006380
J-800107
GS-6350
STL555100
CCG-358057
BBL101304
AMY31493
Q27277127
SY021562
CS-W016252
EN300-21220
Z104494398

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Preclinical and initial clinical studies have demonstrated this compound to be a highly potent inhibitor of thrombin-induced platelet activation, to have excellent oral bioavailability and to have a favorable safety profile."( SCH 530348: a novel oral thrombin receptor antagonist.
Bonaca, MP; Morrow, DA, 2009)		0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Indoleamine 2,3-dioxygenase 1Homo sapiens (human)IC50 (µMol)161.00000.05373.075710.0000AID1798457; AID361930
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (19)

Processvia Protein(s)Taxonomy
regulation of activated T cell proliferationIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of T cell tolerance inductionIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of chronic inflammatory responseIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of type 2 immune responseIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
tryptophan catabolic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
inflammatory responseIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
female pregnancyIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
tryptophan catabolic process to kynurenineIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
response to lipopolysaccharideIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
negative regulation of interleukin-10 productionIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of interleukin-12 productionIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
multicellular organismal response to stressIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
kynurenic acid biosynthetic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
swimming behaviorIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
T cell proliferationIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
negative regulation of T cell proliferationIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
negative regulation of T cell apoptotic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
positive regulation of T cell apoptotic processIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
'de novo' NAD biosynthetic process from tryptophanIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
electron transfer activityIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
heme bindingIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
indoleamine 2,3-dioxygenase activityIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
metal ion bindingIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
tryptophan 2,3-dioxygenase activityIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
cytosolIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
smooth muscle contractile fiberIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
stereocilium bundleIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
cytoplasmIndoleamine 2,3-dioxygenase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID1775064Inhibition of recombinant human IDO1 expressed in Escherichia coli Rosetta (DE3) cells assessed as reduction in kynurenine production using L-tryptophan as substrate incubated for 20 mins by HPLC analysis2021Journal of medicinal chemistry, 02-25, Volume: 64, Issue:4
Azole-Based Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors.
AID361930Inhibition of human recombinant indoleamine 2,3-dioxygenase in presence of L-tryptophan substrate2008Journal of medicinal chemistry, Aug-28, Volume: 51, Issue:16
Structure based development of phenylimidazole-derived inhibitors of indoleamine 2,3-dioxygenase.
AID1572634Down-regulation of c-Myc protein expression in human HT-29 cells assessed as c-Myc protein level at 240 uM after 48 hrs by ELISA (Rvb = 100%)2019Bioorganic & medicinal chemistry, 03-01, Volume: 27, Issue:5
Arylpyridines, arylpyrimidines and related compounds as potential modulator agents of the VEGF, hTERT and c-Myc oncogenes.
AID1572642Down-regulation of VEGFA protein expression in human HT-29 cells assessed as VEGFA protein level at 240 uM after 48 hrs by ELISA (Rvb = 100%)2019Bioorganic & medicinal chemistry, 03-01, Volume: 27, Issue:5
Arylpyridines, arylpyrimidines and related compounds as potential modulator agents of the VEGF, hTERT and c-Myc oncogenes.
AID1572626Down-regulation of VEGFRA mRNA expression in human HT-29 cells assessed as VEGFRA mRNA level at 240 uM after 48 hrs by RT-qPCR analysis (Rvb = 100%)2019Bioorganic & medicinal chemistry, 03-01, Volume: 27, Issue:5
Arylpyridines, arylpyrimidines and related compounds as potential modulator agents of the VEGF, hTERT and c-Myc oncogenes.
AID1572604Selectivity index, ratio of IC50 for HEK293 cells to IC50 for human MCF7 cells2019Bioorganic & medicinal chemistry, 03-01, Volume: 27, Issue:5
Arylpyridines, arylpyrimidines and related compounds as potential modulator agents of the VEGF, hTERT and c-Myc oncogenes.
AID1572602Cytotoxicity against HEK293 cells assessed as decrease in cell viability after 2 days by MTT assay2019Bioorganic & medicinal chemistry, 03-01, Volume: 27, Issue:5
Arylpyridines, arylpyrimidines and related compounds as potential modulator agents of the VEGF, hTERT and c-Myc oncogenes.
AID1572611Down-regulation of hTERT mRNA expression in human HT-29 cells assessed as hTERT mRNA level at 240 uM after 48 hrs by RT-qPCR analysis (Rvb = 100%)2019Bioorganic & medicinal chemistry, 03-01, Volume: 27, Issue:5
Arylpyridines, arylpyrimidines and related compounds as potential modulator agents of the VEGF, hTERT and c-Myc oncogenes.
AID62716Dopamine receptor activation in limbic system of reserpinized rat1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
3-Phenylpiperidines. Central dopamine-autoreceptor stimulating activity.
AID1572600Cytotoxicity against human HT-29 cells assessed as decrease in cell viability after 2 days by MTT assay2019Bioorganic & medicinal chemistry, 03-01, Volume: 27, Issue:5
Arylpyridines, arylpyrimidines and related compounds as potential modulator agents of the VEGF, hTERT and c-Myc oncogenes.
AID1572603Selectivity index, ratio of IC50 for HEK293 cells to IC50 for human HT-29 cells2019Bioorganic & medicinal chemistry, 03-01, Volume: 27, Issue:5
Arylpyridines, arylpyrimidines and related compounds as potential modulator agents of the VEGF, hTERT and c-Myc oncogenes.
AID62721Dopamine receptor activation in striatum of reserpinized rat1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
3-Phenylpiperidines. Central dopamine-autoreceptor stimulating activity.
AID1572601Cytotoxicity against human MCF7 cells assessed as decrease in cell viability after 2 days by MTT assay2019Bioorganic & medicinal chemistry, 03-01, Volume: 27, Issue:5
Arylpyridines, arylpyrimidines and related compounds as potential modulator agents of the VEGF, hTERT and c-Myc oncogenes.
AID1572619Down-regulation of c-Myc mRNA expression in human HT-29 cells assessed as c-Myc mRNA level at 240 uM after 48 hrs by RT-qPCR analysis (Rvb = 100%)2019Bioorganic & medicinal chemistry, 03-01, Volume: 27, Issue:5
Arylpyridines, arylpyrimidines and related compounds as potential modulator agents of the VEGF, hTERT and c-Myc oncogenes.
AID1798457Enzyme Inhibition Assay from Article 10.1021/jm800512z: \\Structure based development of phenylimidazole-derived inhibitors of indoleamine 2,3-dioxygenase.\\2008Journal of medicinal chemistry, Aug-28, Volume: 51, Issue:16
Structure based development of phenylimidazole-derived inhibitors of indoleamine 2,3-dioxygenase.
[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-19902 (22.22)18.7374
1990's0 (0.00)18.2507
2000's3 (33.33)29.6817
2010's3 (33.33)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: 24.13

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 Index24.13 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.79 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.13)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (11.11%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (88.89%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
3,4-dihydroxyphenylacetic acid
3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.		1.9710catechols;
dihydroxyphenylacetic acid		human metabolite
hydrogen
Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.		2.1510elemental hydrogen;
elemental molecule;
gas molecular entity		antioxidant;
electron donor;
food packaging gas;
fuel;
human metabolite
homovanillic acid
Homovanillic Acid: A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.. homovanillate : A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid.. homovanillic acid : A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.		1.9710guaiacols;
monocarboxylic acid		human metabolite;
mouse metabolite
apomorphine
Apomorphine: A derivative of morphine that is a dopamine D2 agonist. It is a powerful emetic and has been used for that effect in acute poisoning. It has also been used in the diagnosis and treatment of parkinsonism, but its adverse effects limit its use.		1.9610aporphine alkaloidalpha-adrenergic drug;
antidyskinesia agent;
antiparkinson drug;
dopamine agonist;
emetic;
serotonergic drug
benzotriazole
benzotriazole: inhibitor of atmospheric metal corrosion; also component of motion picture film & Neva brake fluid. benzotriazole : The simplest member of the class of benzotriazoles that consists of a benzene nucleus fused to a 1H-1,2,3-triazole ring.		2.3110benzotriazolesenvironmental contaminant;
xenobiotic
indazoles
Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.		2.3110indazole
4-phenylpyridine
[no description available]		2.4620phenylpyridine
2-phenylpyridine
2-phenylpyridine: structure given in first source		7.730
squaric acid
[no description available]		2.1110alicyclic ketone;
carbon oxoacid		metabolite
4-phenylpyrimidine
4-phenylpyrimidine : A biaryl that is pyrimidine substituted at position 4 by a phenyl group.		2.3110biaryl;
pyrimidines
alkenes
[no description available]		2.1510
4(5)-phenylimidazole
4(5)-phenylimidazole: tautomeric cpd; cytochrome P450 14alpha-sterol demethylase, CYP51 antagonist		2.5120
honokiol
[no description available]		2.2110biphenyls
1-phenylimidazole
1-phenylimidazole: ligand for cytochrome P-450 & inhibitor of microsomal oxidation		2.3110
1-methyltryptophan
1-methyltryptophan: an immunomodulator. 1-methyltryptophan : A tryptophan derivative that is tryptophan carrying a single methyl substituent at position 1 on the indole.		2.0410indolyl carboxylic acid
vorapaxar
vorapaxar: has antiplatelet activity; structure in first source. vorapaxar : A carbamate ester that is the ethyl ester of [(1R,3aR,4aR,6R,8aR,9S,9aS)-9-{(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]ethynyl}-1-methyl-3-oxododecahydronaphtho[2,3-c]furan-6-yl]carbamic acid. A protease-activated receptor-1 antagonist used (as its sulfate salt) for the reduction of thrombotic cardiovascular events in patients with a history of myocardial infarction (MI) or with peripheral arterial disease. It has been shown to reduce the rate of a combined endpoint of cardiovascular death, MI, stroke and urgent coronary revascularisation.		3.1410carbamate ester;
lactone;
naphthofuran;
organofluorine compound;
pyridines		cardiovascular drug;
platelet aggregation inhibitor;
protease-activated receptor-1 antagonist
ConditionIndicatedRelationship StrengthStudiesTrials
Coronary Thrombosis
Coagulation of blood in any of the CORONARY VESSELS. The presence of a blood clot (THROMBUS) often leads to MYOCARDIAL INFARCTION.		02.9610
Thromboembolism
Obstruction of a blood vessel (embolism) by a blood clot (THROMBUS) in the blood stream.		02.9610
Acute Coronary Syndrome
An episode of MYOCARDIAL ISCHEMIA that generally lasts longer than a transient anginal episode that ultimately may lead to MYOCARDIAL INFARCTION.		02.9610
Atherosclerotic Parkinsonism
[description not available]		01.9710
Parkinson Disease, Secondary
Conditions which feature clinical manifestations resembling primary Parkinson disease that are caused by a known or suspected condition. Examples include parkinsonism caused by vascular injury, drugs, trauma, toxin exposure, neoplasms, infections and degenerative or hereditary conditions. Clinical features may include bradykinesia, rigidity, parkinsonian gait, and masked facies. In general, tremor is less prominent in secondary parkinsonism than in the primary form. (From Joynt, Clinical Neurology, 1998, Ch38, pp39-42)		01.9710