IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-12 DOI: 10.1016/j.tet.2024.134270

引用次数: 0

Corrigendum to “Blue light-promoted N–H insertion of amides, isatins, sulfonamides and imides into arylidiazoacetates: Synthesis of unnatural α-aryl amino acid derivatives” [Tetrahedron 76 (2020) 131316] 蓝光促进酰胺、异肽、磺酰胺和亚胺的 N-H 插入芳基偶氮乙酸酯：非天然 α-芳基氨基酸衍生物的合成" [Tetrahedron 76 (2020) 131316] 的更正

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-09 DOI: 10.1016/j.tet.2024.134254

引用次数: 0

Structural optimization and bioactivity evaluation of 2-(Methylcarbonylamino) thiazole derivatives as novel PDE4B inhibitors 作为新型 PDE4B 抑制剂的 2-（甲基羰基氨基）噻唑衍生物的结构优化和生物活性评估

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-07 DOI: 10.1016/j.tet.2024.134250

{"title":"Structural optimization and bioactivity evaluation of 2-(Methylcarbonylamino) thiazole derivatives as novel PDE4B inhibitors","authors":"","doi":"10.1016/j.tet.2024.134250","DOIUrl":"10.1016/j.tet.2024.134250","url":null,"abstract":"<div>Phosphodiesterase-4 (PDE4) is a protease belonging to the phosphodiesterase family, with a specific function of hydrolyzing intracellular cyclic adenosine monophosphate (cAMP). PDE4 is widely distributed across various human tissues and cells, where it plays a pivotal role in modulating intracellular cAMP levels, particularly in immune and inflammatory cells. Consequently, PDE4 inhibitors have been proven to effectively dampen inflammatory responses in these cells, leading to a reduction in the release of pro-inflammatory factors such as lipid mediators, reactive oxygen species (ROS) hydrolases, cytokines, and chemokines. Despite the considerable interest from both academia and pharmaceutical industries in exploiting this target for drug development, only a handful of PDE4 inhibitors are available in the market. The aim of this study was to identify novel PDE4B inhibitors through a combined approach of computer-aided drug design, synthesis, and activity evaluation. The study implemented three phases of structure optimization from the hit compound MR9, which was previously obtained by virtual screening, with reference to structure-based drug design (SBDD) and ligand-based drug design (LBDD) approaches. The optimized compound MR9-302 (PDE4B IC50 = 2.02 ± 0.2888 μM) exhibited enhanced inhibitory activity compared to MR9.</div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142164592","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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

Green synthesis of imidazoles: The catalytic efficacy of magnetic nanoparticles 咪唑的绿色合成：磁性纳米颗粒的催化功效

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-06 DOI: 10.1016/j.tet.2024.134246

{"title":"Green synthesis of imidazoles: The catalytic efficacy of magnetic nanoparticles","authors":"","doi":"10.1016/j.tet.2024.134246","DOIUrl":"10.1016/j.tet.2024.134246","url":null,"abstract":"<div>In the present scenario, environment-friendly reactions in organic synthesis have a unique and irreplaceable place. In the past, there are significant progress in the development of more nature-friendly and sustainable methods for various organic transformations. The nature-friendly and sustainable methods make a tool named green synthesis which utilizes for the synthesis of various drug candidates. Within perspectives of green synthesis, the magnetic nanoparticles attract considerable attention due to its many characteristics and utilization in the green synthesis. In organic synthesis, magnetic nanoparticles have been used as a green catalyst for the formation of various heterocycles. In the realm of organic compounds, imidazole is considered a preferred and highly valuable motif among aza-heterocycles. It presents a favourable opportunity for discovering lead structures in the quest for new synthetic molecules with potential therapeutic properties and other significant prospects. The synthesis of imidazole due to its exciting profile is very much demanding by using magnetic nanoparticles as a green catalyst. Accordingly, the pure and functionalized magnetic nanoparticles display significant potential in the synthesis of a diverse range of imidazole derivatives. Therefore, this manuscript compiles the current research (from 2004 to present) on the role of environmentally safe pure and functionalized magnetic nanoparticles for generating a wide variety of valuable imidazoles.</div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142150748","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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

Azirine Weinreb amides: Preparation and use in the synthesis of 2-acylated aziridines and azirines 氮丙啶 Weinreb 酰胺：制备并用于合成 2-酰基氮丙啶和氮丙啶

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-06 DOI: 10.1016/j.tet.2024.134255

{"title":"Azirine Weinreb amides: Preparation and use in the synthesis of 2-acylated aziridines and azirines","authors":"","doi":"10.1016/j.tet.2024.134255","DOIUrl":"10.1016/j.tet.2024.134255","url":null,"abstract":"<div>Azirine Weinreb amides (N-methoxy-N-methyl-2H-azirine-2-carboxamides) were synthesized in yields of 35–94 % by the reaction of N,O-dimethylhydroxylamine with 2H-azirine-2-carbonyl chlorides, formed by the catalytic isomerization of 5-chloroisoxazoles. Red-Al reduction of azirine Weinreb amides affects only the azirine C<img>N bond and leaves the C(O)NMeOMe group unaffected, forming stereoselectively 1-unprotected 3-substituted cis-N-methoxy-N-methylaziridine-2-carboxamides. The developed approach is a stereo-complementary addition to the previously proposed method for preparing unprotected trans-N-methoxy-N-methyl-3-phenylaziridine-2-carboxamide. The Weinreb amide group in the synthesized cis-N-methoxy-N-methylaziridine-2-carboxamides was used to prepare cis-2-acyl-3-arylaziridines by reaction with organometallic compounds. The reaction of organomagnesium compounds with azirine Weinreb amides allow the stereoselective preparation of 3-aryl-3-aryl/hetary/alkyl-N-methoxy-N-methylaziridine-2-carboxamides; which, in turn, were used to obtain the corresponding aziridinyl ketones. The reaction of azirine Weinreb amides with bulky substituents in the 3-position of azirine with organometallic compounds occurs only at the C(O)NMeOMe group with retention of the azirine C<img>N bond with the formation of 2-acyl-2H-azirines.</div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142164591","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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

Anti-inflammatory 3,4-seco-triterpenoids from Ganoderma cochlear 灵芝中的 3,4-seco-三萜类抗炎物质

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-06 DOI: 10.1016/j.tet.2024.134240

引用次数: 0

A coumarin-hemicyanine fluorescent probe for simultaneous detection and discrimination of biothiols, HSO3− and S2- 用于同时检测和鉴别生物硫醇、HSO3- 和 S2- 的香豆素-水杨碱荧光探针

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-04 DOI: 10.1016/j.tet.2024.134249

{"title":"A coumarin-hemicyanine fluorescent probe for simultaneous detection and discrimination of biothiols, HSO3− and S2-","authors":"","doi":"10.1016/j.tet.2024.134249","DOIUrl":"10.1016/j.tet.2024.134249","url":null,"abstract":"<div>Biomercaptan, bisulfite (HSO3−) and hydrogen sulfide (H2S) are involved in many physiological and pathological processes in the human body. Therefore, it is of great significance to develop a fluorescent probe that can simultaneously detect and distinguish biological mercaptans from HSO3− and S2−. The probe CDI-1 was synthesized by combining coumarin with hemicyanine. The maximum absorption wavelength of the probe is at 609 nm. After adding Cys/Hcy and GSH, the probe shows varying degrees of blue shift, which can be used to distinguish Cys/Hcy and GSH. After it reacts with Cys/Hcy, the fluorescence intensity of the solution increases about twice, while it increases three times after it reacts with GSH. This phenomenon can also be used to distinguish Cys/Hcy from GSH. The probe CDI-1 can react with Cys completely within 30 min, with Hcy or GSH completely within 80 min, and with HSO3− and S2− quickly within 20 min. The study on the effect of pH on the fluorescence performance of CDI-1 shows that the probe is suitable for detecting biological mercaptan or HSO3−, S2− in weak acid to weak alkali environments. The selectivity study showed that the probe CDI-1 had high specificity for biological mercaptan, HSO3− and S2−. This provides a new and simple method for simultaneous detection of biological mercaptan, HSO3− and S2− ions.</div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142150670","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 β-lactams and transformation to β-amino acid ethyl ester derivatives: Theoretical calculations β-内酰胺的合成及向β-氨基酸乙酯衍生物的转化：理论计算

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-03 DOI: 10.1016/j.tet.2024.134247

引用次数: 0

A concise, stereoselective and scalable synthesis of optically pure (3R,4R)-1-benzyl- and (3R,4R)-1-Boc-3-methyl-4-aminopiperidines 光学纯(3R,4R)-1-苄基和(3R,4R)-1-叔丁氧羰基-3-甲基-4-氨基哌啶的简便、立体选择性和可扩展合成方法

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-02 DOI: 10.1016/j.tet.2024.134239

引用次数: 0

Photoredox-catalyzed self-dimerization and cross-addition as well as Zn(OTf)2-mediated nucleophile coupling: A novel route to structurally diverse 2,2-disubstituted indolin-3-ones 光氧化催化的自二聚化和交叉加成以及 Zn(OTf)2 介导的亲核偶联：获得结构多样的 2,2-二取代吲哚啉-3-酮的新途径

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-09-02 DOI: 10.1016/j.tet.2024.134242

引用次数: 0

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