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Chemistry of Heterocyclic Compounds最新文献

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The synthesis of salts of five-membered heterocyclic compounds based on N-containing cations/anions (microreview) 基于含 N 的阳离子/阴离子的五元杂环化合物盐的合成（微型综述）
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-27 DOI: 10.1007/s10593-024-03324-0
Larisa V. Zhilitskaya, Nina O. Yarosh
{"title":"The synthesis of salts of five-membered heterocyclic compounds based on N-containing cations/anions (microreview)","authors":"Larisa V. Zhilitskaya, Nina O. Yarosh","doi":"10.1007/s10593-024-03324-0","DOIUrl":"https://doi.org/10.1007/s10593-024-03324-0","url":null,"abstract":"\u0000<figure></figure><p>This microreview summarizes the data on the synthesis of salts of five-membered N-heterocyclic compounds published since 2017. The material is systematized on the basis of the number of nitrogen atoms in the five-membered ring.</p><figure><picture><source srcset=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03324-0/MediaObjects/10593_2024_3324_Figd_HTML.png?as=webp\" type=\"image/webp\"/><img alt=\"\" height=\"2\" loading=\"lazy\" src=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03324-0/MediaObjects/10593_2024_3324_Figd_HTML.png\" width=\"685\"/></picture></figure>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":"31 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207508","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
Ring expansion strategy to access functionalized 2-oxazolines (microreview) 获得功能化 2-噁唑啉的扩环策略（微型综述）
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-27 DOI: 10.1007/s10593-024-03326-y
Leyan Liu, Wentong Liu, Huangdi Feng
{"title":"Ring expansion strategy to access functionalized 2-oxazolines (microreview)","authors":"Leyan Liu, Wentong Liu, Huangdi Feng","doi":"10.1007/s10593-024-03326-y","DOIUrl":"https://doi.org/10.1007/s10593-024-03326-y","url":null,"abstract":"\u0000<figure></figure><p>The development of innovative methods for the construction of heterocycles is an important topic in synthetic and medicinal chemistry. Ring expansion strategies, involving the cyclization of strained aza rings, have been well developed in the synthesis of diverse heterocyclic compounds. This microreview summarizes recent advances in the ring expansion reactions of aziridines, oxetanes, and azetidines to access a series of functionalized 2-oxazolines, which are versatile structural motifs in drugs and bioactive molecules.</p><figure><picture><source srcset=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03326-y/MediaObjects/10593_2024_3326_Figd_HTML.png?as=webp\" type=\"image/webp\"/><img alt=\"\" height=\"2\" loading=\"lazy\" src=\"//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs10593-024-03326-y/MediaObjects/10593_2024_3326_Figd_HTML.png\" width=\"685\"/></picture></figure>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":"61 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142226323","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 professor Gunars Duburs, academician of the Latvian Academy of Sciences 献给拉脱维亚科学院院士 Gunars Duburs 教授 90 岁生日
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-23 DOI: 10.1007/s10593-024-03320-4
{"title":"To the 90th birthday of professor Gunars Duburs, academician of the Latvian Academy of Sciences","authors":"","doi":"10.1007/s10593-024-03320-4","DOIUrl":"https://doi.org/10.1007/s10593-024-03320-4","url":null,"abstract":"","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":"22 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-08-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207510","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
2,5-Di(het)arylpyridines: synthesis by ‘‘1,2,4-triazine’’ methodology and photophysical properties 2,5-二（噻）芳基吡啶：用 "1,2,4-三嗪 "方法合成和光物理特性
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-22 DOI: 10.1007/s10593-024-03335-x
Alexei P. Krinochkin, Albert F. Khasanov, Maria I. Valieva, Ekaterina A. Kudryashova, Mallikarjuna R. Guda, Dmitry S. Kopchuk, Olga V. Shabunina, Nataliya N. Mochulskaya, Pavel A. Slepukhin, Grigory V. Zyryanov, Oleg N. Chupakhin
{"title":"2,5-Di(het)arylpyridines: synthesis by ‘‘1,2,4-triazine’’ methodology and photophysical properties","authors":"Alexei P. Krinochkin, Albert F. Khasanov, Maria I. Valieva, Ekaterina A. Kudryashova, Mallikarjuna R. Guda, Dmitry S. Kopchuk, Olga V. Shabunina, Nataliya N. Mochulskaya, Pavel A. Slepukhin, Grigory V. Zyryanov, Oleg N. Chupakhin","doi":"10.1007/s10593-024-03335-x","DOIUrl":"https://doi.org/10.1007/s10593-024-03335-x","url":null,"abstract":"<p>The method for the preparation of 3,6-disubstituted 1,2,4-triazines based on condensation reaction between easily available α-imino esters and isonitrosoacetophenone hydrazones was reported. The significant differences in reaction conditions, ratio of products, and yields between the developed method and the earlier reported approach were demonstrated. The corresponding 2,5-disubstituted pyridines were synthesized from the prepared 1,2,4-triazines, and their photophysical properties were studied. Studies of the photo-physical properties revealed low and moderate luminescence quantum yields, and negligible solvatochromic behavior in case of 4-methoxyphenylpyridine derivative due to the role of donating methoxy group, however, with a low linearity of a Lippert–Mataga plot. Nevertheless, 2,5-disubstituted pyridines are of interest due to simple protocols of synthesis, moderate photophysical properties, and potential applicability in different scientific and industrial areas.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":"316 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142226320","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 first example of a cine-substitution in a series of 1,3-dinitropyrazoles 在 1,3-二硝基吡唑系列中实现 cine 取代的首个实例
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-22 DOI: 10.1007/s10593-024-03330-2
Tatyana K. Shkineva, Svetlana A. Krasnova, Igor L. Dalinger
{"title":"The first example of a cine-substitution in a series of 1,3-dinitropyrazoles","authors":"Tatyana K. Shkineva, Svetlana A. Krasnova, Igor L. Dalinger","doi":"10.1007/s10593-024-03330-2","DOIUrl":"https://doi.org/10.1007/s10593-024-03330-2","url":null,"abstract":"<p>New C–N-bonded bisazoles were obtained by cine-substitution of 1,3-dinitro-1<i>H</i>-pyrazole-4-carbonitrile by the action of <i>N</i>-azoles. Their spectral characteristics were investigated using multinuclear NMR spectroscopy.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":"10 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207514","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
Fused chiral azaheterocycles based on monosubstituted ferrocenes 基于单取代二茂铁的融合手性杂环
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-22 DOI: 10.1007/s10593-024-03322-2
Kyrylo I. Tymoshenko, Vitalii A. Palchykov
{"title":"Fused chiral azaheterocycles based on monosubstituted ferrocenes","authors":"Kyrylo I. Tymoshenko, Vitalii A. Palchykov","doi":"10.1007/s10593-024-03322-2","DOIUrl":"https://doi.org/10.1007/s10593-024-03322-2","url":null,"abstract":"<p>Minireview describes recent (2014–2024) advances in the synthesis of five- to seven-membered azaheterocycles using heteroannulation of monosubstituted ferrocenes. Most of the methods described here are based on asymmetric transition metal catalysis.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":"7 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142226322","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 1,4-dihydroquinoline-3-carboxylates from 2-benzoyl-3-[2-(dialkylamino)aryl]acrylates 从 2-苯甲酰基-3-[2-(二烷基氨基)芳基]丙烯酸酯合成 1,4-二氢喹啉-3-羧酸盐
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-22 DOI: 10.1007/s10593-024-03332-0
Dmitrii S. Ivanov, Alexander Yu. Smirnov, Mikhail S. Baranov
{"title":"The synthesis of 1,4-dihydroquinoline-3-carboxylates from 2-benzoyl-3-[2-(dialkylamino)aryl]acrylates","authors":"Dmitrii S. Ivanov, Alexander Yu. Smirnov, Mikhail S. Baranov","doi":"10.1007/s10593-024-03332-0","DOIUrl":"https://doi.org/10.1007/s10593-024-03332-0","url":null,"abstract":"<p>A method for the synthesis of 1,4-dihydroquinoline-3-carbonyl compounds from 2-benzoyl-3-[2-(dialkylamino)aryl]acrylates <i>via</i> the sequence of 1,5-hydride shift, dealkylation, and cyclization processes was proposed. The reaction products contained a push-pull enamine fragment.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":"7 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207516","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
Unexpected products of the reaction of purine nucleic base perchlorates with acetylacetone causing single-strand breaks in the DNA molecule 嘌呤核酸高氯酸盐与乙酰丙酮反应的意外产物导致 DNA 分子单链断裂
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-22 DOI: 10.1007/s10593-024-03337-9
Polina S. Zdereva, Grigorii V. Bezhenar, Anastasiya N. Sokolova, Boris V. Paponov, Andrey M. Rumyantsev, Elena V. Sambuk, Dmitry N. Maistrenko, Oleg E. Molchanov
{"title":"Unexpected products of the reaction of purine nucleic base perchlorates with acetylacetone causing single-strand breaks in the DNA molecule","authors":"Polina S. Zdereva, Grigorii V. Bezhenar, Anastasiya N. Sokolova, Boris V. Paponov, Andrey M. Rumyantsev, Elena V. Sambuk, Dmitry N. Maistrenko, Oleg E. Molchanov","doi":"10.1007/s10593-024-03337-9","DOIUrl":"https://doi.org/10.1007/s10593-024-03337-9","url":null,"abstract":"<p>The reactions of purine nucleic base perchlorates with the simplest 1,3-diketone – acetylacetone – were studied for the first time. It was demonstrated that adenine reacts with acetylacetone in a 1:2 molar ratio <i>via</i> opening of the pyrimidine fragment of the bicyclic struc- ture, elimination of a one-carbon fragment in the form of a formic acid molecule, and recyclization into 8-(4,6-dimethylpyrimidin-2-yl)- 2,4-dimethylimidazo[1,5-<i>a</i>]pyrimidine. Guanine, in turn, reacted with acetylacetone in a 1:1 ratio and formed 7,9-dimethyl-3<i>H</i>-pyrimido- [2,1-<i>b</i>]purin-10-ium-4-olate. In this case, the direction of heterocyclization differed from that observed in the reaction of guanine with malondialdehyde during the <i>in vitro</i> and <i>in vivo</i> formation of the minor nucleotide base M<sub>1</sub>G. The synthesized compounds were capable of causing single-strand breaks in DNA macromolecules.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":"114 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142226321","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 one-pot synthesis of 3-nitro-2H-thiopyrans and their selective reduction to 3-nitro-3,4-dihydro-2H-thiopyrans 3- 硝基-2H-噻喃的一步合成及其选择性还原为 3-硝基-3,4-二氢-2H-噻喃
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-22 DOI: 10.1007/s10593-024-03329-9
Ivan D. Karpov, Aleksei V. Kolobov, Ilya P. Filippov, Nikolai V. Rostovskii, Konstantin L. Ovchinnikov
{"title":"A one-pot synthesis of 3-nitro-2H-thiopyrans and their selective reduction to 3-nitro-3,4-dihydro-2H-thiopyrans","authors":"Ivan D. Karpov, Aleksei V. Kolobov, Ilya P. Filippov, Nikolai V. Rostovskii, Konstantin L. Ovchinnikov","doi":"10.1007/s10593-024-03329-9","DOIUrl":"https://doi.org/10.1007/s10593-024-03329-9","url":null,"abstract":"<p>A one-pot method for the synthesis of 3-nitro-2<i>H</i>-thiopyrans starting from enamin-3-ones was developed. Reduction of the obtained 3-nitro-2<i>H</i>-thiopyrans with the benzaldehyde/<i>o</i>-phenylenediamine system in butanol led to 3-nitro-3,4-dihydro-2<i>H</i>-thiopyrans.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":"77 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207515","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
Schizocommunin-inspired heterocyclic hybrid molecules 受 Schizocommunin 启发的杂环混合分子
IF 1.5 4区 化学
Chemistry of Heterocyclic Compounds Pub Date : 2024-08-22 DOI: 10.1007/s10593-024-03334-y
Bhawna Chechani, Mukesh Kumar, Dinesh K. Yadav, Siddharth Sharma, Neetu Kumari
{"title":"Schizocommunin-inspired heterocyclic hybrid molecules","authors":"Bhawna Chechani, Mukesh Kumar, Dinesh K. Yadav, Siddharth Sharma, Neetu Kumari","doi":"10.1007/s10593-024-03334-y","DOIUrl":"https://doi.org/10.1007/s10593-024-03334-y","url":null,"abstract":"<p>An effective and environmentally friendly technique for synthesizing hybrid molecules based on schizocommunin has been detailed in this study. This process involves a click reaction utilizing quinazolinones, isatin, and azides. Schizocommunin, a natural bioactive compound recognized for its wide array of biological functions including its anticancer properties, was employed as the foundational scaffold. The resultant triazo compounds originating from schizocommunin were subjected to thorough evaluation for their potential anticancer activity against three human cancer cell lines: MCF-7 (breast cancer), A549 (lung cancer), and PC-3 (prostate cancer), through employment of the MTT assay. One compound from the series showcased a remarkable anticancer efficacy (IC<sub>50</sub> 2.35 ± 0.67 μM) against MCF-7.</p>","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":"57 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142207517","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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