Asian Journal of Organic Chemistry最新文献

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Design and Synthesis of Triazole‐Based Imidazolium Salts as Potent Integrin‐Linked Kinase (ILK) Inhibitors for Anti‐Metastatic Breast Cancer Therapy 三唑基咪唑盐作为抗转移性乳腺癌整合素连接激酶(ILK)抑制剂的设计和合成
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.70161
Alameer Ezat Abdulkareem , Ahmed Hassoon Mageed
{"title":"Design and Synthesis of Triazole‐Based Imidazolium Salts as Potent Integrin‐Linked Kinase (ILK) Inhibitors for Anti‐Metastatic Breast Cancer Therapy","authors":"Alameer Ezat Abdulkareem ,&nbsp;Ahmed Hassoon Mageed","doi":"10.1002/ajoc.70161","DOIUrl":"10.1002/ajoc.70161","url":null,"abstract":"<div><div>Breast cancer metastasis remains a critical challenge, necessitating targeted therapies that disrupt key signaling pathways in tumor progression. Integrin‐linked kinase (ILK), a key regulator of cell adhesion, migration, and survival via the AKT/NF‐κB axis, is a promising target for anti‐metastatic drug development. This study reports the synthesis and evaluation of C2‐substituted and unsubstituted imidazolium–triazole derivatives as potential ILK modulators. Compounds were synthesized using Cu(I)‐catalyzed azide–alkyne cycloaddition and characterized by FTIR, NMR, and mass spectrometry. To explore upstream molecular interactions, docking studies were conducted using the CXCR4 receptor (PDB ID: 3ODU), functionally linked to ILK activation in metastasis. Compound <strong>14</strong> demonstrated high binding affinity (–9.3 kcal/mol), interacting with Trp94, Asp97, and Ile204, and maintained stability during 100 ns molecular dynamics simulations. In vitro cytotoxicity against MCF‐7 cells identified Compound <strong>6</strong> as the most potent (IC<sub>50</sub> = 170.58 ± 0.3 µg/mL), with Compound <strong>14</strong> also showing notable activity (IC<sub>50</sub> = 200.84 ± 0.7 µg/mL). Structure–activity relationship analysis (SAR) revealed that aromatic and hydrophobic groups enhanced efficacy. These results suggest that imidazolium–triazole hybrids are promising modulators of the CXCR4–ILK–AKT/NF‐κB axis and hold potential for further development as anti‐metastatic agents in breast cancer therapy.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e70161"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317791","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
Palladium‐Catalyzed Formal [4 + 2] Benzannulation of 1‐ferrocenyl‐2‐bromobenzene with Alkynes 钯催化的1-二茂铁-2-溴苯与炔烃的正[4 + 2]联环反应
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500272
Jiafeng He , Dr. Pei‐Chao Zhang , Yin‐Lin Li , Dr. Wen‐Bo Li , Prof. Dr. Lu Liu
{"title":"Palladium‐Catalyzed Formal [4 + 2] Benzannulation of 1‐ferrocenyl‐2‐bromobenzene with Alkynes","authors":"Jiafeng He ,&nbsp;Dr. Pei‐Chao Zhang ,&nbsp;Yin‐Lin Li ,&nbsp;Dr. Wen‐Bo Li ,&nbsp;Prof. Dr. Lu Liu","doi":"10.1002/ajoc.202500272","DOIUrl":"10.1002/ajoc.202500272","url":null,"abstract":"<div><div>A Pd‐catalyzed formal [4 + 2] benzannulation of 1‐ferrocenyl‐2‐bromobenzene with diarylacetylenes involving C─C coupling/C─H functionalization processes are developed, which provides a straightforward access to various substituted naphtho‐ferrocenes. This methodology offers a novel and efficient approach to produce polycyclic aromatic hydrocarbons (PAHs). The preliminary investigation shows the chiral phosphine ligand <em>N</em>‐Me‐PC‐Phos has great potential in the asymmetric synthesis of planar naphtho‐ferrocene derivatives.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00272"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317792","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
Fenton‐Like Catalysis: Fe(III)/H2O2‐Mediated Oxidative Scission of Ascorbic Acid to a Sustainable One‐Carbon Approach for Aza‐Heterocycle Synthesis Fenton-Like催化:Fe(III)/ h2o2介导的抗坏血酸氧化裂解为可持续的单碳氮杂环合成方法
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500042
Ariprasanth Ramalingam , Vikraman Ganesh Moorthi , Sreenath Murukesan , Gopal Chandru Senadi
{"title":"Fenton‐Like Catalysis: Fe(III)/H2O2‐Mediated Oxidative Scission of Ascorbic Acid to a Sustainable One‐Carbon Approach for Aza‐Heterocycle Synthesis","authors":"Ariprasanth Ramalingam ,&nbsp;Vikraman Ganesh Moorthi ,&nbsp;Sreenath Murukesan ,&nbsp;Gopal Chandru Senadi","doi":"10.1002/ajoc.202500042","DOIUrl":"10.1002/ajoc.202500042","url":null,"abstract":"<div><div>We report a sustainable and efficient strategy for the synthesis of aza‐heterocycles via oxidative C─C bond cleavage of naturally occurring <em>L</em>‐ascorbic acid, utilized as a renewable one‐carbon (C<sub>1</sub>) synthon. The transformation is promoted by a Fenton‐like Fe(III)/H<sub>2</sub>O<sub>2</sub> catalytic system and exhibits broad functional group tolerance. A wide variety of substituted <em>o</em>‐aminobenzamides were successfully converted into quinazolinone derivatives in moderate to excellent yields. Additionally, other aza‐heterocycles derived from <em>ortho</em>‐substituted anilines were synthesized in moderate yields. The practicality of this protocol was further demonstrated through a one‐pot synthesis starting from isatoic anhydride <strong>1′</strong> and aromatic amines, along with successful gram‐scale reactions. Radical inhibition experiments with TEMPO and control studies in the absence of <em>o</em>‐aminobenzamide support a radical‐mediated oxidative pathway. Furthermore, the in situ formation of glyceraldehyde as a key C<sub>1</sub> intermediate was confirmed by HRMS, providing support for the proposed mechanism. Thus, this method offers an economical and scalable route for the construction of valuable nitrogen‐containing heterocycles from bio‐based feedstocks.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00042"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317738","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
Synthesis and Physical Properties of Salphen‐Conjugated TTF‐Metal Complex [CuII(TTF‐Salphen)]2PF6 salphon -共轭ttf -金属配合物[CuII(TTF-Salphen)]2PF6的合成及物理性质
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500590
Daiki Tauchi , Aoba Kanesaka , So Yokomori , Takuya Shiga , Tomoyuki Akutagawa , Nobuki Kuwabara , Masashi Hasegawa , Hiroyuki Nishikawa
{"title":"Synthesis and Physical Properties of Salphen‐Conjugated TTF‐Metal Complex [CuII(TTF‐Salphen)]2PF6","authors":"Daiki Tauchi ,&nbsp;Aoba Kanesaka ,&nbsp;So Yokomori ,&nbsp;Takuya Shiga ,&nbsp;Tomoyuki Akutagawa ,&nbsp;Nobuki Kuwabara ,&nbsp;Masashi Hasegawa ,&nbsp;Hiroyuki Nishikawa","doi":"10.1002/ajoc.202500590","DOIUrl":"10.1002/ajoc.202500590","url":null,"abstract":"<div><div>A paramagnetic metal complex, [Cu<sup>II</sup>(TTF‐Salphen)], in which a TTF (tetrathiafulvalene) ligand is coordinated through a Salphen coordination site, was synthesized as a potential candidate for a new π‐d system. Electrochemical oxidation afforded its cation radical salt, [Cu<sup>II</sup>(TTF‐Salphen)]<sub>2</sub>PF<sub>6</sub>, as black, block‐shaped crystals. X‐ray crystallographic analysis revealed that both the neutral and cationic complexes possess planar structures and stack in a head‐to‐tail manner to form dimers. The 2:1 stoichiometry of the TTF‐complex to the anion in [Cu<sup>II</sup>(TTF‐Salphen)]<sub>2</sub>PF<sub>6</sub> indicates a partial oxidation state of +0.5 for the TTF moiety. Electrical conductivity measurements of [Cu<sup>II</sup>(TTF‐Salphen)]<sub>2</sub>PF<sub>6</sub> revealed semiconducting behavior, reflecting its one‐dimensional columnar structure, yielded a room‐temperature conductivity of σ<sub>RT</sub> = 1.8 S·cm<sup>−1</sup> and an activation energy of <em>E</em><sub>a</sub> = 0.14 eV. [Cu<sup>II</sup>(TTF‐Salphen)]<sub>2</sub>PF<sub>6</sub> exhibits weak antiferromagnetic interactions between the π‐spins of the TTF moieties and the d‐spins of Cu(II) centers upon cooling, followed by the formation of singlet states by the π‐spins in the TTF moieties below 20 K. Electron spin resonance (ESR) measurements on the powder sample of [Cu<sup>II</sup>(TTF‐Salphen)]<sub>2</sub>PF<sub>6</sub> support the magnetic behavior observed in the magnetic susceptibility measurements.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00590"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317745","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
Organocatalytic Synthesis of δ‐Sultone‐Fused Benzofurans and Indoles by Annulative SuFEx Reactions of β‐Arylethenesulfonyl Fluorides β-芳基磺酰氟环结SuFEx反应有机催化合成δ-磺酮-融合苯并呋喃和吲哚
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500573
Qichao Zhang , Fang Zhang , Qifan Wang , Lin He , Guangfen Du
{"title":"Organocatalytic Synthesis of δ‐Sultone‐Fused Benzofurans and Indoles by Annulative SuFEx Reactions of β‐Arylethenesulfonyl Fluorides","authors":"Qichao Zhang ,&nbsp;Fang Zhang ,&nbsp;Qifan Wang ,&nbsp;Lin He ,&nbsp;Guangfen Du","doi":"10.1002/ajoc.202500573","DOIUrl":"10.1002/ajoc.202500573","url":null,"abstract":"<div><div>An organocatalytic annulative sulfur(VI)‐fluoride exchange (SuFEx) reaction of β‐arylethenesulfonyl fluorides has been reported. Under the catalysis of 10 mol% BTMG and molecular sieves 4 Å, β‐arylethenesulfonyl fluorides undergo Michael addition‐intramolecular SuFEx click reaction with benzofuran‐3(2<em>H</em>)‐ones to give δ‐sultone‐fused benzofurans in 72%–99% yields. Under similar reaction conditions, β‐arylethenesulfonyl fluorides couple with oxindoles to produce δ‐sultone‐fused indoles in 62%–92% yields. In these reactions, molecular sieves 4 Å act as efficient HF scavenger, which avoid the using of stoichiometric silicon additives and bases. Density functional theory (DFT) calculations reveal that the Michael addition is the rate‐determining step for the reaction.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00573"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145316865","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
Amino Acids as Carboxyl Sources for the Palladium‐Catalyzed Remote Selective C(sp2)─H Acyloxylation 氨基酸作为钯催化远距离选择性C(sp2)─H酰基化反应的羧基来源
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500543
Tao Zheng , Qilin Gu , Changqing Shi , Xiangjie Xiao , Prof. Dr. Zheyu Li , Prof. Dr. Wenbo Ma
{"title":"Amino Acids as Carboxyl Sources for the Palladium‐Catalyzed Remote Selective C(sp2)─H Acyloxylation","authors":"Tao Zheng ,&nbsp;Qilin Gu ,&nbsp;Changqing Shi ,&nbsp;Xiangjie Xiao ,&nbsp;Prof. Dr. Zheyu Li ,&nbsp;Prof. Dr. Wenbo Ma","doi":"10.1002/ajoc.202500543","DOIUrl":"10.1002/ajoc.202500543","url":null,"abstract":"<div><div>An efficient palladium‐catalyzed remote selective C(<em>sp</em><sup>2</sup>)─H acyloxylation of arenes and alkenes, assisted by a thioether weak‐coordination directing group, has been developed. This acyloxylation protocol exhibits broad functional group tolerance and affords <em>δ</em>‐position‐selective products in up to 90% yield. Notably, a diverse range of substrates including amino acids, peptide derivatives, and carboxylic acid‐containing drugs is compatible under mild reaction conditions. Preliminary mechanistic studies suggest that an irreversible Pd(II)/Pd(IV) reaction model is likely involved in this process. The directing groups can be further transformed into synthetically useful functional groups or efficiently removed.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00543"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317691","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
Experimental and Theoretical Mechanistic Study on the 6‐Iodo‐2‐pyridone‐Catalyzed Aminolysis of Esters 6-碘-2-吡啶酮催化酯类氨解的实验与理论机理研究
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.70171
Takeshi Yamada , Takeshi Yoshikawa , Nanako Tsuji , Mahiro Tamura , Marin Gogami , Ken Sakata , Manabu Hatano
{"title":"Experimental and Theoretical Mechanistic Study on the 6‐Iodo‐2‐pyridone‐Catalyzed Aminolysis of Esters","authors":"Takeshi Yamada ,&nbsp;Takeshi Yoshikawa ,&nbsp;Nanako Tsuji ,&nbsp;Mahiro Tamura ,&nbsp;Marin Gogami ,&nbsp;Ken Sakata ,&nbsp;Manabu Hatano","doi":"10.1002/ajoc.70171","DOIUrl":"10.1002/ajoc.70171","url":null,"abstract":"<div><div>A rigorous evaluation of 6‐halo‐2‐pyridone in the catalytic aminolysis of esters revealed that 6‐iodo‐2‐pyridone exhibits high catalytic activity, particularly in the presence of phenyl esters. In this reaction, a series of amines and aromatic esters gave the corresponding amides in high yield. To elucidate the reaction mechanism of the 6‐iodo‐2‐pyridone‐catalyzed aminolysis of esters, <sup>1</sup>H NMR experiments, kinetic studies, and density functional theory (DFT) calculations were conducted. The combined results demonstrate that the reaction proceeds via the formation of a 1:1:1 complex comprising the catalyst, the amine, and the phenyl ester. In this context, 6‐iodo‐2‐pyridone thus works as an acid–base bifunctional catalyst, successfully activating both the ester and the amine. Notably, a π–π interaction was observed between the catalyst and the phenyl ester in the transition state. The stereoelectronic effect of iodine most likely contributes to a favorable degree of this π–π interaction, facilitating a smooth transition to the subsequent leaving of phenol. The low energy barrier for the tautomerization between 6‐iodo‐2‐pyridone and 6‐iodo‐2‐hydroxypyridine also facilitates the process.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e70171"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317693","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
Efficient Copper‐Catalyzed, One‐Pot Synthesis of N2‐Aryl Phosphoryl 1,2,3‐Triazole 1‐Oxides 高效铜催化一锅法合成n2 -芳基磷基1,2,3-三唑1-氧化物
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500162
M. Mujahid , Akshay A. Bhavar , Vijay Vara , Rajesh Gonnade , M. Muthukrishnan
{"title":"Efficient Copper‐Catalyzed, One‐Pot Synthesis of N2‐Aryl Phosphoryl 1,2,3‐Triazole 1‐Oxides","authors":"M. Mujahid ,&nbsp;Akshay A. Bhavar ,&nbsp;Vijay Vara ,&nbsp;Rajesh Gonnade ,&nbsp;M. Muthukrishnan","doi":"10.1002/ajoc.202500162","DOIUrl":"10.1002/ajoc.202500162","url":null,"abstract":"<div><div>A simple and facile one‐pot process has been developed for the synthesis of <em>N</em><sup>2</sup>‐aryl phosphoryl 1,2,3‐triazole 1‐oxide derivatives. This new approach utilizes simple and commercially available starting materials, operating under mild conditions. The method employs copper‐catalyzed multicomponent reaction, involving the combination of arylhydrazines, <em>β</em>‐ketophosphonates, and <em>tert</em>‐butyl nitrite. The developed protocol shows excellent functional group tolerance permitting an extensive range of substrate scope up to 92% isolated yield.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00162"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317790","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
Highly Regioselective Butylation of N‐Sulfonyl‐1,2,3‐triazoles by the Formation of Quaternary Carbon‐Centered C(sp3)─N Bonds 通过形成季碳中心C(sp3)─N键的N-磺酰-1,2,3-三唑的高区域选择性丁化反应
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500353
Jian Ji , Jinhua Liu , Yaqi Deng , Zongjing Hu , Prof. Shunying Liu
{"title":"Highly Regioselective Butylation of N‐Sulfonyl‐1,2,3‐triazoles by the Formation of Quaternary Carbon‐Centered C(sp3)─N Bonds","authors":"Jian Ji ,&nbsp;Jinhua Liu ,&nbsp;Yaqi Deng ,&nbsp;Zongjing Hu ,&nbsp;Prof. Shunying Liu","doi":"10.1002/ajoc.202500353","DOIUrl":"10.1002/ajoc.202500353","url":null,"abstract":"<div><div>An efficient example of quaternary carbon‐centered C(sp<sup>3</sup>)─N bond formation has been developed using <em>N</em>‐sulfonyl‐1,2,3‐triazoles and <em>tert</em>‐butyl hydroperoxide with a high regioselectivity in good yields (71%–83%) without any additional catalysts or additives. The unprecedented reaction was possibly promoted by a radical addition to triazoles followed by an aromatic desulfonation process.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00353"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317743","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
N‐Formylation of Amino Acid Esters and Peptides via Peroxide–Mediated Decarboxylative Coupling with α‐Keto Acids 通过过氧化物介导的α-酮酸脱羧偶联的氨基酸酯和肽的n -甲酰化
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500517
Binduja Kadamannil , Anjali Devi Subramanian , Trinadh Ballanki , Mohammad Irshad Hussain , Baby Viswambharan
{"title":"N‐Formylation of Amino Acid Esters and Peptides via Peroxide–Mediated Decarboxylative Coupling with α‐Keto Acids","authors":"Binduja Kadamannil ,&nbsp;Anjali Devi Subramanian ,&nbsp;Trinadh Ballanki ,&nbsp;Mohammad Irshad Hussain ,&nbsp;Baby Viswambharan","doi":"10.1002/ajoc.202500517","DOIUrl":"10.1002/ajoc.202500517","url":null,"abstract":"<div><div><em>N</em>‐formyl amino acids and peptides play a crucial role in protein biosynthesis and in the design and development of antimicrobial peptides. In this study, we report an efficient <em>N</em>‐formylation of amino acid esters and peptides with α‐keto acids via peroxide‐mediated decarboxylative coupling, where only water/tertiary butanol and carbon dioxide were formed as by‐products. H<sub>2</sub>O<sub>2</sub> was found to be ideal for the <em>N</em>‐formylation of substituted amino acids, while TBHP was successful for unprotected amino acid esters and oligopeptides. The methodology was extended for the synthesis of bioactive <em>N</em>‐formyl methionine and f‐MLP. The synthesized library includes <em>N</em>‐ferrocenyl‐<em>N</em>‐formyl amino acid and peptide derivatives, which might serve as a hybrid material for medicinal and electrochemical applications.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00517"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317771","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
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