Compounds > 4-(diethylamino)benzaldehyde
Page last updated: 2024-12-06

4-(diethylamino)benzaldehyde

Description

4-(Diethylamino)benzaldehyde is a yellow crystalline solid used in the synthesis of various organic compounds. It is a key intermediate in the production of dyes, pharmaceuticals, and other fine chemicals. The compound is also a building block for the preparation of Schiff bases, which have applications in catalysis, materials science, and coordination chemistry. Its synthesis typically involves the reaction of N,N-diethylaniline with benzaldehyde in the presence of a catalyst, followed by oxidation of the resulting alcohol. Studies on 4-(diethylamino)benzaldehyde focus on its reactivity, its use in the synthesis of new functional materials, and its potential as a precursor for biologically active compounds. The compound is a versatile building block in organic synthesis and has been used in the preparation of a wide range of products with diverse applications.'

4-(diethylamino)benzaldehyde : A member of the class of benzaldehydes carrying a diethylamino substituent at position 4. [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]

Cross-References

ID SourceID
PubMed CID67114
CHEMBL ID3416563
CHEBI ID86194
SCHEMBL ID195135
MeSH IDM0156278

Synonyms (58)

Synonym
p-diethylaminobenzaldehyde
ai3-05886
nsc 8782
einecs 204-377-4
4-diethylaminobenzaldehyde
nsc-8782
4-(diethylamino)benzaldehyde
p-formyl-n,n-diethylaniline
benzaldehyde, 4-(diethylamino)-
nsc8782
benzaldehyde, p-(diethylamino)-
120-21-8
p-(diethylamino)benzaldehyde
p-diethylaminobenzaldhyde
benzaldehyde,4-diethylamino
inchi=1/c11h15no/c1-3-12(4-2)11-7-5-10(9-13)6-8-11/h5-9h,3-4h2,1-2h
4-diethylaminobenzaldehyde, 99%
STK187548
D0463
AKOS000118909
A804467
4-(diethylamino)-benzaldehyde
s640xwl10h ,
unii-s640xwl10h
FT-0618338
PS-6119
n,n-diethyl-4-formylaniline
BP-21432
4-(diethylamino) benzaldehyde
4-(n,n-diethyl)aminobenzaldehyde
p-n,n-diethylaminobenzaldehyde
4-diethylamino benzaldehyde
p-diethylamino-benzaldehyde
SCHEMBL195135
4-(n,n-diethylamino)benzaldehyde
dtxcid901963
tox21_303895
cas-120-21-8
NCGC00357151-01
dtxsid0021963 ,
CHEBI:86194 ,
W-108483
diethylaminobenzaldehyde, p-
4-(n,n-diethylamine)benzaldehyde
p-(n,n-diethylamino)benzaldehyde
4-formyl-n,n-diethylaniline
4-n,n-diethylamino benzaldehyde
bdbm50076742
CHEMBL3416563 ,
F2190-0606
mfcd00003382
CS-W017361
Q27158973
EN300-18276
HY-W016645
SB66335
4-diethylamino-benzaldehyde
Z57772436
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitorAn EC 1.2.1.* (oxidoreductase acting on donor aldehyde/oxo group with NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of aldehyde dehydrogenase (NAD(+)), EC 1.2.1.3.
[role 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]

Drug Classes (3)

ClassDescription
benzaldehydesAny arenecarbaldehyde that consists of a formyl substituted benzene ring and its substituted derivatives thereof.
tertiary amino compoundA compound formally derived from ammonia by replacing three hydrogen atoms by organyl groups.
aromatic amineAn amino compound in which the amino group is linked directly to an aromatic system.
[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 (11)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LuciferasePhotinus pyralis (common eastern firefly)Potency39.91490.007215.758889.3584AID1224835
AR proteinHomo sapiens (human)Potency12.65310.000221.22318,912.5098AID1259243; AID1259247; AID1259381
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency49.26170.001022.650876.6163AID1224838; AID1224839; AID1224893
progesterone receptorHomo sapiens (human)Potency21.68990.000417.946075.1148AID1346795
retinoid X nuclear receptor alphaHomo sapiens (human)Potency0.71010.000817.505159.3239AID1159527; AID1159531
pregnane X nuclear receptorHomo sapiens (human)Potency48.55770.005428.02631,258.9301AID1346982
thyroid stimulating hormone receptorHomo sapiens (human)Potency61.13060.001628.015177.1139AID1259385
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Retinal dehydrogenase 1Homo sapiens (human)IC50 (µMol)1.03570.02001.04766.7900AID1199888; AID1199901; AID1387301; AID1387315; AID1387316; AID1826420
Aldehyde dehydrogenase, mitochondrialHomo sapiens (human)IC50 (µMol)15.00000.04003.40799.0000AID1387300
Aldehyde dehydrogenase, dimeric NADP-preferring Homo sapiens (human)IC50 (µMol)5.67001.20003.43505.6700AID1826422
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (33)

Processvia Protein(s)Taxonomy
retinoid metabolic processRetinal dehydrogenase 1Homo sapiens (human)
cellular aldehyde metabolic processRetinal dehydrogenase 1Homo sapiens (human)
gamma-aminobutyric acid biosynthetic processRetinal dehydrogenase 1Homo sapiens (human)
fructosamine catabolic processRetinal dehydrogenase 1Homo sapiens (human)
maintenance of lens transparencyRetinal dehydrogenase 1Homo sapiens (human)
retinol metabolic processRetinal dehydrogenase 1Homo sapiens (human)
cellular detoxification of aldehydeRetinal dehydrogenase 1Homo sapiens (human)
negative regulation of cold-induced thermogenesisRetinal dehydrogenase 1Homo sapiens (human)
carbohydrate metabolic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
alcohol metabolic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
ethanol catabolic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
aldehyde catabolic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
regulation of dopamine biosynthetic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
regulation of serotonin biosynthetic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
cellular aldehyde metabolic processAldehyde dehydrogenase, dimeric NADP-preferring Homo sapiens (human)
lipid metabolic processAldehyde dehydrogenase, dimeric NADP-preferring Homo sapiens (human)
xenobiotic metabolic processAldehyde dehydrogenase, dimeric NADP-preferring Homo sapiens (human)
optic cup morphogenesis involved in camera-type eye developmentAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
retinoic acid biosynthetic processAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
apoptotic processAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
locomotory behaviorAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
nucleus accumbens developmentAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
embryonic camera-type eye developmentAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
inner ear morphogenesisAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
retinol metabolic processAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
retinoic acid metabolic processAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
retinal metabolic processAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
positive regulation of apoptotic processAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
embryonic eye morphogenesisAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
neuromuscular process controlling balanceAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
protein homotetramerizationAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
righting reflexAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
olfactory pit developmentAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
face developmentAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
Harderian gland developmentAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (20)

Processvia Protein(s)Taxonomy
retinal dehydrogenase activityRetinal dehydrogenase 1Homo sapiens (human)
aldehyde dehydrogenase (NAD+) activityRetinal dehydrogenase 1Homo sapiens (human)
GTPase activator activityRetinal dehydrogenase 1Homo sapiens (human)
androgen bindingRetinal dehydrogenase 1Homo sapiens (human)
protein bindingRetinal dehydrogenase 1Homo sapiens (human)
aminobutyraldehyde dehydrogenase activityRetinal dehydrogenase 1Homo sapiens (human)
glyceraldehyde-3-phosphate dehydrogenase (NAD+) (non-phosphorylating) activityRetinal dehydrogenase 1Homo sapiens (human)
NAD bindingRetinal dehydrogenase 1Homo sapiens (human)
3-deoxyglucosone dehydrogenase activityRetinal dehydrogenase 1Homo sapiens (human)
benzaldehyde dehydrogenase (NAD+) activityRetinal dehydrogenase 1Homo sapiens (human)
aldehyde dehydrogenase (NAD+) activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
aldehyde dehydrogenase [NAD(P)+] activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
phenylacetaldehyde dehydrogenase activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
electron transfer activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
nitroglycerin reductase activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
glyceraldehyde-3-phosphate dehydrogenase (NAD+) (non-phosphorylating) activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
NAD bindingAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
carboxylesterase activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
aldehyde dehydrogenase (NAD+) activityAldehyde dehydrogenase, dimeric NADP-preferring Homo sapiens (human)
aldehyde dehydrogenase [NAD(P)+] activityAldehyde dehydrogenase, dimeric NADP-preferring Homo sapiens (human)
protein bindingAldehyde dehydrogenase, dimeric NADP-preferring Homo sapiens (human)
alcohol dehydrogenase (NADP+) activityAldehyde dehydrogenase, dimeric NADP-preferring Homo sapiens (human)
benzaldehyde dehydrogenase (NAD+) activityAldehyde dehydrogenase, dimeric NADP-preferring Homo sapiens (human)
3-chloroallyl aldehyde dehydrogenase activityAldehyde dehydrogenase, dimeric NADP-preferring Homo sapiens (human)
retinal dehydrogenase activityAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
aldehyde dehydrogenase [NAD(P)+] activityAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
protein homodimerization activityAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
thyroid hormone bindingAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
NAD+ bindingAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
aldehyde dehydrogenase (NAD+) activityAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
cytoplasmRetinal dehydrogenase 1Homo sapiens (human)
cytosolRetinal dehydrogenase 1Homo sapiens (human)
axonRetinal dehydrogenase 1Homo sapiens (human)
synapseRetinal dehydrogenase 1Homo sapiens (human)
extracellular exosomeRetinal dehydrogenase 1Homo sapiens (human)
mitochondrionAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
mitochondrial matrixAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
extracellular exosomeAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
extracellular spaceAldehyde dehydrogenase, dimeric NADP-preferring Homo sapiens (human)
endoplasmic reticulumAldehyde dehydrogenase, dimeric NADP-preferring Homo sapiens (human)
cytosolAldehyde dehydrogenase, dimeric NADP-preferring Homo sapiens (human)
plasma membraneAldehyde dehydrogenase, dimeric NADP-preferring Homo sapiens (human)
cytoplasmAldehyde dehydrogenase, dimeric NADP-preferring Homo sapiens (human)
cytoplasmAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
cytosolAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
extracellular exosomeAldehyde dehydrogenase family 1 member A3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (25)

Assay IDTitleYearJournalArticle
AID1387301Inhibition of human ALDH1A12018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
Structure-Based Optimization of a Novel Class of Aldehyde Dehydrogenase 1A (ALDH1A) Subfamily-Selective Inhibitors as Potential Adjuncts to Ovarian Cancer Chemotherapy.
AID1387327Inhibition of ALDH1A3 in human PEO1 cells assessed as reduction in aldefluor positive cells at 1 uM incubated for 30 mins by aldefluor assay2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
Structure-Based Optimization of a Novel Class of Aldehyde Dehydrogenase 1A (ALDH1A) Subfamily-Selective Inhibitors as Potential Adjuncts to Ovarian Cancer Chemotherapy.
AID1387300Inhibition of ALDH (unknown origin)2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
Structure-Based Optimization of a Novel Class of Aldehyde Dehydrogenase 1A (ALDH1A) Subfamily-Selective Inhibitors as Potential Adjuncts to Ovarian Cancer Chemotherapy.
AID1826435Cytotoxicity against human H415/15 cells assessed as reduction in cell viability incubated for 72 hrs by AlamarBlue staining based analysis2022Journal of medicinal chemistry, 03-10, Volume: 65, Issue:5
Expansion of the 4-(Diethylamino)benzaldehyde Scaffold to Explore the Impact on Aldehyde Dehydrogenase Activity and Antiproliferative Activity in Prostate Cancer.
AID1826433Antiproliferative activity against human LNCaP cells expressing ALDH1A3 assessed as reduction in cell survival measured after 96 hrs by MTT assay2022Journal of medicinal chemistry, 03-10, Volume: 65, Issue:5
Expansion of the 4-(Diethylamino)benzaldehyde Scaffold to Explore the Impact on Aldehyde Dehydrogenase Activity and Antiproliferative Activity in Prostate Cancer.
AID1199901Inhibition of recombinant human ALDH1A1 using propionaldehyde as substrate preincubated for 2 mins with NAD+ followed by substrate addition by UV-Vis spectrophotometric analysis2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
Characterization of two distinct structural classes of selective aldehyde dehydrogenase 1A1 inhibitors.
AID1199888Inhibition of human ALDH1A1 G458N mutant using propionaldehyde as substrate preincubated for 2 mins with NAD+ followed by substrate addition by UV-Vis spectrophotometric analysis2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
Characterization of two distinct structural classes of selective aldehyde dehydrogenase 1A1 inhibitors.
AID1826437Cytotoxicity against human H431/14 LM cells assessed as reduction in cell viability incubated for 72 hrs by AlamarBlue staining based analysis2022Journal of medicinal chemistry, 03-10, Volume: 65, Issue:5
Expansion of the 4-(Diethylamino)benzaldehyde Scaffold to Explore the Impact on Aldehyde Dehydrogenase Activity and Antiproliferative Activity in Prostate Cancer.
AID1387333Inhibition of ALDH1A3 in human PEO1 cells assessed as reduction in CD133 protein expression incubated for 48 hrs by CD133/2-APC antibody based assay2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
Structure-Based Optimization of a Novel Class of Aldehyde Dehydrogenase 1A (ALDH1A) Subfamily-Selective Inhibitors as Potential Adjuncts to Ovarian Cancer Chemotherapy.
AID1826438Cytotoxicity against human H488/14 RM cells assessed as reduction in cell viability incubated for 72 hrs by AlamarBlue staining based analysis2022Journal of medicinal chemistry, 03-10, Volume: 65, Issue:5
Expansion of the 4-(Diethylamino)benzaldehyde Scaffold to Explore the Impact on Aldehyde Dehydrogenase Activity and Antiproliferative Activity in Prostate Cancer.
AID1826434Antiproliferative activity against human DU145 cells expressing ALDH1A1 assessed as reduction in cell survival measured after 96 hrs by MTT assay2022Journal of medicinal chemistry, 03-10, Volume: 65, Issue:5
Expansion of the 4-(Diethylamino)benzaldehyde Scaffold to Explore the Impact on Aldehyde Dehydrogenase Activity and Antiproliferative Activity in Prostate Cancer.
AID1387314Inhibition of ALDH1A3 in human PEO1 cells assessed as reduction in aldefluor positive cells up to 30 uM incubated for 30 mins by aldefluor assay2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
Structure-Based Optimization of a Novel Class of Aldehyde Dehydrogenase 1A (ALDH1A) Subfamily-Selective Inhibitors as Potential Adjuncts to Ovarian Cancer Chemotherapy.
AID1826422Inhibition of N-terminal-His6 tagged recombinant human ALDH3A1 assessed as reduction in NADPH production using 4-NBA and NADP+ as substrate by fluorimetric analysis2022Journal of medicinal chemistry, 03-10, Volume: 65, Issue:5
Expansion of the 4-(Diethylamino)benzaldehyde Scaffold to Explore the Impact on Aldehyde Dehydrogenase Activity and Antiproliferative Activity in Prostate Cancer.
AID1826421Inhibition of N-terminal-His6 tagged recombinant human ALDH1A3 assessed as reduction in NADH production using hexanal and NAD+ as substrate by fluorimetric analysis2022Journal of medicinal chemistry, 03-10, Volume: 65, Issue:5
Expansion of the 4-(Diethylamino)benzaldehyde Scaffold to Explore the Impact on Aldehyde Dehydrogenase Activity and Antiproliferative Activity in Prostate Cancer.
AID1387328Inhibition of ALDH1A3 in human PEO1 cells assessed as reduction in aldefluor positive cells at 10 uM incubated for 30 mins by aldefluor assay2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
Structure-Based Optimization of a Novel Class of Aldehyde Dehydrogenase 1A (ALDH1A) Subfamily-Selective Inhibitors as Potential Adjuncts to Ovarian Cancer Chemotherapy.
AID1387334Inhibition of ALDH1A3 in human OVCAR5 cells assessed as reduction in CD133 protein expression incubated for 48 hrs by CD133/2-APC antibody based assay2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
Structure-Based Optimization of a Novel Class of Aldehyde Dehydrogenase 1A (ALDH1A) Subfamily-Selective Inhibitors as Potential Adjuncts to Ovarian Cancer Chemotherapy.
AID1387330Inhibition of ALDH1A3 in human OVCAR5 cells assessed as reduction in aldefluor positive cells at 10 uM incubated for 30 mins by aldefluor assay2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
Structure-Based Optimization of a Novel Class of Aldehyde Dehydrogenase 1A (ALDH1A) Subfamily-Selective Inhibitors as Potential Adjuncts to Ovarian Cancer Chemotherapy.
AID1826439Cytotoxicity against human H517/15 RM cells assessed as reduction in cell viability incubated for 72 hrs by AlamarBlue staining based analysis2022Journal of medicinal chemistry, 03-10, Volume: 65, Issue:5
Expansion of the 4-(Diethylamino)benzaldehyde Scaffold to Explore the Impact on Aldehyde Dehydrogenase Activity and Antiproliferative Activity in Prostate Cancer.
AID1387315Inhibition of ALDH1A1 in human MIAPaCa2 cells assessed as reduction in aldefluor positive cells up to 30 uM incubated for 30 mins by aldefluor assay2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
Structure-Based Optimization of a Novel Class of Aldehyde Dehydrogenase 1A (ALDH1A) Subfamily-Selective Inhibitors as Potential Adjuncts to Ovarian Cancer Chemotherapy.
AID1387316Inhibition of ALDH1A1 in human HT-29 cells assessed as reduction in aldefluor positive cells up to 30 uM incubated for 30 mins by aldefluor assay2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
Structure-Based Optimization of a Novel Class of Aldehyde Dehydrogenase 1A (ALDH1A) Subfamily-Selective Inhibitors as Potential Adjuncts to Ovarian Cancer Chemotherapy.
AID1826436Cytotoxicity against human H568/15 RM cells assessed as reduction in cell viability incubated for 72 hrs by AlamarBlue staining based analysis2022Journal of medicinal chemistry, 03-10, Volume: 65, Issue:5
Expansion of the 4-(Diethylamino)benzaldehyde Scaffold to Explore the Impact on Aldehyde Dehydrogenase Activity and Antiproliferative Activity in Prostate Cancer.
AID1387329Inhibition of ALDH1A3 in human OVCAR5 cells assessed as reduction in aldefluor positive cells at 1 uM incubated for 30 mins by aldefluor assay2018Journal of medicinal chemistry, 10-11, Volume: 61, Issue:19
Structure-Based Optimization of a Novel Class of Aldehyde Dehydrogenase 1A (ALDH1A) Subfamily-Selective Inhibitors as Potential Adjuncts to Ovarian Cancer Chemotherapy.
AID1826419Inhibition of N-terminal-His6 tagged recombinant human ALDH1A1 assessed as remaining enzyme activity by measuring fluorescence of NADH using hexanal and NAD+ as substrate at 10 uM by fluorimetric analysis relative to control2022Journal of medicinal chemistry, 03-10, Volume: 65, Issue:5
Expansion of the 4-(Diethylamino)benzaldehyde Scaffold to Explore the Impact on Aldehyde Dehydrogenase Activity and Antiproliferative Activity in Prostate Cancer.
AID1826420Inhibition of N-terminal-His6 tagged recombinant human ALDH1A1 assessed as reduction in NADH production using hexanal and NAD+ as substrate by fluorimetric analysis2022Journal of medicinal chemistry, 03-10, Volume: 65, Issue:5
Expansion of the 4-(Diethylamino)benzaldehyde Scaffold to Explore the Impact on Aldehyde Dehydrogenase Activity and Antiproliferative Activity in Prostate Cancer.
AID1826432Antiproliferative activity against human PC-3 cells expressing ALDH1A1 and ALDH3A1 assessed as reduction in cell survival measured after 96 hrs by MTT assay2022Journal of medicinal chemistry, 03-10, Volume: 65, Issue:5
Expansion of the 4-(Diethylamino)benzaldehyde Scaffold to Explore the Impact on Aldehyde Dehydrogenase Activity and Antiproliferative Activity in Prostate Cancer.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (6.25)18.7374
1990's1 (6.25)18.2507
2000's3 (18.75)29.6817
2010's8 (50.00)24.3611
2020's3 (18.75)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 33.59

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 Index33.59 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index5.18 (4.65)
Search Engine Demand Index35.52 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (33.59)

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%
Other16 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetic acid
Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.		2.0210monocarboxylic acidantimicrobial food preservative;
Daphnia magna metabolite;
food acidity regulator;
protic solvent
acetaldehyde
Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.		1.9810aldehydecarcinogenic agent;
EC 3.5.1.4 (amidase) inhibitor;
electron acceptor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
mutagen;
oxidising agent;
Saccharomyces cerevisiae metabolite;
teratogenic agent
benzaldehyde
[no description available]		2.0310benzaldehydesEC 3.1.1.3 (triacylglycerol lipase) inhibitor;
EC 3.5.5.1 (nitrilase) inhibitor;
flavouring agent;
fragrance;
odorant receptor agonist;
plant metabolite
4-nitrobenzaldehyde
4-nitrobenzaldehyde: RN given refers to parent cpd. 4-nitrobenzaldehyde : A C-nitro compound that is benzaldehyde substituted at the para-position with a nitro group.		2.4110benzaldehydes;
C-nitro compound
theophylline
[no description available]		2.1110dimethylxanthineadenosine receptor antagonist;
anti-asthmatic drug;
anti-inflammatory agent;
bronchodilator agent;
drug metabolite;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
fungal metabolite;
human blood serum metabolite;
immunomodulator;
muscle relaxant;
vasodilator agent
antipyrine
Antipyrine: An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29). antipyrine : A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2.		1.9810pyrazoloneantipyretic;
cyclooxygenase 3 inhibitor;
environmental contaminant;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic
beta-naphthoflavone
beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.		2.0210extended flavonoid;
naphtho-gamma-pyrone;
organic heterotricyclic compound		aryl hydrocarbon receptor agonist
caffeine
[no description available]		2.1110purine alkaloid;
trimethylxanthine		adenosine A2A receptor antagonist;
adenosine receptor antagonist;
adjuvant;
central nervous system stimulant;
diuretic;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
environmental contaminant;
food additive;
fungal metabolite;
geroprotector;
human blood serum metabolite;
mouse metabolite;
mutagen;
plant metabolite;
psychotropic drug;
ryanodine receptor agonist;
xenobiotic
methoxyamine
methoxyamine: analytical reagent for aldehydes and ketones; strong irritant, can probably produce methemoglobinemia; RN given refers to parent cpd; structure		7.4520organooxygen compound
4-aminobenzoic acid
para-Aminobenzoates: Benzoic acids, salts, or esters that contain an amino group attached to carbon number 4 of the benzene ring structure.. 4-aminobenzoate : An aromatic amino-acid anion that is the conjugate base of 4-aminobenzoic acid.		2.2510aminobenzoate;
aromatic amino-acid anion		Escherichia coli metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
carbamylhydrazine
carbamylhydrazine: RN given refers to parent cpd		2.0310carbohydrazide;
monocarboxylic acid amide;
one-carbon compound;
ureas
temozolomide
[no description available]		2.0710imidazotetrazine;
monocarboxylic acid amide;
triazene derivative		alkylating agent;
antineoplastic agent;
prodrug
hydrazine
diamine : Any polyamine that contains two amino groups.		2.2110azane;
hydrazines		EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
win 18446
WIN 18446 : A carboxamide that is 1,8-diaminooctane in which a hydrogen attached to each of the amino groups has been replaced by a dichloroacetyl group. Inhibitor of aldehyde dehydrogenase 1a2 (ALDH1a2). Inhibits the biosynthesis of retinoic acid from retinol in neonatal and adult murine testis. It down-regulates sex related genes in zebrafish.		2.1710organochlorine compound;
secondary carboxamide		EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor
palladium
Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.		2.0310metal allergen;
nickel group element atom;
platinum group metal atom
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		1.9810benzenes;
phenyl acetates
tretinoin
Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.		3.1950retinoic acid;
vitamin A		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
AP-1 antagonist;
human metabolite;
keratolytic drug;
retinoic acid receptor agonist;
retinoid X receptor agonist;
signalling molecule
7-butyl-8-[[4-(3-chlorophenyl)-1-piperazinyl]methyl]-1,3-dimethylpurine-2,6-dione
[no description available]		2.1110piperazines
thiosemicarbazide
thiosemicarbazide: glutamate decarboxylase antagonist; structure given in first source. hydrazinecarbothioamide : A member of the class of thioureas that is thiourea in which a hydrogen of one of the amino groups is replaced by an amino group.		2.0310hydrazines;
thiocarboxamide;
thioureas
4-(2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl)benzoic acid
4-(2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl)benzoic acid: RN refers to (E)-isomer; structure given in first source. arotinoid acid : A retinoid that consists of benzoic acid substituted at position 4 by a 2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-en-1-yl group. It is a synthetic retinoid that acts as a selective agonist for the retinoic acid receptors (RAR).		2.1310benzoic acids;
naphthalenes;
retinoid		antineoplastic agent;
retinoic acid receptor agonist;
teratogenic agent
perfosfamide
[no description available]		1.9710
nad
NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.		2.2510organophosphate oxoanioncofactor;
human metabolite;
hydrogen acceptor;
Saccharomyces cerevisiae metabolite
dacarbazine
(E)-dacarbazine : A dacarbazine in which the N=N double bond adopts a trans-configuration.		2.0710dacarbazine
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Ovary
[description not available]		02.5520
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		02.5520
Cancer of Prostate
[description not available]		02.4110
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.4110
Deafness, Transitory
[description not available]		02.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.6120
Hearing Loss
A general term for the complete or partial loss of the ability to hear from one or both ears.		02.2510
ER-Negative PR-Negative HER2-Negative Breast Cancer
[description not available]		02.1710
Triple Negative Breast Neoplasms
Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.		02.1710
Deficiency, Vitamin A
[description not available]		02.1310
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.5120
Vitamin A Deficiency
A nutritional condition produced by a deficiency of VITAMIN A in the diet, characterized by NIGHT BLINDNESS and other ocular manifestations such as dryness of the conjunctiva and later of the cornea (XEROPHTHALMIA). Vitamin A deficiency is a very common problem worldwide, particularly in developing countries as a consequence of famine or shortages of vitamin A-rich foods. In the United States it is found among the urban poor, the elderly, alcoholics, and patients with malabsorption. (From Cecil Textbook of Medicine, 19th ed, p1179)		02.1310
Benign Neoplasms
[description not available]		02.0710
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.0710
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.0710
Leukemia L 1210
[description not available]		01.9710
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