32268-30-7

Upstream product

• 870-63-3 prenyl bromide 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 115-18-4 2-methyl-3-buten-2-ol 
• 163041-67-6 2-hydroxy-3-(3-methylbut-2-en-1-yl)-4-[(tetrahydro-2H-pyran-2-yl)oxy]benzaldehyde 

Downstream Products

• 54287-99-9 5-hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde 
• 263902-83-6 3-benzoyl-8,8-dimethyl-8H-pyrano[2,3-f]chromen-2-one 
• 310403-17-9 8,8-dimethyl-3-(4-nitro-benzoyl)-8H-pyrano[2,3-f]chromen-2-one 
• 163041-67-6 2-hydroxy-3-(3-methylbut-2-en-1-yl)-4-[(tetrahydro-2H-pyran-2-yl)oxy]benzaldehyde 
• 144506-14-9 Licochalcone C 
• 163041-69-8 2-methoxy-3-(3-methylbut-2-en-1-yl)-4-[(tetrahydro-2H-pyran-2-yl)oxy]benzaldehyde 
• 144506-14-9 licochalcone 
• 523-59-1 seseline 

Relevant academic research and scientific papers

Synthetic methods for Gramniphenols F and G, Cicerfuran, Morunigrol C and its Derivative

The present invention relates to a method for preparing natural benzofurans including gramniphenol F, gramniphenol G, morunigrol C and 3andprime;,5andprime;-di-O-methyl analogues thereof and cicerfuran by using 2,4-dihydroxybenzaldehyde, 5-bromoresorcinol and sesamol. In the method according to the present invention, region-selective prenylation, Ramirez gem-dibromo olefination, Miyaura borylation and Suzuki coupling are used. In addition, the compounds were determined for anti-inflammatory effects through a test for production of nitrogen oxide in liposaccharide-induced RAW-264.7 macrophages. All of the compounds show weak to medium (16-42%) inhibitory activities, are not toxic and have an IC_50 value of 9.1 to 25.2 andmu;M.COPYRIGHT KIPO 2017

Synthetic method for licochalcone C

According to the present invention, licochalcone C is produced by performing C-prenylation using A_2O_3, position selective deprotection and methylation, and general Claisen-Schmidt condensation under a base condition. A [3,3]-sigma bond position transferring reaction promoted by water cannot be applied to licochalcone C synthesis due to a decomposition problem. According to the present invention, it has been confirmed that position selective C-prenylation using Al_2O_3 is a novel method for synthesizing licochalcone C.COPYRIGHT KIPO 2015

Facile synthesis of licochalcone C

Licochalcone C was synthesized from commercially available 2,4-dihydroxybenzaldehde by using regioselective Al2O 3-mediated C-prenylation followed by conventional Claisen-Schmidt condensation in basic condition.

Concise synthesis of licochalcone C and its regioisomer, licochalcone H

Licochalone C (7a) is a retrochalcone isolated from Glycyrrhiza inflata, which shows potent antioxidant properties and inhibition of bacterial growth and cellular respiration. Biological studies have suggested that licochalcone C attenuates the lipopolysaccharide and interferon-gamma induced inflammatory response by decreasing the expression and activity of inducible nitric oxide synthase and modulating the antioxidant network activity of superoxide dismutase, catalase, and glutathione peroxidase activity. Licochalcone C also inhibits NADH-cytochrome C reductase in the membrane fraction of Micrococcus luteus. Since pharmacological activity studies of licochalcone C are ongoing and the yield of the compound is poor from natural product, we report a concise four step synthesis of licochalcone C (7a) and its regioisomer, tentatively called licochalcone H (7b), by employing acid-mediated Claisen-Schmidt condensation as a key step with 6 and 20 % overall yield, respectively.

THERAPEUTIC AGENT

A therapeutic agent and prophylactic agent for a disease accompanying an abnormality in an amount of insulin or insulin response, an agent for an insulin-mimetic action, a food, beverage and feed, an agent for enhancing glucose uptake into a cell, and an agent for inducing differentiation into an adipocyte, characterized in that each comprises as an effective ingredient at least one compound selected from the group consisting of a chalcone compound, an acetophenone compound, a coumarin compound, a phthalide compound, derivatives thereof, and pharmacologically acceptable salts thereof.

Biologically active 1,3-bis-aromatic-prop-2-en-1-ones, 1,3-bis-aromatic-propan-1-ones, and 1,3-bis-aromatic-prop-2-yn-1-ones

The invention relates to the use of 1,3-bis-aromatic-prop-2-en-1-ones (chalcones), 1,3-bis-aromatic-propan-1-ones (dihydrochalcones), and 1,3-bis-aromatic-prop-2-yn-1-ones for the preparation of pharmaceutical compositions for the treatment or prophylaxis of a number of serious diseases including i) conditions relating to harmful effects of inflammatory cytokines, ii) conditions involving infection by Helicobacter species, iii) conditions involving infection by viruses, iv) neoplastic disorders, and v) conditions caused by microorganisms or parasites. The invention also relates to novel chalcones and dihydrochalcones (especially alkoxy substituted variants) having advantageous substitution patterns with respect to their effect as drug substances, and to methods of preparing them, as well as to pharmaceutical compositions comprising the novel chalcones. Moreover, the present invention relates to a method for the isolation of Leishmania fumarate reductase, QSAR methodologies for selecting potent compounds for the above-mentioned purposes.

Natural product-like combinatorial libraries based on privileged structures. 1. General principles and solid-phase synthesis of benzopyrans

Herein we report a novel strategy for the design and construction of natural and natural product-like libraries based on the principle of privileged structures, a term originally introduced to describe structural motifs capable of interacting with a variety of unrelated molecular targets. The identification of such privileged structures in natural products is discussed, and subsequently the 2,2-dimethylbenzopyran moiety is selected as an inaugural template for the construction of natural product-like libraries via this strategy. Initially, a novel solid-phase synthesis of the benzopyran motif is developed employing a unique cycloloading strategy that relies on the use of a new, polystyrene-based selenenyl bromide resin. Once the loading, elaboration, and cleavage of these benzopyrans was established, this new solid-phase method was then thoroughly validated through the construction of six focused combinatorial libraries designed around natural and designed molecules of recent biological interest.

CONSTITUENT OF THE CHINESE CRUDE DRUG "SANG-BAI-PI" (MORUS ROOT BARKS) III. STRUCTURE OF A NEW FLAVANONE DERIVATIVE, SANGGENON F.

From the benzene extract of the Chinese crude drug "Sang-Bai-Pi" (Japanese name "Sohakuhi"), the root barks of Morus sp. (Moraceae), an isoprene substituted flavanone derivative, named sanggenon F, was isolated, for which stucture (I) was proposed on the basis of its spectral and chemical evidence.