15485-65-1Relevant academic research and scientific papers
Microwave-promoted synthesis of polyhydroxydeoxybenzoins in ionic liquids
Hakala, Ullastiina,W?h?l?, Kristiina
, p. 8375 - 8378 (2006)
A microwave-promoted synthesis of polyhydroxydeoxybenzoins and -phenylpropanones has been developed, using bis{(trifluoromethyl)sulfonyl}amine (HNTf2) or BF3·OEt2 in an ionic liquid solvent.
Microwave-Mediated Synthesis of Anticarcinogenic Isoflavones from Soybeans
Chang, Yu-Chen,Nair, Muraleedharan G.,Santell, Ross C.,Helferich, William G.
, p. 1869 - 1871 (1994)
Soybean isoflavonoids, 7,4'-dihydroxyisoflavone (daidzein), 7-hydroxy-4'-methoxyisoflavone (formononetin), 5,7,4'-trihydroxyisoflavone (genistein), and 5,7-dihydroxy-4'-methoxyisoflavone (biochanin A), were synthesized in high yields by cyclization of their corresponding ketones in a conventional microwave oven. Keywords: Microwave synthesis; isoflavones; daidzein; genistein; formononetin; biochanin A
Identification of enterodiol as a masker for caffeine bitterness by using a pharmacophore model based on structural analogues of homoeriodictyol
Ley, Jakob P.,Dessoy, Marco,Paetz, Susanne,Blings, Maria,Hoffmann-Lücke, Petra,Reichelt, Katharina V.,Krammer, Gerhard E.,Pienkny, Silke,Brandt, Wolfgang,Wessjohann, Ludger
, p. 6303 - 6311 (2012)
Starting from previous structure-activity relationship studies of taste modifiers based on homoeriodictyol, dihydrochalcones, deoxybenzoins, and trans-3-hydroxyflavones as obvious analogues were investigated for their masking effect against caffeine. The most active compounds of the newly investigated taste modifiers were phloretin, the related dihydrochalcones 3-methoxy-2′,4,4′-trihydroxydihydrochalcone and 2′,4- dihydroxy-3-methoxydihydrochalcone, and the deoxybenzoin 2-(4-hydroxy-3- methoxyphenyl)-1-(4-hydroxyphenyl)ethanone. Starting with the whole set of compounds showing activity >22%, a (Q)SAR pharmacophore model for maskers of caffeine bitterness was calculated to explain the structural requirements. After docking of the pharmacophore into a structural model of the broadly tuned bitter receptor hTAS2R10 and docking of enterolactone and enterodiol as only very weakly related structures, it was possible to predict qualitatively their modulating activity. Enterodiol (25 mg L-1) reduced the bitterness of the 500 mg L-1 caffeine solution by about 30%, whereas enterolactone showed no masking but a slight bitter-enhancing effect.
A Direct Synthesis of 2-(ω-Carboxyalkyl)isoflavones from ortho-Hydroxylated Deoxybenzoins
Mrug, Galyna P.,Demydchuk, Bohdan A.,Bondarenko, Svitlana P.,Sviripa, Vitaliy M.,Wyrebek, Przemyslaw,Mohler, James L.,Fiandalo, Michael V.,Liu, Chunming,Frasinyuk, Mykhaylo S.,Watt, David S.
supporting information, p. 5460 - 5463 (2018/10/20)
As part of a program focused on the development of new antineoplastic agents based on scaffolds found in natural products, we explored the isoflavone family as potential enzyme inhibitors. We required biotin-modified isoflavones to identify potential biological targets, and we selected the C-2 position in isoflavones as an attachment site for an alkyl group bearing a terminal carboxylic acid to which we could attach a biotin derivative. The base-catalyzed condensation of 2,4-dihydroxy-substituted deoxybenzoins with cyclic anhydrides mediated by a combination of triethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene led to an efficient synthesis of the desired 2-(ω-carboxyalkyl)isoflavones with functional groups at C-5, 6 and 7 and with various substituents in the C-3 phenyl group.
Multifunctional deoxybenzoin-based monomers and resins having reduced flammability
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Page/Page column 10, (2016/08/10)
The invention provides a novel platform for minimal- or non-flammable polymers, which is based purely on hydrocarbon systems and does not need additives of any kind A key feature is that the hydrocarbons disclosed herein are characterized by degradation mechanisms that produce few flammable volatiles. For example, 2,4,4′,6-tetrahydroxydeoxybenzoin is employed as a multifunctional cross-linker in conjunction with bis-epoxydeoxybenzoin, affording new resins that combine excellent physical and mechanical properties with low flammability.
Technical Process for Preparation of Genistein
Filip, Katarzyna,Kleczkowska-Plichta, Ewa,Ara?ny, Zbigniew,Grynkiewicz, Grzegorz,Polowczyk, Magdalena,Gabarski, Krzysztof,Trzcińska, Kinga
, p. 1354 - 1362 (2016/07/23)
Development and scale-up of the synthetic process for genistein preparation are described. The process was designed with consideration for environmental and economical aspects and optimized in a laboratory scale. In a scale up, on every step quantity of the environmentally unfriendly substrates or solvents was reduced without compromising the quality of the final product, and the waste load was significantly diminished. The optimal duration times of the individual stages were determined, and the number of operations was reduced, leading to lowering of energy consumption. Elaborated process secures good yield and quality expected for pharmaceutical substances.
Multifunctional deoxybenzoin-based epoxies: Synthesis, mechanical properties, and thermal evaluation
Szyndler, Megan W.,Timmons, Justin C.,Yang, Zhan H.,Lesser, Alan J.,Emrick, Todd
, p. 4441 - 4446 (2014/10/15)
We describe 2,4,4′,6-tetrahydroxydeoxybenzoin (THDB) as a multifunctional cross-linker in conjunction with bis-epoxydeoxybenzoin (BEDB), affording new resins that combine excellent physical and mechanical properties with low flammability. The char residue and heat release capacity values of the cross-linked epoxies were measured by thermogravimetric analysis (TGA) and pyrolysis combustion flow calorimetry (PCFC), respectively. Resins fabricated from THDB exhibited low total heat release (13 kJ/g) and high char yields (34%), as well as good mechanical properties, making them suitable candidates for consideration in high performance adhesive applications. The desirable heat release and char yield properties of these structures are realized without the presence of any conventional flame retardant, such as halogenated structures or inorganic fillers that are commonly utilized in commercial materials.
Arylalkyl ketones, benzophenones, desoxybenzoins and chalcones inhibit TNF-α induced expression of ICAM-1: Structure-activity analysis
Kumar, Sarvesh,Reddy L, Chandra Shekhar,Kumar, Yogesh,Kumar, Amit,Singh, Brajendra K.,Kumar, Vineet,Malhotra, Shashwat,Pandey, Mukesh K.,Jain, Rajni,Thimmulappa, Rajesh,Sharma, Sunil K.,Prasad, Ashok K.,Biswal, Shyam,Van Der Eycken, Erik,Depass, Anthony L.,Malhotra, Sanjay V.,Ghosh, Balaram,Parmar, Virinder S.
experimental part, p. 368 - 377 (2012/07/31)
The interaction between leukocytes and the vascular endothelial cells (EC) via cellular adhesion molecules plays an important role in the pathogenesis of various inflammatory and autoimmune diseases. Small molecules that block these interactions have been targeted as potential therapeutic agents against acute and chronic inflammatory diseases. In an effort to identify potent intercellular cell adhesion molecule-1 (ICAM-1) inhibitors, a large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones and their analogs (54 in total) have been synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated the possible mechanism for their ICAM-1 inhibitory activities. The most active compound was found to be 79. A large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones as well as their analogs (54 in total) were synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated a possible mechanism of their ICAM-1 inhibitory activities. The most active compound was found to be 79. Copyright
Synthesis of Talosin A and B, two bioactive isoflavonoid glycosides
Wu, Zhongtao,Lian, Gaoyana,Yu, Biao,Wang, Zhenzhongc,Zhao, Yiwuc,Xiao, Wei
scheme or table, p. 1725 - 1730 (2011/07/07)
Talosin A and B, namely genistein 7-O-α-L-6-deoxy-talopyranoside and genistein 4',7-di-O-α-L-6-deoxytalopyranoside, which show excellent antifungal and anti-inflammatory activities, were synthesized concisely.
Synthesis and structure-activity relationship study of deoxybenzoins on relaxing effects of porcine coronary artery
Lu, Tzy-Ming,Kuo, Daih-Huang,Ko, Horng-Huey,Ng, Lean-Teik
experimental part, p. 10027 - 10032 (2011/05/17)
Deoxybenzoins are potent antioxidants and tyrosinase inhibitors with potential to be developed as food preservatives and cosmetic ingredients. To explore the potential in cardiovascular protection, 25 polyphenolic deoxybenzoins were synthesized and evaluated for inhibitory effects on KCl-induced porcine coronary arterial contraction. The results revealed deoxybenzoins are significant inhibitors of KCl-induced arterial contraction. Among those synthesized, two-thirds of the deoxybenzoins exhibited moderate to good efficacy on relaxing contracted artery including 2,4-dihydroxydeoxybenzoin with EC50 = 3.30 μM (Emax = 100%, n = 7) and 2,4-dihydroxy-4′-methoxydeoxybenzoin EC50 = 3.70 μM (E max = 100%, n = 5). Deoxybenzoins displayed an endothelium-dependent relaxing manner on the contracted artery; the contractile responses of neither endothelium denuded nor L-NAME deactivated rings were inhibited. The structure-activity relationships of deoxybenzoin on arterial relaxing effects concluded that the 2,4-dihydroxylated deoxybenzoins presented a potential vascular relaxing pharmacophore, with favoring substitution on ring B in the order of H ≤ p-OMe > p-OH > o-OMe > m,p-diOMe ≤ m-OMe.
