Abstract Naphthoquinones, a diverse group of natural compounds with a 1,4-naphthoquinone core structure, have gained attention for their pharmacological properties. The anticancer activity of these compounds is attributed to their ability to accept electrons, leading to the generation of reactive oxygen species that cause DNA damage and cell death. In recent studies, hydroxy-1,4-naphthoquinone derivatives, including daunorubicin, have shown promising inhibitory effects against several human cancers, such as acute myeloid leukemia, chronic myelogenous leukemia, and Kaposi’s sarcoma. To further explore their potential as anticancer agents, this research article focuses on the design and synthesis of natural product inspired naphthoquinone-based glycohybrids. These glycohybrids are designed based on the structures of bioactive aryl glycosides and quinones, aiming to enhance their binding affinity and specificity towards cancer-related protein targets. The interactions between the synthesized glycohybrids and target proteins through computational docking simulations has been studied and better binding affinity was found.
{"title":"An efficient synthesis of natural product-inspired naphthoquinone fused glycohybrids and their in-silico docking studies","authors":"Ashish Khanna, Ghanshyam Tiwari, Vinay Kumar Mishra, Kavita Singh, Ram Sagar","doi":"10.1055/a-2181-9709","DOIUrl":"https://doi.org/10.1055/a-2181-9709","url":null,"abstract":"Abstract Naphthoquinones, a diverse group of natural compounds with a 1,4-naphthoquinone core structure, have gained attention for their pharmacological properties. The anticancer activity of these compounds is attributed to their ability to accept electrons, leading to the generation of reactive oxygen species that cause DNA damage and cell death. In recent studies, hydroxy-1,4-naphthoquinone derivatives, including daunorubicin, have shown promising inhibitory effects against several human cancers, such as acute myeloid leukemia, chronic myelogenous leukemia, and Kaposi’s sarcoma. To further explore their potential as anticancer agents, this research article focuses on the design and synthesis of natural product inspired naphthoquinone-based glycohybrids. These glycohybrids are designed based on the structures of bioactive aryl glycosides and quinones, aiming to enhance their binding affinity and specificity towards cancer-related protein targets. The interactions between the synthesized glycohybrids and target proteins through computational docking simulations has been studied and better binding affinity was found.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"45 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134885995","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}
Abstract An efficient and convenient synthetic protocol is reported for the synthesis of 2-phenyl-4H-chromen-4-one, 2-phenylquinolin-4(1H)-one, and 11H-benzofuro[3,2-b]chromen-11-one derivatives from 2′-hydroxychalcones, 2′-aminochalcones, and 3-hydroxyflavones, respectively, using transition-metal catalysts and TEMPO as an oxidizing agent. This catalytic heterocyclization approach involves in situ free-radical generation as phenoxyl radicals were detected by EPR spectroscopic study and H2O2 was formed. The present method has numerous advantages, such as high atom-economy, less hazardous synthesis, benign solvent and auxiliaries, easy handling, and broader substrate scope with good to excellent product yields.
{"title":"Oxidative Cyclization Reactions Catalyzed by Designed Transition-Metal Complexes: A New Strategy for the Synthesis of Flavone, Quinolone, and Benzofuran Derivatives","authors":"Kaushik Ghosh, Naseem Ahmed, Apurva Singh, Sain Singh","doi":"10.1055/s-0042-1751489","DOIUrl":"https://doi.org/10.1055/s-0042-1751489","url":null,"abstract":"Abstract An efficient and convenient synthetic protocol is reported for the synthesis of 2-phenyl-4H-chromen-4-one, 2-phenylquinolin-4(1H)-one, and 11H-benzofuro[3,2-b]chromen-11-one derivatives from 2′-hydroxychalcones, 2′-aminochalcones, and 3-hydroxyflavones, respectively, using transition-metal catalysts and TEMPO as an oxidizing agent. This catalytic heterocyclization approach involves in situ free-radical generation as phenoxyl radicals were detected by EPR spectroscopic study and H2O2 was formed. The present method has numerous advantages, such as high atom-economy, less hazardous synthesis, benign solvent and auxiliaries, easy handling, and broader substrate scope with good to excellent product yields.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"90 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134885105","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}
Abstract 1,4-Conjugate addition of arylboronic acids to the glycal enones delivered 2-deoxy-α-aryl-C-glycosides in good yields. The reaction was catalyzed by palladium acetate in the presence of trifluoroacetic acid and 1,10-phenanthroline. A wide range of glycal enones derived from d-glucal, d-galactal, and d-rhamnal participated in the coupling reaction with different arylboronic acids smoothly. Different protecting groups including benzyl, acetyl, pivaloyl, and benzoyl were compatible under optimized conditions.
{"title":"Palladium-Catalyzed Stereocontrolled Synthesis of Aryl-C-Glycosides from Arylboronic Acids and Glycal Enones Through 1,4-Conjugate Addition Reactions","authors":"Jeyakumar Kandasamy, Adesh Kumar Singh, Rapelly Venkatesh","doi":"10.1055/a-2179-8669","DOIUrl":"https://doi.org/10.1055/a-2179-8669","url":null,"abstract":"Abstract 1,4-Conjugate addition of arylboronic acids to the glycal enones delivered 2-deoxy-α-aryl-C-glycosides in good yields. The reaction was catalyzed by palladium acetate in the presence of trifluoroacetic acid and 1,10-phenanthroline. A wide range of glycal enones derived from d-glucal, d-galactal, and d-rhamnal participated in the coupling reaction with different arylboronic acids smoothly. Different protecting groups including benzyl, acetyl, pivaloyl, and benzoyl were compatible under optimized conditions.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"45 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136131059","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}
Abstract A Cp*Rh-catalyzed C–H functionalization/cyclization to afford 2,3-substituted N-secondary alkyl indole derivatives is described. This intermolecular cyclization of N-secondary nitrosoanilines and unsymmetrically substituted alkynes has good performances in yields, substrate scope, and regioselectivities.
{"title":"Rhodium-Catalyzed Regioselective Synthesis of N-Secondary Alkyl Indoles via Intermolecular Cyclization of N-Nitrosoanilines and Unsymmetrical Alkynes","authors":"Yi Dong, Heng Xu, Yiting Chang, Tingting Hou","doi":"10.1055/s-0041-1738453","DOIUrl":"https://doi.org/10.1055/s-0041-1738453","url":null,"abstract":"Abstract A Cp*Rh-catalyzed C–H functionalization/cyclization to afford 2,3-substituted N-secondary alkyl indole derivatives is described. This intermolecular cyclization of N-secondary nitrosoanilines and unsymmetrically substituted alkynes has good performances in yields, substrate scope, and regioselectivities.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"27 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136130094","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}
Indrė Misiūnaitė, Raminta Bajarūnaitė, Rita Buksnaitiene, Algirdas Brukštus, Ieva Žutautė
Electrophile-initiated nucleophilic cyclization of 2-alkynylthiobenzimidazoles is a useful tool for synthesizing new heterocyclic systems. However, halogen-initiated cyclization demonstrates poor selectivity between electrophilic addition and substitution reactions using other imidazole analogues. In this research, several different coinage-metal catalysts were employed to broaden the scope of 7H-imidazo[2,1-b][1,3]thiazines in atom-economic manner. Selective 6-endo-dig pathway reactions were achieved in good to excellent yields using various 2-alkynylthioimidazoles with AuCl as a catalyst in DCE/DCM.
{"title":"Straightforward approach to 5-substituted 7H-imidazo[2,1-b][1,3]thiazines via cyclization of 2-alkynylthioimidazoles","authors":"Indrė Misiūnaitė, Raminta Bajarūnaitė, Rita Buksnaitiene, Algirdas Brukštus, Ieva Žutautė","doi":"10.1055/a-2179-1250","DOIUrl":"https://doi.org/10.1055/a-2179-1250","url":null,"abstract":"Electrophile-initiated nucleophilic cyclization of 2-alkynylthiobenzimidazoles is a useful tool for synthesizing new heterocyclic systems. However, halogen-initiated cyclization demonstrates poor selectivity between electrophilic addition and substitution reactions using other imidazole analogues. In this research, several different coinage-metal catalysts were employed to broaden the scope of 7H-imidazo[2,1-b][1,3]thiazines in atom-economic manner. Selective 6-endo-dig pathway reactions were achieved in good to excellent yields using various 2-alkynylthioimidazoles with AuCl as a catalyst in DCE/DCM.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"158 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136264288","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}
This review article outlines the progress made in the synthesis of substituted naphthalene derivatives. Naphthalene and its derivatives exhibit various biological activities such as anti-inflammatory, anticancer, antiviral, antitubercular, antimicrobial, antihypertensive, antidiabetic, etc. Several strategies have been developed in the past for the construction of naphthalene derivatives, primarily focused on Metal-catalyzed reactions (palladium, copper, zinc, rhodium, platinum, nickel, etc.,) and Lewis acid-catalyzed transformations. This review discusses the preparations of naphthalene derivatives using various salt such as gallium chlorides, gold chlorides, gold bromides, various gold complexes as well as bronsted acids like triflic acid and trifluoroacetic acid, and Lewis acids such as like boron trifluoride etherate. Additionally, miscellaneous reactions involving metal and Lewis acids are explored. The transformational approaches covered in this review include cycloadditions, carboannulations, benzoannulations, electroannulations, rearrangements, and cross-dehydrogenative coupling reactions. Overall this review provides a comprehensive and up-to-date account of the current state of preparations of substituted naphthalenes, highlighting their medicinal and industrial importance.
{"title":"Chemical Synthesis of Substituted Naphthalene Derivatives: A Review","authors":"Mittali Maheswari, Nazar Hussain","doi":"10.1055/a-2179-1338","DOIUrl":"https://doi.org/10.1055/a-2179-1338","url":null,"abstract":"This review article outlines the progress made in the synthesis of substituted naphthalene derivatives. Naphthalene and its derivatives exhibit various biological activities such as anti-inflammatory, anticancer, antiviral, antitubercular, antimicrobial, antihypertensive, antidiabetic, etc. Several strategies have been developed in the past for the construction of naphthalene derivatives, primarily focused on Metal-catalyzed reactions (palladium, copper, zinc, rhodium, platinum, nickel, etc.,) and Lewis acid-catalyzed transformations. This review discusses the preparations of naphthalene derivatives using various salt such as gallium chlorides, gold chlorides, gold bromides, various gold complexes as well as bronsted acids like triflic acid and trifluoroacetic acid, and Lewis acids such as like boron trifluoride etherate. Additionally, miscellaneous reactions involving metal and Lewis acids are explored. The transformational approaches covered in this review include cycloadditions, carboannulations, benzoannulations, electroannulations, rearrangements, and cross-dehydrogenative coupling reactions. Overall this review provides a comprehensive and up-to-date account of the current state of preparations of substituted naphthalenes, highlighting their medicinal and industrial importance.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"144 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136264289","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}
Abstract The thermal electrocyclization of heptatrienyl anions is reviewed. We begin with a succinct background on the importance of cycloheptane rings in complex molecules and a brief survey of approaches to their synthesis. We also review the fundamental aspects of this electrocyclization manifold, relying on the Woodward–Hoffmann rules for pericyclic chemistry. Then we survey the literature, covering the burst of discovery in the late 1960s and early 1970s, and the more sporadic reports in from the 1990s to the present day. 1 Introduction 2 The Electrocyclization of Heptatrienyl Anions 3 Discovery and Early Development (1964–1975) 4 Recent Developments (1996–2023) 5 Concluding Remarks
{"title":"The Electrocyclization of Heptatrienyl Anions","authors":"Arturo Orellana, Samira Komijani","doi":"10.1055/s-0040-1720086","DOIUrl":"https://doi.org/10.1055/s-0040-1720086","url":null,"abstract":"Abstract The thermal electrocyclization of heptatrienyl anions is reviewed. We begin with a succinct background on the importance of cycloheptane rings in complex molecules and a brief survey of approaches to their synthesis. We also review the fundamental aspects of this electrocyclization manifold, relying on the Woodward–Hoffmann rules for pericyclic chemistry. Then we survey the literature, covering the burst of discovery in the late 1960s and early 1970s, and the more sporadic reports in from the 1990s to the present day. 1 Introduction 2 The Electrocyclization of Heptatrienyl Anions 3 Discovery and Early Development (1964–1975) 4 Recent Developments (1996–2023) 5 Concluding Remarks","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"153 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136306452","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}
The reduction of 2-nitrophenylacetic acid to oxindoles promoted by SmI2 is reported for the first time. This reaction involving the reduction of nitro group proceeds through N-O bond cleavage and direct condensation with the neighboring carboxyl group. From a synthetic point of view, a new method for the synthesis of oxindoles in mild neutral conditions is developed.
{"title":"Synthesis of Oxindoles via SmI2-Promoted Reduction of 2-Nitrophenylacetic Acids","authors":"Pengkai Wang, Songlin Zhang","doi":"10.1055/a-2175-1008","DOIUrl":"https://doi.org/10.1055/a-2175-1008","url":null,"abstract":"The reduction of 2-nitrophenylacetic acid to oxindoles promoted by SmI2 is reported for the first time. This reaction involving the reduction of nitro group proceeds through N-O bond cleavage and direct condensation with the neighboring carboxyl group. From a synthetic point of view, a new method for the synthesis of oxindoles in mild neutral conditions is developed.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"67 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135690411","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}
Kei Kitamura, Saki Ise, Tetsuto Tsunoda, Hiroto Kaku
We report herein an iterative assembly of chiral alcohol building blocks utilizing cyanomethylene trimethylphosphorane (CMMP)-mediated Mitsunobu reactions. 1,3-Benzodithiole tetraoxide (BDT) was used as the platform to prepare long-chain saturated compounds with multiple stereocenters en route to polyisoprenoid natural products. Selectively protected chiral 1,3-butanediols played a key role in iterative chain elongation for the construction of 1,5-dimethyl branched arrays with high stereocontrol.
{"title":"Iterative Assembly of Chiral Alcohols Utilizing CMMP-mediated Mitsunobu Reactions","authors":"Kei Kitamura, Saki Ise, Tetsuto Tsunoda, Hiroto Kaku","doi":"10.1055/a-2175-1271","DOIUrl":"https://doi.org/10.1055/a-2175-1271","url":null,"abstract":"We report herein an iterative assembly of chiral alcohol building blocks utilizing cyanomethylene trimethylphosphorane (CMMP)-mediated Mitsunobu reactions. 1,3-Benzodithiole tetraoxide (BDT) was used as the platform to prepare long-chain saturated compounds with multiple stereocenters en route to polyisoprenoid natural products. Selectively protected chiral 1,3-butanediols played a key role in iterative chain elongation for the construction of 1,5-dimethyl branched arrays with high stereocontrol.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"3 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135734387","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}
During the past several decades, Zweifel olefination has emerged as one of the most powerful and reliable tools for constructing C–C double bonds. This reaction features high efficiency, good versatility, nonuse of transition metals, and perfect stereospecificity, which make it superior to many other olefination methods. Since the summary of Zweifel olefination’s 50-years history was published in 2017 by Aggarwal et al., remarkable achievements have been made in terms of employing new organometallic species, proceeding through electrochemical or photochemical pathways, and furnishing new kinds of products. This short review summarizes and discusses the very recent progress in Zweifel olefination and its latest application in natural products synthesis. 1 Introduction 2 Zweifel Olefination with New Organometallic Species 3 Zweifel Olefination with New Migrating Groups 4 Electrochemical and Photocatalyzed Zweifel Olefination 5 New Elimination and Migration Patterns of Zweifel Olefination 6 Zweifel Olefination in Natural Product Synthesis 7 Other Reactions Involving the Zweifel Olefination Mechanism 8 Conclusions and Outlook
{"title":"Recent Progress in Zweifel Olefination: An Update","authors":"Xin Li, Qiuling Song","doi":"10.1055/a-2172-1386","DOIUrl":"https://doi.org/10.1055/a-2172-1386","url":null,"abstract":"During the past several decades, Zweifel olefination has emerged as one of the most powerful and reliable tools for constructing C–C double bonds. This reaction features high efficiency, good versatility, nonuse of transition metals, and perfect stereospecificity, which make it superior to many other olefination methods. Since the summary of Zweifel olefination’s 50-years history was published in 2017 by Aggarwal et al., remarkable achievements have been made in terms of employing new organometallic species, proceeding through electrochemical or photochemical pathways, and furnishing new kinds of products. This short review summarizes and discusses the very recent progress in Zweifel olefination and its latest application in natural products synthesis. \u00001 Introduction \u00002 Zweifel Olefination with New Organometallic Species \u00003 Zweifel Olefination with New Migrating Groups \u00004 Electrochemical and Photocatalyzed Zweifel Olefination \u00005 New Elimination and Migration Patterns of Zweifel Olefination\u00006 Zweifel Olefination in Natural Product Synthesis \u00007 Other Reactions Involving the Zweifel Olefination Mechanism\u00008 Conclusions and Outlook\u0000\u0000","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"1 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-09-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80985763","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}
京公网安备 11010802042870号
京ICP备2023020795号-1
扫码关注我们
求助内容：
应助结果提醒方式：