Page last updated: 2024-11-07

4-(3-chloroanilino)quinazoline

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Description

4-(3-chloroanilino)quinazoline: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID128872
CHEMBL ID329672
SCHEMBL ID136003
MeSH IDM0235759

Synonyms (18)

Synonym
n-(3-chlorophenyl)quinazolin-4-amine
4-anilino quinazoline deriv. 14
chembl329672 ,
bdbm3263
OPREA1_681561
OPREA1_688366
SR-02000000183
88404-44-8
AKOS001614894
(3-chlorophenyl)-quinazolin-4-yl-amine
4-quinazolinamine, n-(3-chlorophenyl)-
4-(3-chloroanilino)quinazoline
4-caq
n-(3-chlorophenyl)-4-quinazolinamine
STL330854
SCHEMBL136003
DTXSID50237026
PD086253
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Acyl-CoA (8-3)-desaturaseHomo sapiens (human)IC50 (µMol)0.01100.01100.01100.0110AID1243190
Epidermal growth factor receptorHomo sapiens (human)IC50 (µMol)0.54020.00000.536910.0000AID1795505; AID1795540; AID1795558; AID1795635; AID320960; AID66596; AID66602; AID69421
Beta-2 adrenergic receptorRattus norvegicus (Norway rat)IC50 (µMol)0.01100.00301.17839.7724AID1243190
Beta-1 adrenergic receptorRattus norvegicus (Norway rat)IC50 (µMol)0.01100.00300.07870.3250AID1243190
Beta-3 adrenergic receptorRattus norvegicus (Norway rat)IC50 (µMol)0.01100.00300.07870.3250AID1243190
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (100)

Processvia Protein(s)Taxonomy
unsaturated fatty acid biosynthetic processAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
long-chain fatty acid biosynthetic processAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
regulation of DNA-templated transcriptionAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
unsaturated fatty acid biosynthetic processAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
cell-cell signalingAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
phospholipid biosynthetic processAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
cellular response to starvationAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
alpha-linolenic acid metabolic processAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
linoleic acid metabolic processAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
regulation of cell differentiationAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
icosanoid biosynthetic processAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
lipid metabolic processAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
cell surface receptor signaling pathwayEpidermal growth factor receptorHomo sapiens (human)
epidermal growth factor receptor signaling pathwayEpidermal growth factor receptorHomo sapiens (human)
positive regulation of cell population proliferationEpidermal growth factor receptorHomo sapiens (human)
MAPK cascadeEpidermal growth factor receptorHomo sapiens (human)
ossificationEpidermal growth factor receptorHomo sapiens (human)
embryonic placenta developmentEpidermal growth factor receptorHomo sapiens (human)
positive regulation of protein phosphorylationEpidermal growth factor receptorHomo sapiens (human)
hair follicle developmentEpidermal growth factor receptorHomo sapiens (human)
translationEpidermal growth factor receptorHomo sapiens (human)
signal transductionEpidermal growth factor receptorHomo sapiens (human)
epidermal growth factor receptor signaling pathwayEpidermal growth factor receptorHomo sapiens (human)
activation of phospholipase C activityEpidermal growth factor receptorHomo sapiens (human)
salivary gland morphogenesisEpidermal growth factor receptorHomo sapiens (human)
midgut developmentEpidermal growth factor receptorHomo sapiens (human)
learning or memoryEpidermal growth factor receptorHomo sapiens (human)
circadian rhythmEpidermal growth factor receptorHomo sapiens (human)
positive regulation of cell population proliferationEpidermal growth factor receptorHomo sapiens (human)
diterpenoid metabolic processEpidermal growth factor receptorHomo sapiens (human)
peptidyl-tyrosine phosphorylationEpidermal growth factor receptorHomo sapiens (human)
cerebral cortex cell migrationEpidermal growth factor receptorHomo sapiens (human)
positive regulation of cell growthEpidermal growth factor receptorHomo sapiens (human)
lung developmentEpidermal growth factor receptorHomo sapiens (human)
positive regulation of cell migrationEpidermal growth factor receptorHomo sapiens (human)
positive regulation of superoxide anion generationEpidermal growth factor receptorHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylationEpidermal growth factor receptorHomo sapiens (human)
response to cobalaminEpidermal growth factor receptorHomo sapiens (human)
response to hydroxyisoflavoneEpidermal growth factor receptorHomo sapiens (human)
cellular response to reactive oxygen speciesEpidermal growth factor receptorHomo sapiens (human)
peptidyl-tyrosine autophosphorylationEpidermal growth factor receptorHomo sapiens (human)
ERBB2-EGFR signaling pathwayEpidermal growth factor receptorHomo sapiens (human)
negative regulation of epidermal growth factor receptor signaling pathwayEpidermal growth factor receptorHomo sapiens (human)
negative regulation of protein catabolic processEpidermal growth factor receptorHomo sapiens (human)
vasodilationEpidermal growth factor receptorHomo sapiens (human)
positive regulation of phosphorylationEpidermal growth factor receptorHomo sapiens (human)
ovulation cycleEpidermal growth factor receptorHomo sapiens (human)
hydrogen peroxide metabolic processEpidermal growth factor receptorHomo sapiens (human)
negative regulation of apoptotic processEpidermal growth factor receptorHomo sapiens (human)
positive regulation of MAP kinase activityEpidermal growth factor receptorHomo sapiens (human)
tongue developmentEpidermal growth factor receptorHomo sapiens (human)
positive regulation of cyclin-dependent protein serine/threonine kinase activityEpidermal growth factor receptorHomo sapiens (human)
positive regulation of DNA repairEpidermal growth factor receptorHomo sapiens (human)
positive regulation of DNA replicationEpidermal growth factor receptorHomo sapiens (human)
positive regulation of bone resorptionEpidermal growth factor receptorHomo sapiens (human)
positive regulation of DNA-templated transcriptionEpidermal growth factor receptorHomo sapiens (human)
positive regulation of vasoconstrictionEpidermal growth factor receptorHomo sapiens (human)
negative regulation of mitotic cell cycleEpidermal growth factor receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIEpidermal growth factor receptorHomo sapiens (human)
regulation of JNK cascadeEpidermal growth factor receptorHomo sapiens (human)
symbiont entry into host cellEpidermal growth factor receptorHomo sapiens (human)
protein autophosphorylationEpidermal growth factor receptorHomo sapiens (human)
astrocyte activationEpidermal growth factor receptorHomo sapiens (human)
positive regulation of fibroblast proliferationEpidermal growth factor receptorHomo sapiens (human)
digestive tract morphogenesisEpidermal growth factor receptorHomo sapiens (human)
positive regulation of smooth muscle cell proliferationEpidermal growth factor receptorHomo sapiens (human)
neuron projection morphogenesisEpidermal growth factor receptorHomo sapiens (human)
epithelial cell proliferationEpidermal growth factor receptorHomo sapiens (human)
positive regulation of epithelial cell proliferationEpidermal growth factor receptorHomo sapiens (human)
regulation of peptidyl-tyrosine phosphorylationEpidermal growth factor receptorHomo sapiens (human)
protein insertion into membraneEpidermal growth factor receptorHomo sapiens (human)
response to calcium ionEpidermal growth factor receptorHomo sapiens (human)
regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionEpidermal growth factor receptorHomo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionEpidermal growth factor receptorHomo sapiens (human)
positive regulation of synaptic transmission, glutamatergicEpidermal growth factor receptorHomo sapiens (human)
positive regulation of glial cell proliferationEpidermal growth factor receptorHomo sapiens (human)
morphogenesis of an epithelial foldEpidermal growth factor receptorHomo sapiens (human)
eyelid development in camera-type eyeEpidermal growth factor receptorHomo sapiens (human)
response to UV-AEpidermal growth factor receptorHomo sapiens (human)
positive regulation of mucus secretionEpidermal growth factor receptorHomo sapiens (human)
regulation of ERK1 and ERK2 cascadeEpidermal growth factor receptorHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeEpidermal growth factor receptorHomo sapiens (human)
cellular response to amino acid stimulusEpidermal growth factor receptorHomo sapiens (human)
cellular response to mechanical stimulusEpidermal growth factor receptorHomo sapiens (human)
cellular response to cadmium ionEpidermal growth factor receptorHomo sapiens (human)
cellular response to epidermal growth factor stimulusEpidermal growth factor receptorHomo sapiens (human)
cellular response to estradiol stimulusEpidermal growth factor receptorHomo sapiens (human)
cellular response to xenobiotic stimulusEpidermal growth factor receptorHomo sapiens (human)
cellular response to dexamethasone stimulusEpidermal growth factor receptorHomo sapiens (human)
positive regulation of canonical Wnt signaling pathwayEpidermal growth factor receptorHomo sapiens (human)
liver regenerationEpidermal growth factor receptorHomo sapiens (human)
cell-cell adhesionEpidermal growth factor receptorHomo sapiens (human)
positive regulation of protein kinase C activityEpidermal growth factor receptorHomo sapiens (human)
positive regulation of G1/S transition of mitotic cell cycleEpidermal growth factor receptorHomo sapiens (human)
positive regulation of non-canonical NF-kappaB signal transductionEpidermal growth factor receptorHomo sapiens (human)
positive regulation of prolactin secretionEpidermal growth factor receptorHomo sapiens (human)
positive regulation of miRNA transcriptionEpidermal growth factor receptorHomo sapiens (human)
positive regulation of protein localization to plasma membraneEpidermal growth factor receptorHomo sapiens (human)
negative regulation of cardiocyte differentiationEpidermal growth factor receptorHomo sapiens (human)
neurogenesisEpidermal growth factor receptorHomo sapiens (human)
multicellular organism developmentEpidermal growth factor receptorHomo sapiens (human)
positive regulation of kinase activityEpidermal growth factor receptorHomo sapiens (human)
cell surface receptor protein tyrosine kinase signaling pathwayEpidermal growth factor receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (30)

Processvia Protein(s)Taxonomy
C-5 sterol desaturase activityAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
linoleoyl-CoA desaturase activityAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
oxidoreductase activityAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
omega-6 fatty acid desaturase activityAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
acyl-CoA delta5-desaturase activityAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
oxidoreductase activity, acting on paired donors, with oxidation of a pair of donors resulting in the reduction of molecular oxygen to two molecules of waterAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
epidermal growth factor receptor activityEpidermal growth factor receptorHomo sapiens (human)
virus receptor activityEpidermal growth factor receptorHomo sapiens (human)
chromatin bindingEpidermal growth factor receptorHomo sapiens (human)
double-stranded DNA bindingEpidermal growth factor receptorHomo sapiens (human)
MAP kinase kinase kinase activityEpidermal growth factor receptorHomo sapiens (human)
protein tyrosine kinase activityEpidermal growth factor receptorHomo sapiens (human)
transmembrane receptor protein tyrosine kinase activityEpidermal growth factor receptorHomo sapiens (human)
transmembrane signaling receptor activityEpidermal growth factor receptorHomo sapiens (human)
epidermal growth factor receptor activityEpidermal growth factor receptorHomo sapiens (human)
integrin bindingEpidermal growth factor receptorHomo sapiens (human)
protein bindingEpidermal growth factor receptorHomo sapiens (human)
calmodulin bindingEpidermal growth factor receptorHomo sapiens (human)
ATP bindingEpidermal growth factor receptorHomo sapiens (human)
enzyme bindingEpidermal growth factor receptorHomo sapiens (human)
kinase bindingEpidermal growth factor receptorHomo sapiens (human)
protein kinase bindingEpidermal growth factor receptorHomo sapiens (human)
protein phosphatase bindingEpidermal growth factor receptorHomo sapiens (human)
protein tyrosine kinase activator activityEpidermal growth factor receptorHomo sapiens (human)
transmembrane receptor protein tyrosine kinase activator activityEpidermal growth factor receptorHomo sapiens (human)
ubiquitin protein ligase bindingEpidermal growth factor receptorHomo sapiens (human)
identical protein bindingEpidermal growth factor receptorHomo sapiens (human)
cadherin bindingEpidermal growth factor receptorHomo sapiens (human)
actin filament bindingEpidermal growth factor receptorHomo sapiens (human)
ATPase bindingEpidermal growth factor receptorHomo sapiens (human)
epidermal growth factor bindingEpidermal growth factor receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (28)

Processvia Protein(s)Taxonomy
mitochondrionAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
endoplasmic reticulum membraneAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
membraneAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
intracellular membrane-bounded organelleAcyl-CoA (8-3)-desaturaseHomo sapiens (human)
endosomeEpidermal growth factor receptorHomo sapiens (human)
plasma membraneEpidermal growth factor receptorHomo sapiens (human)
ruffle membraneEpidermal growth factor receptorHomo sapiens (human)
Golgi membraneEpidermal growth factor receptorHomo sapiens (human)
extracellular spaceEpidermal growth factor receptorHomo sapiens (human)
nucleusEpidermal growth factor receptorHomo sapiens (human)
cytoplasmEpidermal growth factor receptorHomo sapiens (human)
endosomeEpidermal growth factor receptorHomo sapiens (human)
endoplasmic reticulum membraneEpidermal growth factor receptorHomo sapiens (human)
plasma membraneEpidermal growth factor receptorHomo sapiens (human)
focal adhesionEpidermal growth factor receptorHomo sapiens (human)
cell surfaceEpidermal growth factor receptorHomo sapiens (human)
endosome membraneEpidermal growth factor receptorHomo sapiens (human)
membraneEpidermal growth factor receptorHomo sapiens (human)
basolateral plasma membraneEpidermal growth factor receptorHomo sapiens (human)
apical plasma membraneEpidermal growth factor receptorHomo sapiens (human)
cell junctionEpidermal growth factor receptorHomo sapiens (human)
clathrin-coated endocytic vesicle membraneEpidermal growth factor receptorHomo sapiens (human)
early endosome membraneEpidermal growth factor receptorHomo sapiens (human)
nuclear membraneEpidermal growth factor receptorHomo sapiens (human)
membrane raftEpidermal growth factor receptorHomo sapiens (human)
perinuclear region of cytoplasmEpidermal growth factor receptorHomo sapiens (human)
multivesicular body, internal vesicle lumenEpidermal growth factor receptorHomo sapiens (human)
intracellular vesicleEpidermal growth factor receptorHomo sapiens (human)
protein-containing complexEpidermal growth factor receptorHomo sapiens (human)
receptor complexEpidermal growth factor receptorHomo sapiens (human)
Shc-EGFR complexEpidermal growth factor receptorHomo sapiens (human)
basal plasma membraneEpidermal growth factor receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1795540Kinase Inhibition Assay from Article 10.1021/jm9503613: \\Tyrosine Kinase Inhibitors. 8. An Unusually Steep Structure-Activity Relationship for Analogues of 4-(3-Bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a Potent Inhibitor of the Epidermal Growth1996Journal of medicinal chemistry, Jan-05, Volume: 39, Issue:1
Tyrosine kinase inhibitors. 8. An unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor.
AID1795635EGFR assay from Article 10.1016/0968-0896(96)00107-1: \\Tyrphostins IV--highly potent inhibitors of EGF receptor kinase. Structure-activity relationship study of 4-anilidoquinazolines.\\1996Bioorganic & medicinal chemistry, Aug, Volume: 4, Issue:8
Tyrphostins IV--highly potent inhibitors of EGF receptor kinase. Structure-activity relationship study of 4-anilidoquinazolines.
AID1795505Kinase Inhibition Assay from Article 10.1021/jm00018a008: \\Tyrosine kinase inhibitors. 5. Synthesis and structure-activity relationships for 4-[(phenylmethyl)amino]- and 4-(phenylamino)quinazolines as potent adenosine 5'-triphosphate binding site inhibito1995Journal of medicinal chemistry, Sep-01, Volume: 38, Issue:18
Tyrosine kinase inhibitors. 5. Synthesis and structure-activity relationships for 4-[(phenylmethyl)amino]- and 4-(phenylamino)quinazolines as potent adenosine 5'-triphosphate binding site inhibitors of the tyrosine kinase domain of the epidermal growth fa
AID1795558Kinase Inhibition Assay from Article 10.1021/jm9903949: \\Tyrosine kinase inhibitors. 16. 6,5,6-tricyclic benzothieno[3, 2-d]pyrimidines and pyrimido[5,4-b-] and -[4,5-b]indoles as potent inhibitors of the epidermal growth factor receptor tyrosine kinase.\\1999Journal of medicinal chemistry, Dec-30, Volume: 42, Issue:26
Tyrosine kinase inhibitors. 16. 6,5,6-tricyclic benzothieno[3, 2-d]pyrimidines and pyrimido[5,4-b-] and -[4,5-b]ĭndoles as potent inhibitors of the epidermal growth factor receptor tyrosine kinase.
AID1243190Inhibition of liver delta-5 desaturase (unknown origin)2015Bioorganic & medicinal chemistry letters, Sep-15, Volume: 25, Issue:18
Design, synthesis, and in vivo activity of novel inhibitors of delta-5 desaturase for the treatment of metabolic syndrome.
AID1303326Antiproliferative activity against human SMMC7721 cells over expressing EGFR after 48 hrs by MTT assay2016Bioorganic & medicinal chemistry letters, 06-01, Volume: 26, Issue:11
Facile and efficient synthesis and biological evaluation of 4-anilinoquinazoline derivatives as EGFR inhibitors.
AID1303325Antiproliferative activity against human HepG2 cells over expressing EGFR after 48 hrs by MTT assay2016Bioorganic & medicinal chemistry letters, 06-01, Volume: 26, Issue:11
Facile and efficient synthesis and biological evaluation of 4-anilinoquinazoline derivatives as EGFR inhibitors.
AID320960Inhibition of EGFR2008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Discovery of kinase inhibitors by high-throughput docking and scoring based on a transferable linear interaction energy model.
AID66596Concentration needed to inhibit the phosphorylation of a 14-residue fragment of phospholipase C-gamma1 by Epidermal growth factor receptor (prepared from human A431 carcinoma cell vesicles by immunoaffinity chromatography)1999Journal of medicinal chemistry, Dec-30, Volume: 42, Issue:26
Tyrosine kinase inhibitors. 16. 6,5,6-tricyclic benzothieno[3, 2-d]pyrimidines and pyrimido[5,4-b-] and -[4,5-b]ĭndoles as potent inhibitors of the epidermal growth factor receptor tyrosine kinase.
AID66602Evaluation of inhibitory activity against phospholipase C-gamma1 phosphorylation by Epidermal growth factor receptor enzyme isolated from A431 cells.1995Journal of medicinal chemistry, Sep-01, Volume: 38, Issue:18
Tyrosine kinase inhibitors. 5. Synthesis and structure-activity relationships for 4-[(phenylmethyl)amino]- and 4-(phenylamino)quinazolines as potent adenosine 5'-triphosphate binding site inhibitors of the tyrosine kinase domain of the epidermal growth fa
AID69421Concentration required to inhibit the phosphorylation of a 14-residue fragment of phospholipase C gamma 1 by Epidermal growth factor receptor from A431 cell vesicles1996Journal of medicinal chemistry, Jan-05, Volume: 39, Issue:1
Tyrosine kinase inhibitors. 8. An unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor.
AID1303324Antiproliferative activity against human NCI-H1975 cells over expressing EGFR after 48 hrs by MTT assay2016Bioorganic & medicinal chemistry letters, 06-01, Volume: 26, Issue:11
Facile and efficient synthesis and biological evaluation of 4-anilinoquinazoline derivatives as EGFR inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (62.50)18.2507
2000's1 (12.50)29.6817
2010's2 (25.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.42

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 Index12.42 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.62 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.42)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]