Organic & Biomolecular Chemistry最新文献_第10页

Selective 1,1- and 1,2-dibromination of phenylethanes in the presence of NaBr/NaBrO3/H2SO4 as the bromination reagent† 在 NaBr/NaBrO3/H2SO4 作为溴化试剂的情况下，选择性地对苯乙烷进行 1,1- 和 1,2- 二溴反应。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob01016g

引用次数: 0

Transition metal-catalyzed C(sp2/sp3)–H α-fluoroalkenylation from gem-(bromo/di)fluoroalkenes to monofluoroalkenes: scope, mechanisms, and synthetic applications 过渡金属催化的 C（sp2/sp3）-H α-氟烯烃化反应：范围、机理和合成应用。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob01044b

{"title":"Transition metal-catalyzed C(sp2/sp3)–H α-fluoroalkenylation from gem-(bromo/di)fluoroalkenes to monofluoroalkenes: scope, mechanisms, and synthetic applications","authors":"","doi":"10.1039/d4ob01044b","DOIUrl":"10.1039/d4ob01044b","url":null,"abstract":"<div>Organofluorines have a broad range of industrial applications, such as pharmaceuticals, liquid crystal displays (LCDs), solar cells, textiles, and construction coatings, and are used in peptidomimetics, surfactants, refrigerants, anesthetics, and agrochemicals. Among them are versatile monofluoroalkenes that play a crucial role in medicinal and synthetic chemistry. The synthetic strategies for this class of molecules are limited, and prior efforts frequently suffered from poor atom- and step-economies. As a surrogate pathway for traditional cross-coupling transformations, transition metal (TM)-catalyzed C–H direct α-fluoroalkenylation overcomes these obstacles and provides straightforward techniques to access monofluoroalkenes. Nevertheless, substrate scope is still a challenge for catalysis, where gem-bromofluoroalkene synthons are applicable with electronically biased substrates such as azoles, while gem-difluoroalkene-based strategies are limited to substrates containing N-based directing groups. Herein, we review the cutting-edge fluoroalkenylation research for direct synthesis of monofluoroalkenes achieved during the last decade (2013–2023). This review is divided into two main parts: the first part discusses TM-catalyzed direct α-fluoroalkenylation via the merging of C–H activation and C(sp2)–Br cleavage strategies using gem-bromofluoroalkenes, and the second part describes the same reaction, albeit with C(sp2)–F cleavage of highly explored gem-difluoroolefins. Our review surveys all previously reported monofluoroalkenes in this research area, including their preparation techniques, stereoselectivity, and yield percentages. Furthermore, optimal conditions, reactant scope, mechanistic investigations, synthetic applications, benefits, and drawbacks of each presented methodology are critically discussed.</div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/ob/d4ob01044b?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141970083","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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Atropisomeric 1-phenylbenzimidazoles affecting microtubule organization: influence of axial chirality† 影响微管组织的异构体 1-苯基苯并咪唑：轴向手性的影响。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob00863d

{"title":"Atropisomeric 1-phenylbenzimidazoles affecting microtubule organization: influence of axial chirality†","authors":"","doi":"10.1039/d4ob00863d","DOIUrl":"10.1039/d4ob00863d","url":null,"abstract":"<div>Benzimidazoles are frequently used in medicinal chemistry. Their anticancer effect is among the most prominent biological activities exhibited by this scaffold. Although numerous benzimidazole derivatives have been synthesized, possible atropisomerism of ortho-substituted 1-phenylbenzimidazoles has been largely overlooked. The aim of this research was to synthesize a small library of novel atropisomeric benzimidazole derivatives and explore their biological activity in various cancer and normal human cell lines. The new unique structural motif provides an interesting 3D architecture with axial chirality, which further contributes to molecular complexity and specificity. Racemates and their separated atropisomers arrested the cell cycle, caused apoptosis, and affected microtubule organization in cancer cells in vitro at different intensities. Moreover, this phenomenon was also verified by the inhibition of endothelial cell migration. These results showed that (+)-atropisomers, especially 5n, exhibit a stronger effect and show promise as agents for cancer therapy.</div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/ob/d4ob00863d?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141578326","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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

Photoredox-catalyzed C(sp2)–H trifluoromethylation of 3-methylene-isoindolin-1-ones under metal-free conditions† 无金属条件下光氧化催化 3-亚甲基异吲哚啉-1-酮的 C(sp2)-H 三氟甲基化反应。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob01046a

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A novel tumor theranostic strategy based on metabolic glycoengineering and disulfidptosis†‡ 基于代谢糖工程和二硫化硫的新型肿瘤治疗策略。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/d4ob01027b

引用次数: 0

Switching the regioselectivity of acid-catalyzed reactions of arylnaphtho[2,1-b]furans via a [1,2]-aryl shift† 通过 [1,2]- 芳基转变转换芳基萘并[2,1-b]呋喃的酸催化反应的区域选择性。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-08-28 DOI: 10.1039/D4OB01223B

I. S. Mekeda, R. Yu. Balakhonov and V. Z. Shirinian

{"title":"Switching the regioselectivity of acid-catalyzed reactions of arylnaphtho[2,1-b]furans via a [1,2]-aryl shift†","authors":"I. S. Mekeda, R. Yu. Balakhonov and V. Z. Shirinian","doi":"10.1039/D4OB01223B","DOIUrl":"10.1039/D4OB01223B","url":null,"abstract":"The [1,2]-aryl shift reaction was used to synthesize naphtho[2,1-b]furans as promising fluorescent scaffolds for organic electronics. The target compounds are furan analogues of phenanthrene formally accessed by isosteric replacement of the CH<img>CH moiety with an oxygen atom. The straightforward and robust approach involving a [1,2]-aryl shift as a key step provides easy access to a wide range of naphtho[2,1-b]furans with the possibility of late-stage functionalization. Efficient switching of the regioselectivity of acid-catalyzed reactions of arylnaphtho[2,1-b]furans via a [1,2]-aryl shift has been demonstrated. A one-pot protocol involving sequential intramolecular condensation/[1,2]-aryl shift/intermolecular oxidative aromatic coupling to provide access to binaphtho[2,1-b]furan analogues of BINOL was developed. The advantage of these compounds lies in the strong variation in chemical properties and spectral performance depending on the nature and position of the aryl substituent, which facilitates the synthesis of compounds with desired spectral characteristics and opens up prospects for their further use in electronics, biotechnologies and organic synthesis.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142118417","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

Exploring 2-mercapto-N-arylacetamide analogs as promising anti-melanogenic agents: in vitro and in vivo evaluation† 探索 2-巯基-N-芳基乙酰胺类似物作为有前途的抗黑色素生成剂：体外和体内评估。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-08-27 DOI: 10.1039/D4OB01225A

Hee Jin Jung, Hye Soo Park, Hye Jin Kim, Hyeon Seo Park, Young Eun Kim, Da Eun Jeong, Sang Gyun Noh, Yujin Park, Pusoon Chun, Hae Young Chung and Hyung Ryong Moon

{"title":"Exploring 2-mercapto-N-arylacetamide analogs as promising anti-melanogenic agents: in vitro and in vivo evaluation†","authors":"Hee Jin Jung, Hye Soo Park, Hye Jin Kim, Hyeon Seo Park, Young Eun Kim, Da Eun Jeong, Sang Gyun Noh, Yujin Park, Pusoon Chun, Hae Young Chung and Hyung Ryong Moon","doi":"10.1039/D4OB01225A","DOIUrl":"10.1039/D4OB01225A","url":null,"abstract":"Based on the hypothesis that the 2-mercaptoacetamide moiety chelates the copper ions of tyrosinase, 2-mercapto-N-arylacetamide (2-MAA) analogs were designed and synthesized as potential tyrosinase inhibitors. Four 2-MAA analogs showed low IC50 values ranging from 0.95 to 2.0 μM against mushroom tyrosinase, which was 12–26 times lower than that of kojic acid (IC50 value = 24.3 μM). However, according to a copper ion chelation experiment performed, the 2-MAA analogs did not participate in chelation with copper ions. To identify the mode of inhibition of the 2-MAA analogs, kinetic studies were performed, and the results were supported by docking results. In addition, docking simulation results suggested that the 2-MAA analogs strongly inhibited tyrosinase activity because of the hydrogen bonding of the amide NH group and the hydrophobic interaction of the aryl ring instead of chelation with copper ions. In experiments using B16F10 cells, 2-MAA analogs were shown to inhibit melanin production by inhibiting cellular tyrosinase activity. Western blotting showed that in addition to directly inhibiting tyrosinase activity, analog 7 also has an anti-melanogenic effect by inhibiting the expression of microphthalmia-associated transcription factor (MITF) and tyrosinase. The 2-MAA analogs showed no appreciable cytotoxicity against HaCaT and B16F10 cells, making them suitable for dermal applications. In a depigmentation experiment using zebrafish embryos, analogs 1 and 2 showed more potent depigmentation effects than kojic acid even at 1000 times lower concentration than that of kojic acid. These results suggest that the 2-MAA analogs are promising anti-melanogenic agents that can inhibit most tyrosinases in various species.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142102246","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

Catalyst-free reactions of anilines with β-chloroenones: synthesis of α-chloroenaminones and 1,4-benzodiazepines. 苯胺与 β-氯烯酮的无催化剂反应：合成 α-氯烯酮和 1,4-苯并二氮杂卓。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-08-27 DOI: 10.1039/d4ob00954a

Sundaram Suresh, Sowndarya Palla, Dai-Ru Chung, Hung-Sheng Chien, Bo-Xun Du, Jivan Shinde, Veerababurao Kavala, Ching-Fa Yao

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Aerobic oxidative C–C bond formation through C–H bond activation catalysed by flavin and iodine† 在黄素和碘的催化下，通过 C-H 键活化形成有氧氧化 C-C 键。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-08-27 DOI: 10.1039/D4OB01317D

Hazuki Miyake, Nico Ishige, Hayaki Okai and Hiroki Iida

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BODIPYs α-appended with distyryl-linked aryl bisboronic acids: single-step cell staining and turn-on fluorescence binding with d-glucose† BODIPYs α-与二芳基连接的芳基双硼酸：单步细胞染色和与 D-葡萄糖的荧光结合。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-08-27 DOI: 10.1039/D4OB01013B

Adil Alkaş, Joshua M. Kofsky, Em C. Sullivan, Daisy Nebel, Katherine N. Robertson, Chantelle J. Capicciotti, David L. Jakeman, Erin R. Johnson and Alison Thompson

引用次数: 0