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TBAB-catalyzed assisted C-C/C-N bond formations: An efficient approach to dihydrobenzo[b][1,8]naphthyridin derivatives via metal free Cascade annulation TBAB 催化辅助 C-C/C-N 键形成：通过无金属级联环化获得二氢苯并[b][1,8]萘啶衍生物的有效方法
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-08-02 DOI: 10.1080/00397911.2024.2379447
Jiming Liu , Xinghua Zheng , Wenjun Luo , Zhengwang Chen , Fei Ling
{"title":"TBAB-catalyzed assisted C-C/C-N bond formations: An efficient approach to dihydrobenzo[b][1,8]naphthyridin derivatives via metal free Cascade annulation","authors":"Jiming Liu ,&nbsp;Xinghua Zheng ,&nbsp;Wenjun Luo ,&nbsp;Zhengwang Chen ,&nbsp;Fei Ling","doi":"10.1080/00397911.2024.2379447","DOIUrl":"10.1080/00397911.2024.2379447","url":null,"abstract":"<div><p>An eco-friendly, metal-free approach for synthesizing dihydrobenzo[<em>b</em>][1,8]naphthyridine derivatives has been established. This method employs <em>ortho</em>-chloroquinolin-α,β-unsaturated ketones as dipolarophiles and acyclic enaminones as amphiphilic nucleophiles, enabling a formal [3 + 3] annulation reaction under phase-transfer catalysis to offed the targeted products. It boasts transition-metal-free conditions, broad functional group compatibility, and straightforward operational procedures.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 15","pages":"Pages 1252-1262"},"PeriodicalIF":1.8,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141942790","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
1,4,5,8-tetrasubstituted dihydroanthracene-based triptycene trisquinones: Synthesis, structural, and physicochemical characterization 1,4,5,8-四取代二氢蒽基三庚烯三醌：合成、结构和理化特性分析
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-08-02 DOI: 10.1080/00397911.2024.2381074
Chang-Seok Hyun , Joohwan Eo , Ji Eon Kwon , Byeong-Kwan An
{"title":"1,4,5,8-tetrasubstituted dihydroanthracene-based triptycene trisquinones: Synthesis, structural, and physicochemical characterization","authors":"Chang-Seok Hyun ,&nbsp;Joohwan Eo ,&nbsp;Ji Eon Kwon ,&nbsp;Byeong-Kwan An","doi":"10.1080/00397911.2024.2381074","DOIUrl":"10.1080/00397911.2024.2381074","url":null,"abstract":"<div><p>1,4,5,8-tetrasubstituted dihyroanthracene-based triptycene trisquinones (TT) molecules, THAO-TT and <em>tris</em>(THAO)-TT, were synthesized by Diels–Alder reaction between TT and 1,4,5,8-tetrakis(hexyloxy)anthracene to produce the extended triptycene derivatives containing electron-accepting functionality. The prepared THOA-TT and <em>tris</em>(THOA)-TT exhibited excellent thermal stability owing to the rigid TT framework. The optical and redox properties of THOA-TT and <em>tris</em>(THOA)-TT were controlled by the homoconjugation between the benzoquinone units and the peripheral units through the connecting methine groups.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 15","pages":"Pages 1263-1272"},"PeriodicalIF":1.8,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141802653","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 and characterization of new highly fluorinated phosphoramidates bearing different alkylamino groups 带有不同烷基氨基的新型高氟化磷酰胺的合成与表征
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-08-02 DOI: 10.1080/00397911.2024.2382784
Samar Argoubi , M. A. Sanhoury , I. Zerough , E. Manoury , I. Chehidi
{"title":"Synthesis and characterization of new highly fluorinated phosphoramidates bearing different alkylamino groups","authors":"Samar Argoubi ,&nbsp;M. A. Sanhoury ,&nbsp;I. Zerough ,&nbsp;E. Manoury ,&nbsp;I. Chehidi","doi":"10.1080/00397911.2024.2382784","DOIUrl":"10.1080/00397911.2024.2382784","url":null,"abstract":"<div><p>Seventeen new highly fluorinated phosphoramidates containing alkylamino moieties of the type (R<sub>F</sub>O)<sub>2</sub>P(O)NHR (R = CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>, (CH<sub>2</sub>)<sub>3</sub>CH<sub>3</sub>, (CH<sub>2</sub>)<sub>4</sub>-CH<sub>3</sub>, CH(CH<sub>3</sub>)<sub>2</sub>, C<sub>6</sub>H<sub>11</sub>, CH<sub>2</sub>CH<sub>2</sub>-C<sub>6</sub>H<sub>5</sub>, CH<sub>2</sub>-C<sub>6</sub>H<sub>5</sub> or C<sub>6</sub>H<sub>5</sub>; R<sub>F</sub> = CH<sub>2</sub>CF<sub>3</sub>, CH<sub>2</sub>C<sub>2</sub>F<sub>5</sub> or CH<sub>2</sub>CH<sub>2</sub>C<sub>6</sub>F<sub>13</sub>) were synthesized. These compounds were obtained through the reaction of primary amines with bis(polyfluoroalkyl)phosphites as phosphorylating agents, using molecular iodine as a mild catalyst and in the presence of H<sub>2</sub>O<sub>2.</sub>This method was chosen out of various literature common methods, which were thoroughly investigated using <sup>31</sup>P NMR spectroscopy. In addition, the variation in reaction rates among different phosphites was studied and compared with previous research findings. The title phosphoramidates were fully characterized using multinuclear (<sup>1</sup>H,<sup>13</sup>C,<sup>31</sup>P, and <sup>19</sup>F) NMR, IR, and HRMS techniques.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 15","pages":"Pages 1273-1283"},"PeriodicalIF":1.8,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141813488","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
Hantzsch reaction: The important key for pyridine/dihydropyridine synthesis 汉兹奇反应：吡啶/二氢吡啶合成的重要关键
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-08-02 DOI: 10.1080/00397911.2024.2377738
{"title":"Hantzsch reaction: The important key for pyridine/dihydropyridine synthesis","authors":"","doi":"10.1080/00397911.2024.2377738","DOIUrl":"10.1080/00397911.2024.2377738","url":null,"abstract":"<div><p>Pyridines and its derivatives are an important class of heterocyclic compounds of low molecular weight. They have been used in the treatment of a various diseases like cardiovascular disease, antioxidant, antibacterial, anti-tubercular, anticancer, anticoagulant, etc. In 1882, Arthur Hantzsch reported pyridine derivative synthesis using different aldehydes, 2 molecules β-keto ester and ammonium acetate to give a Hantzsch ester or 1,4-dihydropyridine derivatives. This review article focuses on different protocols for Hantzsch reaction using different catalysts like β-cyclodextrin–polyurethane polymer (β-CDPU), chitosan nanoparticles (NPs), salicylic acid, p-toluenesulfonic acid (p-TSA), alginic acid, Fe-TUD-1, PdRuNi@GO, Ceric Ammonium Nitrate (CAN), sulfate polyborate, etc. for the synthesis of pyridine derivatives.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 15","pages":"Pages 1221-1244"},"PeriodicalIF":1.8,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141584941","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-step synthesis of sugar nucleotides under optimized conditions 在优化条件下一步合成糖核苷酸
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-08-02 DOI: 10.1080/00397911.2024.2380063
Kota Fujihara , Hatsuo Yamamura , Atsushi Miyagawa
{"title":"One-step synthesis of sugar nucleotides under optimized conditions","authors":"Kota Fujihara ,&nbsp;Hatsuo Yamamura ,&nbsp;Atsushi Miyagawa","doi":"10.1080/00397911.2024.2380063","DOIUrl":"10.1080/00397911.2024.2380063","url":null,"abstract":"<div><p>Sugar nucleotides are essential substrates used for synthesizing bioactive oligosaccharides in enzymatic reactions, however, their preparation via chemical and enzyme reactions is challenging. Therefore, we investigated the synthesis of sugar nucleotides under optimal conditions using a facile one-step reaction. Seven sugar nucleotides were synthesized via an optimized one-step reaction in 40–80% yield, exhibiting a preference for 1,2-trans glycoside. Moreover, a gram-scale synthesis of UDP-galactose resulted in a 46% (578 mg) yield.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 15","pages":"Pages 1245-1251"},"PeriodicalIF":1.8,"publicationDate":"2024-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141829533","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
BF3‧OEt2 promoted synthesis of 9-fluorenlidene appended 2-hydrazinopyridine imines from (phenylethynyl)-fluorene and 2-hydrazinopyridine derivatives BF3‧OEt2 促进从（苯乙炔基）-芴和 2-肼基吡啶衍生物合成 9-亚芴基 2-肼基吡啶亚胺的过程
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-08-01 DOI: 10.1080/00397911.2024.2385538
Suresh Snoxma Smile , Harichandran Gurusamy , Ponnusamy Shanmugam
{"title":"BF3‧OEt2 promoted synthesis of 9-fluorenlidene appended 2-hydrazinopyridine imines from (phenylethynyl)-fluorene and 2-hydrazinopyridine derivatives","authors":"Suresh Snoxma Smile ,&nbsp;Harichandran Gurusamy ,&nbsp;Ponnusamy Shanmugam","doi":"10.1080/00397911.2024.2385538","DOIUrl":"10.1080/00397911.2024.2385538","url":null,"abstract":"<div><p>Reaction of 9-fluorene propargylic alcohols and substituted-2-hydrazinopyridine using BF<sub>3</sub>·OEt<sub>2</sub> as a Lewis acid catalyst afforded 9-fluorenlidene appended 2-hydrazinopyridine imine derivatives has been developed. The scope of the reaction is demonstrated by selecting a range of fluorene propargylic alcohols and substituted 2-hydrazinopyridine imines. All the synthesized molecules were characterized using various spectroscopic and analytical techniques including <sup>1</sup>H NMR,<sup>13</sup>C NMR, and Mass spectrometry. A plausible reaction mechanism for forming title compounds via propargylic allenyl carbocation is postulated. The synthetic utility of products thus formed is demonstrated by utilizing Suzuki coupling.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 17","pages":"Pages 1413-1422"},"PeriodicalIF":1.8,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141882958","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 and synthesis of mono/bis isoxazoline and pyrroline pendant chromone derivatives-anti-cancer activity 单/双异噁唑啉和吡咯啉垂铬酮衍生物的设计与合成--抗癌活性
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-07-17 DOI: 10.1080/00397911.2024.2375768
Jayaprakash Rao Yerrabelly , Subbanarasimhulu Porala , Venkateshwar Reddy Kasireddy , Hemasri Yerrabelly , Ramakrishna Kancha
{"title":"Design and synthesis of mono/bis isoxazoline and pyrroline pendant chromone derivatives-anti-cancer activity","authors":"Jayaprakash Rao Yerrabelly ,&nbsp;Subbanarasimhulu Porala ,&nbsp;Venkateshwar Reddy Kasireddy ,&nbsp;Hemasri Yerrabelly ,&nbsp;Ramakrishna Kancha","doi":"10.1080/00397911.2024.2375768","DOIUrl":"10.1080/00397911.2024.2375768","url":null,"abstract":"<div><p>A simple and efficient route for the synthesis of a series of new mono/bis isoxazolines, and pyrroline linked chromone heterocyclic hybrids has been developed from 2-aminochromone <em>via</em> key intermediate mono and 2-(diallylamino)chromen-4-one. The intermediate subjected to the [1,3] dipolar cycloaddition with <em>insitu</em> generated nitrile oxides and ring-closing metathesis to generate the regio selective Isoxazolines and 3-pyrrolines. All the derivatives were screened for their anti-cancer activity (Cell viability), compared to the standard drug Imatinib. Compounds <strong>13b</strong> and <strong>13e, 14b</strong> and <strong>14g</strong> showed good inhibition at 10 µM concentration.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 14","pages":"Pages 1168-1176"},"PeriodicalIF":1.8,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141613378","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
Studies in synthesis and anticancer activity of 6-aminocoumarin/piperazine hybrids 6-aminocoumarin/piperazine 杂交化合物的合成和抗癌活性研究
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-07-17 DOI: 10.1080/00397911.2024.2377285
Jayashree V. Patil , Shubhangi S. Soman , Anjali Singh , Suresh Balakrishanan
{"title":"Studies in synthesis and anticancer activity of 6-aminocoumarin/piperazine hybrids","authors":"Jayashree V. Patil ,&nbsp;Shubhangi S. Soman ,&nbsp;Anjali Singh ,&nbsp;Suresh Balakrishanan","doi":"10.1080/00397911.2024.2377285","DOIUrl":"10.1080/00397911.2024.2377285","url":null,"abstract":"<div><p>Breast cancer and lung cancer causes a high rate of mortality all over the world. Pursuing our efforts toward searching for efficient anticancer agents herein a series of coumarin/piperazine hybrids <strong>10a-f</strong>, <strong>12a-d</strong>, <strong>14</strong> were synthesized and subsequently assessed for their potential <em>In Vitro</em> anticancer activity, against A549 (Lung cancer) and MCF-7 (breast cancer) cell lines using MTT assay. Encouragingly, all the synthesized compounds displayed varying degrees of effectiveness, ranging from good to moderate activity against these two cancer cell lines. However, amongst all the compounds synthesized, compound <strong>12c</strong> exhibited notably higher potency against both A549 and MCF-7 cell lines, with an IC<sub>50</sub> of <strong>0.40 µM</strong> and <strong>0.51 µM,</strong> respectively. Additionally, the study delved deeper by conducting EtBr/AO assays, unveiling the induction of apoptosis. Furthermore, investigations into Reactive Oxygen Species (ROS) were conducted by using DCFH-DA dye. To understand the behavioral patterns and selectivity of the synthesized compounds, computational techniques were employed alongside experimental analysis. Utilizing density functional theory (DFT) calculations, electronic and structural characteristics were determined for compound <strong>12c</strong> These calculations were then compared and associated with the observed biological effects. Additionally, molecular docking was utilized to investigate how compounds <strong>12c</strong> interacted with crucial apoptotic genes, specifically targeting p53 and caspase 3. Compound <strong>12c</strong> exhibited docking scores of −8.4 kcal/mol and −7.9 kcal/mol for p53 and caspase 3 respectively. Lastly, an <em>in Silico</em> ADME study was performed to evaluate the compounds’ potential as drug candidates.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 14","pages":"Pages 1186-1208"},"PeriodicalIF":1.8,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141640245","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
Recent advances of 9,10-phenanthrenequinone (PQ) in photoredox catalysis 9,10-菲醌 (PQ) 在光氧化催化方面的最新进展
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-07-17 DOI: 10.1080/00397911.2024.2358521
{"title":"Recent advances of 9,10-phenanthrenequinone (PQ) in photoredox catalysis","authors":"","doi":"10.1080/00397911.2024.2358521","DOIUrl":"10.1080/00397911.2024.2358521","url":null,"abstract":"<div><p>Recently, photoredox catalysis using 9,10-phenanthrenequinone (PQ) has emerged as an efficient method for the transformation of various organic compounds. Low cost and good availability make it a promising alternate to typical transition metal complex-based photocatalysts. It has emerged as an alternative in photoredox catalysis highlighting recent advancement in organic transformation using (PQ) as photocatalyst.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 14","pages":"Pages 1129-1146"},"PeriodicalIF":1.8,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141153248","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 indole derivatives from the S3•−-mediated intramolecular cyclization of o-alkynylanilines 通过 S3--介导的邻炔基苯胺分子内环化合成吲哚衍生物
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-07-17 DOI: 10.1080/00397911.2024.2373164
{"title":"Synthesis of indole derivatives from the S3•−-mediated intramolecular cyclization of o-alkynylanilines","authors":"","doi":"10.1080/00397911.2024.2373164","DOIUrl":"10.1080/00397911.2024.2373164","url":null,"abstract":"<div><p>A new method for the synthesis of 2-(phenyl)indole via the cyclization of 2-(phenylethynyl)aniline in the presence of K<sub>2</sub>S was established, which was used to prepare 2-(phenyl)indole derivatives in high yields (66%-93%). Mechanistic studies have revealed that a trisulfur radical anion (S<sub>3</sub><sup>•−</sup>) is generated from K<sub>2</sub>S, which acts as an initiator for the intramolecular addition of the alkyne and the amino group in <em>o</em>-alkynylaniline, ultimately leading to the formation of the indole derivative. This method provides a new way to prepare 2-(phenyl)indoles and a novel application of S<sub>3</sub><sup>•−</sup> in organic synthesis.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 14","pages":"Pages 1147-1158"},"PeriodicalIF":1.8,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141584942","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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