Organic & Biomolecular Chemistry最新文献_第8页

Synthesis and structural confirmation of selaginpulvilin X. 舍拉金木素 X 的合成和结构确认。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-17 DOI: 10.1039/d4ob01529k

Tereza Havlíková, Sundaravelu Nallappan, Ivana Císařová, Lukas Rycek

引用次数: 0

C3-Chlorination of C2-substituted benzo[b]thiophene derivatives in the presence of sodium hypochlorite. C2 取代的苯并[b]噻吩衍生物在次氯酸钠存在下的 C3 氯化反应。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-17 DOI: 10.1039/d4ob01185f

Vincent Conrad Oppenheimer, Peter Le, Cathy Tran, Haobin Wang, Marino J E Resendiz

{"title":"C3-Chlorination of C2-substituted benzo[b]thiophene derivatives in the presence of sodium hypochlorite.","authors":"Vincent Conrad Oppenheimer, Peter Le, Cathy Tran, Haobin Wang, Marino J E Resendiz","doi":"10.1039/d4ob01185f","DOIUrl":"https://doi.org/10.1039/d4ob01185f","url":null,"abstract":"Benzo[b]thiophene rings are common synthons for the development of novel drugs and materials, and thus, the discovery of facile ways for their functionalization is of value. In this work, a new method for the C3-chlorination of C2-substituted benzothiophene derivatives is described. The chlorine source is sodium hypochlorite pentahydrate (NaOCl·5H2O), and optimal transformations occur in aqueous acetonitrile at 65-75 °C to provide the corresponding C3-halogenated products in variable yields (30-65%). The reaction occurs in the presence of vinyl and alkyl groups, while the presence of alcohols leads to competing oxidation reactions at the heterobenzylic position. The presence of a carbonyl group at the C2-position inhibited the halogenation reaction, while the use of benzofuran led to a highly exothermic reaction, presumably via the formation of a peroxide intermediate. Reactions carried out at lower temperatures led to side reactions associated with competing oxidative processes. To gain a better understanding of the mechanism of the reaction, DFT calculations were carried out, where the heteroatom enables the formation of a hypochlorous acidium ion that serves to generate a C2-C3 chloronium ion intermediate in a step-wise manner, which in turn leads to the formation of an S-stabilized C2-carbocation that undergoes re-aromatization to the corresponding C3-chlorinated products. To probe potential synthetic applications, a model C3-chloro derivative was coupled with phenylboronic acid using standard Suzuki-Miyaura coupling conditions.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11484177/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453675","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

Recognition of mixed-sequence double-stranded DNA regions using chimeric Invader/LNA probes. 使用嵌合 Invader/LNA 探针识别混合序列双链 DNA 区域。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-16 DOI: 10.1039/d4ob01403k

Michaela E Everly, Raymond G Emehiser, Patrick J Hrdlicka

{"title":"Recognition of mixed-sequence double-stranded DNA regions using chimeric Invader/LNA probes.","authors":"Michaela E Everly, Raymond G Emehiser, Patrick J Hrdlicka","doi":"10.1039/d4ob01403k","DOIUrl":"https://doi.org/10.1039/d4ob01403k","url":null,"abstract":"Development of robust oligonucleotide-based probe technologies, capable of recognizing specific regions of double-stranded DNA (dsDNA) targets, continues to attract considerable attention due to the promise of tools for modulation of gene expression, diagnostic agents, and new modalities against genetic diseases. Our laboratory pursues the development of various strand-invading probes. These include Invader probes, i.e., double-stranded oligonucleotide probes with one or more +1 interstrand zipper arrangements of intercalator-functionalized nucleotides like 2'-O-(pyren-1-yl)methyl-RNA monomers, and chimeric Invader/γPNA probes, i.e., heteroduplex probes between individual Invader strands and complementary γPNA strands. Here we report on the biophysical properties and dsDNA-recognition characteristics of a new class of chimeric probes-chimeric Invader/LNA probes-which are comprised of densely modified Invader strands and fully modified complementary LNA strands. The chimeric Invader/LNA probes form labile and distorted heteroduplexes, due to an apparent incompatibility between intercalating pyrene moieties and LNA strands. In contrast, the individual Invader and LNA strands form very stable duplexes with complementary DNA, which provides the driving force for near-stoichiometric recognition of model double-stranded DNA targets with single base-pair accuracy. The distinctive properties of chimeric Invader/LNA probes unlock exciting possibilities in molecular biology, and diagnostic and therapeutic fields.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11482323/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453693","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-catalysed radical difluoromethylation/cyclization of N-acryloyl-2-arylbenzimidazole to access CF₂H-substituted benzimidazo[2,1-a]isoquinolin-6(5H)-ones. 光氧化催化的 N-丙烯酰基-2-芳基苯并咪唑自由基二氟甲基化/环化反应，获得 CF2H 取代的苯并咪唑并[2,1-a]异喹啉-6(5H)-酮。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-15 DOI: 10.1039/d4ob01413h

Jinwei Yuan, Hongzhao Qu, Wenfeng Jia, Jinling Li, Liangru Yang, Yongmei Xiao, Yanli Yin, Lingbo Qu

引用次数: 0

Base-promoted cascade vinylogous Michael/Michael addition of alkylidene succinimides for the construction of penta-substituted cyclopentanes. 碱促进的亚烷基琥珀酰亚胺级联乙烯基迈克尔/迈克尔加成反应，用于构建五代环戊烷。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-15 DOI: 10.1039/d4ob01455c

Peiyao Liang, Siyi Chen, Xin Liu, Shenghan Teng, Shoulei Wang

引用次数: 0

Photochemical alkylation of quinoxalin-2(1H)-ones with N,N,N',N'-tetraalkylethylenediamine. 喹喔啉-2(1H)-酮与 N,N,N',N'-四烷基乙二胺的光化学烷基化反应。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-15 DOI: 10.1039/d4ob01494d

Yaqing Zhu, Yi Zhang, Xia Zhao, Kui Lu

引用次数: 0

Silver-catalyzed regioselective synthesis of pyrano heterocycles: a versatile route to samoquasine A derivatives. 银催化的吡喃杂环的区域选择性合成：获得翅果喹啉 A 衍生物的多功能途径。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-15 DOI: 10.1039/d4ob01446d

Kapil Chahal, Ravikumar Badhavath, Simran Kaur Matharu, Anjana Vinod, Damera Vani, Vijaya Rani Potluri, Balasubramanian Sridhar, Kallu Rajender Reddy

引用次数: 0

Electrochemical oxidative site-selective direct C-H activation of tanshinone IIA. 丹参酮 IIA 的电化学氧化位点选择性直接 C-H 活化。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-15 DOI: 10.1039/d4ob01479k

Jingyi Zhang, Shan Han, Siao Lu, Minghan Li, Zixun Gao, Linyu Zheng, Yulin Feng, Fangling Lu

引用次数: 0

Synthesis of biaryl-based carbazoles via C-H functionalization and exploration of their anticancer activities. 通过 C-H 功能化合成双芳基咔唑并探索其抗癌活性。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-15 DOI: 10.1039/d4ob01392a

Ramandeep Kaur, Haritha Dilip, Sivapriya Kirubakaran, Srinivasarao Arulananda Babu

{"title":"Synthesis of biaryl-based carbazoles via C-H functionalization and exploration of their anticancer activities.","authors":"Ramandeep Kaur, Haritha Dilip, Sivapriya Kirubakaran, Srinivasarao Arulananda Babu","doi":"10.1039/d4ob01392a","DOIUrl":"https://doi.org/10.1039/d4ob01392a","url":null,"abstract":"The synthesis of a library of new biaryl-based carbazoles via bidentate directing group-assisted C-H functionalization and preliminary screening of the anticancer properties of biaryl-based carbazoles is reported. While various classes of modified carbazoles are known for their applications in materials and medicinal chemistry, to our knowledge, the biological activities of designed biaryl-based carbazoles have been rarely known. Given the prominence of carbazoles in research in medicinal chemistry, we envisioned the scope for new scaffolds of carbazole-based biaryl structures. We screened the synthesized biaryl-based carbazoles for their anticancer properties against various cancer cell lines such as HeLa (cervical cancer), HCT116 (colon cancer), MDA-MB-231 and MDA-MB-468 (breast cancer). In addition, the hits were also tested in the human embryonic kidney cell line HEK293T to assess their impact on the viability of normal human cells in the presence of these compounds. In this preliminary study, we identified some of the biaryl-based carbazoles as lead compounds with anticancer activities.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453701","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

Synthesis, antioxidant and structural properties of modified ebselen derivatives and conjugates. 改性依布硒衍生物和共轭物的合成、抗氧化性和结构特性。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-15 DOI: 10.1039/d4ob01400f

Adrian I Doig, Kai N Sands, Bienca Boongaling, Wen Zhou, Thomas G Back

{"title":"Synthesis, antioxidant and structural properties of modified ebselen derivatives and conjugates.","authors":"Adrian I Doig, Kai N Sands, Bienca Boongaling, Wen Zhou, Thomas G Back","doi":"10.1039/d4ob01400f","DOIUrl":"https://doi.org/10.1039/d4ob01400f","url":null,"abstract":"Ebselen is a drug in clinical trials for several diseases and degenerative conditions where oxidative stress is implicated. A series of novel ebselen analogues was synthesized, including hydroxy-, alkoxy- and aminomethylene derivatives, as well as hybrid species where the ebselen selenium atom is shared with other potent antioxidant structures, such as cyclic selenenyl sulfide, cyclic seleninate ester and spirodioxyselenurane moieties. Conjugates of ebselen with cholesterol, prednisolone and the radical inhibitor BHT were also prepared. The products were tested for antioxidant activity in an NMR-based assay by measuring the rate of consumption of benzyl thiol or the production of dibenzyl disulfide in the presence of hydrogen peroxide when catalyzed by the ebselen analogues. Activities ranged from 12 to 0.12 times that of ebselen. The oxidation of the 2-hydroxymethylene derivative of ebselen was faster than thiolysis in the initial step and the overall rate was further accelerated under basic conditions. The corresponding selenenyl sulfide analogue underwent very slow disproportionation under neutral conditions that was enhanced by the presence of a base catalyst. During investigation of possible fluxional behaviour of a bis-amide analogue, an unusual tetraphenyphosphonium salt of a tricoordinate selenium pincer anion was discovered with exceptionally potent catalytic activity, 130 times that of ebselen. In addition to rate measurements, X-ray crystallography and DFT computational methods were also employed to gain further structural and mechanistic insights.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453703","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