Tetrahedron Letters最新文献

A convenient ammonium chloride facilitated mild and efficient synthesis of Benzazepinoindole derivatives through a Pictet-Spengler reaction*

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-03-19 DOI: 10.1016/j.tetlet.2025.155529

Chibisree Elanchezhian , Diksha Bansal , Pooja Sivaganesan , Gokulprasanth Nataraj , Mrinal Kanti Das , Saikat Chaudhuri

{"title":"A convenient ammonium chloride facilitated mild and efficient synthesis of Benzazepinoindole derivatives through a Pictet-Spengler reaction*","authors":"Chibisree Elanchezhian , Diksha Bansal , Pooja Sivaganesan , Gokulprasanth Nataraj , Mrinal Kanti Das , Saikat Chaudhuri","doi":"10.1016/j.tetlet.2025.155529","DOIUrl":"10.1016/j.tetlet.2025.155529","url":null,"abstract":"<div><div>Benzazepinoindoles are a promising class of compounds in the growing field of heterocyclic chemistry due to their intriguing pharmacological properties. The tetrahydro-benzazepinoindole scaffold, in particular, holds great promise as a versatile framework for drug discovery, especially in the development of antiproliferative and anti-inflammatory agents. In present work, we proposed the synthesis of tetrahydro-benzazepinoindoles starting from alkylated indole and benzaldehyde derivatives using NH<sub>4</sub>Cl, and methanol as solvent. This approach is designed to achieve high efficiency and good to excellent yields, while accommodating diverse functional groups to enhance structural diversity. The scalability of this method was demonstrated through successful gram-scale reactions, highlighting its utility in practical applications. The synthesized compounds were characterized using advanced techniques, including <sup>1</sup>H NMR, <sup>13</sup>C NMR, <sup>19</sup>F NMR, DEPT-135, IR and mass spectrometry, confirming their structural integrity. This work provides a streamlined and reliable strategy for the synthesis of tetrahydro-benzazepinoindoles, contributing to advancements in synthetic methodology and paving the way for the development of novel bioactive molecules with significant therapeutic potential.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155529"},"PeriodicalIF":1.5,"publicationDate":"2025-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143654773","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 aerobic C-3 thiocyanation of indoles using carbon dots as photoredox catalyst 利用碳点作为光氧化催化剂，在可见光诱导下进行吲哚的有氧 C-3 硫氰化反应

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-03-15 DOI: 10.1016/j.tetlet.2025.155545

Pritesh Khobrekar , Sandesh Bugde

引用次数: 0

Synthesis and Structural Confirmation of PyHOPO and its Applicability in Racemization Reduction in Solid-Phase Peptide Synthesis

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-03-10 DOI: 10.1016/j.tetlet.2025.155520

Kwazi Masuku , Anamika Sharma , Sikabwe Noki , Sizwe Zamisa , Ayman El-Faham , Beatriz G. de la Torre , Fernando Albericio

引用次数: 0

Construction of Amidines via palladium-catalyzed three-component reaction of Arylacetylenes, t-Butylisonitrile and O-benzoyl Hydroxylamines

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-03-06 DOI: 10.1016/j.tetlet.2025.155534

Jianquan Hong, Feng Zheng, Xiaoyu Wang, Mingyu Ma, Yupeng Yang, Lianguang Huo, Shuai Huang, Changge Zheng

引用次数: 0

Synthesis of spiroisoxazoline oxindoles by base-promoted annulation of oxime esters and isatins

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-03-06 DOI: 10.1016/j.tetlet.2025.155506

Si-Wei Chen , Xu-Hua Hu , Ling Wu , Chun-Bao Miao , Xun-Xiang Guo

引用次数: 0

Synthesis of Ortho-nitrochalcones by solvent-free grinding method: Facilitating the synthesis of 2,3-Disubstituted Quinoline N-oxides via bimolecular reaction

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-03-05 DOI: 10.1016/j.tetlet.2025.155533

Sai Wang , Wangyuan Zhan , Deguang Huang , XiaoFeng Zhang

引用次数: 0

Greener synthesis of Pyrroloacridine-1(2H)-one and 1,8-Dioxodecahydroacridine derivatives: Ascorbic acid mediated OrganocatalyticApproach

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-03-03 DOI: 10.1016/j.tetlet.2025.155518

Saptadwipa Bhattacharjee, Puja Basak, Pranab Ghosh

引用次数: 0

Nitration of deactivated aromatic compounds using Lithium nitrate

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-03-03 DOI: 10.1016/j.tetlet.2025.155515

Weihao Ma , J. Tyler McBride , Robert S. Phillips

引用次数: 0

Synthesis of bis-sulfonium lipids and their antibacterial ability

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-03-03 DOI: 10.1016/j.tetlet.2025.155528

Chengcai Liu , Xiaodong Zhou , Xinrui Bi , Peiyu Chen , Wanning Li , Jing Li

引用次数: 0

One-pot synthesis and anti-proliferative activity of hindered 5-amino-1-alkylimidazole-4-carboxamides

IF 1.5 4区化学

Tetrahedron Letters Pub Date : 2025-03-03 DOI: 10.1016/j.tetlet.2025.155517

Yamei Zhang , Zijuan Yang , Yong Xie , Yeming Wang

{"title":"One-pot synthesis and anti-proliferative activity of hindered 5-amino-1-alkylimidazole-4-carboxamides","authors":"Yamei Zhang , Zijuan Yang , Yong Xie , Yeming Wang","doi":"10.1016/j.tetlet.2025.155517","DOIUrl":"10.1016/j.tetlet.2025.155517","url":null,"abstract":"<div><div>One-pot procedure was developed for the synthesis of hindered 5-amino-1-alkylimidazole-4-carboxamides by using bulky alkyl amines with trimethyl orthoformate and 2-amino-2-cyanoacetamide. Under optimized conditions, the reactivity of a series of steric hindrance substrates was examined, producing the corresponding hindered 5-amino-1-alkylimidazole-4-carboxamides with good to excellent yields. This synthetic method has several advantages including metal- and additive-free, short reaction time and wide substrate scope with good to excellent yields. Besides, 5-amino-1-(4-fluorobenzyl)-1<em>H</em>-imidazole-4-carboxamide (<strong>3j</strong>) exhibited potent antiproliferative activity against A375(B-RAF<sup>V600E</sup>) cells as a novel anti-tumor agent, and the molecular docking model showed that carboxamide moiety of <strong>3j</strong> was a key active functional group, forming two hydrogen bonds with Lys483 and Phe595，which was similar to the function of sulfonamide of vemurafenib. To our delight, the imidazole scaffold of <strong>3j</strong> formed a novel hydrogen bond with Asp594, and there was π…π interaction between the phenyl group of <strong>3j</strong> and Phe583, which were different from binding mode of vemurafenib. The binding mode between <strong>3j</strong> and B-RAF<sup>V600E</sup> kinase provided a reasonable explanation for <strong>3j</strong> as a potential B-RAF<sup>V600E</sup> kinase inhibitor.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155517"},"PeriodicalIF":1.5,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143580730","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