13709-07-4

Upstream product

• 1194-98-5 2,5-Dihydroxybenzaldehyde 
• 107-30-2 chloromethyl methyl ether 
• 2150-46-1 Methyl 2,5-dihydroxybenzoate 
• 40931-12-2 (2,5-Bis-methoxymethoxy-phenyl)-methanol 

Downstream Products

• 40931-14-4 ethyl (E)-3-[2,5-bis(methoxymethoxy)phenyl]prop-2-enoate 
• 156424-40-7 (2,5-Bis-methoxymethoxy-phenyl)-(2-[1,3]dioxolan-2-yl-phenyl)-methanol 
• 131223-63-7 2-hydroxy-5-(methoxymethoxy)benzaldehyde 
• 908588-41-0 (R)-5-(2,5-dihydroxyphenyl)-3-(4-methylpent-3-en-1-yl)furan-2(5H)-one 
• 1580541-84-9 (R)-5-[2',5'-bis(methoxymethoxyphenyl)]-3-(4''-methylnona-3''-en-1''-yl)-2(5H)-furanone 

Relevant academic research and scientific papers

Design, synthesis, and evaluation of a water soluble C5-monoketone type curcumin analogue as a potent amyloid β aggregation inhibitor

A structure activity relationship study of curcumin analogues for the inhibition of amyloid β aggregation is described. Optimization of the o-phenol and olefin spacer resulted in the identification of the C5-monoketone type curcumin analogue AY1319, which

Hydroxylated chalcones with dual properties: Xanthine oxidase inhibitors and radical scavengers

In this study, we evaluated the abilities of a series of chalcones to inhibit the activity of the enzyme xanthine oxidase (XO) and to scavenge radicals. 20 mono- and polyhydroxylated chalcone derivatives were synthesized by Claisen-Schmidt condensation reactions and then tested for inhibitory potency against XO, a known generator of reactive oxygen species (ROS). In parallel, the ability of the synthesized chalcones to scavenge a stable radical was determined. Structure-activity relationship analysis in conjunction with molecular docking indicated that the most active XO inhibitors carried a minimum of three hydroxyl groups. Moreover, the most effective radical scavengers had two neighboring hydroxyl groups on at least one of the two phenyl rings. Since it has been proposed previously that XO inhibition and radical scavenging could be useful properties for reduction of ROS-levels in tissue, we determined the chalcones' effects to rescue neurons subjected to ROS-induced stress created by the addition of β-amyloid peptide. Best protection was provided by chalcones that combined good inhibitory potency with high radical scavenging ability in a single molecule, an observation that points to a potential therapeutic value of this compound class.

POLYMERIZABLE COMPOUND, POLYMERIZABLE COMPOSITION, POLYMER, OPTICALLY ANISOTROPIC BODY, AND METHOD FOR PRODUCING POLYMERIZABLE COMPOUND

A polymerizable compound has a practical low melting point, excellent solubility in a general-purpose solvent, and can produce an optical film at low cost, exhibits low reflected luminance, and achieves uniform conversion of polarized light over a wide wavelength band, an optically anisotropic article. A carbonyl compound is useful as a raw material for producing the polymerizable compound. (In the formula (I), Y1 to Y8 represent —C(═O)—O—, G1 and G2 represent a C1-20 divalent linear aliphatic group, Z1 and Z2 represent a C2-10 alkenyl group that is unsubstituted, or substituted with a halogen atom, Ax represents a C2-30 organic group with at least one aromatic ring, Ay represents a hydrogen atom or C1-20 alkyl group, A1 represents a trivalent aromatic group, A2 and A3 represent a C3-30 divalent alicyclic hydrocarbon group, A4 and A5 represent a C6-30 divalent aromatic group or the like, and Q1 represents a hydrogen atom.)

Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure-activity relationship

To explore the structure-activity relationships on the inhibitory activity of flavanonols against nitric oxide (NO) production in inflammatory cells, we synthesized 19 flavanonols which shared a common 3,5,7-trihydroxychroman scaffold. A range of substitutions was included in the B ring in order to investigate the structure-activity relationship. We also succeeded in isolating stereoisomers from 16 of the flavanonols using chiral column chromatography. The inhibitory effects of these compounds on NO production were examined in RAW 264.7 cells (a murine macrophage-like cell line), which were activated by lipopolysaccharide (LPS). We only observed inhibitory activity against NO production in (2R,3R) stereoisomers, while the inhibitory activities of (2S,3S) stereoisomers were significantly weaker. We also evaluated the free radical scavenging potential of the flavanonols using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Each stereoisomer indicated the equivalent DPPH scavenging potential as expected. The radical scavenging activity was not correlated with the inhibitory activity against NO. The inhibition of NO production by flavanonols is stereospecific and cannot simply be explained by their radical scavenging activity. We propose the possible existence of a 'target' molecule for flavanonols which is involved in the production and/or regulation of NO in RAW 264.7 cells.

Concise syntheses and biological activities of ganomycin I and fornicin A

The first enantioselective syntheses of ganomycin I, a meroterpenoid isolated from the Vietnamese mushroom Ganoderma colossum, and the related meroterpenoid fornicin A were accomplished. Our methodology for the total syntheses of these compounds featured the construction of the butenolide moiety by asymmetric dihydroxylation followed by Julia-Kocienski type olefin formation and ring-closing metathesis reactions. The absolute configurations of the two natural products were determined by comparisons of specific rotation. A cell-based assay of the synthetic compounds with transfected human embryonic kidney 293 tetoff (E-PR293) cells indicated that ganomycin I possesses cytotoxicity and fornicin A possesses weak anti-HIV-1 protease activity without cytotoxicity.

Concise Syntheses and Biological Activities of Ganomycin i and Fornicin A

The first enantioselective syntheses of ganomycin I, a meroterpenoid isolated from the Vietnamese mushroom Ganoderma colossum, and the related meroterpenoid fornicin A were accomplished. Our methodology for the total syntheses of these compounds featured the construction of the butenolide moiety by asymmetric dihydroxylation followed by Julia-Kocienski type olefin formation and ring-closing metathesis reactions. The absolute configurations of the two natural products were determined by comparisons of specific rotation. A cell-based assay of the synthetic compounds with transfected human embryonic kidney 293 tet-off (E-PR293) cells indicated that ganomycin I possesses cytotoxicity and fornicin A possesses weak anti-HIV-1 protease activity without cytotoxicity.

Synthesis of flavonoids and their effects on aldose reductase and sorbitol accumulation in streptozotocin-induced diabetic rat tissues

Aldose reductase, the key enzyme of the polyol pathway, and oxidative stress are known to play important roles in the complications of diabetes. A drug with potent inhibition of aldose reductase and oxidative stress, therefore, would be a most promising drug for the prevention of diabetic complications. The purpose of this study was to develop new compounds with these dual-effects through synthesis of chalcone derivatives and by examining the structure-activity relationships on the inhibition of rat lens aldose reductase as well as on antioxidant effects. A series of 35 flavonoid derivatives were synthesized by Winget's condensation, oxidation, and reduction of appropriate acetophenones with appropriate benzaldehydes. The inhibitory activity of these derivatives on rat lens aldose reductase and their antioxidant effects, measured using Cu2+ chelation and radical scavenging activities on 1,1-diphenyl-picrylhydrazyl in-vitro, were evaluated. Their effect on sorbitol accumulation in the red blood cells, lenses and sciatic nerves of streptozotocin-induced diabetic rats was also estimated. Among the new flavonoid derivatives synthesized, those with the 2′,4′-dihydroxyl groups in the A ring such as 2,4,2′,4′-tetrahydroxychalcone (22), 2,2′,4′-trihydroxychalcone (11), 2′,4′-dihydroxy-2,4-dimethylchalcone (21) and 3,4,2′,4′-tetrahydroxychalcone (18) were found to possess the highest rat lens aldose reductase inhibitory activity in-vitro, their IC50 values (concentration of inhibitors giving 50 % inhibition of enzyme activity) being 1.6 × 10-7, 3.8 × 10-7, 4.0 × 10-7 and 4.6 × 10-7 M, respectively. All of the chalcones tested except 3, 18, 23 with o-dihydroxy or hydroquinone moiety showed a weak free radical scavenging activity. In the in-vivo experiments, however, compound 18 with o-dihydroxy moiety in the B ring showed the strongest inhibitory activity in the accumulation of sorbitol in the tissues. It also showed the strongest activity in transition metal chelation and free radical scavenging activity. Of the 35 4,2′-dihydroxyl and 2′,4′-dihydroxyl derivatives of flavonoid synthesized, including chalcone, flavone, flavanone, flavonol and dihydrochalcone, some chalcone derivatives synthesized were found to possess aldose reductase inhibition and antioxidant activities in-vitro as well as inhibition in the accumulation of sorbitol in the tissues in-vivo. 3,4,2′,4′-Tetrahydroxychalcone (18, butein) was the most promising compound for the prevention or treatment of diabetic complications.