917813-62-8

Usage

Chemical class

Ketone
A ketone is a type of organic compound with a carbonyl group (C=O) bonded to two carbon atoms.

Structure

Conjugated dienone
The compound has two carbon-carbon double bonds (C=C) separated by a single bond (C-C), creating a conjugated system.

Phenyl groups

Two
The compound contains two phenyl groups, which are aromatic rings consisting of six carbon atoms and six hydrogen atoms.

Methoxymethoxy substituents

Multiple
The phenyl groups have methoxymethoxy substituents, which are functional groups containing an oxygen atom bonded to two methoxy groups.

Stereochemistry

(1E,4E)
The compound has a specific stereochemistry, with the double bonds at the 1st and 4th positions being in the E (entgegen) configuration.

Potential applications

Industrial and research
The compound may have potential uses in various industrial and research applications, but further study is needed to fully understand its properties and potential uses.

Derivative

1,4-pentadien-3-one
The compound is a derivative of 1,4-pentadien-3-one, which is a conjugated dienone compound.

Complexity

Complex organic compound
The compound has a long and specific name, indicating its complex structure and the presence of multiple functional groups.

Upstream product

• 76280-61-0 3,5-di-[(methoxymethyl)oxy]benzaldehyde 
• 67-64-1 acetone 

Relevant academic research and scientific papers

BIS(ARYLMETHYLIDENE)ACETONE COMPOUND, ANTI-CANCER AGENT, CARCINOGENESIS-PREVENTIVE AGENT, INHIBITOR OF EXPRESSION OF Ki-Ras, ErbB2, c-Myc AND CYCLINE D1, BETA-CATENIN-DEGRADING AGENT, AND p53 EXPRESSION ENHANCER

It has been demanded to improve the poor solubility of curcumin to develop an anti-tumor compound capable of inhibiting the growth of various cancer cells at a low concentration. Thus, disclosed is a novel synthetic compound, a bis(arylmethylidene)acetone, which has both of an excellent anti-tumor activity and a chemo-preventive activity. A bis(arylmethylidene)acetone (i.e., a derivative having a curcumin skeleton) which is an anti-tumor compound and has a chemo-preventive activity is synthesized and screened. A derivative having enhanced anti-tumor activity and chemo-preventive activity can be synthesized.

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.