122-48-5Relevant articles and documents
A Hantzsch Amido Dihydropyridine as a Transfer Hydrogenation Reagent for α,β-Unsaturated Ketones
Van Arman, Scott A.,Zimmet, Austin J.,Murray, Ian E.
, p. 3528 - 3532 (2016)
An improved synthesis of the bis-methylamido Hantzsch dihydropyridine is described. The Hantzsch amide is demonstrated to be an effective transfer hydrogenation reagent using α,β-unsaturated ketones as the test case. Unreacted Hantzsch amide and the bis-methylamidopyridine byproduct are effectively removed by extraction in contrast to the commonly used Hantzsch diethyl ester. Several examples are given with the reaction being more effective for conjugated aromatic substrates than for aliphatics.
Synthesis of raspberry and ginger ketones by nickel boride-catalyzed hydrogenation of 4-arylbut-3-en-2-ones
Bandarenko, Mikhail,Kovalenko, Vitaly
, p. 885 - 888 (2014)
Raspberry and ginger ketones have been synthesized in good yield by the hydrogenation of the corresponding unsaturated precursors 4-(4′- hydroxyphenyl)but-3-en-2-one and 4-(4′-hydroxy-3′-methoxyphenyl)but- 3-en-2-one, respectively, using a freshly prepared suspension of nickel boride in methanol as catalyst.
Reduction of solid-supported olefins and alkynes
Dickson, David P.,Toh, Christine,Lunda, Menaka,Yermolina, Maria V.,Wardrop, Duncan J.,Landrie, Chad L.
, p. 9535 - 9538 (2009)
(Chemical Equation Presented) The reduction of carbon-carbonmultiple bonds in alkynes and olefins supported on a polystyrene resin has been investigated. Homogeneous catalysis by titanocene reagents is effective for the stereoselective preparation of cis-
GINGEROL DERIVATIVE HAVING INHIBITORY ACTIVITY AGAINST BIOFILM FORMATION AND PHARMACEUTICAL COMPOSITION COMPRISING SAME AS EFFECTIVE INGREDIENT FOR PREVENTING OR TREATING BIOFILM-CAUSED INFECTION SYMPTOM
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, (2020/09/22)
The present invention relates to a gingerol derivative having inhibitory activity against biofilm formation and a pharmaceutical composition for preventing or treating infections caused by biofilms including the gingerol derivative as an active ingredient. The gingerol derivative of the present invention exhibits significantly improved binding affinity for LasR and inhibitory activity against biofilm formation. Therefore, the gingerol derivative of the present invention can act on various membrane surfaces where biofilms tend to form and can effectively inhibit the formation of the corresponding biofilms. In addition, the use of the pharmaceutical composition according to the present invention can fundamentally prevent or treat a variety of infections caused by biofilms due to the presence of the gingerol derivative in the pharmaceutical composition.
Chemoselective and metal-free reduction of α,β-unsaturated ketones by: In situ produced benzeneselenol from O -(tert -butyl) Se-phenyl selenocarbonate
Ballarotto, Marco,Siciliano, Carlo,Temperini, Andrea
, p. 33706 - 33717 (2020/10/22)
The carbon-carbon double bond of arylidene acetones and chalcones can be selectively reduced with benzeneselenol generated in situ by reacting O-(tert-butyl) Se-phenyl selenocarbonate with hydrochloric acid in ethanol. This mild, metal-free and experimentally simple reduction procedure displays considerable functional-group compatibility, products are obtained in good to excellent yields, and the use of toxic Se/CO mixture and NaSeH, or the smelly and air-sensitive benzeneselenol, is avoided. This journal is
Discovery and Characterization of Pure RhlR Antagonists against Pseudomonas aeruginosa Infections
Nam, SangJin,Ham, So-Young,Kwon, Hongmok,Kim, Han-Shin,Moon, Suhyun,Lee, Jeong-Hoon,Lim, Taehyeong,Son, Sang-Hyun,Park, Hee-Deung,Byun, Youngjoo
, p. 8388 - 8407 (2020/09/21)
Pseudomonas aeruginosa (P. aeruginosa) is an opportunistic human pathogen that forms biofilms and produces virulence factors via quorum sensing (QS). Blocking the QS system in P. aeruginosa is an excellent strategy to reduce biofilm formation and the production of virulence factors. RhlR plays an essential role in the QS system of P. aeruginosa. We synthesized 55 analogues based on the chemical structure of 4-gingerol and evaluated their RhlR inhibitory activities using the cell-based reporter strain assay. Comprehensive structure-activity relationship studies identified the alkynyl ketone 30 as the most potent RhlR antagonist. This compound displayed selective RhlR antagonism over LasR and PqsR, strong inhibition of biofilm formation, and reduced production of virulence factors in P. aeruginosa. Furthermore, the survival rate of Tenebrio molitor larvae treated with 30 in vivo greatly improved. Therefore, compound 30, a pure RhlR antagonist, can be utilized for developing QS-modulating molecules in the control of P. aeruginosa infections.
Heterogeneous Catalytic Synthesis of Zingerone and Dehydrozingerone
Chistyakov, A. V.,Chistyakova, P. A.,Tsodikov, M. V.
, p. 1080 - 1086 (2020/10/02)
Abstract: Results of a single-stage heterogeneous catalytic synthesis of zingerone and dehydrozingerone have been described. The prospects of the proposed approach have been shown; the main kinetic laws governing the reaction have been revealed. Optimum conditions for zingerone and dehydrozingerone synthesis providing a yield of the target products of 45.8 and 76.2%, respectively, have been found.
Preparation method of (E)-1-(4-hydroxy-3-methoxyphenyl)-4-ene-3-decalone
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, (2018/07/15)
The invention discloses a preparation method of (E)-1-(4-hydroxy-3-methoxyphenyl)-4-ene-3-decalone and relates to the field of medicinal chemistry. The method comprises the steps as follows: 1) 4-(4-hydroxy-3-methoxyphenyl)-2-butanone is dissolved in a halogenated hydrocarbon solvent, pyrrolidine or piperidine is added at the room temperature, and the mixture reacts for 15-120 min; 2) a halogenated hydrocarbon solution of n-hexaldehyde is added, and the mixture reacts for 2-24 h; 3) an inorganic base solution is added, the mixture reacts for 1-24 h, aftertreatment is performed, and a compoundshown in formula (1) is prepared. Reactions at the room temperature are conducted with inorganic base and other weak bases, and the total yield is 78% or above. The method has mild reaction conditionsand is convenient to operate and suitable for industrial production.
Structure-Activity Relationships of 6- and 8-Gingerol Analogs as Anti-Biofilm Agents
Choi, Hyunsuk,Ham, So-Young,Cha, Eunji,Shin, Yujin,Kim, Han-Shin,Bang, Jeong Kyu,Son, Sang-Hyun,Park, Hee-Deung,Byun, Youngjoo
, p. 9821 - 9837 (2017/12/26)
Pseudomonas aeruginosa is a causative agent of chronic infections in immunocompromised patients. Disruption of quorum sensing circuits is an attractive strategy for treating diseases associated with P. aeruginosa infection. In this study, we designed and synthesized a series of gingerol analogs targeting LasR, a master regulator of quorum sensing networks in P. aeruginosa. Structure-activity relationship studies showed that a hydrogen-bonding interaction in the head section, stereochemistry and rotational rigidity in the middle section, and optimal alkyl chain length in the tail section are important factors for the enhancement of LasR-binding affinity and for the inhibition of biofilm formation. The most potent compound 41, an analog of (R)-8-gingerol with restricted rotation, showed stronger LasR-binding affinity and inhibition of biofilm formation than the known LasR antagonist (S)-6-gingerol. This new LasR antagonist can be used as an early lead compound for the development of anti-biofilm agents to treat P. aeruginosa infections.
Selective hydrogenation of conjugated unsaturated ketones containing a hydroxyaryl substituent in the β-position
Kovalenko,Pratsko
, p. 24 - 28 (2017/03/16)
A high selectivity was achieved in the Ni2B-catalyzed hydrogenation of α,β-unsaturated ketones containing a hydroxyaryl (phenolic) substituent in the β-position. The developed hydrogenation procedure was used to synthesize natural compounds of the phenylpropane series and their structural analogs.
