Bulletin of the Chemical Society of Japan最新文献_第6页

Synthesis and Biological Evaluation of Siladenoserinol A Analogs Possessing a Diastereomeric 6,8-Dioxabicyclo[3.2.1]octane Skeleton 具有6,8-二恶二环[3.2.1]辛烷非对映体骨架的硅腺苷丝氨酸醇A类似物的合成及生物学评价

3区化学

Bulletin of the Chemical Society of Japan Pub Date : 2023-10-06 DOI: 10.1246/bcsj.20230197

Masahito Yoshida, Kohei Sasaoka, Kohei Hano, Yoshiyuki Sugiyama, Yuki Hitora, Takayuki Doi, Sachiko Tsukamoto, Hideo Kigoshi

{"title":"Synthesis and Biological Evaluation of Siladenoserinol A Analogs Possessing a Diastereomeric 6,8-Dioxabicyclo[3.2.1]octane Skeleton","authors":"Masahito Yoshida, Kohei Sasaoka, Kohei Hano, Yoshiyuki Sugiyama, Yuki Hitora, Takayuki Doi, Sachiko Tsukamoto, Hideo Kigoshi","doi":"10.1246/bcsj.20230197","DOIUrl":"https://doi.org/10.1246/bcsj.20230197","url":null,"abstract":"The efficient synthesis of siladenoserinol analogs possessing a diastereomeric 6,8-dioxabicyclo[3.2.1]octane (6,8-DOBCO) skeleton has been achieved from commercially available carbohydrates as a chiral source. In this synthesis, we successfully determined the reaction conditions for the one-pot transformation using (PPh3)AuCl/AgSbF6/2,6-di-tert-butylpyridine (2,6-DTBP), leading to the desired bicycloketal without losing the TBS group. Elongation of two side chains by the Julia–Kocienski olefination and Horner–Wadsworth–Emmons reaction and subsequent chemoselective sulfamation furnished the two desired diastereomers from the corresponding carbohydrates, respectively. The inhibitory activities of the synthetic diastereomeric analogs against the p53–Hdm2 interaction were slightly weaker than that of natural siladenoserinol A, resulting in the fact that the stereochemistry on the 6,8-DOBCO skeleton would be one of the fundamental factors to control the potency of inhibition of the p53–Hdm2 interaction but not an essential one. We successfully achieved the synthesis of siladenoserinol A analogs through one-pot bicycloketal formation using a catalytic amount of (PPh3)AuCl/AgSbF6 and AlCl3. Biological evaluation of the natural product and synthetic analogs revealed that the stereochemistry on the 6,8-DOBCO skeleton would be one of the fundamental factors to control the potency of inhibition of the p53–Hdm2 interaction but not an essential one.","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":"45 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135303643","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Small Molecule Activation Based on Novel Heavier Group 13/15 Interelement Compounds, λ³,λ³-Phosphanylalumanes 基于新型重基团13/15元素间化合物λ3，λ3-磷酰烯醛的小分子活化

3区化学

Bulletin of the Chemical Society of Japan Pub Date : 2023-10-06 DOI: 10.1246/bcsj.20230186

Tatsuya Yanagisawa, Yoshiyuki Mizuhata, Norihiro Tokitoh

{"title":"Small Molecule Activation Based on Novel Heavier Group 13/15 Interelement Compounds, λ3,λ3-Phosphanylalumanes","authors":"Tatsuya Yanagisawa, Yoshiyuki Mizuhata, Norihiro Tokitoh","doi":"10.1246/bcsj.20230186","DOIUrl":"https://doi.org/10.1246/bcsj.20230186","url":null,"abstract":"As a new entry of heteroatom-heteroatom bond species, λ3,λ3-phosphanylalumanes, having an unperturbed P–Al single-bond species are expected to show high reactivity due to the separation of Lewis acid/base moieties, which can be extended to develop novel small molecule activation reactions using single-bond and saturated-compounds. We have designed novel λ3,λ3-phosphanylalumanes, which have all-carbon protecting groups on the λ3-P and λ3-Al moieties, respectively. This account highlights the synthesis and availability of phosphanylalumane derivatives. We demonstrate the addition reactions of phosphanylalumanes toward alkynes to give unique unsaturated C2-vicinal P/Al-based frustrated Lewis pairs and the resulting alkyne-adducts are found to undergo transformation into unique ring-compounds. Furthermore, reversible addition reactions of a λ3,λ3-phosphanylalumane toward alkenes will also be described together with the results obtained with other small molecules. As a new entry of interelement bond species, novel λ3,λ3-phosphanylalumanes are designed. Addition reactions of phosphanylalumanes toward alkynes are found to give unique unsaturated C2-vicinal P/Al-based FLPs and the resulting alkyne-adducts undergo transformation into unique ring-compounds. Furthermore, reversible addition reactions of a λ3,λ3-phosphanylalumane toward alkenes are also investigated.","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":"36 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135303641","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Surface-mediated dynamic cooperative motions in azobenzene polymer films 偶氮苯聚合物薄膜中表面介导的动态协同运动

3区化学

Bulletin of the Chemical Society of Japan Pub Date : 2023-09-29 DOI: 10.1246/bcsj.20230219

Takahiro Seki

{"title":"Surface-mediated dynamic cooperative motions in azobenzene polymer films","authors":"Takahiro Seki","doi":"10.1246/bcsj.20230219","DOIUrl":"https://doi.org/10.1246/bcsj.20230219","url":null,"abstract":"Azobenzene (1,2-diphenyldiazene in IUPAC name) is a widely studied simple rodlike photochromic molecule. The trans- (E) to cis- (Z) photoisomerization of this molecule was discovered long time (nearly 90 years) ago. Nevertheless, the allure and utilities of this molecule never get faded and does not surrender a leading position among many other organic photochromic molecules. New applications for photoswitching molecular and macromolecular systems are still being proposed extensively. When the azobenzene molecule is linked with liquid crystals (LCs) and polymer systems, a number of fascinating motility functions have been newly realized. This article overviews our research activities using azobenzene-containing monolayers and LC polymer films. The topics range surface photoalignment of LCs both from solid surface and free surface, photoalignment of hierarchical structures such as mesohybrids and block copolymers, photomechanical motions and morphological switching in block copolymer monolayers, high-density brushes of azobenzene side chain LC polymers (SCLCPs), photo-triggered mass migrations in azobenzene SCLCP films and polymer motions via Marangoni flow etc. Demonstrations of these dynamic photofunctions are expected to provide great opportunities toward practical smart applications. This account overviews our research activities using azobenzene-containing polymer monolayers and liquid crystalline (LC) materials undertaken over 35 years. The topics cover the surface photoalignment of LC materials both from solid surface and free surface, photoalignment of hierarchical structures, photomechanical motions and morphological switching in monolayers, phototriggered mass migrations etc. Dynamic photoresponsive systems are expected to provide wide opportunities toward practical smart applications.","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":"52 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135132674","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Stability and Metastability of Li₃YCl₆ and Li₃HoCl₆ Li3YCl6和Li3HoCl6的稳定性和亚稳态

3区化学

Bulletin of the Chemical Society of Japan Pub Date : 2023-09-27 DOI: 10.1246/bcsj.20230132

Hiroaki Ito, Yuki Nakahira, Naoki Ishimatsu, Yosuke Goto, Aichi Yamashita, Yoshikazu Mizuguchi, Chikako Moriyoshi, Takashi Toyao, Ken-ichi Shimizu, Hiroshi Oike, Masanori Enoki, Nataly Carolina Rosero-Navarro, Akira Miura, Kiyoharu Tadanaga

{"title":"Stability and Metastability of Li3YCl6 and Li3HoCl6","authors":"Hiroaki Ito, Yuki Nakahira, Naoki Ishimatsu, Yosuke Goto, Aichi Yamashita, Yoshikazu Mizuguchi, Chikako Moriyoshi, Takashi Toyao, Ken-ichi Shimizu, Hiroshi Oike, Masanori Enoki, Nataly Carolina Rosero-Navarro, Akira Miura, Kiyoharu Tadanaga","doi":"10.1246/bcsj.20230132","DOIUrl":"https://doi.org/10.1246/bcsj.20230132","url":null,"abstract":"Metastable solid electrolytes exhibit superior conductivity compared to stable ones, making them a subject of considerable interest. However, their synthesis of the metastable phase is affected by multiple thermodynamic and kinetic parameters, leading to ambiguity in the organization of stability and metastability. In this study, we organized remnant and intermediate metastability based on temperature. The intermediate metastable phase, which is less stable than the temperature-independent stable phase, typically transforms into the stable phase(s) at high temperatures. In contrast, the remnant metastable phase is formed by first obtaining most stable phase at specific temperatures and then “trapping” it by rapidly changing the temperature. By investigating Li+ conducting chlorides, Li3MCl6 (M = Y and Ho), we demonstrated that heating starting materials to approximately 600 K produced low-temperature Li3MCl6 phase with one formula unit while further heating resulted in high-temperature Li3MCl6 phase with three formula units. Annealing of quenched Li3MCl6 at 573 K resulted in a phase transition from the high-temperature to low-temperature phase, indicating that the high-temperature phase was remnant metastable at low temperatures. This study organizes remnant and intermediate metastability. The intermediate metastable phase, which is less stable than the thermodynamically independent stable phase, typically transforms into the stable phase(s) at high temperatures. In contrast, the remnant metastable phase once becomes the most stable phase under specific thermodynamic conditions, like such as ice in a freezer, and is then trapped by upon changing the conditions rapidly.","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":"9 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135477193","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Bacteriophage-Conjugated Fluorescent Nanoemulsion as a Novel Optical Probe for Highly Selective Bacterial Detection 噬菌体共轭荧光纳米乳作为一种高选择性细菌检测的新型光学探针

3区化学

Bulletin of the Chemical Society of Japan Pub Date : 2023-09-23 DOI: 10.1246/bcsj.20230200

Shin-ya Sekida, Takatoshi Chisaka, Jumpei Uchiyama, Iyo Takemura-Uchiyama, Shigenobu Matsuzaki, Yosuke Niko, Shingo Hadano, Shigeru Watanabe

{"title":"Bacteriophage-Conjugated Fluorescent Nanoemulsion as a Novel Optical Probe for Highly Selective Bacterial Detection","authors":"Shin-ya Sekida, Takatoshi Chisaka, Jumpei Uchiyama, Iyo Takemura-Uchiyama, Shigenobu Matsuzaki, Yosuke Niko, Shingo Hadano, Shigeru Watanabe","doi":"10.1246/bcsj.20230200","DOIUrl":"https://doi.org/10.1246/bcsj.20230200","url":null,"abstract":"Infectious diseases mortality decreased due to effective drugs and healthcare. However, global health remains threatened by infectious diseases. New methods to rapid and accurate bacterial detection have attracted considerable attention. Fluorescence detection of whole bacterial cells offers high sensitivity, quantitative analysis, and simple operation. A highly fluorescent bioconjugated probe improves sensitivity and selectivity. This study presents a novel, bright fluorescent probe comprising a bacteriophage and a fluorescent nanoemulsion (fNE) as biorecognition and signal transduction elements, respectively. We demonstrate that fluorescence microscopy imaging using the S. aureus-specific phage, S13’-fNE (phage-fNE), detects S. aureus in the presence of E. coli or S. pseudintermedius, another closely related Staphylococci, in a highly selective manner. Furthermore, fNEs with high dye loadings exhibit considerably greater brightness compared to the fluorescent dye alone, making them suitable for sensitive fluorescence imaging. Phage-fNEs can quantitatively detect S. aureus at 104–108 colony-forming units per milliliter (CFU mL−1), with a limit of detection of 8 × 104 CFU mL−1. This result is comparable to the lowest value achieved by microscopic bacterial detection, with no preconcentration or enzymatic signal enhancement methods used. Bioconjugated fNEs open new avenues for highly selective and sensitive fluorescent detection of bacteria. This study presents a novel, bright fluorescent probe comprising a bacteriophage and a fluorescent nanoemulsion (fNE) as biorecognition and signal transduction elements, respectively. We demonstrate that fluorescence microscopy imaging using the S. aureus-specific phage, S13’-fNE (phage-fNE), detects S. aureus in the presence of E. coli or S. pseudintermedius, another closely related Staphylococci, in a highly selective manner.","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":"17 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135959849","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Structural effect on the dielectric constant of hydrocarbon liquids: A molecular dynamics study using the Drude polarizable force field 结构对烃类液体介电常数的影响:基于德鲁德极化力场的分子动力学研究

3区化学

Bulletin of the Chemical Society of Japan Pub Date : 2023-09-23 DOI: 10.1246/bcsj.20230100

Kohei Sasaki, Takefumi Yamashita

引用次数: 0

Ferroelectric Photovoltaic Effect in the Ordered Smectic Phases of Chiral π-Conjugated Liquid Crystals: Improved Current-Voltage Characteristics by Efficient Fixation of Polar Structure 手性π共轭液晶有序近晶相中的铁电光伏效应:极性结构的有效固定改善了电流-电压特性

3区化学

Bulletin of the Chemical Society of Japan Pub Date : 2023-09-22 DOI: 10.1246/bcsj.20230185

Atsushi Seki, Masahiro Funahashi, Ken’ichi Aoki

引用次数: 0

Controlled Chemical Construction in Nature: Unified Biogenesis Accounting for Synthesis of Fungal Dimeric Anhydrides 自然界中的受控化学结构:真菌二聚酸酐合成的统一生物成因计算

3区化学

Bulletin of the Chemical Society of Japan Pub Date : 2023-09-16 DOI: 10.1246/bcsj.20230187

Atsushi Minami

引用次数: 0

Carbon-neutral energy cycle via highly selective electrochemical reactions using biomass derivable organic liquid energy carriers 利用生物质衍生有机液体能量载体，通过高选择性电化学反应实现碳中性能量循环

3区化学

Bulletin of the Chemical Society of Japan Pub Date : 2023-09-16 DOI: 10.1246/bcsj.20230172

Takashi Fukushima, Manabu Higashi, Miho Yamauchi

引用次数: 0

Understanding Molecular Transfer Between Aqueous Phase and Reverse Micelles and its Application to Bioassays in Microfluidics 了解水相和反胶束之间的分子转移及其在微流体生物检测中的应用

3区化学

Bulletin of the Chemical Society of Japan Pub Date : 2023-09-16 DOI: 10.1246/bcsj.20230179

Mao Fukuyama

引用次数: 0