Letters in Organic Chemistry最新文献

Tröger’s Base Derivative-catalyzed Ugi-Smiles Reaction Involving Aliphatic Aldehydes Tröger的碱衍生物催化Ugi-Smiles反应涉及脂肪醛

4区化学

Letters in Organic Chemistry Pub Date : 2025-10-23 DOI: 10.2174/0115701786415168251005160724

Meng Dong, Hao Cui, Yu Wan, Yuan Rui, Hui Wu

引用次数: 0

Humic Acid as a Recyclable Green Catalyst for the Synthesis of Imines from Carbonyl Compounds and Primary Amines at Room Temperature 腐植酸作为可循环绿色催化剂用于羰基化合物和伯胺在室温下合成亚胺

4区化学

Letters in Organic Chemistry Pub Date : 2025-10-06 DOI: 10.2174/0115701786395176250828052806

Zeyi Liu, Miao Zhou, Zijian Yang, Yichun Wang, Hongshe Wang

{"title":"Humic Acid as a Recyclable Green Catalyst for the Synthesis of Imines from Carbonyl Compounds and Primary Amines at Room Temperature","authors":"Zeyi Liu, Miao Zhou, Zijian Yang, Yichun Wang, Hongshe Wang","doi":"10.2174/0115701786395176250828052806","DOIUrl":"https://doi.org/10.2174/0115701786395176250828052806","url":null,"abstract":"Imines are important intermediates for the synthesis of fine chemicals, pharmaceuticals, and agricultural chemicals. The development of green and sustainable synthetic methods is always a high priority of modern synthetic chemistry. Catalysts with environmental sustainability and high catalytic performance are of great research interest for sustainable catalysis. Humic acid is a class of natural and refractory high molecular weight organic matter. The chemical structure of humic acid contains a large number of functional groups such as carboxyls, hydroxyls, and aromatic rings, indicating that it comprises quinones, phenols, sugar, polypeptides, and other compounds. Humic acid is a green, biodegradable, commercially available, inexpensive and homogeneous recyclable organocatalyst. In this article, humic acid was used to catalyze the condensation of aldehydes or ketones with primary amines to the corresponding imines. In order to optimize the reaction conditions, the condensation reaction of benzaldehyde and aniline was selected as a model reaction. The effects of catalysts, catalyst loading and solvents on the formation of imines were systematically investigated. Under the optimized conditions, the methodology was successfully applied for the synthesis of a series of imines at room temperature in high yields and can be easily scaled up to the gram scale. The results showed that the catalyst humic acid exhibited excellent activity in the synthesis of imines from carbonyl compounds and primary amines. Importantly, the catalyst humic acid is effectively recycled and reused eight times with no significant decrease in the yield of the product. Our strategy provides a sustainable, efficient route for the green synthesis and large-scale production of imines at room temperature.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"23 3","pages":"171-179"},"PeriodicalIF":0.0,"publicationDate":"2025-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147899687","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

Chemoselectivity Profiling in the Alkylation of 2-Chloroethylurea Derivatives with Secondary Amines 2-氯乙基脲衍生物与仲胺烷基化反应的化学选择性分析

4区化学

Letters in Organic Chemistry Pub Date : 2025-01-24 DOI: 10.2174/0115701786357824250117052847

Hongyin Wang, Liang Yu, Yafen Yu, Yihao Wang, Ni An, Ni An, Dong Cai

引用次数: 0

Synthesis and Anticancer Activity Evaluation of N-(3,4,5-Trimethoxycinnamoyl)anthranilic Acid Derivatives N-（3,4,5-三甲氧基肉桂基）苯甲酸衍生物的合成及抗癌活性评价

4区化学

Letters in Organic Chemistry Pub Date : 2025-01-24 DOI: 10.2174/0115701786355190241214054126

Tri-Thuc D. Nguyen, Linh C. Phan, Nhat-Linh N. Dao, Phuong-Thuy T. Phan, Da-Huong H. Phan, Tuan-Anh Nguyen Pham

{"title":"Synthesis and Anticancer Activity Evaluation of N-(3,4,5-Trimethoxycinnamoyl)anthranilic Acid Derivatives","authors":"Tri-Thuc D. Nguyen, Linh C. Phan, Nhat-Linh N. Dao, Phuong-Thuy T. Phan, Da-Huong H. Phan, Tuan-Anh Nguyen Pham","doi":"10.2174/0115701786355190241214054126","DOIUrl":"https://doi.org/10.2174/0115701786355190241214054126","url":null,"abstract":"There is an urgent need to search for more efficient, better-tolerated anticancer drugs. Tranilast, a synthetic analog of tryptophan metabolite, has been shown to inhibit the growth of various cancer cells. In our previous study, the tranilast analog TRA01 [N-(3,4,5-trimethoxycinnamoyl) anthranilic acid] was identified as a promising agent against the proliferation of MCF-7 and HepG2 cell lines along with good binding affinity on the transforming growth factor beta 1 (TGFβ1) target. To further explore the structure-activity relationship, a series of N-(3,4,5-trimethoxycinnamoyl) anthranilic acid derivatives 5a–i were successfully synthesized via a two-step synthetic procedure based on N-acylation and Knoevenagel-Doebner reactions and their structures were determined using 1H-NMR, 13C-NMR, and MS spectra. The derivatives (5a–i) were evaluated for in vitro activity using MTT assay and in silico docking on TGFβ1 target by AutoDockTools–1.5.6 software. The bioactivity results of 5a–i showed 12.30–27.04% and 19.13–46.23% inhibition on proliferation of MCF-7 and HepG2 cell lines at 100 μM concentration, respectively, with the fluorinated derivatives (5a and 5e) possessing the strongest inhibitory activities. The molecular docking also found the best binding affinity of 5a (-8.70 Kcal/mol) and 5e (-8.71 Kcal/mol) on the TGF&#946;1 target. The SAR result revealed that substituents on the benzene ring of anthranilic acid were not favored for anticancer activity. Although these derivatives exhibited weak anticancer properties, the good binding affinity to the TGF&#946;1 target suggested certain potential of this scaffold for further study on this target.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"22 7","pages":"580-590"},"PeriodicalIF":0.0,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147881769","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: 1

How Enzyme Selectivity and Immobilization Affect Catalytic Yields in Lipase-Catalyzed Processes 酶的选择性和固定化如何影响脂肪酶催化过程的催化产量

IF 0.8 4区化学

Letters in Organic Chemistry Pub Date : 2024-09-10 DOI: 10.2174/0115701786330890240826053103

Ibrahim Karume

{"title":"How Enzyme Selectivity and Immobilization Affect Catalytic Yields in Lipase-Catalyzed Processes","authors":"Ibrahim Karume","doi":"10.2174/0115701786330890240826053103","DOIUrl":"https://doi.org/10.2174/0115701786330890240826053103","url":null,"abstract":": Herein, the influence of structural attributes, including the interactions of lipases with support systems, substrates, products/byproducts, and the media environment, on enzyme stability, selectivity and activity are discussed. Substrates/products, such as methanol, glycerol, phenolic acids and polyphenols, can inhibit lipase activity by influencing the mass flow of the reactants and products or by enzyme denaturation, which is also caused by extreme pH, high temperatures, and digestive action of most organic solvents. Immobilization techniques that involve chemical bonding between the functional groups of the support and the amino acids of the lipase maintain the enzyme’s active conformation via the formation of stable secondary structures. Functionalized metal nanoparticles and metal and covalent organic frameworks (COFs and MOFs) covalently bond to lipases, reducing the reliance of the active site conformation on hydrogen bonding and disulfide bonds. The crystallinity of COFand MOF-immobilized lipases allows them to be used in contrasting media environments and at high temperatures, which increases the reaction kinetics and improves the catalytic yield. On the other hand, inert support systems such as silica promote catalytic yields by minimizing protein leaching, which fairly maintains the amount of the preloaded lipase. The structure of substrates also plays a large role, whereas some lipases strictly prefer narrow substrates. In contrast, others, such as Candida species lipases, are liberal and allow substrates of varying bulkiness/steric hindrances.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"64 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142227747","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

Photochemical Dimerization of Indones: A DFT Study 印度尼西亚的光化学二聚化：DFT 研究

IF 0.8 4区化学

Letters in Organic Chemistry Pub Date : 2024-09-03 DOI: 10.2174/0115701786313908240822100732

Maurizio D' Auria

引用次数: 0

Rapid and Metal-Free Green Synthesis of Coumarins Catalyzed by Humic Acid 腐植酸催化香豆素的快速无金属绿色合成

IF 0.8 4区化学

Letters in Organic Chemistry Pub Date : 2024-09-03 DOI: 10.2174/0115701786318539240822112936

Ling Wei, Yichun Wang, Qixuan Huang, Hongshe Wang

{"title":"Rapid and Metal-Free Green Synthesis of Coumarins Catalyzed by Humic Acid","authors":"Ling Wei, Yichun Wang, Qixuan Huang, Hongshe Wang","doi":"10.2174/0115701786318539240822112936","DOIUrl":"https://doi.org/10.2174/0115701786318539240822112936","url":null,"abstract":": In recent years, numerous methods have been developed for the synthesis of coumarins via Pechmann reaction catalyzed by various catalysts. Although each of the synthetic strategies previously reported has its own merit, most of these methods are associated with certain disadvantages, including the use of commercially unavailable metal catalysts and organic solvents, low yields, and long reaction times. Therefore, the development of a highly efficient, green, and sustainable catalytic methodology for the synthesis of coumarins is still desirable. Humic acid has been found to be an efficient catalyst for the synthesis of coumarins via the Pechmann reaction at 80oC under solvent-free conditions. The methodology enables the synthesis of structurally diverse coumarins from phenols and β-keto esters within 5-8 min in high yields (91-99%). The green, commercially available, inexpensive organocatalyst can be effectively recycled and reused five times with no significant dropdown in the yield of the product. The method reported has the advantages of high yield, no need for metal catalysts, short reaction time, simple operation, and green and reusable catalyst.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"41 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142224405","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

An Efficient Metal-Free Methodology for the Synthesis of Hydrazo-Linked 5-(4-aryl)-1H-1,2,4-Triazoles 合成 5-(4-芳基)-1H-1,2,4-三唑的高效无金属方法学

IF 0.8 4区化学

Letters in Organic Chemistry Pub Date : 2024-08-28 DOI: 10.2174/0115701786332586240819074232

Neha Rani, Deepak K. Aneja, Mayank Kinger, Rinku Soni, Monika Sihag, Sandeep Malik, Kirti Bhardwaj

{"title":"An Efficient Metal-Free Methodology for the Synthesis of Hydrazo-Linked 5-(4-aryl)-1H-1,2,4-Triazoles","authors":"Neha Rani, Deepak K. Aneja, Mayank Kinger, Rinku Soni, Monika Sihag, Sandeep Malik, Kirti Bhardwaj","doi":"10.2174/0115701786332586240819074232","DOIUrl":"https://doi.org/10.2174/0115701786332586240819074232","url":null,"abstract":"Hydrazo compounds have displayed significant roles in both biological and physical aspects, such as spinamycin as a potent growth inhibitor against fungi and rat sarcoma cells, hydrazo tocopherol as a component of vitamin E, and electron-rich hydrazo-linked triazines as energetic materials. In this study, a metal-free approach was proposed for the synthesis of hydrazo-linked 5-(4- aryl)-1H-1,2,4-triazoles. The methods for the synthesis of 5-(4-aryl)-1H-1,2,4-triazoles initiated by the reaction of aldehyde with semicarbazide. The resulted compound, 5-(4-aryl)-1H-1,2,4-triazol-3- ol, upon reaction with phosphorous oxychloride yielded 3-chloro-5-(4-aryl)-1H-1,2,4-triazoles. These synthesized compounds upon fusión with various aryl and hetero aryl substituted hydrazines provided desired hydrazo moieties. Synthesized hydrazo compounds were characterized by spectroscopic techniques, viz. 1H-NMR, FT-IR and mass spectrometry. In this study, a series of novel hydrazo- linked 5-(4-aryl)-1H-1,2,4-triazoles were synthesized. The methodology proposed in this study eliminates the use of complicated procedures and heavy metals.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"36 1","pages":""},"PeriodicalIF":0.8,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142185363","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

Ce(OTf)3-Catalyzed Synthesis of Glucopyranurono-6,1-Lactone: A Key Intermediate for Obtaining Glycoconjugates of Peptidic Fragments of Arenastatin A Ce(OTf)3催化合成吡喃葡萄糖醛酸-6,1-内酯：获得阿瑞司他丁 A 肽片段糖苷共轭物的关键中间体

IF 0.8 4区化学

Letters in Organic Chemistry Pub Date : 2024-08-28 DOI: 10.2174/0115701786325021240817182955

A. Mezrai, L. Mrah, Z. Khiati, A. Keniche

引用次数: 0

Continuous Flow Synthesis of Amides in Bio-Derived Solvent GVL 在生物衍生溶剂 GVL 中连续流合成酰胺

IF 0.8 4区化学

Letters in Organic Chemistry Pub Date : 2024-08-23 DOI: 10.2174/0115701786313379240815113722

Xu-Yang Mu, Rui Zhu, Li-Jie Yu, Wen-Long Wang

引用次数: 0