Journal of Synthetic Organic Chemistry Japan最新文献_第2页

The Search for Inhibitors of the Ubiquitin-proteasome System from Natural Sources by Cell-based Screening in Reporter-expressing Cells 在报告蛋白表达细胞中筛选天然来源的泛素-蛋白酶体系统抑制剂

4区化学

Journal of Synthetic Organic Chemistry Japan Pub Date : 2023-11-01 DOI: 10.5059/yukigoseikyokaishi.81.1073

Yuki Hitora, Sachiko Tsukamoto

{"title":"The Search for Inhibitors of the Ubiquitin-proteasome System from Natural Sources by Cell-based Screening in Reporter-expressing Cells","authors":"Yuki Hitora, Sachiko Tsukamoto","doi":"10.5059/yukigoseikyokaishi.81.1073","DOIUrl":"https://doi.org/10.5059/yukigoseikyokaishi.81.1073","url":null,"abstract":"The ubiquitin-proteasome system (UPS) regulates cellular protein degradation to maintain protein homeostasis (proteostasis). The UPS mainly consists of three steps, ubiquitination, deubiquitination, and protein degradation. In the ubiquitination process, a series of enzymes, the ubiquitin-activating enzyme (E1), ubiquitin-conjugating enzyme (E2), and ubiquitin ligase (E3), catalyze the formation of a polyubiquitin chain on target proteins. Prior to the degradation of the polyubiquitinated proteins by the proteasome, deubiquitination enzymes remove this polyubiquitin chain and cleave it into monoubiquitin molecules. The UPS plays a key role in controlling proteostasis and multiple signaling pathways. Dysfunction of the UPS has been implicated in the development of various diseases, including cancer, neurodegenerative diseases, and autoimmune diseases. Therefore, UPS inhibitors that disrupt protein degradation are promising as drug leads. In our study, we searched for natural products (NPs) that inhibit UPS-dependent proteolysis using dual-reporter HeLa cells expressing UbG76V-green fluorescent protein (GFP) and the oxygen-dependent degradation domain of HIF1α fused to luciferase (ODD-Luc). Here we report our research on NPs that inhibit the UPS using these cell-based reporter assays.","PeriodicalId":17123,"journal":{"name":"Journal of Synthetic Organic Chemistry Japan","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135565177","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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Have fun! 玩得开心!

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Journal of Synthetic Organic Chemistry Japan Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.991

Ryo Takita

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Total Synthesis of Resin Glycoside Merremoside D Using Key Glycosylation Methodologies 用关键糖基化方法合成树脂糖苷Merremoside D

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Journal of Synthetic Organic Chemistry Japan Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.988

Naruki Konishi

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Dual Functionalization of Organic Compounds via Oxidation of Halogen 卤素氧化作用下有机化合物的双官能化

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Journal of Synthetic Organic Chemistry Japan Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.951

Katsuhiko Moriyama

{"title":"Dual Functionalization of Organic Compounds via Oxidation of Halogen","authors":"Katsuhiko Moriyama","doi":"10.5059/yukigoseikyokaishi.81.951","DOIUrl":"https://doi.org/10.5059/yukigoseikyokaishi.81.951","url":null,"abstract":"Dual functionalization in organic synthesis is an elegant and powerful method for simultaneously introducing two different functional groups regio-selectively into a target molecule. We herein describe our recent work on retained dual functionalization and dehydrogenative dual functionalization via oxidation of halogen. For the dehydrogenative dual functionalization by oxidation of bromide ion, a catalytic dual functionalization of ethers through dealkylation-oxidation-bromination accompanied by C-O bond cleavage via aerobic oxidation of bromide was developed to obtain α-bromo ketones. Furthermore, a nitrite-catalyzed ring-contraction reaction of substituted tetrahydropyrans by oxidation of bromide under aerobic conditions was discovered to provide 2-acyltetrahydrofurans. We also succeeded a regio-selective Csp2-Csp2 bromo-amination of indole derivatives via the 1,3-migration of imides on indolyl(phenyl)iodonium imides and a remote Csp2-Csp3 iodo-amination of 2-methyl indole derivatives with iodinating reagents to furnish the corresponding halo-amino-indole derivatives via formation of indolyl(phenyl)iodonium imides from indole derivatives, bis(sulfonyl)imides, and (diacetoxy)iodobenzene as the retained dual functionalization using hypervalent iodine (III).","PeriodicalId":17123,"journal":{"name":"Journal of Synthetic Organic Chemistry Japan","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134934687","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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超強酸共役塩基二重官能基化反応エレクトロクロミズムアトロプ異性体超强酸共轭碱基双官能团化反应电致染色质异构体

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Journal of Synthetic Organic Chemistry Japan Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.994

健男坂井, 克彦森山, 尚張本, 侑祐石垣, 理北川

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Synthesis and Functional Control of Near-infrared Electrochromic Molecules Based on Redox-active Para-quinodimethane Scaffolds 基于氧化还原活性对醌二甲烷支架的近红外电致变色分子的合成及功能控制

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Journal of Synthetic Organic Chemistry Japan Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.963

Takashi Harimoto, Yusuke Ishigaki

{"title":"Synthesis and Functional Control of Near-infrared Electrochromic Molecules Based on Redox-active Para-quinodimethane Scaffolds","authors":"Takashi Harimoto, Yusuke Ishigaki","doi":"10.5059/yukigoseikyokaishi.81.963","DOIUrl":"https://doi.org/10.5059/yukigoseikyokaishi.81.963","url":null,"abstract":"In recent years, near-infrared (NIR) dyes, exhibiting absorption in the NIR region (750-2500 nm), has been applied to various optical applications such as security marking, photovoltaic cells and chemotherapy of deep tissues in vivo. Electrochromic systems capable of switching NIR absorption are attractive from the viewpoint of applications for material and life science, and thus several examples have been reported to date. The development of organic-based materials is needed to reduce the environmental impact and improve biocompatibility. However, since the redox states of organic NIR dyes are generally unstable, the switching of NIR absorption based on quantitative redox interconversion is still a challenging issue regarding reversibility and durability during their interconversion. To construct organic electrochromic systems capable of ON/OFF switching of NIR-absorbing properties, we have focused on the non-aromatic π-conjugated para-quinodimethane (p-QD) skeleton. Herein, we have shown several studies on the synthesis and functional control of NIR electrochromic molecules based on redox-active p-QD scaffolds. We have elucidated the spectroscopic and electrochemical properties of various arylated quinodimethane derivatives and demonstrated that p-QD building blocks can be versatile components for the development of NIR switchable organic electrochromic systems.","PeriodicalId":17123,"journal":{"name":"Journal of Synthetic Organic Chemistry Japan","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134936028","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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炭素-窒素不斉軸を有するアトロプ異性キナゾリノンの化学具有碳氮不对称轴的阿托普异构喹唑酮化学

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Journal of Synthetic Organic Chemistry Japan Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.978

Azusa Sato, Yuuki Fujimoto, Osamu Kitagawa

{"title":"炭素-窒素不斉軸を有するアトロプ異性キナゾリノンの化学","authors":"Azusa Sato, Yuuki Fujimoto, Osamu Kitagawa","doi":"10.5059/yukigoseikyokaishi.81.978","DOIUrl":"https://doi.org/10.5059/yukigoseikyokaishi.81.978","url":null,"abstract":"Recently, atropisomers owing to the rotational restriction around an N-C single bond (N-C axially chiral compounds) have received much attention in the field of synthetic organic chemistry. In particular, the catalytic enantioselective synthesis of various N-C axially chiral compounds and their application to asymmetric reactions have been reported by many groups. Bioactive compounds possessing an N-C axially chiral structure have also been known. The typical example of such bioactive N-C axially chiral compounds is quinazolin-4-one derivatives bearing an ortho-substituted phenyl group at 3-position. However, the catalytic asymmetric synthesis of N-C axially chiral quinazlolin-4-one derivatives has never been reported. We succeeded in the enantioselective synthesis of 3-(2-bromophenyl)quinazolin-4-one derivatives (GABA agonist, mebroqualone derivatives) through chiral Pd-catalyzed reductive asymmetric desymmetrization with 3-(2,6-dibromophenyl)quinazolin-4-ones. Furthermore, it was found that the reaction of various alkyl halides with the enolate prepared from quinazolinone products proceeds in a highly diastereoselective manner by the asymmetric induction due to the N-C axial chirality. The self-disproportionation of enantiomers (SDE) and crystal structure (chirality-dependent halogen bond) in mebroqualone derivatives, the preparation of N-C axially chiral quinazolinones bearing an ortho-fluorophenyl group, and the creation of isotopic atropisomers based on N-C axially chiral quinazolinone scaffold are also described.","PeriodicalId":17123,"journal":{"name":"Journal of Synthetic Organic Chemistry Japan","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134934686","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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硫黄官能基をα位に有するケトンのパン酵母不斉還元硫官能团在α位的酮的面包酵母不齐还原

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Journal of Synthetic Organic Chemistry Japan Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.995

Toshiyuki Itoh

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Studies on Tetracyanocyclopentadienides in Synthetic Organic Chemistry 合成有机化学中四氰环戊二烯类化合物的研究

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Journal of Synthetic Organic Chemistry Japan Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.941

Takeo Sakai

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電気陽性な典型元素の励起状態を利用する光反応の開発利用电阳性典型元素激发态的光反应的开发

4区化学

Journal of Synthetic Organic Chemistry Japan Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.930

Yuki Nagashima, Masanobu Uchiyama, Ken Tanaka

{"title":"電気陽性な典型元素の励起状態を利用する光反応の開発","authors":"Yuki Nagashima, Masanobu Uchiyama, Ken Tanaka","doi":"10.5059/yukigoseikyokaishi.81.930","DOIUrl":"https://doi.org/10.5059/yukigoseikyokaishi.81.930","url":null,"abstract":"Photoinduced reactions have received much attention as a powerful tool to access kinetically or thermodynamically prohibited reactions on the ground state. However, these reactions have been developed mainly by using electro-negative elements such as C, O, N, halogens as well as transition-metals. On the other hand, we have revealed the nature of chemical species including electro-positive main-group elements, such as boron (B), silicon (Si), and tin (Sn), on the excited state, developing the highly reactive and selective photoinduced reactions. For diboron (B-B) reagents, we designed the anionic photo-absorbing borate complex to enable a quadruple borylation reaction of terminal alkynes under ultraviolet irradiation. For stannyl (Sn) species, we revealed that the illumination of stannyl anions generates the excited triplet stannyl diradicals, which showed the orthogonality to traditional reagents (cations, anions, and radicals) to enable hydrostannylation of alkynes and defluorostannylation of fluoroarenes. For silylborane (Si-B) reagents, we developed dearomative triple elementalization (carbo-silaboration) reactions of quinolines by the excitation of silyl-borate complexes without the need for any catalyst.","PeriodicalId":17123,"journal":{"name":"Journal of Synthetic Organic Chemistry Japan","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134934688","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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