(1E,4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one, also known as **chalcone**, is an important organic compound that has been extensively studied for its potential applications in various fields. Let's break down its structure and significance.
**Structure and Properties:**
* **Chalcone** is a yellow crystalline solid with a characteristic aromatic odor.
* It consists of a **penta-1,4-dien-3-one** backbone, which is a five-carbon chain with alternating double and single bonds and a ketone group at the third carbon.
* Two **4-methoxyphenyl** groups (benzene rings with a methoxy group at the para position) are attached at the first and fifth carbons of the chain.
* The (1E,4E) designation indicates the configuration of the double bonds, meaning they are in a trans (E) configuration.
**Importance in Research:**
Chalcone is a versatile molecule with numerous applications in research, including:
* **Pharmacology:**
* **Anti-inflammatory and analgesic properties:** Chalcone and its derivatives have shown promise in treating inflammatory diseases like arthritis, and reducing pain.
* **Anti-cancer activity:** Chalcone analogs have exhibited activity against various cancer cell lines, demonstrating potential as anti-cancer drugs.
* **Antimicrobial activity:** Chalcones have shown effectiveness against bacteria, fungi, and viruses, suggesting potential use in antimicrobial therapies.
* **Antioxidant properties:** Chalcones can scavenge free radicals, protecting cells from oxidative damage and potentially preventing diseases like heart disease and cancer.
* **Materials Science:**
* **Organic electronics:** Chalcones can serve as building blocks for organic semiconductors used in solar cells, LEDs, and other electronic devices.
* **Liquid crystals:** Chalcone derivatives have been incorporated into liquid crystal displays due to their optical properties and ability to align in response to electric fields.
* **Agricultural Research:**
* **Pesticide and fungicide development:** Chalcone analogs have been investigated for their potential as natural pesticides and fungicides, offering a more environmentally friendly approach to pest control.
**Why is Chalcone Important for Research?**
Chalcone's importance stems from its unique combination of features:
* **Biological activity:** Its diverse biological properties, including anti-inflammatory, anti-cancer, and antimicrobial effects, make it a promising lead compound for drug discovery.
* **Structural versatility:** The chalcone scaffold can be easily modified by attaching different substituents to the phenyl rings, allowing for the synthesis of a wide range of derivatives with tailored properties.
* **Natural occurrence:** Chalcones are found in various plants, suggesting their potential for developing natural remedies and agrochemicals.
**In Summary:**
(1E,4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one, or chalcone, is a crucial molecule in research due to its biological activity, structural flexibility, and potential applications in pharmaceuticals, materials science, and agriculture.
ID Source | ID |
---|---|
PubMed CID | 715840 |
CHEMBL ID | 584437 |
CHEBI ID | 183767 |
SCHEMBL ID | 2744098 |
SCHEMBL ID | 2744101 |
Synonym |
---|
50764-85-7 |
bis(4-methoxybenzylidene)acetone |
MEGXP0_001779 |
nsc-677239 |
1,4-pentadien-3-one, 1,5-bis(4-methoxyphenyl)- |
nsc 401196 |
1,4-pentadien-3-one, 1,5-bis(p-methoxyphenyl)- |
(1e,4e)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one |
1,4-pentadien-3-one, 1,5-bis(4-methoxyphenyl)-, (1e,4e)- |
nsc677239 |
nsc-401196 |
2051-07-2 |
STK325157 |
HMS1552C13 |
AKOS001325277 |
1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one |
di-p-anisylideneacetone |
CHEMBL584437 , |
go-y013 |
CHEBI:183767 |
37951-12-5 |
BBL002419 |
di-(4,4'-dimethoxy)-benzylidene-acetone |
(1e,4e)-1,5-bis(4-methoxyphenyl)-3-penta-1,4-dienone |
A816101 |
F0415-0075 |
dianisylidene acetone |
1,5-bis(4-methoxyphenyl)-1,4-pentadien-3-one |
AB01134828-03 |
SCHEMBL2744098 |
SCHEMBL2744101 |
(1e,4e)-1,5-bis(4-methoxyphenyl)-1,4-pentadien-3-one # |
dianisylideneacetone |
IOZVKDXPBWBUKY-LQIBPGRFSA-N |
di(4-methoxybenzylidene)acetone |
trans,trans-bis(4-methoxybenzylidene)acetone |
trans,trans-1,5-bis(4-methoxyphenyl)-1,4-pentadien-3-one |
trans,trans-bis(4-methoxystyryl) ketone |
B4467 |
trans,trans-bis(4-methoxybenzal)acetone |
AS-67184 |
AS-69064 |
bdbm50488795 |
(1e,4e)-1,5-bis(4-methoxyphenyl)-1,4-pentadien-3-one |
mfcd00014901 |
1,5-di(4-methoxyphenyl)penta-1,4-dien-3-one |
Z234853558 |
NCGC00336197-01 |
1,5-bis-(4-methoxy-phenyl)-penta-1,4-dien-3-one |
D89083 |
1,5-bis(p-methoxyphenyl)-1,4-pentadien-3-one |
C1T5NW58W3 , |
go-y-013 |
A873973 |
1,5-bis-(4-methoxyphenyl)-3-pentadienone |
unii-c1t5nw58w3 |
CS-W014550 |
DTXSID401347720 |
Class | Description |
---|---|
methoxybenzenes | Any aromatic ether that consists of a benzene skeleton substituted with one or more methoxy groups. |
[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] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1415617 | Antifungal activity against fluconazole-resistant Candida tropicalis clinical isolate 087 in presence of 8 ug/ml fluconazole by broth microdilution method | 2017 | MedChemComm, May-01, Volume: 8, Issue:5 | Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant |
AID1415618 | Antifungal activity against fluconazole-resistant Candida krusei clinical isolate 2159 in presence of 8 ug/ml fluconazole by broth microdilution method | 2017 | MedChemComm, May-01, Volume: 8, Issue:5 | Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant |
AID1415616 | Antifungal activity against fluconazole-resistant Candida albicans clinical isolate 103 in presence of 8 ug/ml fluconazole by broth microdilution method | 2017 | MedChemComm, May-01, Volume: 8, Issue:5 | Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant |
AID594784 | Cytotoxic activity against human HeLa cells after 24 to 48 hrs by MTT assay | 2011 | Bioorganic & medicinal chemistry letters, May-15, Volume: 21, Issue:10 | Dibenzylideneacetone analogues as novel Plasmodium falciparum inhibitors. |
AID664956 | Cytotoxicity against human PANC1 cells after 72 hrs by MTT assay | 2012 | European journal of medicinal chemistry, Jul, Volume: 53 | Synthesis and evaluation of curcumin-related compounds for anticancer activity. |
AID664955 | Cytotoxicity against human PC3 cells after 72 hrs by MTT assay | 2012 | European journal of medicinal chemistry, Jul, Volume: 53 | Synthesis and evaluation of curcumin-related compounds for anticancer activity. |
AID458185 | Growth inhibition of human HCT116 cells after 48 hrs by MTS assay | 2010 | Bioorganic & medicinal chemistry, Feb, Volume: 18, Issue:3 | Structure-activity relationship of C5-curcuminoids and synthesis of their molecular probes thereof. |
AID593867 | Displacement of [125I]IMPY from amyloid beta (1 to 42) aggregate after 2 hrs by gamma counting | 2011 | Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7 | Synthesis and structure-affinity relationships of novel dibenzylideneacetone derivatives as probes for β-amyloid plaques. |
AID1415613 | Antifungal activity against fluconazole-resistant Candida krusei clinical isolate 2159 by broth microdilution method | 2017 | MedChemComm, May-01, Volume: 8, Issue:5 | Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant |
AID1415615 | Antifungal activity against fluconazole-resistant Candida tropicalis clinical isolate 087 by broth microdilution method | 2017 | MedChemComm, May-01, Volume: 8, Issue:5 | Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant |
AID1415614 | Antifungal activity against fluconazole-resistant Candida albicans clinical isolate 103 by broth microdilution method | 2017 | MedChemComm, May-01, Volume: 8, Issue:5 | Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant |
AID594786 | Antiplasmodial activity against blood stage of chloroquine-sensitive Plasmodium falciparum 3D7 infected in human O positive erythrocytes after 48 hrs by SYBR green-I based fluorescence assay | 2011 | Bioorganic & medicinal chemistry letters, May-15, Volume: 21, Issue:10 | Dibenzylideneacetone analogues as novel Plasmodium falciparum inhibitors. |
AID664957 | Cytotoxicity against human HT-29 cells after 72 hrs by MTT assay | 2012 | European journal of medicinal chemistry, Jul, Volume: 53 | Synthesis and evaluation of curcumin-related compounds for anticancer activity. |
AID594785 | Antiplasmodial activity against blood stage of chloroquine-resistant Plasmodium falciparum isolate RKL9 infected in human O positive erythrocytes after 48 hrs by SYBR green I-based fluorescence assay | 2011 | Bioorganic & medicinal chemistry letters, May-15, Volume: 21, Issue:10 | Dibenzylideneacetone analogues as novel Plasmodium falciparum inhibitors. |
AID588519 | A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities | 2011 | Antiviral research, Sep, Volume: 91, Issue:3 | High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. |
AID540299 | A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis | 2010 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21 | Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. |
AID1159607 | Screen for inhibitors of RMI FANCM (MM2) intereaction | 2016 | Journal of biomolecular screening, Jul, Volume: 21, Issue:6 | A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway. |
[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 | 0 (0.00) | 29.6817 |
2010's | 8 (100.00) | 24.3611 |
2020's | 0 (0.00) | 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 moderate demand-to-supply ratio for research on this compound.
| This Compound (24.36) 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 | 8 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |