Chemistry of Heterocyclic Compounds最新文献_第5页

The synthesis and properties of [1,2] dithiolopyridine derivatives (microreview) 1,2]二硫环吡啶衍生物的合成及其性质（微综述

IF 1.5 4区化学

Chemistry of Heterocyclic Compounds Pub Date : 2024-04-11 DOI: 10.1007/s10593-024-03288-1

Victor V. Dotsenko, Anna E. Sinotsko

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Recent advances in the synthesis of thiazolo[4,5-b]pyridines. Part 1: Focus on pyridine annulation to thiazole ring (microreview) 噻唑并[4,5-b]吡啶合成的最新进展。第 1 部分：聚焦吡啶环化至噻唑环（微综述）

IF 1.5 4区化学

Chemistry of Heterocyclic Compounds Pub Date : 2024-04-11 DOI: 10.1007/s10593-024-03289-0

Taras I. Chaban, Olena V. Klenina, Ihor H. Chaban, Maryan I. Lelyukh

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A cascade reaction of 4-amino-substituted 6-hydrazinyl-1,3,5-triazin-2(1H)-ones with triethyl orthoacetate 4-氨基取代的 6-肼基-1,3,5-三嗪-2(1H)-酮与原乙酸三乙酯的级联反应

IF 1.5 4区化学

Chemistry of Heterocyclic Compounds Pub Date : 2024-04-08 DOI: 10.1007/s10593-024-03294-3

Anna V. Zavodskaya, Victor E. Parfenov, Olga V. Golovina, Vladimir V. Bakharev

{"title":"A cascade reaction of 4-amino-substituted 6-hydrazinyl-1,3,5-triazin-2(1H)-ones with triethyl orthoacetate","authors":"Anna V. Zavodskaya, Victor E. Parfenov, Olga V. Golovina, Vladimir V. Bakharev","doi":"10.1007/s10593-024-03294-3","DOIUrl":"https://doi.org/10.1007/s10593-024-03294-3","url":null,"abstract":"The reaction of 4-amino-substituted 6-hydrazinyl-1,3,5-triazin-2(1H)-ones with triethyl orthoacetate proceeded as a cascade reaction. The initially formed 7-amino-substituted 3-methyl[1,2,4]triazolo[4,3-a][1,3,5]triazin-5(1H)-ones underwent a Dimroth-type rearrangement with the formation of 5-amino-substituted 2-methyl[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(3H)-ones. The latter underwent alkylation at three positions: at the exocyclic oxygen atom with the formation of 7-ethoxy-2-methyl[1,2,4]triazolo[1,5-a][1,3,5]triazines, at the N-3 nitrogen atom with the formation of 3-ethyl-2-methyl[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(3H)-ones, and at the N-1 nitrogen atom to form 1-ethyl-2-methyl[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(3H)-ones. For the latter compound, a retro-Dimroth-type rearrangement occurred with the formation of betaine-type 7-amino-substituted 2-ethyl-3-methyl[1,2,4]triazolo[4,3-a][1,3,5]triazin- 2-ium-5-olates. A possible mechanism for the alkylation of 5-amino-substituted 2-methyl[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(3H)-ones with ortho esters was proposed.","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140566907","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}

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A novel facile approach to obtain phenytoin and thiophenytoin using new deep eutectic solvent-like mixtures of urea, thiourea, and KOH 利用尿素、硫脲和 KOH 的新型深共晶溶剂混合物快速获得苯妥英和硫苯妥英的新方法

IF 1.5 4区化学

Chemistry of Heterocyclic Compounds Pub Date : 2024-04-08 DOI: 10.1007/s10593-024-03300-8

Elena V. Khovrenko, Vadim Yu. Baula, Viktoria V. Shtrykova, Vera Yu. Kuksenok, Victor D. Filimonov

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A synthesis of triacetyl-substituted 1,2,3,4-tetrahydropyridine by the reaction of 3-[(alkylsulfanyl)methyl]pentane-2,4-diones with aniline 通过 3-[(烷基硫)甲基]戊烷-2,4-二酮与苯胺的反应合成三乙酰基取代的 1,2,3,4-四氢吡啶

IF 1.5 4区化学

Chemistry of Heterocyclic Compounds Pub Date : 2024-04-08 DOI: 10.1007/s10593-024-03301-7

Larisa A. Baeva, Rail R. Gataullin, Radik M. Nugumanov

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Thiazolo[5,4-b]indole derivatives as additives to cardioplegic solutions with increased time of preventing hypothermic ischemia 作为心脏麻痹溶液添加剂的噻唑并[5,4-b]吲哚衍生物可延长低体温缺血的预防时间

IF 1.5 4区化学

Chemistry of Heterocyclic Compounds Pub Date : 2024-04-08 DOI: 10.1007/s10593-024-03297-0

Oleg A. Loskutov, Kostiantyn P. Melnykov, Serhiy V. Ryabukhin, Eduard B. Rusanov, Illya A. Chaikovsky, Oleksiy V. Khavryuchenko, Dmytro O. Dziuba, Dmytro M. Volochnyuk

{"title":"Thiazolo[5,4-b]indole derivatives as additives to cardioplegic solutions with increased time of preventing hypothermic ischemia","authors":"Oleg A. Loskutov, Kostiantyn P. Melnykov, Serhiy V. Ryabukhin, Eduard B. Rusanov, Illya A. Chaikovsky, Oleksiy V. Khavryuchenko, Dmytro O. Dziuba, Dmytro M. Volochnyuk","doi":"10.1007/s10593-024-03297-0","DOIUrl":"https://doi.org/10.1007/s10593-024-03297-0","url":null,"abstract":"A set of 1-(2-amino-4H-thiazolo[5,4-b]indol-4-yl)ethan-1-one derivatives and their formally \"hydrated\" counterparts 1-(2-amino-8bhydroxy-3a,8b-dihydro-4H-thiazolo[5,4-b]indol-4-yl)ethan-1-ones were synthesized and characterized by both spectral methods and single crystal X-ray diffraction studies. The obtained compounds as additives to Bretschneider's solution (trade name Custodiol) were tested on an isolated rat heart, as a classical model for the period of hypothermic ischemia. The experiments showed that adding the synthesized compounds to classical Bretschneider's solution increases the prevention time of the hypoxic injury of the myocardium by at least 45 min of exposure without oxygen supplements and significant histological changes. The \"hydrated\" forms showed much better results than the parent ones. Meanwhile, it was found that additive activity correlates with the substance's solubility in Custodiol. This data could be a milestone for the further medicinal chemistry project with the goal of developing a new generation of perfusion and flushing compositions for increasing the duration of open heart surgery.","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140566702","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}

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Discovery of indole-3-acetic acid derivatives containing 1,3,4-thiadiazole thioether and amide moieties as novel antibacterial agents 发现含有 1,3,4-噻二唑硫醚和酰胺分子的吲哚-3-乙酸衍生物作为新型抗菌剂

IF 1.5 4区化学

Chemistry of Heterocyclic Compounds Pub Date : 2024-04-08 DOI: 10.1007/s10593-024-03298-z

Chenghao Tang, Jiali Shao, Chou Si, Xiumei Yang, Xiuhong Hu, Pei Li, Xiang Wang

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The reaction of 4-hydroxy-6H-1,3-oxazin-6-ones with amidines – a route to access new 1,3,5-triazine derivatives 4-羟基-6H-1,3-恶嗪-6-酮与酰胺的反应--获得新的 1,3,5-三嗪衍生物的途径

IF 1.5 4区化学

Chemistry of Heterocyclic Compounds Pub Date : 2024-04-08 DOI: 10.1007/s10593-024-03292-5

Polina O. Levshukova, Denis A. Kolesnik, Margarita O. Dosina, Igor P. Yakovlev, Lidiya A. Tunguskova, Elena V. Kuvaeva, Tamara L. Semakova, Galina V. Ksenofontova, Yurii G. Pokhodnya

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Novel iminocoumarin imidazo[4,5-b]pyridine derivatives: design, synthesis, and biological evaluation 新型亚氨基香豆素咪唑并[4,5-b]吡啶衍生物：设计、合成和生物学评价

IF 1.5 4区化学

Chemistry of Heterocyclic Compounds Pub Date : 2024-04-08 DOI: 10.1007/s10593-024-03296-1

Ida Boček Pavlinac, Kristina Starčević, Leentje Persoons, Mihailo Banjanac, Vedrana Radovanović, Dirk Daelemans, Marijana Hranjec

{"title":"Novel iminocoumarin imidazo[4,5-b]pyridine derivatives: design, synthesis, and biological evaluation","authors":"Ida Boček Pavlinac, Kristina Starčević, Leentje Persoons, Mihailo Banjanac, Vedrana Radovanović, Dirk Daelemans, Marijana Hranjec","doi":"10.1007/s10593-024-03296-1","DOIUrl":"https://doi.org/10.1007/s10593-024-03296-1","url":null,"abstract":"Herein, we present the design, synthesis, and biological activity of novel iminocoumarin imidazo[4,5-b]pyridine derivatives. The prepared compounds were designed to study the type of substituent in position 6 of the coumarin nucleus as well as the type of the substituent at the N atom of imidazo[4,5-b]pyridine core for their effect on the biological activity. Therefore, all compounds were tested for their antiproliferative action on several human cancer cell lines in vitro, for their antioxidative activity, antibacterial activity on several bacterial strains, and for their antiviral activity on several viruses. The results of the evaluation of biological activity revealed that the tested derivatives did not display significant biological activities. The majority of the tested compounds were not active at all, while some derivatives showed low activity in these assays. Therefore, we could conclude that the biological potential of 6-substituted iminocoumarin derivatives is very low – the substitution in position 6 of the coumarin nucleus, in comparison to 7-substituted iminocoumarins, strongly decreases biological activity.","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140566827","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}

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Synthesis and in vitro anticancer evaluation of functionalized 5-(4-piperazin-1-yl)-2-aryloxazoles and 5-[(4-arylsulfonyl)piperazin-1-yl]-2-phenyloxazoles 功能化 5-(4-哌嗪-1-基)-2-芳基噁唑和 5-[(4-芳基磺酰基)哌嗪-1-基]-2-苯基噁唑的合成和体外抗癌评估

IF 1.5 4区化学

Chemistry of Heterocyclic Compounds Pub Date : 2024-04-08 DOI: 10.1007/s10593-024-03295-2

Oleksandr O. Severin, Stepan G. Pilyo, Viktoriia S. Moskvina, Olga V. Shablykina, Yevgen A. Karpichev, Volodymyr S. Brovarets

{"title":"Synthesis and in vitro anticancer evaluation of functionalized 5-(4-piperazin-1-yl)-2-aryloxazoles and 5-[(4-arylsulfonyl)piperazin-1-yl]-2-phenyloxazoles","authors":"Oleksandr O. Severin, Stepan G. Pilyo, Viktoriia S. Moskvina, Olga V. Shablykina, Yevgen A. Karpichev, Volodymyr S. Brovarets","doi":"10.1007/s10593-024-03295-2","DOIUrl":"https://doi.org/10.1007/s10593-024-03295-2","url":null,"abstract":"This research focuses on the synthesis and in vitro anticancer evaluation of functionalized 2-aryl-5-(4-piperazin-1-yl)oxazoles and 5-[(4-arylsulfonyl) piperazin-1-yl]-2-phenyloxazoles. Oxazoles are a versatile class of compounds with diverse biological activities, making them attractive targets in medicinal chemistry. We incorporated amino and sulfonamide functionalities into the oxazole scaffold, as they have shown potential for interacting with biological targets. The synthesis of target oxazole derivatives was accomplished using 2-aroylamino-3,3-dichloroacrylonitriles as starting materials and employing efficient reaction conditions. The resulting compounds exhibited structural features that make them promising candidates for further chemical modifications and biological evaluations. Additionally, a series of sulfonamides were synthesized from 5-(piperazin-1-yl)oxazole-4-carbonitrile hydrochloride, offering diverse bioactivity and versatile structural characteristics. However, no potent inhibitors of malignant cell growth were identified among the tested compounds. Nevertheless, we categorized the investigated substances into two distinct groups based on their activity profile. Group A, comprising sulfonamides, displayed pronounced anticancer activity against breast cancer and melanoma cell lines. On the other hand, group B, the 2-aryl-5-(4-R-piperazin-1-yl)oxazole-4-carbonitriles, exhibited a moderate effect primarily on renal cancer cell lines. These findings provide valuable insights for further structural modifications in the quest for more potent anticancer agents.","PeriodicalId":9770,"journal":{"name":"Chemistry of Heterocyclic Compounds","volume":null,"pages":null},"PeriodicalIF":1.5,"publicationDate":"2024-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140566619","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}

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