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New Selective Inhibitors of α-Glucosidase for the Treatment of Type 2 Diabetes Mellitus 治疗 2 型糖尿病的新型α-葡萄糖苷酶选择性抑制剂
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-02-14 DOI: 10.1002/hlca.202300222
Takwa Khanchouch, Aurélie Vallin, Urjwan Alali, Mohammed Benazza, Rym Abidi, Véronique Bonnet
{"title":"New Selective Inhibitors of α-Glucosidase for the Treatment of Type 2 Diabetes Mellitus","authors":"Takwa Khanchouch,&nbsp;Aurélie Vallin,&nbsp;Urjwan Alali,&nbsp;Mohammed Benazza,&nbsp;Rym Abidi,&nbsp;Véronique Bonnet","doi":"10.1002/hlca.202300222","DOIUrl":"10.1002/hlca.202300222","url":null,"abstract":"<p>Type 2 diabetes mellitus is a metabolic dreadful disease caused by an uncontrolled glucose level in the bloodstream, particularly high after a meal. Inhibitors of glucosidases, involved in the digestion of carbohydrates, can regulate this post-prandial increase in glucose concentration. The traditional drugs act as competitive inhibitors of both pancreatic α-amylase and α-glucosidases and this unselective inhibition is behind severe gastrointestinal side effects related to the concomitant inhibition of α-amylase. We described herein some perglycosylated cyclodextrins as efficient and selective inhibitors of α-glucosidase with low micromolar IC<sub>50</sub> (3.64-7.98 μM) compared to the acarbose (IC<sub>50</sub> 212 μM), clinically used for patients suffering from type 2 diabetes. On the other hand, they do not inhibit α-amylase (IC<sub>50</sub>&gt;500 μM). Structure/activity relationship rationalization suggests multiple interactions between the described inhibitors and α-glucosidase, which support the existence of both active site and allosteric interactions.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2024-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300222","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139770799","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
N-Methyl-N-Alkylaminocyclopentanes: Powerful and Selective β-d-Glucocerebrosidase Inhibitors N-甲基-N-烷基氨基环戊烷：强效、选择性β-D-葡糖脑抑制剂
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-02-13 DOI: 10.1002/hlca.202300219
Patrick Weber, Roland Fischer, Seyed A. Nasseri, Bettina M. Pabst, Herwig Prasch, Arnold E. Stütz, Martin Thonhofer, Stephen G. Withers, Werner Windischhofer, Tanja M. Wrodnigg
{"title":"N-Methyl-N-Alkylaminocyclopentanes: Powerful and Selective β-d-Glucocerebrosidase Inhibitors","authors":"Patrick Weber,&nbsp;Roland Fischer,&nbsp;Seyed A. Nasseri,&nbsp;Bettina M. Pabst,&nbsp;Herwig Prasch,&nbsp;Arnold E. Stütz,&nbsp;Martin Thonhofer,&nbsp;Stephen G. Withers,&nbsp;Werner Windischhofer,&nbsp;Tanja M. Wrodnigg","doi":"10.1002/hlca.202300219","DOIUrl":"10.1002/hlca.202300219","url":null,"abstract":"<p>Building upon a previously established (2+3)-cycloaddition strategy, a series of <i>N</i>,<i>N</i>-dialkylated aminocyclopentanes was synthesized using a partially protected eno-furanose as the starting point. The resulting <i>N</i>-methylisoxazolidine was subsequently transformed into the corresponding aminocyclopentane, which was further <i>N</i>-alkylated, yielding a collection of compounds with potential as inhibitors and pharmacological chaperones of β-<span>d</span>-glucocerebrosidase. A comprehensive screening involving a range of biologically relevant glycosidases unveiled that these compounds exhibit remarkable potency and selectivity as inhibitors of human lysosomal β-<span>d</span>-glucocerebrosidase. However, none of these compounds exhibit significant activity enhancement of Morbus Gaucher related p.N409S/p.L483P mutant β-<span>d</span>-glucocerebrosidase.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2024-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139770839","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}
引用次数: 0
Development of a Novel Measurement Setup to Study and Predict Electrostatic Discharges in Agitated Glass-Lined Vessels 开发用于研究和预测搅拌搪玻璃容器中静电放电的新型测量装置
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-02-12 DOI: 10.1002/hlca.202300223
Benedikt Robert Brönnimann, Daniel Egli-Tedesco, Klaus Schwenzfeuer, Andreas Zogg
{"title":"Development of a Novel Measurement Setup to Study and Predict Electrostatic Discharges in Agitated Glass-Lined Vessels","authors":"Benedikt Robert Brönnimann,&nbsp;Daniel Egli-Tedesco,&nbsp;Klaus Schwenzfeuer,&nbsp;Andreas Zogg","doi":"10.1002/hlca.202300223","DOIUrl":"10.1002/hlca.202300223","url":null,"abstract":"<p>Two glass lined reactors in a launch platform facility operated by Syngenta have been damaged during the crystallization of an organic compound due to electrostatic discharges. The goal of this work was to design and commission a novel setup to measure charges and currents generated by this slurry in a laboratory-scale reactor. An improved and more sophisticated setup was then proposed for possible implementation in Syngenta's own laboratories. With this novel setup, the electrostatic charging of stirred suspensions involving nonconductive solvents could be accurately measured in the context of a case study that involved the suspension that led to liner damages in the production facilities of Syngenta.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2024-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300223","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139770830","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Benzylic C(sp3)‐H Azidation: Copper vs Iron Catalysis 苄基 C(sp3)-H 氮化：铜催化与铁催化
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-02-09 DOI: 10.1002/hlca.202400004
Angel Rentería-Gómez, Rubén O Torres-Ochoa, Pierre Palamini, Raphael Simonet-Davin, Qian Wang, J. Waser, Jieping Zhu
{"title":"Benzylic C(sp3)‐H Azidation: Copper vs Iron Catalysis","authors":"Angel Rentería-Gómez, Rubén O Torres-Ochoa, Pierre Palamini, Raphael Simonet-Davin, Qian Wang, J. Waser, Jieping Zhu","doi":"10.1002/hlca.202400004","DOIUrl":"https://doi.org/10.1002/hlca.202400004","url":null,"abstract":"The generation of benzylic radicals through hydrogen atom abstraction (HAT) has been a recent research focus and various C(sp3)‐H bond functionalization protocols have been developed relying on this elementary step. We report herein copper‐ and iron‐catalyzed C(sp3)‐H benzylic azidation reactions using mCPBA and NFSI as oxidant, respectively, and TMSN3 as azide source. The reaction is thought to be initiated via intermolecular abstraction of benzylic hydrogen by the in situ generated heteroatom‐centered radicals. The Fe(OTf)3‐catalyzed azidation protocol displays good chemoselectivity as it takes place preferentially at the secondary and tertiary benzylic C(sp3)‐H bonds over the primary benzylic and tertiary aliphatic carbons. Efforts on the development of catalytic enantioselective processes are also documented.","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2024-02-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139848393","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}
引用次数: 0
Benzylic C(sp3)−H Azidation: Copper vs Iron Catalysis 苄基 C(sp3)-H 氮化：铜催化与铁催化
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-02-09 DOI: 10.1002/hlca.202400004
Angel Rentería-Gómez, Rubén O. Torres-Ochoa, Pierre Palamini, Raphaël Simonet-Davin, Qian Wang, Jérôme Waser, Jieping Zhu
{"title":"Benzylic C(sp3)−H Azidation: Copper vs Iron Catalysis","authors":"Angel Rentería-Gómez,&nbsp;Rubén O. Torres-Ochoa,&nbsp;Pierre Palamini,&nbsp;Raphaël Simonet-Davin,&nbsp;Qian Wang,&nbsp;Jérôme Waser,&nbsp;Jieping Zhu","doi":"10.1002/hlca.202400004","DOIUrl":"10.1002/hlca.202400004","url":null,"abstract":"<p>The generation of benzylic radicals through hydrogen atom abstraction (HAT) has been a recent research focus and various C(sp<sup>3</sup>)−H bond functionalization protocols have been developed relying on this elementary step. We report herein copper- and iron-catalyzed C(sp<sup>3</sup>)−H benzylic azidation reactions using <i>m</i>CPBA and NFSI as oxidant, respectively, and TMSN<sub>3</sub> as azide source. The reaction is thought to be initiated <i>via</i> intermolecular abstraction of benzylic hydrogen by the <i>in situ</i> generated heteroatom-centered radicals. The Fe(OTf)<sub>3</sub>-catalyzed azidation protocol displays good chemoselectivity as it takes place preferentially at the secondary and tertiary benzylic C(sp<sup>3</sup>)−H bonds over the primary benzylic and tertiary aliphatic carbons. Efforts on the development of catalytic enantioselective processes are also documented.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2024-02-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400004","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139788534","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Design and Synthesis of Dialkylarylphosphine Urea Ligands and their Application in Palladium-Catalyzed Cross-Coupling Reactions 二烷基芳基膦脲配体的设计与合成及其在钯催化交叉偶联反应中的应用
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-02-09 DOI: 10.1002/hlca.202300244
Lupita S. Aguirre, Levi T. Litwiller, Alexis N. Lugo, Andy A. Thomas
{"title":"Design and Synthesis of Dialkylarylphosphine Urea Ligands and their Application in Palladium-Catalyzed Cross-Coupling Reactions","authors":"Lupita S. Aguirre,&nbsp;Levi T. Litwiller,&nbsp;Alexis N. Lugo,&nbsp;Andy A. Thomas","doi":"10.1002/hlca.202300244","DOIUrl":"10.1002/hlca.202300244","url":null,"abstract":"<p>We describe herein the design and synthesis of a new class of dialkylarylphosphine ligands incorporating a Lewis-basic urea subunit. The ligand synthesis consisted of six linear steps and was enabled by the discovery of a new N-to-N alkyl migration reaction. This new series of dialkylarylphosphine urea ligands were applied in common palladium-catalyzed cross-coupling reactions for the formation of carbon-carbon and carbon-nitrogen bonds in moderate to high yields.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2024-02-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300244","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139769452","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Functionalization of Cubane Formation of C−C and C−Heteroatom Bonds 立方体的官能化 形成 C-C 键和 C 杂原子键
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-02-02 DOI: 10.1002/hlca.202300200
Tomohiro Yasukawa, Katja S. Håheim, Janine Cossy
{"title":"Functionalization of Cubane Formation of C−C and C−Heteroatom Bonds","authors":"Tomohiro Yasukawa,&nbsp;Katja S. Håheim,&nbsp;Janine Cossy","doi":"10.1002/hlca.202300200","DOIUrl":"https://doi.org/10.1002/hlca.202300200","url":null,"abstract":"<p>Functionalized cubanes are attractive scaffolds for medicinal chemists as they are bioisosteres of benzene rings. The replacement of a benzene ring by a cubane, in a bioactive compound, can have a beneficial effect on the biological activity of such compound. Thus, the design of new molecular cubyl building blocks is of importance. In this review, we will focus on the functionalization of cubanes by creating C−C, C−heteroatom bonds e. g. C−N, C−O, C−B, C−P and C−S bonds. Different methods are reported involving organometallics, radicals, and ionic species. Mechanisms are included when relevant.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2024-02-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300200","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139739148","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A Scalable and Chromatography-Free Synthesis of N,N-Bis(9,9-dimethyl-9H-fluoren-2-yl)-3′,3′,4′,7′-tetramethyl-2′,3′-dihydrospiro[fluorene-9,1′-indene]-2-amine, a new Hole Transport Material for Organic Solar Cells 一种用于有机太阳能电池的新型空穴传输材料--N,N-双（9,9-二甲基-9H-芴-2-基）-3′,3′,4′,7′-四甲基-2′,3′-二氢螺[芴-9,1′-茚]-2-胺的规模化无色谱法合成方法
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-02-02 DOI: 10.1002/hlca.202300220
Yves Aeschi, Thorsten M. Beck, Ulrich Berens, Alexander Ernst
{"title":"A Scalable and Chromatography-Free Synthesis of N,N-Bis(9,9-dimethyl-9H-fluoren-2-yl)-3′,3′,4′,7′-tetramethyl-2′,3′-dihydrospiro[fluorene-9,1′-indene]-2-amine, a new Hole Transport Material for Organic Solar Cells","authors":"Yves Aeschi,&nbsp;Thorsten M. Beck,&nbsp;Ulrich Berens,&nbsp;Alexander Ernst","doi":"10.1002/hlca.202300220","DOIUrl":"10.1002/hlca.202300220","url":null,"abstract":"<p>The title triarylamine <i>N</i>,<i>N</i>-bis(9,9-dimethyl-9<i>H</i>-fluoren-2-yl)-3′,3′,4′,7′-tetramethyl-2′,3′-dihydrospiro[fluorene-9,1′-indene]-2-amine is a new hole transport material for organic solar cells. After investigating different discovery approaches (<i>Schemes 1 + 2</i>), a multi gram-scale synthetic sequence was developed (<i>Scheme 4</i>). The key intermediate 2-bromo-9-(2,5-dimethylphenyl)-9<i>H</i>-fluorene was accessible from 2-bromo-9-fluorenone by either the sequence <i>Grignard</i> reaction, Et<sub>3</sub>SiH/BF<sub>3</sub> reduction or by direct arylation of the corresponding 2-bromo-9-fluorenol. Alkylation at C(9) of 2-bromo-9-(2,5-dimethylphenyl)-9<i>H</i>-fluorene with methallyl chloride and cyclization by an intramolecular <i>Friedel-Crafts</i> alkylation led to the key building block 2-bromo-3′,3′,4′,7′-tetramethyl-2′,3′-dihydrospiro[fluorene-9,1′-indene] (<i>Scheme 4</i>). A <i>Buchwald-Hartwig</i> coupling was employed (<i>Scheme 3 + 4</i>) for the assembly of the final triarylamines. The developed gram-scale synthesis of the title compound is scalable and chromatography-free with an overall yield &gt;25 % over 5 steps.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2024-02-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139664746","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}
引用次数: 0
Novel Rearrangements of Guaiane Sesquiterpenes 胍类倍半萜的新型重排
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-01-29 DOI: 10.1002/hlca.202300205
Paul L. Türtscher, Gerhard Brunner, Andreas Goeke
{"title":"Novel Rearrangements of Guaiane Sesquiterpenes","authors":"Paul L. Türtscher,&nbsp;Gerhard Brunner,&nbsp;Andreas Goeke","doi":"10.1002/hlca.202300205","DOIUrl":"10.1002/hlca.202300205","url":null,"abstract":"<p>Guaiane sesquiterpenes are an important class of biologically active natural products. Several oxygenated bicyclic but also tricyclic derivatives show unprecedented olfactory activity with great importance in perfumery. Their <i>in vivo</i> syntheses are largely controlled by the intrinsic selectivities of terpene synthases and only a few rearrangements of their hydroazulene skeletons were reported, mostly resulting into terpenoids with decalin motives. Using α-guaiene and bulnesene, complex rearrangements into novel tri and tetracyclic terpenoids are described herein. The cationic rearrangement mechanisms of their formation based on subsequent 1,2-H and alkyl shifts promoted by substoichiometric amounts of ethylaluminum dichloride.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2024-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139578287","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}
引用次数: 0
Synthesis and Cell-Based Evaluation of Umifenovir Analogues as Anti-SARS-CoV-2 Agents 作为抗 SARS-CoV-2 药物的 Umifenovir 类似物的合成和基于细胞的评估
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-01-18 DOI: 10.1002/hlca.202300208
Hiroaki Tanaka, Seiya Miyagi, Tomoko Morita, Hiroaki Ishii, Natsuki Mori, Kaho Oishi, Takemasa Sakaguchi, Toyonobu Usuki
{"title":"Synthesis and Cell-Based Evaluation of Umifenovir Analogues as Anti-SARS-CoV-2 Agents","authors":"Hiroaki Tanaka,&nbsp;Seiya Miyagi,&nbsp;Tomoko Morita,&nbsp;Hiroaki Ishii,&nbsp;Natsuki Mori,&nbsp;Kaho Oishi,&nbsp;Takemasa Sakaguchi,&nbsp;Toyonobu Usuki","doi":"10.1002/hlca.202300208","DOIUrl":"10.1002/hlca.202300208","url":null,"abstract":"<p>Umifenovir is a broad-spectrum antiviral agent used to treat influenza in China and Russia, and it has been studied as an antiviral agent for the treatment of coronavirus disease 2019 (COVID-19). We have previously reported the synthesis of novel umifenovir analogues and their biological evaluation with a focus on their inhibitory activity against the binding of the spike glycoprotein (S-protein) of severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) and the angiotensin-converting enzyme 2 (ACE2) receptor; however, no strong inhibitory activity was observed from these analogues. In the present study, an additional set of umifenovir analogues was synthesized with replacement of the substituents at the 2-, 3-, and 4-positions of the indole, and a cell-based assay using SARS-CoV-2 (B.1.1) was performed to examine the antiviral activity of the analogues. We found that one of the newly synthesized umifenovir analogues exhibited antiviral activity and reduced the viral load to 0.06 % as compared to the control when it was assessed in the presence of nafamostat and marimastat, which inhibit cell-surface viral entry. In contrast, when this analogue was evaluated without the addition of nafamostat or marimastat, it exhibited less antiviral activity, suggesting that the umifenovir analogue would exert antiviral activity mainly by inhibiting endosome-mediated viral entry.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2024-01-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300208","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139514785","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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