Page last updated: 2024-12-07

1-(4'-nitrophenyl)-2-aminopropane-1,3-diol

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

Description

1-(4'-nitrophenyl)-2-aminopropane-1,3-diol, also known as **nitropropanolamine** or **NPN**, is a synthetic compound with a unique chemical structure that has garnered significant research interest for its potential applications in various fields.

**Chemical Structure:**

NPN is a chiral molecule that combines structural elements of both **propanolamine** (a common pharmaceutical ingredient) and **nitrobenzene** (a potent aromatic compound).

**Importance in Research:**

1. **Pharmacology:**
- **Potential Antidepressant Activity:** Research suggests that NPN may exhibit antidepressant-like effects through its interaction with neurotransmitter systems like serotonin and dopamine.
- **Anti-inflammatory Effects:** Preliminary studies indicate that NPN may possess anti-inflammatory properties, potentially stemming from its ability to modulate the inflammatory response.
- **Antifungal Activity:** NPN has demonstrated antifungal activity against certain fungal species, making it a potential candidate for the development of new antifungal treatments.

2. **Materials Science:**
- **Liquid Crystals:** NPN's unique molecular structure makes it a potential component for liquid crystal displays, offering novel functionalities and improved performance characteristics.

3. **Biochemistry and Molecular Biology:**
- **Probing Protein Function:** NPN can serve as a valuable tool for studying protein interactions and functions due to its ability to bind to specific proteins.

4. **Chemical Synthesis:**
- **Novel Synthesis Methods:** NPN's complex structure has driven the development of innovative synthetic routes, leading to advancements in organic chemistry and synthetic methodology.

**Challenges and Future Directions:**

While NPN's potential is significant, there are challenges associated with its research and development:

- **Toxicity:** NPN's nitro group raises concerns about potential toxicity. Further research is needed to determine its safety profile and establish safe dosage limits.
- **Clinical Trials:** Clinical trials are necessary to validate NPN's efficacy and safety for therapeutic applications.
- **Scale-up and Manufacturing:** Large-scale production of NPN needs to be optimized for cost-effectiveness and environmental sustainability.

Despite these challenges, the unique properties and potential applications of NPN make it a compelling target for continued research. Further exploration of its pharmacological, materials science, and chemical synthesis aspects promises to yield valuable insights and potentially lead to significant advancements in diverse scientific fields.

1-(4'-nitrophenyl)-2-aminopropane-1,3-diol: chloramphenicol minus dichloroacetamide side chain; RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID92743
CHEMBL ID25280
SCHEMBL ID251728
MeSH IDM0081971

Synonyms (62)

Synonym
BB 0257067
MLS001049025
smr000387020
1,3-propanediol, 2-amino-1-(4-nitrophenyl)-
CBDIVE_003085
CBDIVE_006305
OPREA1_299899
EU-0000552
119-62-0
1, 2-amino-1-(p-nitrophenyl)-
1-(p-nitrophenyl)-2-amino-1,3-propanediol
nsc163951
1, 2-amino-1-(4-nitrophenyl)-
nsc-163951
STK386820
2-amino-1-(4-nitrophenyl)propane-1,3-diol
CHEMBL25280
AKOS000118828
NCGC00246273-01
BBL002381
2-amino-1-(4-nitrophenyl)-1,3-propanediol
einecs 221-001-4
(s(r*,r*))-2-amino-1-(p-nitrophenyl)propane-1,3-diol
nsc 12466
HMS2268H24
1-(4'-nitrophenyl)-2-aminopropane-1,3-diol
unii-8fb0b566g6
8fb0b566g6 ,
ai3-62046
einecs 204-338-1
1,3-propanediol, 2-amino-1-(p-nitrophenyl)-
nsc 163951
(r*,r*)-(1)-2-amino-1-(p-nitrophenyl)propane-1,3-diol
einecs 222-997-3
FT-0600616
FT-0634580
AM20050390
AB00601071-07
SCHEMBL251728
AB00601071-09
AKOS016050620
d-threo-2-amino-1-(4-nitrophenyl)-1,3-propanediol
1,3-propanediol, 2-amino-1-(4-nitrophenyl)-, [r-(r*,r*)]-
OCYJXSUPZMNXEN-UHFFFAOYSA-N
2-amino-1-(4-nitrophenyl)-1,3-propanediol #
phenylaceticacid
cambridge id 5104423
F0322-0027
mfcd00066778
mfcd00007359
2-bromo-6-chlorophenylboronicacid
dextramine
VS-01059
1-(4-nitrophenyl)-2-aminopropane-1,3-diol
(r*,r*)-( inverted exclamation marka)-2-amino-1-(p-nitrophenyl)propane-1,3-diol
SB44222
SY066624
SB79368
DTXSID501020866
EN300-16771
F87036
Z235472440

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
"CLRM-IMP-A present in drugs and dosage form can alter the therapeutic effects and adverse reaction of a drug considerably, it is mandatory to have a precise method for the estimation of impurities to safeguard the public health."( Synthesis, Analytical Characterization and Spectroscopic Investigation of Chloramphenicol Impurity A for the Quality Control of Chloramphenicol and its Formulation as Per International Compendium.
Ali, F; Kumar, R; Parveen, S; Singh, GN; Wadhwa, A, 2020
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency3.98110.044717.8581100.0000AID485294
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency22.38720.177814.390939.8107AID2147
glp-1 receptor, partialHomo sapiens (human)Potency3.54810.01846.806014.1254AID624172
thioredoxin reductaseRattus norvegicus (Norway rat)Potency89.12510.100020.879379.4328AID588453; AID588456
lysosomal alpha-glucosidase preproproteinHomo sapiens (human)Potency11.22020.036619.637650.1187AID1466; AID2242
muscleblind-like protein 1 isoform 1Homo sapiens (human)Potency28.18380.00419.962528.1838AID2675
Neuronal acetylcholine receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency11.22023.548118.039535.4813AID1466
Neuronal acetylcholine receptor subunit beta-2Rattus norvegicus (Norway rat)Potency11.22023.548118.039535.4813AID1466
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (19)

Assay IDTitleYearJournalArticle
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.
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.
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
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.
AID198284Evaluated for the inhibition constant determined from the Dixon and slope vs. inhibitor concentration plots; No data1980Journal of medicinal chemistry, Dec, Volume: 23, Issue:12
Analogues of chloramphenicol: circular dichroism spectra, inhibition of ribosomal peptidyltransferase, and possible mechanism of action.
AID198281Evaluated for the concentration required for a 50% inhibition of N-acetyl-L-[14C] phenylalanylpuromycin formation; No data1980Journal of medicinal chemistry, Dec, Volume: 23, Issue:12
Analogues of chloramphenicol: circular dichroism spectra, inhibition of ribosomal peptidyltransferase, and possible mechanism of action.
AID26319pKa value is determined; No data1980Journal of medicinal chemistry, Dec, Volume: 23, Issue:12
Analogues of chloramphenicol: circular dichroism spectra, inhibition of ribosomal peptidyltransferase, and possible mechanism of action.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
AID1159537qHTS screening for TAG (triacylglycerol) accumulators in algae2017Plant physiology, Aug, Volume: 174, Issue:4
Identification and Metabolite Profiling of Chemical Activators of Lipid Accumulation in Green Algae.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (26.09)18.7374
1990's3 (13.04)18.2507
2000's1 (4.35)29.6817
2010's6 (26.09)24.3611
2020's7 (30.43)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.60

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 Index11.60 (24.57)
Research Supply Index3.18 (2.92)
Research Growth Index4.78 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.60)

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%
Other23 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]