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Encapsulation of Cofacial Diarylacetylene Dimers Using [ 用[]包封共面二芳基乙炔二聚体
IF 0.6 4区 化学
Heterocycles Pub Date : 2023-11-29 DOI: 10.3987/com-23-14921
2]Daisy Chain Rotaxane Strategy
{"title":"Encapsulation of Cofacial Diarylacetylene Dimers Using [","authors":"2]Daisy Chain Rotaxane Strategy","doi":"10.3987/com-23-14921","DOIUrl":"https://doi.org/10.3987/com-23-14921","url":null,"abstract":"<span>[</span><span>c</span><span>2]Daisy chain rotaxanes are mechanically interlocked molecules that can cofacially assemble two </span><span>π</span><span>-conjugated molecules. In this study, we employed a rotaxane architecture to encapsulate diarylacetylene dimers modified with an electron-withdrawing or electron-donating substituent in two permethylated </span><span>α</span><span>-cyclodextrins. Solvent- and concentration-dependent </span><span>1</span><span>H nuclear magnetic resonance measurements indicated the selective formation of the cofacial dimers. These dimers were mechanically interlocked by condensation with 4-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}-3,5-dimethylaniline to obtain the corresponding [</span><span>c</span><span>2]daisy chain rotaxanes (up to 68% yield). UV-visible absorption and fluorescence spectra revealed that the diarylacetylene substituents modulated the optical properties of the rotaxanes. </span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":null,"pages":null},"PeriodicalIF":0.6,"publicationDate":"2023-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138495436","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
Evaluation of 4,4'-Diaminodiphenylmethane as a Platform for Proton, 4,4′-二氨基二苯甲烷作为质子平台的评价
IF 0.6 4区 化学
Heterocycles Pub Date : 2023-11-29 DOI: 10.3987/com-23-14922
p
{"title":"Evaluation of 4,4'-Diaminodiphenylmethane as a Platform for Proton,","authors":"p","doi":"10.3987/com-23-14922","DOIUrl":"https://doi.org/10.3987/com-23-14922","url":null,"abstract":"<span>4,4'-Diaminodiphenylmethane (DPM)-based fluorescent probes have been reported. We designed a new fluorescent probe </span><span>1</span><span>, having bis(4-methoxyphenyl)maleimide and an amino group as a fluorophore and a sensing part, respectively, in which DPM was used as a platform for sensing molecules to utilize its advantage. The fluorescence intensity of </span><span>1</span><span> increased upon adding trifluoroacetic acid in MeCN, CH</span><span>2</span><span>Cl</span><span>2</span><span>, and toluene, indicating that </span><span>1</span><span> showed as a proton sensor. The fluorescence spectral change of </span><span>1</span><span> was observed in a mixture of MeCN and various pH buffers. Moreover, </span><span>1</span><span> behaved as a metal (zinc or nickel) ion sensor with 2-formylpyridine by forming the Schiff base skeleton. The metal ion sensing behavior of </span><span>1</span><span> could be applied to an AND circuit. </span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":null,"pages":null},"PeriodicalIF":0.6,"publicationDate":"2023-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138495437","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
Chemical Structures 化学结构
IF 0.6 4区 化学
Heterocycles Pub Date : 2023-11-24 DOI: 10.3987/com-23-14924
a
{"title":"Chemical Structures","authors":"a","doi":"10.3987/com-23-14924","DOIUrl":"https://doi.org/10.3987/com-23-14924","url":null,"abstract":"<span>From the peels of </span><span>Citrus sphaerocarpa</span><span>, two new limonoids, sphaerocarpain Ⅰ</span><span> </span><span>and Ⅱ were isolated together with five known compounds including methyl deacetylnomilinate and ichangin. The chemical structures of the new compounds were elucidated based on chemical/physicochemical evidence.</span><span> </span><span>For sphaerocarpain Ⅰ and Ⅱ, the absolute configuration was established by comparison of experimental and predicted electronic circular dichroism (ECD) data. Among the isolated compounds, sphaerocarpain I, II, methyl deacetylnomilinate and ichangin showed cytotoxic activity against both human neuroblastoma cells (SH-SY5Y) and human glioblastoma cells (U-251 MG). <br/></span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":null,"pages":null},"PeriodicalIF":0.6,"publicationDate":"2023-11-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138495435","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
Diterpene Glycosides Derived from 二萜苷源自
IF 0.6 4区 化学
Heterocycles Pub Date : 2023-11-17 DOI: 10.3987/com-23-14919
Have Immunomodulatory Effects
{"title":"Diterpene Glycosides Derived from","authors":"Have Immunomodulatory Effects","doi":"10.3987/com-23-14919","DOIUrl":"https://doi.org/10.3987/com-23-14919","url":null,"abstract":"<span>Senescence-associated secretory phenotype (SASP) factors, involved in inflammation and tumorigenesis, can be inhibited by CD39, which degrades extracellular ATP. In this study, we analysed the chemical composition of the extracts of </span><span>Aster spathulifolius</span><span>, a coastal medicinal plant belonging to the Asteraceae family, and thereafter, isolated and determined the structures of the active components. We also treated THP-1 cells with the </span><span>A. spathulifolius</span><span> extracts and observed CD39 expression. Nine secondary metabolites, including a new diterpene glycoside </span><span>1</span><span>, were isolated. Compounds </span><span>1</span><span> and </span><span>3</span><span>–</span><span>7</span><span> substantially promoted CD39 expression in THP-1 cells, and compound </span><span>3</span><span>, the abundant component, showed the strongest effect in this regard, possibly degrading ATP and inhibiting the SASP. <br/></span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":null,"pages":null},"PeriodicalIF":0.6,"publicationDate":"2023-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138495434","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 of Protected L,L-Cyclotryptophyltyrosine, a Key Unit of Tryptorubin A 色氨酸a关键单元保护性L-环色氨酸的合成
IF 0.6 4区 化学
Heterocycles Pub Date : 2023-11-16 DOI: 10.3987/com-23-14913
Ryohei Nokura, Mayu Senda, Haruhiko Fukaya, and Yukio Hitotsuyanagi
{"title":"Synthesis of Protected L,L-Cyclotryptophyltyrosine, a Key Unit of Tryptorubin A","authors":"Ryohei Nokura, Mayu Senda, Haruhiko Fukaya, and Yukio Hitotsuyanagi","doi":"10.3987/com-23-14913","DOIUrl":"https://doi.org/10.3987/com-23-14913","url":null,"abstract":"<span>A protected form of </span><span>L</span><span>,</span><span>L</span><span>-cyclotryptophyltyrosine, a key structure of the bicyclic hexapeptide tryptorubin A isolated from </span><span>Streptomyces</span><span> sp. CLI2509, was synthesized. Treatment of Boc-</span><span>L</span><span>-Trp-3-borono-</span><span>L</span><span>-Tyr(Me)-OMe, obtained from the coupling reaction of Boc-</span><span>L</span><span>-Trp-OH and H</span><span>2</span><span>N-3-iodo-</span><span>L</span><span>-Tyr(Me)-OMe and the subsequent borylation of iodide, with Cu(OAc)</span><span>2</span><span>, pyridine, and 4 Å molecular sieves in dichloromethane at 30 °C for 48 h at a concentration of 0.001 M gave protected </span><span>L</span><span>,</span><span>L</span><span>-cyclotryptophyltyrosine in 58% yield. The structure of obtained protected </span><span>L</span><span>,</span><span>L</span><span>-cyclotryptophyltyrosine was confirmed by X-ray crystallography, revealing the presence of a pyramidal indole nitrogen atom. </span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":null,"pages":null},"PeriodicalIF":0.6,"publicationDate":"2023-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138495433","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 Properties of Novel Thiophene Polycyclic Aromatic Hydrocarbons Based on Pyrene and Their Radical Cations 基于芘及其自由基阳离子的新型噻吩多环芳烃的合成与性质
IF 0.6 4区 化学
Heterocycles Pub Date : 2023-11-16 DOI: 10.3987/com-23-14916
Shunjie Li and Jian Chen
{"title":"Synthesis and Properties of Novel Thiophene Polycyclic Aromatic Hydrocarbons Based on Pyrene and Their Radical Cations","authors":"Shunjie Li and Jian Chen","doi":"10.3987/com-23-14916","DOIUrl":"https://doi.org/10.3987/com-23-14916","url":null,"abstract":"<span>Two new thiophene-modified pyrene derivatives, 4,5,9,10-tetra- (2-(5-methyl)thienyl)-2,7-di-</span><span>tert</span><span>-butylpyrene </span><span>(1)</span><span> and 4,5,9,10-tetra- (2-(5-methoxy)thienyl)-2,7-di-</span><span>tert</span><span>-butylpyrene </span><span>(2)</span><span>, were designed and synthesized via Friedel</span><span>–</span><span>Crafts alkylation and Stille coupling reactions of pyrene. The stable monoradical cations </span><span>1</span><span>•+</span><span> and </span><span>2</span><span>•+</span><span> based on the thiophene-modified pyrene derivatives were generated by the one-electron oxidation of the pyrene-based thiophene polycyclic aromatic groups with Ag[Al(OR</span><span>F</span><span>)</span><span>4</span><span>] (OR</span><span>F</span><span> = OC(CF</span><span>3</span><span>)</span><span>3</span><span>). Their structures and properties were investigated using </span><span>1</span><span>H nuclear magnetic resonance spectroscopy, ultraviolet</span><span>–</span><span>visible spectrophotometry, X-ray diffraction, density functional theory calculations, and electron paramagnetic resonance spectroscopy. The electron spin density was mainly concentrated on the pyrene ring, with a minor spillover to the peripheral thienyl moieties. Compound </span><span>1</span><span>•+</span><span>, which is the first reported monoradical cation of thiophene-modified pyrene, is expected to have broad application prospects in the fields of semiconductors and optoelectronic materials.<br/></span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":null,"pages":null},"PeriodicalIF":0.6,"publicationDate":"2023-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138495432","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
Diversity-Oriented, One Step Synthesis of Chromeno[2,3- 面向多样性，一步合成铬二甲基[2,3-]
IF 0.6 4区 化学
Heterocycles Pub Date : 2023-11-15 DOI: 10.3987/com-23-14920
]Indoles and Thiochromeno[2,3-
{"title":"Diversity-Oriented, One Step Synthesis of Chromeno[2,3-","authors":"]Indoles and Thiochromeno[2,3-","doi":"10.3987/com-23-14920","DOIUrl":"https://doi.org/10.3987/com-23-14920","url":null,"abstract":"<span>A general and efficient synthesis of tetracyclic chromeno[2,3-</span><span>b</span><span>]indoles, thiochromeno[2,3-</span><span>b</span><span>]indoles and 6</span><span>H</span><span>-indolo[2,3-</span><span>b</span><span>]quinolines has been achieved through a microwave-assisted, metal free, base catalyzed domino Knoevenagel condensation, intramolecular cyclization process starting from simple indoline-2-thiones and 2-substituted benzaldehyde derivatives. This approach provides a straightforward, atom economical and concise route to access a range of otherwise not easily available heterocycles in good yields.<br/></span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":null,"pages":null},"PeriodicalIF":0.6,"publicationDate":"2023-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138495431","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 of Thiosemicarbazone Derivatives of 3-Formyl- 3-甲酰基-硫代氨基脲衍生物的合成
IF 0.6 4区 化学
Heterocycles Pub Date : 2023-11-10 DOI: 10.3987/com-23-14870
-pyrazolylmethyleneindoles and Their Antifungal Activities
{"title":"Synthesis of Thiosemicarbazone Derivatives of 3-Formyl-","authors":"-pyrazolylmethyleneindoles and Their Antifungal Activities","doi":"10.3987/com-23-14870","DOIUrl":"https://doi.org/10.3987/com-23-14870","url":null,"abstract":"<span>In order to discover natural-product-based </span><span>antifungal</span><span> candidates, a series of new </span><span>thiosemicarbazone derivatives of 3-formyl-</span><span>N</span><span>-pyrazolylmethyleneindoles</span><span> were prepared. Some derivatives showed good </span><span>antifungal</span><span> activities. Against </span><span>Curvularia lunata</span><span>,</span><span> compound </span><span>I-2</span><span> showed 2.2 times </span><span>antifungal activity</span><span> compared to the </span><span>precursor indole</span><span>. Against</span><span> Valsa mali</span><span>,</span><span> compound </span><span>Ⅰ-1</span><span> exhibited 1.7 times </span><span>antifungal</span><span> activity compared to </span><span>indole.</span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":null,"pages":null},"PeriodicalIF":0.6,"publicationDate":"2023-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138495430","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 of Hepta-arbutin-branched β-Cyclodextrins at Their Primary Sides 七熊果苷支链β-环糊精的合成
IF 0.6 4区 化学
Heterocycles Pub Date : 2023-11-06 DOI: 10.3987/com-23-14908
Click Reaction
{"title":"Synthesis of Hepta-arbutin-branched β-Cyclodextrins at Their Primary Sides","authors":"Click Reaction","doi":"10.3987/com-23-14908","DOIUrl":"https://doi.org/10.3987/com-23-14908","url":null,"abstract":"<span>This paper describes</span><span> the synthesis of β-cyclodextrin (CD) based arbutin (4-hydroxyphenyl β-glucopyanoside) conjugates as a model for drug delivery molecules. We introduced three variants of hepta-ar</span><span>butin-branched CDs at their primary side. Of these, two incorporated oligo(ethylene)chains within their spacer</span><span>s to demonstrate the effect of varying spatial characteristics between the β-glucopyanoside moieties. Due to the sterically hindered position on the primary side of β-CD, we employed a highly efficient cl</span><span>ick chemistry reaction.<br/></span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":null,"pages":null},"PeriodicalIF":0.6,"publicationDate":"2023-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138495429","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, Antioxidant Activity 合成、抗氧化活性
IF 0.6 4区 化学
Heterocycles Pub Date : 2023-11-06 DOI: 10.3987/com-23-14915
a
{"title":"Synthesis, Antioxidant Activity","authors":"a","doi":"10.3987/com-23-14915","DOIUrl":"https://doi.org/10.3987/com-23-14915","url":null,"abstract":"<span>3-[2-(5-Aryl-3-phenyl-4,5-dihydro-1</span><span>H</span><span>-pyrazol-1-yl)thiazol-4-yl]-4- hydroxy-6-methyl-2</span><span>H</span><span>-pyran-2-ones </span><span>6a-h</span><span> were synthesized </span><span>via</span><span> the ring closure reactions of 3-phenyl-5-aryl-4,5-dihydropyrazole-1-carbothioamides </span><span>3a-h</span><span> with 3-(bromoacetyl)-4-hydroxy-6-methyl-2</span><span>H</span><span>-pyran-2-one </span><span>5</span><span>. The new synthesized thiazolyl-pyrazolinyl-pyran-2-one compounds were evaluated for their potential antioxidant activity by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical method. The molecular docking of the synthesized compounds on DPPH oxidase protein showed a high binding affinity, confirming the experimental results recorded. The synthesized compounds deserve a consideration for further analyses regarding the control of oxidative stress and their use as possible antioxidant agents in the pharmaceutical industry.<br/></span>","PeriodicalId":13166,"journal":{"name":"Heterocycles","volume":null,"pages":null},"PeriodicalIF":0.6,"publicationDate":"2023-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138495428","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
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