108102-77-8Relevant articles and documents
Synthesis of Novel Dibenzylbutyrolactones as Dimethylmatairesinol Analogues
Heidary Alizadeh, Babak,Foroumadi, Alireza,Kobarfard, Farzad,Saeedi, Mina,Shafiee, Abbas
, p. 1693 - 1698 (2015)
In this work, (R)-4-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one was prepared though an efficient and novel method starting from (S)-5-((benzyloxy)methyl)dihydrofuran-2(3H)-one. Then, it was utilized as a versatile starting material for the synthesis of novel dimethylmatairesinol analogues; dibenzylbutyrolactone derivatives, via the reaction of the later compound and various aromatic aldehydes.
Synthesis and pharmacological characterisation of arctigenin analogues as antagonists of AMPA and kainate receptors
Butts, Craig P.,Collingridge, Graham L.,Jane, David E.,Mallah, Shahida,Molnár, Elek,Re?nik, Lisa-Maria,Thatcher, Robert J.,Willis, Christine L.
, p. 9154 - 9162 (2021/11/16)
(-)-Arctigenin and a series of new analogues have been synthesised and then tested for their potential as AMPA and kainate receptor antagonists of human homomeric GluA1 and GluK2 receptors expressed in HEK293 cells using a Ca2+ influx assay. In general, these compounds showed antagonist activity at both receptors with greater activity evident at AMPARs. Schild analysis indicates that a spirocyclic analogue 6c acts as a non-competitive antagonist. Molecular docking studies in which 6c was docked into the X-ray crystal structure of the GluA2 tetramer suggest that (-)-arctigenin and its analogues bind in the transmembrane domain in a similar manner to the known AMPA receptor non-competitive antagonists GYKI53655 and the antiepileptic drug perampanel. The arctigenin derivatives described herein may serve as novel leads for the development of drugs for the treatment of epilepsy. This journal is
Discovery of stereospecific cytotoxicity of (8R,8′R)-trans-arctigenin against insect cells and structure-activity relationship on aromatic ring
Nishi, Kosuke,Nishimoto, Asuka,Nishiwaki, Hisashi,Sugahara, Takuya,Yamauchi, Satoshi
supporting information, (2020/04/29)
One of the arctigenin stereoisomers, (8R,8′R)-trans-form 1, showed stereospecific cytotoxicity against insect cells, Sf9 and NIAS-AeAl-2 cells. By the comparison with other stereoisomers, the most importance of the 8′R stereochemistry for the higher activities was clarified. On the other hand, the wider range of activity level among stereoisomers against cancer cells, HL-60, was not observed. The structure-activity relationship research using derivatives bearing (8R,8′R)-trans-form was performed to show the same level of activities of 3-iodo, 4-iodo, and 3,4-methylenedioxy derivatives 28, 29, and 36 as (8R,8′R)-trans-arctigenin 1. In the examination of thiono derivatives, 4-iodo thiono and 3,4-methylenedioxy thiono derivatives 66, 67 showed similar level of activities to that of (8R,8′R)-trans-arctigenin 1. The expression of ribosomal 28S rRNA gene of Sf9 cells was increased by (8R,8′R)-trans-arctigenin 1, whereas a degradation of DNA was not observed.
Method of making synthetic high efficiency having a specific lactone Β - phenylmethyl (by machine translation)
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, (2018/03/24)
The present invention discloses a method for efficiently synthesizing beta-benzyl butyrolactone having a specific configuration. The method is characterized in that phenylpropionic acid or a derivative thereof is adopted as a starting material, the phenylpropionic acid or the derivative thereof and an oxazolidone chiral prosthetic group are subjected to condensation, a haloacetic acid ester attacks the carbonyl ortho position carbon of the phenylpropionic acid under the effect of a large steric hindrance organic alkali, the prosthetic group is hydrolyzed and recovered after the specific chiral center is successfully constructed, and the corresponding product is subjected to an intramolecular ester exchange reaction to generate the beta-benzyl butyrolactone having the specific configuration. According to the present invention, the prepared beta-benzyl butyrolactone can be used for chemical synthesis of a lot of dibenzyl type lignins having potential medicinal values, and has characteristics of cheap and readily available raw materials, short step, high yield, and high optical purity.
Self-sufficient Baeyer-Villiger monooxygenases: Effective coenzyme regeneration for biooxygenation by fusion engineering
Torres Pazmino, Daniel E.,Snajdrova, Radka,Baas, Bert-Jan,Ghobrial, Michael,Mihovilovic, Marko D.,Fraaije, Marco W.
supporting information; scheme or table, p. 2275 - 2278 (2009/02/08)
(Chemical Presented) Two-in-one biocatalysts were engineered by the covalent fusion of NADPH-dependent Baeyer-Villiger monooxygenases to a phosphite dehydrogenase for coenzyme regeneration (see scheme). Not only the purified fusion proteins, but also whole cells and crude cell extracts containing the enzyme conjugates, could be used to catalyze biotransformations with high efficiency. NADP+=nicotinamide adenine dinucleotide phosphate.
Novel chemo-enzymatic process for the preparation of opticaly enriched beta-benzyl-gamma-butyrolactones
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Page 4, (2010/02/05)
The present invention relates to a novel process for the preparation of optically enriched substituted R(+)β-benzyl-γ-butyrolactones of the general formula 1, 1wherein, R1 and R2 independently represent the following groups, R1=R2=H, OH, —OCnH2n+1 (n=1 to 8), NH2, and/or CF3, R1 and R2 together represents —O(CH2)mO— where m=2 to 4.
Highly diastereoselective alkylation of vicinal dianions of chiral succinic acid derivatives: A new general strategy to (R)-β-arylmethyl-γ- butyrolactones
Pohmakotr, Manat,Soorukram, Darunee,Tuchinda, Patoomratana,Prabpai, Samran,Kongsaeree, Palangpon,Reutrakul, Vichai
, p. 4315 - 4318 (2007/10/03)
The vicinal dianions derived from chiral succinic acid derivatives, 1,4-bis[(4R,5S)-3,4-dimethyl-2-oxo-5-phenylimidazolidin-1-yl]butane-1,4-dione and 1,4-bis[(4S,5R)-3,4-dimethyl-2-oxo-5-phenylimidazolidin-1-yl]butane-1,4- dione react with arylmethyl bromides with high diastereo- and regio-selectivity to provide the corresponding chiral α-arylmethylated succinic acid derivatives; the (R)-products are converted into (R)-β-arylmethyl-γ- butyrolactones and (R)-α-arylmethyl-γ-butyrolactones.
Catalytic enantioselective conjugate reduction of lactones and lactams
Hughes, Gregory,Kimura, Masanari,Buchwald, Stephen L.
, p. 11253 - 11258 (2007/10/03)
A dramatic acceleration of the enantioselective copper-catalyzed conjugate reduction of α,β-unsaturated lactones, lactams, and esters is reported upon addition of alcohol additives. Good to excellent yields and enantioselectivities were realized using a catalyst generated in situ from CuCl2·H2O, t-BuONa, p-tol-BINAP, and PMHS, and this methodology was applied to the synthesis of (-)-Paroxetine.
Enantioselective synthesis of benzylbutyrolactones from 5-hydroxyfuran-2(5H)-one. New chiral synthons for dibenzylbutyrolactone lignans by a chemoenzymatic route
Brinksma, Jelle,Van Der Deen, Hanneke,Van Oeveren, Arjan,Feringa, Ben L.
, p. 4159 - 4163 (2007/10/03)
A chemoenzymatic method is described for the asymmetric synthesis of benzylbutyrolactones. (R)-5-Acetoxyfuran-2(5H)-one (12) was obtained with ee > 99% in a multigram scale catalytic esterification using immobilized lipase PS. The addition of lithiated dithianes to chiral synthon 12 was followed by an effective multistep reduction to produce enantiomerically pure benzylbutyrolactones.
Synthesis and anti-HIV activity of dibenzylbutyrolactone lignans
Yang, Li-Ming,Lin, Shwu-Jiuan,Yang, Tsang-Hsiung,Lee, Kuo-Hsiung
, p. 941 - 944 (2007/10/03)
Five optically active dibenzylbutyrolactone lignans were synthesized through a lipase-catalyzed transesterification route and evaluated for their inhibitory activity against HIV-1 replication in acutely infected H9 cells. Compounds 1 and 2 demonstrated anti-HIV replication activity with an EC50 values of 2.2 and 0.16 μg/ml and a therapeutic index values of 9.1 and 5, respectively. Structure-antiviral activity relationships are discussed.
