1-(2-phenanthrenyl)ethanone, also known as **2-acetylphenanthrene**, is an organic compound with the molecular formula C16H12O. It is a ketone with a phenanthrene ring system.
**Importance in Research:**
2-acetylphenanthrene has been investigated in various research areas, including:
* **Organic synthesis:** It serves as a versatile building block for the synthesis of complex organic molecules. Its reactivity and structural features allow for the formation of various functional groups and ring systems.
* **Materials science:** It has potential applications in the development of organic electronic materials, such as organic light-emitting diodes (OLEDs), due to its luminescent properties.
* **Biological studies:** It has been explored as a potential lead compound for the development of novel drugs, particularly in areas like anti-cancer and anti-inflammatory therapies.
* **Environmental chemistry:** It has been studied as a model compound for investigating the photodegradation and biodegradation of polycyclic aromatic hydrocarbons (PAHs), which are environmental pollutants.
**Specific Applications:**
* **Synthesis of phenanthrene derivatives:** 2-acetylphenanthrene can be readily converted into various phenanthrene derivatives through reactions like Wittig reactions, Grignard reactions, and aldol condensations.
* **Preparation of fluorescent probes:** Its luminescent properties have been utilized for the development of fluorescent probes for sensing applications, such as detecting metal ions or biological molecules.
* **Anti-cancer activity:** Some studies have suggested that 2-acetylphenanthrene exhibits anti-cancer activity against certain cancer cell lines, possibly by inducing apoptosis or inhibiting cell proliferation.
**Overall, 1-(2-phenanthrenyl)ethanone is a valuable research compound with potential applications in various fields, including organic synthesis, materials science, biological studies, and environmental chemistry.**
**Note:** It is important to note that the biological and medicinal properties of 2-acetylphenanthrene are still under investigation, and further research is needed to fully understand its potential and limitations.
ID Source | ID |
---|---|
PubMed CID | 80060 |
CHEMBL ID | 1524777 |
CHEBI ID | 117210 |
SCHEMBL ID | 49935 |
Synonym |
---|
AKOS005443236 |
2-acetylphenanthrene |
1-(2-phenanthryl)ethanone |
methyl 2-phenanthryl ketone |
5960-69-0 |
nsc-402640 |
nsc402640 |
ethanone, 1-(2-phenanthrenyl)- |
smr000161383 |
MLS000324982 |
AO-638/40897172 |
1-(phenanthren-2-yl)ethanone |
STK366111 |
2-acetylphenanthrene, 98% |
CHEBI:117210 |
1-phenanthren-2-ylethanone |
A832380 |
NCGC00247241-01 |
einecs 227-730-4 |
nsc 402640 |
HMS2181D14 |
1-(2-phenanthrenyl)ethanone |
FT-0610979 |
SCHEMBL49935 |
1-(phenanthren-2-yl)ethan-1-one |
DS-1144 |
CHEMBL1524777 |
Q27203844 |
DTXSID60208282 |
J-507712 |
mfcd00001171 |
SB66667 |
CS-W013143 |
SY110183 |
Class | Description |
---|---|
phenanthrenes | Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof. |
[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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Luciferase | Photinus pyralis (common eastern firefly) | Potency | 21.3313 | 0.0072 | 15.7588 | 89.3584 | AID588342 |
thioredoxin reductase | Rattus norvegicus (Norway rat) | Potency | 25.1189 | 0.1000 | 20.8793 | 79.4328 | AID588453 |
phosphopantetheinyl transferase | Bacillus subtilis | Potency | 89.1251 | 0.1413 | 37.9142 | 100.0000 | AID1490 |
ATAD5 protein, partial | Homo sapiens (human) | Potency | 12.3727 | 0.0041 | 10.8903 | 31.5287 | AID504466; AID504467 |
Microtubule-associated protein tau | Homo sapiens (human) | Potency | 2.5119 | 0.1800 | 13.5574 | 39.8107 | AID1460 |
aldehyde dehydrogenase 1 family, member A1 | Homo sapiens (human) | Potency | 25.1189 | 0.0112 | 12.4002 | 100.0000 | AID1030 |
P53 | Homo sapiens (human) | Potency | 44.6684 | 0.0731 | 9.6858 | 31.6228 | AID504706 |
heat shock 70kDa protein 5 (glucose-regulated protein, 78kDa) | Homo sapiens (human) | Potency | 2.2387 | 0.0165 | 25.3078 | 41.3999 | AID602332 |
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1 | Homo sapiens (human) | Potency | 10.0000 | 0.0018 | 15.6638 | 39.8107 | AID894 |
chromobox protein homolog 1 | Homo sapiens (human) | Potency | 89.1251 | 0.0060 | 26.1688 | 89.1251 | AID540317 |
nuclear factor erythroid 2-related factor 2 isoform 2 | Homo sapiens (human) | Potency | 14.5810 | 0.0041 | 9.9848 | 25.9290 | AID504444 |
nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 28.1838 | 0.0079 | 8.2332 | 1,122.0200 | AID2546 |
Vpr | Human immunodeficiency virus 1 | Potency | 10.0000 | 1.5849 | 19.6264 | 63.0957 | AID651644 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. 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. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. 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. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. 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. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 1 (20.00) | 29.6817 |
2010's | 3 (60.00) | 24.3611 |
2020's | 1 (20.00) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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.
| This Compound (12.56) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 5 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |