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Chemistry of Heterocyclic Compounds最新文献

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Design, synthesis, and anti-inflammatory activity of novel 20-O-substituted camptothecin carbamate derivatives 新型 20-O 取代喜树碱氨基甲酸酯衍生物的设计、合成和抗炎活性
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-22 DOI: 10.1007/s10593-024-03338-8
Yazhao Zhu, Chuanhao Wang, Rongxue Lv, Hang Yang, Yongchang Wang, Yuelin Wu
{"title":"Design, synthesis, and anti-inflammatory activity of novel 20-O-substituted camptothecin carbamate derivatives","authors":"Yazhao Zhu, Chuanhao Wang, Rongxue Lv, Hang Yang, Yongchang Wang, Yuelin Wu","doi":"10.1007/s10593-024-03338-8","DOIUrl":"https://doi.org/10.1007/s10593-024-03338-8","url":null,"abstract":"<p>Twelve novel camptothecin derivatives with a carbamate substituent at position 20 were designed and synthesized. Most of the targeted compounds indicated potent anti-inflammatory activity in a lipopolysaccharide stimulation of peritoneal macrophage model. Among them, the benzyl(methyl)amine derivative showed the most pronounced anti-inflammatory activity at a concentration of 1 μM and TNF-α inhibitory rate is increased by 10.2% compared to the lead compound (<i>N</i>,<i>N</i>-dimethylethylenediamine derivative).</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207513","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}
引用次数: 0
Synthesis of fluorinated six-membered nitrogen heterocycles using microwave irradiation 利用微波辐照合成氟化六元氮杂环
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-22 DOI: 10.1007/s10593-024-03323-1
Chandra Prakash, Ram Singh
{"title":"Synthesis of fluorinated six-membered nitrogen heterocycles using microwave irradiation","authors":"Chandra Prakash, Ram Singh","doi":"10.1007/s10593-024-03323-1","DOIUrl":"https://doi.org/10.1007/s10593-024-03323-1","url":null,"abstract":"<p>The presence of one or more fluorine atoms in six-membered nitrogen heterocycles significantly impacts their chemical and physical properties, making them important in various applications, including pharmaceuticals and agrochemicals. This review, therefore, surveys the recent advances (mostly from 2010 onwards) in the synthesis of fluorinated six-membered N-heterocyclic compounds, including both the use of fluorinated starting materials and the introducing of fluorine atoms in the heterocyclic core and in either case exploring the benefits of microwave-assisted processes.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207512","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}
引用次数: 0
To the 90th birthday of academician of the Russian Academy of Sciences, professor, doctor of chemical sciences O. N. Chupakhin 献给俄罗斯科学院院士、化学科学博士、教授奥-尼-丘帕金九十华诞
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-21 DOI: 10.1007/s10593-024-03321-3
{"title":"To the 90th birthday of academician of the Russian Academy of Sciences, professor, doctor of chemical sciences O. N. Chupakhin","authors":"","doi":"10.1007/s10593-024-03321-3","DOIUrl":"https://doi.org/10.1007/s10593-024-03321-3","url":null,"abstract":"","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207521","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}
引用次数: 0
Visible-light-induced Ir-catalyzed site-selective C−H trifluoromethylation of 3-substituted 1,2-benzoxazoles 可见光诱导的 Ir 催化的 3-取代 1,2-苯并恶唑的 C-H 三氟甲基化位点选择性反应
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-21 DOI: 10.1007/s10593-024-03336-w
Ming-Ming Xiao, Ming-Qing Hua, Fang-You Mou, Heng-Ying Xiong
{"title":"Visible-light-induced Ir-catalyzed site-selective C−H trifluoromethylation of 3-substituted 1,2-benzoxazoles","authors":"Ming-Ming Xiao, Ming-Qing Hua, Fang-You Mou, Heng-Ying Xiong","doi":"10.1007/s10593-024-03336-w","DOIUrl":"https://doi.org/10.1007/s10593-024-03336-w","url":null,"abstract":"<p>A new protocol for visible-light-induced C–H trifluoromethylation at C-4 position of 1,2-benzoxazoles has been disclosed with Togni reagent II at room temperature in the presence of <i>fac</i>-Ir(ppy)<sub>3</sub>. This approach features simple operation, high efficiency, and specific selectivity.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207511","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}
引用次数: 0
A novel method for the synthesis of 2-arylquinolin-4(1H)-ones 合成 2-芳基喹啉-4(1H)-酮的新方法
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-21 DOI: 10.1007/s10593-024-03333-z
Nikolai A. Arutiunov, Anna M. Zatsepilina, Anna A. Aksenova, Dmitrii A. Aksenov, Alexander V. Aksenov
{"title":"A novel method for the synthesis of 2-arylquinolin-4(1H)-ones","authors":"Nikolai A. Arutiunov, Anna M. Zatsepilina, Anna A. Aksenova, Dmitrii A. Aksenov, Alexander V. Aksenov","doi":"10.1007/s10593-024-03333-z","DOIUrl":"https://doi.org/10.1007/s10593-024-03333-z","url":null,"abstract":"<p>A simple one-pot method for the synthesis of 2-substituted quinolin-4(1<i>H</i>)-ones from synthetically accessible 2-(2-aryl(alkyl)- 3-oxoindolin-2-yl)-2-phenylacetonitriles was developed.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207519","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}
引用次数: 0
The synthesis of 1-oxa-9-azaspiro[5.5]undecane derivatives and optimization of antituberculosis activity thereof 1-oxa-9-azaspiro[5.5]undecane 衍生物的合成及其抗结核活性的优化
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-21 DOI: 10.1007/s10593-024-03328-w
Kristina Yu. Komarova, Alexey Yu. Lukin, Lyubov V. Vinogradova, Maxim E. Zhuravlev, Marine Z. Dogonadze, Tatiana I. Vinogradova, Maxim A. Gureev, Mikhail V. Chudinov, Dmitry V. Dar’in
{"title":"The synthesis of 1-oxa-9-azaspiro[5.5]undecane derivatives and optimization of antituberculosis activity thereof","authors":"Kristina Yu. Komarova, Alexey Yu. Lukin, Lyubov V. Vinogradova, Maxim E. Zhuravlev, Marine Z. Dogonadze, Tatiana I. Vinogradova, Maxim A. Gureev, Mikhail V. Chudinov, Dmitry V. Dar’in","doi":"10.1007/s10593-024-03328-w","DOIUrl":"https://doi.org/10.1007/s10593-024-03328-w","url":null,"abstract":"<p>The aim of this work was to synthesize and study the antituberculosis activity of spirocyclic inhibitors of the MmpL3 protein of <i>M</i>. <i>tu- berculosis</i> containing the 1-oxa-9-azaspiro[5.5]undecane scaffold. Optimization of the initial structure was performed with consideration of the results of molecular docking. The resulting compounds, characterized by the chemical diversity of the peripheral fragment, showed high activity against the antibiotic-sensitive strain H37Rv and some multiresistant strains of <i>M</i>. <i>tuberculosis</i>, exceeding the activity of the comparator drug.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142226324","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}
引用次数: 0
Improved synthesis of two quisqualic acid analogs containing hydantoin and imidazolidinone moieties 含有海因和咪唑烷酮分子的两种奎奎宁酸类似物的改进合成方法
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-21 DOI: 10.1007/s10593-024-03331-1
Aleksandr P. Makhin, Vasily S. Miturich, Matvey V. Vavilov, Maria S. Lyakhovich, Anastasia A. Andrianova, Renata I. Zagitova, Vladimir I. Shmygarev, Anastasia A. Fadeeva, Oleg N. Yatskin, Olga A. Belozerova, Aristides Tsatsakis, Ilia V. Yampolsky, Zinaida M. Kaskova
{"title":"Improved synthesis of two quisqualic acid analogs containing hydantoin and imidazolidinone moieties","authors":"Aleksandr P. Makhin, Vasily S. Miturich, Matvey V. Vavilov, Maria S. Lyakhovich, Anastasia A. Andrianova, Renata I. Zagitova, Vladimir I. Shmygarev, Anastasia A. Fadeeva, Oleg N. Yatskin, Olga A. Belozerova, Aristides Tsatsakis, Ilia V. Yampolsky, Zinaida M. Kaskova","doi":"10.1007/s10593-024-03331-1","DOIUrl":"https://doi.org/10.1007/s10593-024-03331-1","url":null,"abstract":"<p>In the light of recent progress in the development of SARS-CoV-2 main protease inhibitors, the synthesis of their key fragment, heterocyclic amino acids, is of great interest. Here, we report a method for the preparation of two new quisqualic acid analogs containing hydantoin and imidazolidinone moieties. The hydantoin analog was obtained using an amide ester cyclization, while the imidazolidinone unit was constructed by reductive amination and subsequent cyclization of a substituted ethylenediamine with carbonyldiimidazole. The presented approach provides the convergent synthesis of target analogs in 8 and 5 steps respectively.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207518","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}
引用次数: 0
Cascade assembling of aldehydes and two molecules of dimedone into 4H-spiro[1-benzofuran-2,1'-cyclohexane]-2',4,6'-triones under column chromatography-free protocol at room temperature 在室温无柱色谱条件下，醛和两分子二甲基酮级联组装成 4H-螺[1-苯并呋喃-2,1'-环己烷]-2',4,6'-三酮
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-21 DOI: 10.1007/s10593-024-03327-x
Michail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Ryzhkova, Kirill A. Karpenko, Varvara M. Kalashnikova
{"title":"Cascade assembling of aldehydes and two molecules of dimedone into 4H-spiro[1-benzofuran-2,1'-cyclohexane]-2',4,6'-triones under column chromatography-free protocol at room temperature","authors":"Michail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Ryzhkova, Kirill A. Karpenko, Varvara M. Kalashnikova","doi":"10.1007/s10593-024-03327-x","DOIUrl":"https://doi.org/10.1007/s10593-024-03327-x","url":null,"abstract":"<p>A new type of one-pot Knoevenagel–Michael reaction with the following NBS-induced cyclization was found: a direct one-pot transformation of aldehydes and two molecules of dimedone into substituted 4<i>H</i>-spiro[1-benzofuran-2,1'-cyclohexane]-2',4,6'-triones in 86–95% yields. This one-pot process is a very efficient and convenient way to access substituted 4<i>H</i>-spiro[1-benzofuran-2,1'-cyclohexane]-2',4,6'-triones – useful compounds for different biomedical applications with reasonable and nonexpensive starting materials. Mild and facile conditions of this chemical cascade one-pot process, as well as non-chromatographic isolation procedure lead to excellent substance yields.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207520","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}
引用次数: 0
3-Spiroandrostene-substituted 1,3,4-thiadiazolines 3-螺蒽取代的 1,3,4-噻二唑啉类化合物
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-06-28 DOI: 10.1007/s10593-024-03317-z
Alexander V. Komkov, Leonid G. Menchikov, Andrey S. Dmitrenok, Natalya G. Kolotyrkina, Igor V. Zavarzin
{"title":"3-Spiroandrostene-substituted 1,3,4-thiadiazolines","authors":"Alexander V. Komkov, Leonid G. Menchikov, Andrey S. Dmitrenok, Natalya G. Kolotyrkina, Igor V. Zavarzin","doi":"10.1007/s10593-024-03317-z","DOIUrl":"https://doi.org/10.1007/s10593-024-03317-z","url":null,"abstract":"<p>A method for the synthesis of 1,3,4-thiadiazoline spiro steroids <i>via</i> ring A by the reaction of steroid 3-ketones with oxamic acid thiohydrazides was developed. It was shown that if a keto group was present both in ring A and in ring D of the precursor steroid, the reaction occurred only at the keto group of ring A. A number of new steroidal 3-spiroandrostene-substituted 1,3,4-thiadiazolines were obtained, which could be easily acetylated at the thiadiazole NH group.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-06-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141511946","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}
引用次数: 0
A method for the synthesis of spiro-1,3,4-thiadiazolines 一种合成螺-1,3,4-噻二唑啉的方法
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-06-28 DOI: 10.1007/s10593-024-03316-0
Alexander V. Komkov, Leonid G. Menchikov, Andrey S. Dmitrenok, Natalya G. Kolotyrkina, Igor V. Zavarzin
{"title":"A method for the synthesis of spiro-1,3,4-thiadiazolines","authors":"Alexander V. Komkov, Leonid G. Menchikov, Andrey S. Dmitrenok, Natalya G. Kolotyrkina, Igor V. Zavarzin","doi":"10.1007/s10593-024-03316-0","DOIUrl":"https://doi.org/10.1007/s10593-024-03316-0","url":null,"abstract":"<p>A method for the synthesis of spiro-1,3,4-thiadiazolines by the reaction of cyclic ketones with oxamic acid thiohydrazides was developed. A number of new nonsteroidal spiro-1,3,4-thiadiazolines was obtained in high yields.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-06-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141511947","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}
引用次数: 0
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