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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 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-11-01 DOI: 10.5059/yukigoseikyokaishi.81.1073
Yuki Hitora, Sachiko Tsukamoto
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.
泛素-蛋白酶体系统(UPS)调节细胞蛋白质降解以维持蛋白质稳态。UPS主要包括三个步骤:泛素化、去泛素化和蛋白质降解。在泛素化过程中,泛素活化酶(E1)、泛素偶联酶(E2)、泛素连接酶(E3)等一系列酶在靶蛋白上催化形成多泛素链。在蛋白酶体降解多泛素化蛋白之前,去泛素化酶去除多泛素链并将其切割成单泛素分子。UPS在控制蛋白平衡和多种信号通路中起关键作用。UPS功能障碍与多种疾病的发展有关,包括癌症、神经退行性疾病和自身免疫性疾病。因此,破坏蛋白质降解的UPS抑制剂有望成为药物先导。在我们的研究中,我们使用表达ubg76v绿色荧光蛋白(GFP)和HIF1α氧依赖性降解结构域融合荧光素酶(ODD-Luc)的双报告细胞HeLa细胞寻找抑制ups依赖性蛋白水解的天然产物(NPs)。在这里,我们报告了使用这些基于细胞的报告基因测定法对抑制UPS的NPs的研究。
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引用次数: 0
Have fun! 玩得开心!
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.991
Ryo Takita
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引用次数: 0
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
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.988
Naruki Konishi
Resin glycosides are known as glycolipids isolated from plants of the Convolvulaceae families, which have been used as major constituents of traditional folk medicines. However, their isolation, structure determination, and biological activities have been hampered due to poor production because of their complicated structural diversity. In this short review, total synthesis of resin glycoside merremoside D by two research groups is described.
树脂苷是一种从旋花科植物中分离出来的糖脂类物质,已被用作传统民间药物的主要成分。然而,由于其复杂的结构多样性,导致其分离、结构鉴定和生物活性的研究受阻。本文综述了两个研究小组对树脂糖苷merremoside D的全合成。
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引用次数: 0
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
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.951
Katsuhiko Moriyama
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).
有机合成中的双官能团化是一种简便而有效的方法,可以同时在目标分子中选择性地引入两个不同的官能团。本文介绍了我们最近通过卤素氧化对保留双官能化和脱氢双官能化的研究。针对溴离子氧化脱氢双官能化反应,提出了脱烷基-氧化-溴化催化双官能化反应,同时溴离子有氧氧化裂解C-O键,得到α-溴酮。此外,还发现在好氧条件下,亚硝酸盐催化溴化氧化取代四氢吡喃的缩环反应可生成2-酰基四氢呋喃。我们还通过亚胺在吲哚基(苯基)碘亚胺上的1,3迁移,成功地实现了吲哚衍生物的区域选择性Csp2-Csp2溴胺化,并利用碘化试剂对2-甲基吲哚衍生物进行了Csp2-Csp3碘胺化,通过吲哚衍生物、双(磺酰基)亚胺和(二乙酰氧基)碘苯形成吲哚基(苯基)碘亚胺,获得了相应的卤氨基吲哚衍生物(III)。
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引用次数: 0
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
4区 化学 Q4 CHEMISTRY, ORGANIC 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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引用次数: 0
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
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.963
Takashi Harimoto, Yusuke Ishigaki
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.
近年来,近红外(NIR)染料在近红外区域(750- 2500nm)表现出吸收特性,已被广泛应用于安全标记、光伏电池和体内深部组织化疗等光学领域。从材料和生命科学的应用角度来看,能够切换近红外吸收的电致变色系统是有吸引力的,因此迄今为止已经报道了几个例子。为了减少对环境的影响,提高生物相容性,需要发展有机基材料。然而,由于有机近红外染料的氧化还原状态通常是不稳定的,基于定量氧化还原相互转化的近红外吸收开关仍然是一个具有挑战性的问题,涉及到它们在相互转化过程中的可逆性和持久性。为了构建具有nir吸收特性的ON/OFF开关的有机电致变色体系,我们重点研究了非芳香族π共轭对醌二甲酯(p-QD)骨架。在此,我们对基于氧化还原活性p-QD支架的近红外电致变色分子的合成和功能控制进行了研究。我们已经阐明了各种芳基化喹诺二甲烷衍生物的光谱和电化学性质,并证明了p-QD构建块可以作为开发近红外可切换有机电致变色系统的通用组件。
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引用次数: 0
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
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.978
Azusa Sato, Yuuki Fujimoto, Osamu Kitagawa
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.
近年来,由于围绕一个N-C单键的旋转限制而形成的对映异构体(N-C轴向手性化合物)在合成有机化学领域受到了广泛的关注。特别是各种N-C轴向手性化合物的催化对映选择性合成及其在不对称反应中的应用已被许多研究小组报道。具有N-C轴向手性结构的生物活性化合物也已被发现。这种具有生物活性的N-C轴向手性化合物的典型例子是在3位上含有邻取代苯基的喹唑啉-4- 1衍生物。然而,催化不对称合成N-C轴手性喹唑啉-4- 1衍生物尚未见报道。我们通过手性pd催化3-(2,6-二溴苯基)喹唑啉-4-酮的还原不对称脱对称,成功地对映选择性合成了3-(2-溴苯基)喹唑啉-4-酮衍生物(GABA激动剂,甲溴喹酮衍生物)。此外,由于N-C轴向手性的不对称诱导,各种烷基卤化物与喹唑啉酮产物制备的烯醇酯的反应具有高度的非对映选择性。本文还介绍了甲溴喹酮衍生物中对映体(SDE)和晶体结构(手性依赖卤素键)的自歧化,含邻氟苯基的N-C轴向手性喹唑啉酮的制备,以及基于N-C轴向手性喹唑啉酮支架的同位素异位异构体的制备。
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引用次数: 0
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
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.995
Toshiyuki Itoh
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引用次数: 0
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
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.941
Takeo Sakai
Tetra- and pentacyanocyclopentadienides (TCCP and PCCP) are superacid conjugate bases stabilized by the mesomeric and inductive effects of cyano groups and the aromaticity of the cyclopentadienide ring. We have developed an efficient synthetic method for various TCCP and PCCP using tetracyanothiophene and sulfones, followed by substituent transformations. We conducted a series of application studies using our synthetic method for tetra- and pentacyanocyclopentadienides. NanoGoblin, the doll-shaped ion pair of TCCP, catalyzed methanolysis of the cyclic acetal in the anthropomorphic molecule NanoKid. The cyano groups of TCCP acted as hindrances to rotation of CAr-O bonds in 3,3′-BINOL esters. TCCP exhibited high lipophilicity, which was utilized in anionic phase transfer reactions and the ion-pair extraction of quaternary ammonium cations. Lastly, the weakly basic nature of PCCP was helpful in the Au/Ag-catalyzed cyclization-3-aza-Cope-Mannich cascade, enabling us to achieve the total synthesis of cephalotaxine.
四、五氰环戊二烯化合物(TCCP和PCCP)是由氰基的中间体效应和诱导效应以及环戊二烯环的芳香性稳定的超羧酸共轭碱。我们开发了一种利用四氰噻吩和砜进行取代基转化的高效合成各种TCCP和PCCP的方法。我们利用我们的合成方法对四、五氰环戊二烯进行了一系列的应用研究。NanoGoblin是TCCP的玩偶状离子对,它催化了拟人分子NanoKid中环缩醛的甲醇分解。TCCP的氰基对3,3 ' -BINOL酯中CAr-O键的旋转起阻碍作用。TCCP具有较高的亲脂性,可用于阴离子相转移反应和季铵离子的离子对萃取。最后,PCCP的弱碱性有助于Au/ ag催化环化-3-aza- cope - mannich级联,使我们能够实现头孢他啶的全合成。
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引用次数: 0
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 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-10-01 DOI: 10.5059/yukigoseikyokaishi.81.930
Yuki Nagashima, Masanobu Uchiyama, Ken Tanaka
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.
光诱导反应作为一种研究基态上动力学或热力学上被禁止的反应的有力工具,受到了广泛的关注。然而,这些反应主要是通过使用电负性元素如C、O、N、卤素以及过渡金属来发展的。另一方面,揭示了硼(B)、硅(Si)、锡(Sn)等电正主族元素在激发态上的性质,形成了高活性和选择性的光诱导反应。对于二硼(B-B)试剂,我们设计了阴离子光吸收硼酸盐配合物,使末端炔在紫外线照射下发生四重硼化反应。对于锡基(Sn),我们发现在锡基阴离子的照射下会产生激发的三态锡基二自由基,这与传统试剂(阳离子、阴离子和自由基)具有正交性,可以实现炔的氢锡化和氟芳烃的去氟锡化。对于硅硼烷(Si-B)试剂,我们在不需要任何催化剂的情况下,通过激发硅硼酸盐配合物,开发了喹啉类化合物的脱芳三元素化(碳硅硼化)反应。
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引用次数: 0
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Journal of Synthetic Organic Chemistry Japan
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