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Synthesis of a new heterocyclic system: pyrimidine structural analogues of natural integrastatins A, B 新杂环系统的合成：天然整合素 A、B 的嘧啶结构类似物
Synlett Pub Date : 2024-01-05 DOI: 10.1055/a-2239-6657
S. Chikunov, Irina Pustolaikina, Yuri V. Gatilov, I. Kulakov
{"title":"Synthesis of a new heterocyclic system: pyrimidine structural analogues of natural integrastatins A, B","authors":"S. Chikunov, Irina Pustolaikina, Yuri V. Gatilov, I. Kulakov","doi":"10.1055/a-2239-6657","DOIUrl":"https://doi.org/10.1055/a-2239-6657","url":null,"abstract":"In this paper for the first time we report simple one-step synthesis of 5-methyl-11,12-dihydro-5H-5,11-epoxybenzo[7,8]oxocino[4,3-d]pyrimidine derivatives by acid-catalyzed cyclization reaction of various 4-methyl-5-acetyl pyrimidine derivatives with salicylic aldehyde. It was shown that 2-substituted 4-methyl-5-acetylpyrimidines successfully react to form a cyclization product. At the same time, 4-methyl-5-acetylpyrimidines with a substituent in the 6th position do not enter into the cyclization reaction. This may be caused by the negative effect of substituents in the 6th position, which hinder the free rotation of the acetyl group and prevent the formation of a stable pre-reaction complex. The structure of the obtained 5-methyl-11,12-dihydro-5H-5,11-epoxybenzo[7,8]oxocino[4,3-d]pyrimidine derivatives was confirmed using 1H, 13C spectroscopy, mass spectrometry and X-ray diffraction analysis.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"16 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139382770","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Aromatic residue positioning influences helical peptoid structure in aqueous solution 芳香族残基定位影响水溶液中的螺旋蛋白胨结构
Synlett Pub Date : 2024-01-04 DOI: 10.1055/a-2238-5394
Jwwad M. Javed, Katherine Scukas, Michelle T. Nguyen, Amelia Fuller
{"title":"Aromatic residue positioning influences helical peptoid structure in aqueous solution","authors":"Jwwad M. Javed, Katherine Scukas, Michelle T. Nguyen, Amelia Fuller","doi":"10.1055/a-2238-5394","DOIUrl":"https://doi.org/10.1055/a-2238-5394","url":null,"abstract":"Water-soluble peptidomimetics, including peptoids, are promising functional surrogates for biologically relevant, amphiphilic, helical peptides. Twenty amphiphilic peptoid hexamers with predicted helical structures were designed, prepared and studied using circular dichroism (CD) spectroscopy. The site-specific contributions of aromatic and charged residues to the helical structure of peptoid hexamers in aqueous solution was evaluated, revealing that aromatic residue positioning most significantly impacts structure.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"62 11","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139386905","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Condensation of amines with S-methyl thiouronium salts: an another entry for the synthesis of amidines 胺与 S-甲基硫代鎓盐的缩合：合成脒的又一途径
Synlett Pub Date : 2024-01-02 DOI: 10.1055/a-2236-9522
T. Swaroop, Rahym Bakyyev, K. Rangappa, Lokman Torun
{"title":"Condensation of amines with S-methyl thiouronium salts: an another entry for the synthesis of amidines","authors":"T. Swaroop, Rahym Bakyyev, K. Rangappa, Lokman Torun","doi":"10.1055/a-2236-9522","DOIUrl":"https://doi.org/10.1055/a-2236-9522","url":null,"abstract":"In this article, we have presented condensation of primary aryl and alkyl amines with S-methyl thiouronium salts to get N,N,N'-trisubstituted amidines. High yields, short reaction times and fair substrate scope are the noteworthy features of this protocol. Surprisingly, reaction of thiouronium salt with 4-aminopyridine yielded (4-methoxyphenyl)(piperidin-1-yl)methanone.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"101 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139391481","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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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