68081-13-0

Upstream product

• 38552-39-5 1,5-bis(3,4-dimethoxyphenyl)-1,4-pentadien-3-one 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 68081-12-9 1,5-bis(3,4-dimethoxyphenyl)-3-pentanone 

Downstream Products

• 68080-86-4 1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalene 
• 68081-07-2 4-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-2H-naphthalen-1-one 

Relevant academic research and scientific papers

Antimicrobial Activity of Monoketone Curcuminoids Against Cariogenic Bacteria

We evaluated the antimicrobial activity of 25 monoketone curcuminoids (MKCs) against a representative panel of cariogenic bacteria in terms of their minimum inhibitory concentration (MIC) values. Curcumin A (10) displayed promising activity against Streptococcus mutans (MIC?=?50?μg/ml) and Streptococcus mitis (MIC?=?50?μg/ml) as well as moderate activity against S.?sanguinis (MIC?=?100?μg/ml), Lactobacillus casei (MIC?=?100?μg/ml), and Streptococcus salivarius (MIC?=?200?μg/ml). Results indicated higher activity of compound 10 than that of its bis-β-diketone analog. Additionally, compounds 3a (1,5-bis(4-methylphenyl)pentan-3-one) and 7b (1,5-bis(4-bromophenyl)pentan-3-ol) were moderately active against S.?mitis (MIC?=?100?μg/ml) and S.?salivarus (MIC?=?200?μg/ml).

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.