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Synthesis and antiproliferative evaluation of novel chrysin selenocyanates
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-02-01 DOI: 10.1080/00397911.2024.2445860
Zhiping Liu , Lijie Che , Yunlong Ban , Maixia Liu , Xiyan Tang , Yanmin Huang , Jianguo Cui , Chunfang Gan
{"title":"Synthesis and antiproliferative evaluation of novel chrysin selenocyanates","authors":"Zhiping Liu ,&nbsp;Lijie Che ,&nbsp;Yunlong Ban ,&nbsp;Maixia Liu ,&nbsp;Xiyan Tang ,&nbsp;Yanmin Huang ,&nbsp;Jianguo Cui ,&nbsp;Chunfang Gan","doi":"10.1080/00397911.2024.2445860","DOIUrl":"10.1080/00397911.2024.2445860","url":null,"abstract":"<div><div>Selenocyano fragments with distinct structural characteristics were successfully incorporated into the 5- and 7-positions of chrysin via etherification and esterification of its hydroxyl groups. Eleven novel chrysin selenocyanates were synthesized, and their structures characterized by NMR and HRMS. The activities of all compounds were evaluated against human cervical cancer cell lines HeLa, ovarian cancer cell lines SKOV-3, and breast carcinoma cell lines MCF-7 using MTT assays. Results indicated that esterified chrysin derivatives significantly inhibited HeLa cells, while alkylated chrysin ethers showed notable activity against SKOV-3 and MCF-7 cells. Compounds <strong>5c</strong> and <strong>5e</strong> exhibited the strongest inhibitory effects on SKOV-3 cells, with IC<sub>50</sub> values of 2.27 ± 0.19 μM and 2.51 ± 0.33 μM, respectively. The introduction of diselenocyanate at both the 5- and 7-positions demonstrated superior inhibitory activity compared to a single selenocyanate at the 7-position alone. The findings may aid in designing novel chemotherapeutic drugs.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 3","pages":"Pages 259-269"},"PeriodicalIF":1.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143097177","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
One-pot multicomponent reaction: Synthesis, characterization and antibacterial evaluation of novel tri and tetra-substituted imidazoles
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-02-01 DOI: 10.1080/00397911.2024.2447087
Bahgat R. M. Hussein , Hayam H. Mohammed , Eman A. Ahmed , Omran A. Omran
{"title":"One-pot multicomponent reaction: Synthesis, characterization and antibacterial evaluation of novel tri and tetra-substituted imidazoles","authors":"Bahgat R. M. Hussein ,&nbsp;Hayam H. Mohammed ,&nbsp;Eman A. Ahmed ,&nbsp;Omran A. Omran","doi":"10.1080/00397911.2024.2447087","DOIUrl":"10.1080/00397911.2024.2447087","url":null,"abstract":"<div><div>Using one-pot multicomponent reactions, two new series of imidazoles (<strong>4a–o</strong> and <strong>6a–d</strong>), were synthesized due to their great biological activity. The first series was accomplished by the reaction of <em>O</em>-alkyl vanillins <strong>1a–c</strong>, ammonium acetate <strong>2</strong>, and benzil derivatives <strong>3a–e</strong> in ethanol, while the second series was obtained by reacting <em>O</em>-alkyl vanillins <strong>1a</strong>, ammonium acetate <strong>2</strong>, benzil <strong>3a</strong>, and amino compounds (aniline <strong>5a</strong> or amino acids <strong>5b–d</strong>) in acetic acid. The <em>in vitro</em> antibacterial activity of the novel synthetic imidazoles was assessed against strains of gram positive bacteria, such as <em>Bacillus cereus</em> and <em>Staphylococcus aureus</em>, and gram negative bacteria, such as <em>Pseudomonas aeruginosa</em> and <em>Escherichia coli</em>. The findings indicated that some of the evaluated items have promising antibacterial agents, especially imidazoles <strong>4d</strong> and <strong>4e</strong> for (+G) bacteria and imidazoles <strong>4c</strong> and <strong>4f</strong> for (−G) bacteria.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 3","pages":"Pages 270-280"},"PeriodicalIF":1.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143097171","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
Guanidine HCl: a green organo-catalyst for effective multicomponent synthesis of benzodiazepine derivatives under aquatic environment
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-02-01 DOI: 10.1080/00397911.2025.2457439
Omkar C. Dongare , Pradeep U. Yadav , Yatin U. Gadkari
{"title":"Guanidine HCl: a green organo-catalyst for effective multicomponent synthesis of benzodiazepine derivatives under aquatic environment","authors":"Omkar C. Dongare ,&nbsp;Pradeep U. Yadav ,&nbsp;Yatin U. Gadkari","doi":"10.1080/00397911.2025.2457439","DOIUrl":"10.1080/00397911.2025.2457439","url":null,"abstract":"<div><div>An efficient and environmentally friendly methodology has been developed for the synthesis of 1,5-benzodiazepine derivatives, employing catalytic amounts of guanidine hydrochloride in aqueous conditions. The desired compounds were obtained with high yields by combining variously substituted aryl aldehydes with o-phenylene diamine and dimedone. The protocol offers several advantages, including a rapid reaction time, the use of greener solvents, simple workup procedures, and an uncomplicated purification process, ensuring energy efficiency and versatility. Also, the catalyst can be recycled up to 4-5 cycles without compromising the overall yield, adding to the overall merit of this method. Furthermore, green chemistry metrics such as EcoScale, E-Factor, and Process Mass Intensity (PMI) were employed to evaluate the environmental impact of the process thoroughly.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 5","pages":"Pages 394-404"},"PeriodicalIF":1.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143377645","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
New route to preparation of loxoprofen through Mizoroki-Heck reaction as the key step
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-02-01 DOI: 10.1080/00397911.2024.2441331
Huansheng Chen , Dandan Tang , Long Lin , Wei Yuan , Yu Chen , Xianhua Pan
{"title":"New route to preparation of loxoprofen through Mizoroki-Heck reaction as the key step","authors":"Huansheng Chen ,&nbsp;Dandan Tang ,&nbsp;Long Lin ,&nbsp;Wei Yuan ,&nbsp;Yu Chen ,&nbsp;Xianhua Pan","doi":"10.1080/00397911.2024.2441331","DOIUrl":"10.1080/00397911.2024.2441331","url":null,"abstract":"<div><div>The current study describes a new preparation of loxoprofen. The whole process includes five steps from cheap cyclopentanone and methyl 4-bromophenylacetate as the starting materials. The key ­intermediate is obtained through Mizoroki-Heck reaction of 2-methylenecyclopentanone and methyl 2-(4-bromophenyl)propanoate. The desired loxoprofen is yielded through hydrogenation followed by hydrolysis in 56% overall yield with 99.7% purity.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 3","pages":"Pages 236-250"},"PeriodicalIF":1.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143097180","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 of multifunctionalized allyl isothiocyanates via isomerization of Morita-Baylis-Hillman adduct-derived allylic thiocyanates
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-02-01 DOI: 10.1080/00397911.2024.2441336
Sang Gyu Shin , Hyun-Woo Oh , Byung Chang Kim , Jaeseung Ok , Seung In Lee , Sung Pyo Youn , Hyun Hee Bae , Ji Yoon Park , Jin Woo Han , Chang Hoon Lee
{"title":"Synthesis of multifunctionalized allyl isothiocyanates via isomerization of Morita-Baylis-Hillman adduct-derived allylic thiocyanates","authors":"Sang Gyu Shin ,&nbsp;Hyun-Woo Oh ,&nbsp;Byung Chang Kim ,&nbsp;Jaeseung Ok ,&nbsp;Seung In Lee ,&nbsp;Sung Pyo Youn ,&nbsp;Hyun Hee Bae ,&nbsp;Ji Yoon Park ,&nbsp;Jin Woo Han ,&nbsp;Chang Hoon Lee","doi":"10.1080/00397911.2024.2441336","DOIUrl":"10.1080/00397911.2024.2441336","url":null,"abstract":"<div><div>An efficient method to synthesize functionalized allyl isothiocyanates in moderate yields has been demonstrated, based on the isomerization of Morita-Baylis-Hillman adduct-derived allylic thiocyanates. This methodology offers obvious advantages such as easy purification, atom economy, and a broad scope of substrates.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 3","pages":"Pages 251-258"},"PeriodicalIF":1.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143097178","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
Unlocking the imidazole ring: A comprehensive review of synthetic strategies
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-02-01 DOI: 10.1080/00397911.2024.2414201
Peter Solo , M. Arockia Doss
{"title":"Unlocking the imidazole ring: A comprehensive review of synthetic strategies","authors":"Peter Solo ,&nbsp;M. Arockia Doss","doi":"10.1080/00397911.2024.2414201","DOIUrl":"10.1080/00397911.2024.2414201","url":null,"abstract":"<div><div>Imidazole, a five-membered heterocyclic compound, has multipurpose applications for its bioactivity, uses in charge transport materials, and NLO materials. The review provides a comprehensive survey of the synthetic strategies of imidazole from various starting materials, highlighting their percentage yield and mechanistic insights. The most popular starting materials for the syntheses of imidazole include diketones, cyanides, imines, amidines, imidamides, di-amines, and oximes. Although the selection of a particular synthetic strategy will depend largely on the desired imidazole derivative, the survey consists of more than a century of research on imidazole synthetic procedures, starting with Heinrich Debus synthesis in 1858 till the present day. Most recent advancements and future perspectives in the field have been explored. The study will help researchers choose the most suitable starting material, catalyst, solvent, or reaction conditions for the synthesis of various imidazole derivatives.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 3","pages":"Pages 183-235"},"PeriodicalIF":1.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143097179","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
Electrochemical Fe-catalyzed deoxygenative alkoxycarbonylation of imidazoheterocycles with carbazates
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-02-01 DOI: 10.1080/00397911.2025.2458623
Jun-Qi Zhang , Hangfei Huang , Ying Fu
{"title":"Electrochemical Fe-catalyzed deoxygenative alkoxycarbonylation of imidazoheterocycles with carbazates","authors":"Jun-Qi Zhang ,&nbsp;Hangfei Huang ,&nbsp;Ying Fu","doi":"10.1080/00397911.2025.2458623","DOIUrl":"10.1080/00397911.2025.2458623","url":null,"abstract":"<div><div>Imidazo[1,2-a]pyridine derivatives possess widespread applications in the pharmaceutical industry and bioactive natural products. The diverse functionalization of this skeleton has attracted much attention from chemists. Herein, we reported an electrochemical deoxygenative alkoxycarbonylation of imidazoheterocycles by using electrons as the traceless oxidant under mild and oxidant-free conditions. Notably, our strategy provided a green and practical approach for introducing ester group into imidazo[1,2-a]pyridine derivatives by employing easily available and bench-stable carbazates as ester source.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 5","pages":"Pages 422-432"},"PeriodicalIF":1.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143377775","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
Deprotection of nucleosides by lysine-assisted methanolysis of esters and amides
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-01-31 DOI: 10.1080/00397911.2025.2456103
Jyothi Dhuguru , Brandon English , Ryan W. Dellinger , Marie E. Migaud
{"title":"Deprotection of nucleosides by lysine-assisted methanolysis of esters and amides","authors":"Jyothi Dhuguru ,&nbsp;Brandon English ,&nbsp;Ryan W. Dellinger ,&nbsp;Marie E. Migaud","doi":"10.1080/00397911.2025.2456103","DOIUrl":"10.1080/00397911.2025.2456103","url":null,"abstract":"<div><div>A deacylation method was developed based on lysine-assisted methanolysis of nucleoside-derived esters and arylamides. The present methodology complements well-established deacylation methods, using a minimum molar equivalency of lysine and methanol under mild heating to generate the deacylated nucleoside and recyclable lysine and volatile methyl esters as byproducts. A variety of acylated canonical nucleosides and hydrolytically labile non-canonical nucleosides like nicotinamide riboside (NR) and its reduced form (NRH) were deprotected under such lysine-assisted conditions, demonstrating the versatility of this approach. Having determined this one-pot process’s <em>E</em>-factor and reaction mass index, we find this method greener than the more established deacylation processes.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 5","pages":"Pages 381-393"},"PeriodicalIF":1.8,"publicationDate":"2025-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143377774","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
Selectfluor-mediated oxidative deamination: A scalable approach to aromatic aldehydes synthesis
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-01-31 DOI: 10.1080/00397911.2025.2458625
Chengkan Gao , Lin Li , Xiangyang Lin , Renming Pan , Wenfang Zheng
{"title":"Selectfluor-mediated oxidative deamination: A scalable approach to aromatic aldehydes synthesis","authors":"Chengkan Gao ,&nbsp;Lin Li ,&nbsp;Xiangyang Lin ,&nbsp;Renming Pan ,&nbsp;Wenfang Zheng","doi":"10.1080/00397911.2025.2458625","DOIUrl":"10.1080/00397911.2025.2458625","url":null,"abstract":"<div><div>The catalyst-free oxidative deamination without over-oxidation constitutes a considerable challenge in the synthesis of aromatic aldehydes. Herein, we introduce a Selectfluor-mediated Lewis acid system that achieves the oxidative deamination of benzylic amines with α-C-H bond activation to yield aromatic aldehydes. Noteworthy features include the direct use of Selectfluor that can activate the α-C-H bond under catalyst- and base-free conditions via the in-situ dehydrofluorination effect. The approach is demonstrated for a broad scope of benzylic amines without over-oxidation and accomplishes 200 mmol scale synthesis.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 5","pages":"Pages 433-441"},"PeriodicalIF":1.8,"publicationDate":"2025-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143377776","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
Design, synthesis, anticancer evaluation and molecular docking studies of different aryl derivatives of azaindole-pyrimidine-1,3,4-oxadiazoles
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-01-29 DOI: 10.1080/00397911.2025.2457440
Vankayala Ramesh Babu , V. D. N. Kumar Abbaraju , Reddymasu Sreenivasulu , Dasari Sravani , Singamsetty Rangaswamy , Ravi Kumar Kapavarapu , Deva H.Puranam , Farha Farahim
{"title":"Design, synthesis, anticancer evaluation and molecular docking studies of different aryl derivatives of azaindole-pyrimidine-1,3,4-oxadiazoles","authors":"Vankayala Ramesh Babu ,&nbsp;V. D. N. Kumar Abbaraju ,&nbsp;Reddymasu Sreenivasulu ,&nbsp;Dasari Sravani ,&nbsp;Singamsetty Rangaswamy ,&nbsp;Ravi Kumar Kapavarapu ,&nbsp;Deva H.Puranam ,&nbsp;Farha Farahim","doi":"10.1080/00397911.2025.2457440","DOIUrl":"10.1080/00397911.2025.2457440","url":null,"abstract":"<div><div>The aryl-azaindole-pyrimidine-1,3,4-oxadiazole derivatives (<strong>12a–j</strong>) were synthesized by Suzuki coupling reaction between bromo-azaindole-1,3,4-oxadiaole intermediate <strong>10</strong> and various aryl boronic acids (<strong>11a–j</strong>) by using of Pd(dppf)Cl<sub>2</sub> and K<sub>2</sub>CO<sub>3</sub> in 1,4-dioxane/H<sub>2</sub>O. Here, the Suzuki coupling mechanism starts with the oxidative addition followed by transmetallation and ends with reductive elimination. These derivatives were screened in vitro anticancer applications against four human cancer cell lines including MCF-7, A549, Colo-205, and A2780 by employing of MTT method, the well-known chemotherapeutic agent as etoposide used as positive control. Among them, compound <strong>12a</strong> bearing 3,4,5-trimethoxy substituent on the aryl moiety displayed good activity as compared with positive control against MCF-7, A549, Colo-205, and A2780 cell lines with IC<sub>50</sub> values of 1.10 ± 0.84 µM, 1.07 ± 0.067 µM, 1.20 ± 0.95 µM, and 1.34 ± 0.66 µM respectively. Compounds <strong>12a</strong> and <strong>12b</strong> primarily engage in hydrophobic interactions such as pi-pi stacked, amide-pi stacked, pi-alkyl, and alkyl interactions. Specifically, nucleotides DG13, DA12, and arg503 display pi-pi stacked and amide-pi stacked interactions.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 5","pages":"Pages 405-421"},"PeriodicalIF":1.8,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143377777","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
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