Chemical & pharmaceutical bulletin最新文献

筛选
英文 中文
Structure-Signal Relationships of the δ-Opioid-Receptor (DOR)-Selective Agonist KNT-127-Part II: Quinoline Ring Modifications for Enhanced G-Protein Signaling and Reduced β-Arrestin Recruitment. δ-阿片受体(DOR)选择性激动剂knt -127的结构-信号关系——第二部分:喹啉环修饰增强g蛋白信号传导和减少β-阻滞蛋白募集。
IF 1.5 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c24-00796
Keita Kajino, Tomoya Sugai, Tomoya Kakumoto, Ryoji Kise, Riko Suzuki, Akihisa Tokuda, Yuki Sekiya, Risako Katamoto, Noriki Kutsumura, Yasuyuki Nagumo, Takatsugu Hirokawa, Asuka Inoue, Tsuyoshi Saitoh
{"title":"Structure-Signal Relationships of the δ-Opioid-Receptor (DOR)-Selective Agonist KNT-127-Part II: Quinoline Ring Modifications for Enhanced G-Protein Signaling and Reduced β-Arrestin Recruitment.","authors":"Keita Kajino, Tomoya Sugai, Tomoya Kakumoto, Ryoji Kise, Riko Suzuki, Akihisa Tokuda, Yuki Sekiya, Risako Katamoto, Noriki Kutsumura, Yasuyuki Nagumo, Takatsugu Hirokawa, Asuka Inoue, Tsuyoshi Saitoh","doi":"10.1248/cpb.c24-00796","DOIUrl":"https://doi.org/10.1248/cpb.c24-00796","url":null,"abstract":"<p><p>The δ-opioid receptor (DOR) continues to attract attention as a therapeutic target for the development of safer analgesics due to its ability to mediate pain relief with a lower risk of adverse effects compared to the μ-opioid receptor (MOR). Building upon our previous findings on KNT-127, a DOR-selective agonist with a morphinan scaffold, this study further explores the structure-signal relationships between quinoline ring modifications and the signaling bias toward Gi-protein activation while minimizing β-arrestin-2 recruitment. Our findings highlight the critical role of the 5'-position in modulating signaling bias. Bulky hydrophobic substituents, such as isopropoxy and cyclohexanoxy groups, effectively reduce β-arrestin-2 recruitment without compromising DOR binding affinity or Gi-protein activation. Molecular-docking and molecular dynamics simulations provided mechanistic insights, showing that these modifications change ligand interactions with the V281<sup>6.55</sup>-W284<sup>6.58</sup>-L300<sup>7.35</sup> sub-pocket, thus selectively favoring Gi-protein signaling. These insights clarify the key interactions for the signaling bias in DOR agonists, offering a new framework for the design of DOR-targeted therapies with an improved therapeutic profile.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 4","pages":"336-348"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143974449","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Two New Halimanes with a γ-Lactone from Croton argyratus. 含γ-内酯的两个新哈利曼类化合物。
IF 1.5 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c24-00734
Kanami Watanabe, Yohei Saito, Shuichi Fukuyoshi, Katsunori Miyake, David J Newman, Barry R O'Keefe, Kuo-Hsiung Lee, Kyoko Nakagawa-Goto
{"title":"Two New Halimanes with a γ-Lactone from Croton argyratus.","authors":"Kanami Watanabe, Yohei Saito, Shuichi Fukuyoshi, Katsunori Miyake, David J Newman, Barry R O'Keefe, Kuo-Hsiung Lee, Kyoko Nakagawa-Goto","doi":"10.1248/cpb.c24-00734","DOIUrl":"https://doi.org/10.1248/cpb.c24-00734","url":null,"abstract":"<p><p>The phytochemical investigation of the rainforest plant Croton argyratus (Euphorbiaceae) led to the isolation of two halimane-type diterpenes, crotargyolides A (1) and B (2), with an uncommon γ-lactone ring at C-5 and C-9, together with a crotofolane-type diterpene, 3-hydroxylated crotofolin C (3, crokocrotogenoid A), and the known clerodane diterpenes, junceic acid (4) and epoxyjunceic acid (5). The structures of the newly isolated compounds were elucidated by various NMR techniques, high resolution (HR)MS analysis, and electronic circular dichroism (ECD) spectroscopy. The proposed biosynthetic pathway of 1 from 4 was discussed. Crotargyolide A (1) and known compounds 4 and 5 were evaluated for antiproliferative activity and displayed no growth inhibitory effect toward all tested tumor cell lines.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 3","pages":"162-167"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143584880","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Crystalline Phase Transitions of 5'-O-Triethylsilyl-2'-deoxy-5-azacytidine under Varying Temperature and Humidity Conditions and Its Closed Storage Stability. 5'- o -三乙基硅基-2'-脱氧-5-氮杂胞苷在变温变湿条件下的结晶相变及其密闭贮存稳定性
IF 1.5 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c24-00676
Masaru Sudo, Makoto Otsuka, Takahiro Matsumoto, Yoshitaka Nakata, Tetsuo Sasaki
{"title":"Crystalline Phase Transitions of 5'-O-Triethylsilyl-2'-deoxy-5-azacytidine under Varying Temperature and Humidity Conditions and Its Closed Storage Stability.","authors":"Masaru Sudo, Makoto Otsuka, Takahiro Matsumoto, Yoshitaka Nakata, Tetsuo Sasaki","doi":"10.1248/cpb.c24-00676","DOIUrl":"https://doi.org/10.1248/cpb.c24-00676","url":null,"abstract":"<p><p>5'-O-Triethylsilyl-2'-deoxy-5-azacytidine (5'-O-TesDAC) is a prodrug developed to counteract deamination by cytidine deaminase and spontaneous hydrolytic cleavage of the triazine ring. In this study, we have evaluated the physical properties of the crystal forms to determine the optimal crystal form for solid pharmaceutical development. Therefore, the crystalline morphology of 5'-O-TesDAC was assessed using terahertz spectroscopy, in addition to conventional methods (thermal analysis, powder X-ray diffraction, IR absorption spectroscopy and dynamic vapor sorption). Terahertz spectroscopy has the feature of being able to sensitively capture structural changes between lattices and molecules because the absorptions of the terahertz region correspond to those of skeletal vibrations, intermolecular vibrations, and/or lattice vibrations. For this reason, in the evaluation of crystal polymorphism, terahertz spectroscopy was considered to complement methods that have conventionally been used. Furthermore, the metastable state evaluated in this study rapidly transitions to hemihydrate at relative humidity (RH) above 10%, so it could not be measured using attenuated total reflectance-Fourier transform IR (ATR-FTIR), which is performed under atmosphere, whereas terahertz spectroscopy allowed measurements with the sample chamber exposed to dry air easily. The chemical stability was evaluated through a stability test that measured the amount of the main degradation product of each crystalline form using HPLC. As a result, four crystalline forms of 5'-O-TesDAC were identified. The characterization of 5'-O-TesDAC in this study provides valuable information for optimizing the manufacturing parameters of the formulation and selecting appropriate packaging materials for pharmaceutical development.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 4","pages":"374-381"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143968190","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Investigation of the Relationship between the Chemical Stability of Itraconazole Adsorbed on Silica during Humidification and NMR Relaxation Using Time-Domain NMR. 用时域核磁共振研究伊曲康唑在二氧化硅上吸附湿化过程中的化学稳定性与核磁共振弛豫的关系。
IF 1.5 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c25-00056
Kotaro Okada, Myu Hirota, Shungo Kumada, Yoshirnori Onuki
{"title":"Investigation of the Relationship between the Chemical Stability of Itraconazole Adsorbed on Silica during Humidification and NMR Relaxation Using Time-Domain NMR.","authors":"Kotaro Okada, Myu Hirota, Shungo Kumada, Yoshirnori Onuki","doi":"10.1248/cpb.c25-00056","DOIUrl":"https://doi.org/10.1248/cpb.c25-00056","url":null,"abstract":"<p><p>Silica powder is an essential pharmaceutical ingredient, which in some combinations with drugs, causes chemical instability of the drug adsorbed on it. NMR measurements have been used to determine the drug adsorption state; however, the relationship between drug chemical stability and NMR relaxation, one of the NMR processes, is yet to be thoroughly studied. This work investigated the relationship between the chemical stability of itraconazole (ITZ)-adsorbed silica and its NMR relaxation. NMR can specifically observe <sup>1</sup>H nuclei, and this feature was exploited to study only the T<sub>1</sub> relaxation of these nuclei in the drug, excluding the silica signal composed of Si and O. ITZ, a poorly water-soluble model drug, was physically adsorbed on nonporous silica (Aerosil 200, AER), and mesoporous silica (Sylysia 320), and the <sup>1</sup>H T<sub>1</sub> relaxation was measured before storage using the time domain (TD)-NMR technique. The amount of ITZ degradant adsorbed in the silicas was also measured after storage at humidified conditions. Then, the relationship between the degradant amount of ITZ-adsorbed silica after storage and the T<sub>1</sub> relaxation rate (1/T<sub>1</sub>) before storage was investigated. The ITZ-adsorbed silicas showed a positive correlation between the degradant amount and the 1/T<sub>1</sub> value. ITZ-adsorbed AER showed a strong positive correlation (R<sup>2</sup> = 0.751). Thus, the 1/T<sub>1</sub> value may be an efficient parameter to determine the chemical stability of ITZ adsorbed on nonporous silica. The 1/T<sub>1</sub> value measurement by TD-NMR could provide new insight for evaluating the chemical stability of solid dosage forms containing silica.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 5","pages":"419-426"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143985233","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of Glycosylated 3-(3-Amino-3-carboxypropyl)uridine: A Minimum Unit of GlycoRNA. 糖基化3-(3-氨基-3-羧基丙基)尿苷的合成:GlycoRNA的最小单位。
IF 1.5 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c25-00091
Kazuyuki Ishii, Hikaru Yarita, Shino Manabe
{"title":"Synthesis of Glycosylated 3-(3-Amino-3-carboxypropyl)uridine: A Minimum Unit of GlycoRNA.","authors":"Kazuyuki Ishii, Hikaru Yarita, Shino Manabe","doi":"10.1248/cpb.c25-00091","DOIUrl":"https://doi.org/10.1248/cpb.c25-00091","url":null,"abstract":"<p><p>N-Glycosylated RNA (glycoRNA) has been identified on the cell surface, and 3-(3-amino-3-carboxypropyl)uridine has been reported as a conjugation site of N-glycans on RNA. Although the association of glycoRNAs with various diseases has been reported, their biosynthetic mechanisms and biological roles remain unexplored. Here, we report the preparation of two species of N-glycan-conjugated 3-(3-amino-3-carboxypropyl)uridine as the minimal units of glycoRNA. Our synthesized glycoRNA unit would contribute to future biochemical research on glycoRNAs.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 5","pages":"488-490"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144172824","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of the Tricyclic ABC-Ring System of Veratridine. 缬曲啶三环abc环体系的合成。
IF 1.5 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c25-00156
Keita Shiono, Keisuke Fukaya, Ayami Amano, Daisuke Urabe
{"title":"Synthesis of the Tricyclic ABC-Ring System of Veratridine.","authors":"Keita Shiono, Keisuke Fukaya, Ayami Amano, Daisuke Urabe","doi":"10.1248/cpb.c25-00156","DOIUrl":"https://doi.org/10.1248/cpb.c25-00156","url":null,"abstract":"<p><p>Veratridine is a neurotoxic compound classified into the cevanine group of the Veratrum alkaloids and is characterized by its highly functionalized hexacyclic structure. Here, we report the synthesis of the ABC-ring system of veratridine from a known cis-decalin. The cis-decalin was synthesized from 1,5-pentanediol by modification of a literature method. A site-selective acylation of the C3-hydroxy group with 3,4-dimethoxybenzoyl chloride, a chemo- and stereoselective (allyl)<sub>2</sub>Zn-mediated C9-allylation, and ring closing metathesis were employed as key transformations to construct the ABC-ring system of veratridine.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 5","pages":"491-496"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144172922","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of [1-13C]2-Oxoglutaric Acid and 13C Breath Tests Designed to Assess TCA Cycle Flux. [1-13C]2-氧戊二酸的合成及13C呼吸试验评估TCA循环通量
IF 1.3 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c25-00400
Hidemichi Mitome, Kiyoshi Miura, Tomihiro Miyada, Ginjiro Kato, Mieko Takenishi, Kumiko Ono, Nanami Torada, Honoka Kutsuna, Kazuki Akira
{"title":"Synthesis of [1-<sup>13</sup>C]2-Oxoglutaric Acid and <sup>13</sup>C Breath Tests Designed to Assess TCA Cycle Flux.","authors":"Hidemichi Mitome, Kiyoshi Miura, Tomihiro Miyada, Ginjiro Kato, Mieko Takenishi, Kumiko Ono, Nanami Torada, Honoka Kutsuna, Kazuki Akira","doi":"10.1248/cpb.c25-00400","DOIUrl":"https://doi.org/10.1248/cpb.c25-00400","url":null,"abstract":"<p><p>Several approaches for synthesizing [1-<sup>13</sup>C]2-oxoglutaric acid were attempted, and the synthesis was successfully achieved in 4 steps from trimethylsilyl <sup>13</sup>C-cyanide. The <sup>13</sup>C-breath tests on rats were conducted by orally administering the newly synthesized [1-<sup>13</sup>C]2-oxoglutaric acid, the previously prepared [1'-<sup>13</sup>C]citric acid, and [1-<sup>13</sup>C]acetic acid as a control drug, and the results were compared. The results indicate that [1-<sup>13</sup>C]2-oxoglutaric acid and [1'-<sup>13</sup>C]citric acid may serve as potential substrates for assessing the TCA cycle flux.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 9","pages":"807-812"},"PeriodicalIF":1.3,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145032895","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photo-Enhanced Aqueous Solubilization of Azobenzene-Incorporated Lipids. 偶氮苯脂类的光增强水溶液增溶作用。
IF 1.5 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c25-00252
Shusuke Tomoshige, Yushi Kawasaki, Junki Morimoto, Naohiro Sato, Yuichi Hashimoto, Minoru Ishikawa
{"title":"Photo-Enhanced Aqueous Solubilization of Azobenzene-Incorporated Lipids.","authors":"Shusuke Tomoshige, Yushi Kawasaki, Junki Morimoto, Naohiro Sato, Yuichi Hashimoto, Minoru Ishikawa","doi":"10.1248/cpb.c25-00252","DOIUrl":"https://doi.org/10.1248/cpb.c25-00252","url":null,"abstract":"<p><p>Lipids, including fatty acids and phospholipids, play crucial roles in biological systems and are widely utilized in pharmaceutical and biomedical applications. However, their inherent hydrophobicity poses significant challenges for formulation and administration. In this study, we aimed to enhance the aqueous solubility of lipidic compounds by leveraging light-responsive molecular design. We synthesized azo-lipids by incorporating azobenzene units into a fatty acid and phosphatidylcholine, hypothesizing that light-induced trans-cis isomerization would improve solubility. The synthesized compounds exhibited reversible photoisomerization upon alternating UV (365 nm) and visible light irradiation, as confirmed by UV-vis spectroscopy and reverse-phase HPLC. The solubilization of these azo-lipids was quantified under UV-unirradiated and irradiated conditions. Azobenzene-incorporated phosphatidylcholine 2 exhibited a drastic increase in solubilization from 2.030 to 1008 µM (496-fold) after UV irradiation. This significant improvement was attributed to efficient photoisomerization and molecular bending in the cis, cis conformation, reducing intermolecular interactions. Our findings suggest that this on-demand aqueous solubilization strategy offers a novel approach for improving the handling, storage, and potential therapeutic administration of lipid-based compounds.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 6","pages":"568-573"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144526590","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Bioinspired Total Synthesis of Polycyclic Natural Products. 多环天然产物的生物启发全合成。
IF 1.5 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c24-00843
Hayato Ishikawa
{"title":"Bioinspired Total Synthesis of Polycyclic Natural Products.","authors":"Hayato Ishikawa","doi":"10.1248/cpb.c24-00843","DOIUrl":"10.1248/cpb.c24-00843","url":null,"abstract":"<p><p>Despite the great strides in biopharmaceuticals and monoclonal antibodies today, natural products remain highly attractive as drug candidates. Therefore, building a library of natural products through total synthesis is critically important for drug discovery. This perspective article details the collective total synthesis of polycyclic natural products using \"bioinspired reactions\" that mimic natural product biosynthesis. It discusses the total syntheses of 20 natural products, including dimeric diketopiperazine alkaloids, monoterpenoid indole alkaloids, and iridoid glycosides, each achieved in fewer than 14 steps starting from commercially available materials.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 2","pages":"67-77"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143078591","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Total Synthesis and Antibacterial Activity of 5-Geranyloxy-7-hydroxycoumarin and Murrayacoumarin A. 5-香叶氧基-7-羟基香豆素和木耳香豆素A的合成及抗菌活性研究
IF 1.5 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2025-01-01 DOI: 10.1248/cpb.c25-00127
Takahito Kuribara, Honoka Yuba, Hina Saito, Akiko Takaya, Masami Ishibashi, Tetsuhiro Nemoto
{"title":"Total Synthesis and Antibacterial Activity of 5-Geranyloxy-7-hydroxycoumarin and Murrayacoumarin A.","authors":"Takahito Kuribara, Honoka Yuba, Hina Saito, Akiko Takaya, Masami Ishibashi, Tetsuhiro Nemoto","doi":"10.1248/cpb.c25-00127","DOIUrl":"10.1248/cpb.c25-00127","url":null,"abstract":"<p><p>Coumarins are widely found in medicinal plants and exhibit diverse biological properties, including antibacterial activities. Herein, we report the total synthesis of 5-geranyloxy-7-hydroxycoumarin, 5-geranyloxy-7-methoxycoumarin, and Murrayacoumarin A. The asymmetric synthesis of (+)-Murrayacoumarin A was achieved via regioselective asymmetric dihydroxylation, allowing the determination of absolute configuration at the C7'-position. In addition, the antibacterial activities of the synthesized natural products and their derivatives were evaluated.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 5","pages":"484-487"},"PeriodicalIF":1.5,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144141550","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
0
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
相关产品
×
本文献相关产品
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术官方微信