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Effect of Noise Filtering in an Ultraviolet Detector of UHPLC on the Statistical Reliability of Chemometrically Evaluated Repeatability. 超高效液相色谱紫外检测器中的噪声滤波对化学计量学评估重复性统计可靠性的影响
IF 1.5 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c24-00393
Akira Kotani, Koichi Machida, Ryo Watanabe, Hideki Hakamata
{"title":"Effect of Noise Filtering in an Ultraviolet Detector of UHPLC on the Statistical Reliability of Chemometrically Evaluated Repeatability.","authors":"Akira Kotani, Koichi Machida, Ryo Watanabe, Hideki Hakamata","doi":"10.1248/cpb.c24-00393","DOIUrl":"https://doi.org/10.1248/cpb.c24-00393","url":null,"abstract":"<p><p>A noise filter, which is usually attached to a detector for chromatography, was applied for the improvement of a signal-to-noise ratio (S/N) on a chromatogram. The objective of this paper is to elucidate the effect of noise filtering in an UV detector of ultra HPLC (UHPLC) on the statistical reliability of chemometrically evaluated repeatability by the function of mutual information (FUMI) theory. To examine the statistical reliability of chemometrically evaluated repeatability in the UHPLC system associated with noise filtering, the standard deviation (SD) values of the area in baseline fluctuations with peak region k (s(k)) were obtained from six chromatograms with noise filtering. Further, the average of s(k) values (σ̂) was calculated from the s(k) values (n = 6) to be alternatively applied as the population SD. All s(k)/σ̂ values were within the 95% confidence intervals (CIs) at the freedom degree of 50, indicating the chemometrically estimated relative SD (RSD) of a peak area and RSD by repeated measurements of at least 50 times had equivalent reliability.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142131932","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
Recyclable 2-Fluoropyridine Derivative as a Storage for Highly Electrophilic 1,1-Bis(triflyl)ethylene. 可回收的 2-氟吡啶衍生物作为高亲电性 1,1-双(三烯丙基)乙烯的储存剂。
IF 1.5 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c24-00499
Hikaru Yanai, Shoki Hoshikawa, Hiromu Watanabe, Hiroshi Kaneko, Hidemasa Nakaminami, Takashi Matsumoto
{"title":"Recyclable 2-Fluoropyridine Derivative as a Storage for Highly Electrophilic 1,1-Bis(triflyl)ethylene.","authors":"Hikaru Yanai, Shoki Hoshikawa, Hiromu Watanabe, Hiroshi Kaneko, Hidemasa Nakaminami, Takashi Matsumoto","doi":"10.1248/cpb.c24-00499","DOIUrl":"https://doi.org/10.1248/cpb.c24-00499","url":null,"abstract":"<p><p>As an easy-to-handle reagent for the in situ generation of outstandingly electrophilic Tf<sub>2</sub>C=CH<sub>2</sub> (Tf=CF<sub>3</sub>SO<sub>2</sub>), we have designed and synthesised a novel 4-substituted 2-fluoropyridinium zwitterion, in which a partially fluorinated alkyl group is attached to the pyridinium 4-position. Its zwitterionic nature has been well characterised by quantum chemical bonding analysis. By using this reagent, a wide variety of organic compounds, including commercial bioactive agents, were successfully decorated by the strongly acidic or ionic functionality. Remarkably, the 4-substituted 2-fluoropyridine derivative, which results from the zwitterion with the generation of Tf<sub>2</sub>C=CH<sub>2</sub>, can be rapidly separated and recovered from the reaction mixture appropriately using distillation, organic solvent extraction, or fluorous solid phase extraction techniques. Such multi-optionality for the purification methods favours in the isolation of the strongly acidic and/or ionic products.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142380118","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
Development of a Fluorescence Probe for Detecting Nitroreductase Activity Based on Steric Repulsion-Induced Twisted Intramolecular Charge Transfer (sr-TICT). 基于立体斥力诱导的分子内扭转电荷转移(sr-TICT)的检测硝基还原酶活性的荧光探针的开发。
IF 1.5 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c24-00486
Mizuki Sugimoto, Eita Sasaki, Hisashi Ohno, Takayuki Ikeno, Sota Yamada, Kenjiro Hanaoka
{"title":"Development of a Fluorescence Probe for Detecting Nitroreductase Activity Based on Steric Repulsion-Induced Twisted Intramolecular Charge Transfer (sr-TICT).","authors":"Mizuki Sugimoto, Eita Sasaki, Hisashi Ohno, Takayuki Ikeno, Sota Yamada, Kenjiro Hanaoka","doi":"10.1248/cpb.c24-00486","DOIUrl":"10.1248/cpb.c24-00486","url":null,"abstract":"<p><p>Twisted intramolecular charge transfer (TICT) is a phenomenon involving intramolecular charge transfer together with intramolecular rotation upon photoexcitation, and in general this excited state of fluorescent dyes undergoes non-radiative decay (producing no fluorescence). We recently discovered that the magnitude of TICT in rhodamine derivatives could be regulated by altering the size of the substituents on the xanthene moiety, generating differing degrees of intramolecular steric repulsion. To further illustrate the usefulness and generality of this strategy, we describe here an application of quinone methide chemistry, which is widely used as a fluorescence off/on switching reaction for fluorescence probes detecting enzymatic activity, to construct a steric repulsion-induced (sr)-TICT-based fluorescence probe targeting nitroreductase (NTR) activity. The developed probe was almost non-fluorescent in phosphate-buffered saline (PBS) due to strong induction of the TICT state. On the other hand, when the probe was incubated with NTR and nicotinamide adenine dinucleotide (NADH), a large fluorescence increase was observed over time. We confirmed that the enzymatic reaction proceeded as expected, i.e., the nitro group of the probe was reduced to the corresponding amino group, followed by spontaneous elimination of iminoquinone methide. These results suggest that our simple design strategy based on the sr-TICT mechanism, i.e., controlling intramolecular steric repulsion, would be applicable to the development of fluorescence probes for a variety of enzymes.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142307185","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 and Cytotoxicity of Cyclic Octapeptide Surugamides with Varied N-Acyl Moieties. 具有不同 N-酰基的环状八肽素酰胺的合成与细胞毒性
IF 1.5 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c24-00533
Kenichi Matsuda, Shinya Niikura, Rintaro Ichihara, Kei Fujita, Anna M Strasser, Rokusuke Yoshikawa, Jiro Yasuda, Yoshiki Hiramatsu, Hironori Hayashi, Eiichi N Kodama, Toshiyuki Wakimoto
{"title":"Synthesis and Cytotoxicity of Cyclic Octapeptide Surugamides with Varied N-Acyl Moieties.","authors":"Kenichi Matsuda, Shinya Niikura, Rintaro Ichihara, Kei Fujita, Anna M Strasser, Rokusuke Yoshikawa, Jiro Yasuda, Yoshiki Hiramatsu, Hironori Hayashi, Eiichi N Kodama, Toshiyuki Wakimoto","doi":"10.1248/cpb.c24-00533","DOIUrl":"10.1248/cpb.c24-00533","url":null,"abstract":"<p><p>Surugamides are a group of non-ribosomal peptides produced by Streptomyces spp. Several derivatives possess acyl groups, which are proposed to be attached to a lysine side chain after backbone-macrocyclization during biosynthesis. To date, five different acyl groups have been identified in nature, yet their impacts on biological activity remain underexplored. Here we synthesized surugamide B derivatives with varied acyl moieties. Biological evaluations revealed that larger hydrophobic acyl groups on lysine ε-NH<sub>2</sub> enhance cytotoxicity.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142307187","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
The Impact of Adding a Cationic Metal Salt and Curcumin to Monoammonium Glycyrrhizic Acid on Its Solubilizing Capacity and Gelation. 甘草酸单铵中添加阳离子金属盐和姜黄素对其增溶能力和凝胶化的影响
IF 1.5 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c24-00399
Kenta Ando, Hiromasa Uchiyama, Katsuhiko Minoura, Kazunori Kadota, Yuichi Tozuka
{"title":"The Impact of Adding a Cationic Metal Salt and Curcumin to Monoammonium Glycyrrhizic Acid on Its Solubilizing Capacity and Gelation.","authors":"Kenta Ando, Hiromasa Uchiyama, Katsuhiko Minoura, Kazunori Kadota, Yuichi Tozuka","doi":"10.1248/cpb.c24-00399","DOIUrl":"https://doi.org/10.1248/cpb.c24-00399","url":null,"abstract":"<p><p>Monoammonium glycyrrhizic acid (MAG), a glycyrrhizic acid monoammonium salt, is a naturally derived low-molecular-weight gelling agent with surface-active properties. It has the capacity to individually facilitate the preparation of gel-solubilized drugs. As MAG is an anionic surfactant with carboxyl groups, the addition of counterions may affect micelle formation and gelation. In this study, the solubilization and gelling properties of MAG were investigated following the addition of metal salts (NaCl and KCl). The addition of metal salts resulted in a decrease in the critical micelle concentration and an increase in gel hardness. Supersaturation of curcumin (CUR) was maintained by the addition of metal salts because of increased micelle number and viscosity. When the gel hardness was compared between formulations with and without CUR, a significant reduction in hardness was observed with the solubilization of CUR. The addition of KCl prevented the decrease in the hardness of gels containing CUR compared to the addition of NaCl. Put together, the addition of metal salts had a noteworthy impact on micelle and gel formation of MAG. In particular, the addition of KCl was more effective in the preparation of gel-solubilized CUR.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142342559","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
Development of Fast Disintegrating Tablets Containing Loxoprofen Sodium by HYDROFLASH Manufacturing Method 采用 HYDROFLASH 生产方法开发含洛索洛芬钠的快速崩解片剂
IF 1.7 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c23-00520
Aya Kuwata, Tetsuo Ono, Yuri Tsuchiya, Etsuo Yonemochi
{"title":"Development of Fast Disintegrating Tablets Containing Loxoprofen Sodium by HYDROFLASH Manufacturing Method","authors":"Aya Kuwata, Tetsuo Ono, Yuri Tsuchiya, Etsuo Yonemochi","doi":"10.1248/cpb.c23-00520","DOIUrl":"https://doi.org/10.1248/cpb.c23-00520","url":null,"abstract":"</p><p>In order to create and offer superior pharmaceuticals for consumers who wish to be relieved of headache and fever as soon as possible, we established HYDROFLASH manufacturing method that enables us to offer fast disintegration tablets containing loxoprofen sodium (LX), which are difficult to disintegrate. As a result of screening excipients, tablets using mannitol showed the fastest disintegration time, about 2 min. From the result of viscosity measurement, we found that LX produced higher viscosity when dissolved in water. This suggests that tablets containing LX disintegrate slower by inhibiting the penetration of water into the tablet due to the viscosity caused of LX. Therefore, we created a manufacturing method to make it easy for water to penetrate the tablet. It is possible to achieve fastest disintegration in about 30 s for tablets containing LX by granulating in a fluidized-bed with spraying of the dispersion of light anhydrous silicic acid (LASA). LX-containing tablets manufactured by the HYDROFLASH method disintegrated immediately after contact with water. Furthermore, it was observed that LASA was uniformly dotted on the surface of tablets by HYDROFLASH method, compared with other manufacturing methods. We considered that by fluidized-bed granulation with LASA dispersion (HYDROFLASH manufacturing method), water permeates through LASA on the tablet surface regardless of viscosity of LX. Futhermore, LX-containing tablets by the HYDROFLASH method showed that the dissolution rate of LX was nearly 100% at 5 min after starting the test. We considered that the initial dissolution became faster because of the fast disintegration.</p>\u0000<p></p>\u0000<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/cpb/72/1/72_c23-00520/figure/72_c23-00520.png\"/>\u0000<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139082068","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
Sulfonate Derivatives Containing a Kakuol Moiety as Potential Fungicidal Candidates: Design, Synthesis and Antifungal Activity Evaluation. 含 Kakuol 分子的磺酸盐衍生物作为潜在的杀真菌候选化合物:设计、合成和抗真菌活性评估。
IF 1.7 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c23-00857
Guoqing Sui, Lili Shu, Ailing Zhang, Dan Li, Shuhua Cao
{"title":"Sulfonate Derivatives Containing a Kakuol Moiety as Potential Fungicidal Candidates: Design, Synthesis and Antifungal Activity Evaluation.","authors":"Guoqing Sui, Lili Shu, Ailing Zhang, Dan Li, Shuhua Cao","doi":"10.1248/cpb.c23-00857","DOIUrl":"10.1248/cpb.c23-00857","url":null,"abstract":"<p><p>As a part of our continuing exploration to discover new potential promising fungicide candidates, eighteen sulfonate derivatives (3a-3r) containing a kakuol moiety were designed and synthesized. Synthetic sulfonate derivatives were tested comprehensively for antifungal activities against four plant pathogenic fungi (Botrytis (B.) cinerea, Valsa (V.) mali, Fusarium (F.) graminearum, Sclerotinia (S.) sclerotiorum), and their structure activity relationships were summarized. Especially, derivatives 3i and 3j exhibited remarkable activity against V. mali, with the inhibition rates of 99.8 and 100%, which were slightly superior to that of carbendazim (98.9%), a reference fungicide. Moreover, derivatives 3a, 3k and 3q possess the broader antifungal spectrum against three tested plant pathogenic fungi with inhibition rates over 60%. Structure-activity relationship (SAR) analysis indicated that the introduction of 2-F or 3-F into the benzene ring would give rise to a remarkable increase of the antifungal activity against V. mali.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139721801","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
8-Iodoisoquinolinone, a Conformationally Rigid Highly Reactive 2-Iodobenzamide Catalyst for the Oxidation of Alcohols by Hypervalent Iodine. 8-碘异喹啉酮--一种构象刚性高活性 2-碘苯甲酰胺催化剂,用于高价碘氧化醇。
IF 1.7 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c23-00887
Takayuki Yakura, Tomoya Fujiwara, Kanna Asakubo, Hema Naga Lakshmi Perumalla, Mitsuha Uzu, Takashi Okitsu, Kengo Kasama, Hisanori Nambu
{"title":"8-Iodoisoquinolinone, a Conformationally Rigid Highly Reactive 2-Iodobenzamide Catalyst for the Oxidation of Alcohols by Hypervalent Iodine.","authors":"Takayuki Yakura, Tomoya Fujiwara, Kanna Asakubo, Hema Naga Lakshmi Perumalla, Mitsuha Uzu, Takashi Okitsu, Kengo Kasama, Hisanori Nambu","doi":"10.1248/cpb.c23-00887","DOIUrl":"10.1248/cpb.c23-00887","url":null,"abstract":"<p><p>The first lactam-type 2-iodobenzamide catalysts, 8-iodoisoquinolinones 8 (IB-lactam) and 9 (MeO-IB-lactam), were developed. These catalysts have a conformationally rigid 6/6 bicyclic lactam structure and are more reactive than the previously reported catalysts 2-iodobenzamides 4 (IBamide) and 5 (MeO-IBamide) for the oxidation of alcohols. The lactam structure could form an efficient intramolecular I---O interaction, depending on the size of the lactam ring.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139989448","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
Development of Methodologies toward the Unified Synthesis of Ellagitannins. 开发鞣花丹宁统一合成方法。
IF 1.7 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c23-00920
Kazutada Ikeuchi
{"title":"Development of Methodologies toward the Unified Synthesis of Ellagitannins.","authors":"Kazutada Ikeuchi","doi":"10.1248/cpb.c23-00920","DOIUrl":"10.1248/cpb.c23-00920","url":null,"abstract":"<p><p>Ellagitannins, a class of polyphenols with divergent structures, have attracted considerable attention from synthetic organic chemists. The basic structures in ellagitannins contain esters of D-glucose with galloyl or hexahydroxyldiphenoyl groups, as well as diaryl ether structures. Thus, the synthesis methodologies of such components have been developed by various groups, including our group. This review describes the synthetic methods reported by our group during 2017-2023, aimed at increasing the number of ellagitannins that can be chemically synthesized. In addition, recent related reports are introduced.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140331560","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
Concise Synthesis of 11-Noriridoids via Pauson-Khand Reaction. 通过 Pauson-Khand 反应简易合成 11-去甲酰亚胺。
IF 1.7 4区 医学
Chemical & pharmaceutical bulletin Pub Date : 2024-01-01 DOI: 10.1248/cpb.c24-00190
Ryuji Kouda, Kazuki Yamamoto, Akira Katsuyama, Satoshi Ichikawa, Fumika Yakushiji
{"title":"Concise Synthesis of 11-Noriridoids via Pauson-Khand Reaction.","authors":"Ryuji Kouda, Kazuki Yamamoto, Akira Katsuyama, Satoshi Ichikawa, Fumika Yakushiji","doi":"10.1248/cpb.c24-00190","DOIUrl":"https://doi.org/10.1248/cpb.c24-00190","url":null,"abstract":"<p><p>Iridoids, which are a class of monoterpenoids, are attractive synthetic targets due to their diversely substituted cis-fused cyclopenta[c]pyran skeletons. Additionally, various biological activities of iridoids raise the value of synthetic studies on this class of compounds. Here, our synthetic efforts toward 11-noriridoids; (±)-umbellatolide B (6), (±)-10-O-benzoylglobularigenin (9) and 1-O-pentenylaucubigenin (34) are described. For the efficient synthesis of target compounds, common synthetic intermediates (tricyclic enones 17 and 26) were prepared by the Pauson-Khand reaction. The cleavage of the acetal bond on the tricyclic enones and 1,2-reduction introduced the two hydroxy groups on the cyclopentane ring of the core scaffold. Furthermore, the C3-C4 olefin part was constructed by the syn-elimination of a thiocarbonate moiety to obtain 34. The developed synthetic routes for 6, 9, and 34 will be useful for the preparation of iridoid analogs that have a polyfunctionalized core skeleton.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":null,"pages":null},"PeriodicalIF":1.7,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141310092","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
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