458533-66-9

Usage

Uses

Used in Organic Synthesis:
(1E,4E)-1,5-bis(3-methoxyphenyl)penta-1,4-dien-3-one is utilized as a key intermediate in organic synthesis for the development of various chemical compounds. Its unique structure allows for versatile reactions and the creation of a wide range of products.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (1E,4E)-1,5-bis(3-methoxyphenyl)penta-1,4-dien-3-one is employed as a starting material for the synthesis of new drugs. Its potential biological activities and medicinal properties make it a promising candidate for the development of therapeutic agents.
Used in Material Science:
Due to its structural features, (1E,4E)-1,5-bis(3-methoxyphenyl)penta-1,4-dien-3-one may also find applications in material science. Its conjugated system and chemical properties could contribute to the development of new materials with specific properties for various applications.
Further research on (1E,4E)-1,5-bis(3-methoxyphenyl)penta-1,4-dien-3-one's properties, reactivity, and applications is ongoing, which may lead to the discovery of additional uses across different industries.

Upstream product

• 591-31-1 3-methoxy-benzaldehyde 
• 67-64-1 acetone 

Downstream Products

• 223137-71-1 1,5-bis-(2-bromo-5-methoxyphenyl)-3-pentanone 
• 223137-87-9 2,2′,3,3′-tetrahydro-1,1′-spirobi[indene]-7,7′-diol 
• 223137-87-9 (R)-2,2',3,3'-tetrahydro-1,1'-spirobi[indene]-7,7'-diol 
• 223137-87-9 (R)-2,2',3,3'-tetrahydro-1,1'-spirobi[indene]-7,7'-diol 
• 223137-67-5 1,5-bis(3-methoxyphenyl)-3-pentanone 

Relevant academic research and scientific papers

Synthesis and Cytotoxicity of Diarylpentanoids against Sensitive CCRF-CEM and Multidrug-Resistant CEM/ADR5000 Leukemia Cells

This article described the synthesis and biological investigation of a series of symmetric diarylpentanoids, characterized by a dienone moiety and by a different pattern of substitution on the two phenyl rings. The series of compounds 1a–p were tested aga

Supramolecular polymeric aggregation behavior and its impact on catalytic properties of imidazolium based hydrophilic ionic liquids

Ionic Liquids (ILs) self-assemble to form supramolecular polymeric clusters/aggregates. The aggregation behavior of ILs influences its activity in the organic synthesis. However, the precise role of ILs in organic reactions is still unknown. It is, therefore, important to comprehend the supramolecular polymeric aggregation behavior of ILs. We are exploring the supramolecular polymeric aggregation behavior of ILs using Electrospray Ionization Mass Spectrometry (ESI-MS). We have synthesized four hydrophilic ILs (1–4) and investigated their aggregation behavior and its impact on catalytic activity in Carbon-Carbon bond formation (Knoevenagel and Claisen-Schmidt condensation). Here, we show that the aggregation behavior of ILs depends on the type and nature of cation and anion. ESI-MS (?ve) spectra reveals two different type of aggregation i.e. [CnAn+1]? & [A2 + H+]?. We have found that catalytic activity increases with increased [CnAn+1]? supramolecular aggregation. Consequently, highest yield of products obtained in ILs which show decreased anion-anion aggregation [A2 + H+]? abundance in ESI-MS. We anticipate our results to be a starting point for the establishment of desired ILs for organic synthesis.

Mechanistically Inspired Route toward Hexahydro-2H-chromenes via Consecutive [4 + 2] Cycloadditions

Utilizing two robust C-C bond-forming reactions, the Baylis-Hillman reaction and the Diels-Alder reaction, we report a highly enantio-, regio-, and diastereoselective synthesis of hexahydro-2H-chromenes via two sequential [4 + 2] cycloadditions. These tandem and formal cycloadditions have also been performed as a "one-pot" sequence to access the corresponding heterocycles constituting up to five contiguous stereocenters in excellent yields and stereoselectivity.

Structure-activity relationship of C5-curcuminoids and synthesis of their molecular probes thereof

A series of novel analogues of 1,5-bis(4-hydroxy-3-methoxyphenyl)-penta-(1E,4E)-1,4-dien-3-one (C5-curcumin), which is a natural analogue of curcumin isolated from the rhizomes of Curcuma domestica Val. (Zingiberacea), were synthesized and evaluated for their cytotoxicities against human colon cancer cell line HCT-116 to conclude the SAR of C5-curcuminoids for further development of their use in cancer chemotherapy: (1) Bis(arylmethylidene)acetone serves as a promising skeleton for eliciting cytotoxicity. (2) The 3-oxo-1,4-pentadiene structure is essential for eliciting cytotoxicity. (3) As for the extent of the aromatic substituents, hexasubstituted compounds exhibit strong activities, in which 3,4,5-hexasubstitution results in the highest potency. (5) The symmetry between two aryl rings is not an essential requirement for bis(arylmethylidene)acetones to elicit cytotoxicity. (6) para-Positions allows the installation of additional functional groups for use as molecular probes. By taking advantage of the SAR diagram, we have elaborated several advanced derivatives having GI50 of single-digit micromolar potencies that will function as molecular probes to target and/or report key biomolecules interacting with curcumin and C5-curcumin.

Method and compounds for cancer treatment utilizing NFkB as a direct or ultimate target for small molecule inhibitors

A method is described for cancer treatment through NFκB inhibition. NFκB is a direct or ultimate target for small molecule inhibitors. These small molecule inhibitors are aimed at suppression of NFκB directly or by indirect suppression of IKK, SFK kinases, or other upstream kinases. The present invention includes small molecule inhibitors comprising three, five, and seven carbon unsaturated spacers having one or two carbonyls, flanked by substituted aryl rings. The small molecule inhibitors can be symmetrical or unsymmetrical.

Anti-oxidant activities of curcumin and related enones

The natural product curcumin (diferuloylmethane, 1,7-bis(4-hydroxy-3- methoxyphenyl)-1,6-heptadiene-3,5-dione), obtained from the spice turmeric, exhibits numerous biological activities including anti-cancer, anti-inflammatory, and anti-angiogenesis activities. Some of these biological activities may derive from its anti-oxidant properties. There are conflicting reports concerning the structural/electronic basis of the anti-oxidant activity of curcumin. Curcumin is a symmetrical diphenolic dienone. A series of enone analogues of curcumin were synthesized that included: (1) curcumin analogues that retained the 7-carbon spacer between the aryl rings; (2) curcumin analogues with a 5-carbon spacer; and (3) curcumin analogues with a 3-carbon spacer (chalcones). These series included members that retained or were devoid of phenolic groups. Anti-oxidant activities were determined by the TRAP assay and the FRAP assay. Most of the analogues with anti-oxidant activity retained the phenolic ring substituents similar to curcumin. However, a number of analogues devoid of phenolic substituents were also active; these non-phenolic analogues are capable of forming stable tertiary carbon-centered radicals.

Curcumin analogs with anti-tumor and anti-angiogenic properties

The present invention is directed to curcumin analogs exhibiting anti-tumor and anti-angiogenic properties, pharmaceutical formulations including such compounds and methods of using such compounds.

1,1'-Spirobiindane-7,7'-diol: A novel, C2-symmetric chiral ligand

A novel, C2-symmetric chiral diol (16) was prepared in six steps from m-anisaldehyde and resolved via its bis-L-menthoxycarboxylate.