Zsuzsanna Szalai , Boldizsár S. Tóth , Csenge Horváth , Marcell Bohus , Angéla Takács , László Kőhidai , Ágnes Gömöry , László Drahos , György Keglevich
{"title":"The Synthesis of Nonsymmetric α‐hydroxy‐ethylidenebisphosphonic Derivatives by the Pudovik Reaction, Their Reactions, and Cytotoxic Activity","authors":"Zsuzsanna Szalai , Boldizsár S. Tóth , Csenge Horváth , Marcell Bohus , Angéla Takács , László Kőhidai , Ágnes Gömöry , László Drahos , György Keglevich","doi":"10.1002/ajoc.202500596","DOIUrl":"10.1002/ajoc.202500596","url":null,"abstract":"<div><div>Nonsymmetric α‐hydroxy‐ethylidenebisphosphonic (HEBP) derivatives were synthesized by the Pudovik reaction of dialkyl α‐oxo‐ethylphosphonates (DAOEPs) and P‐reagents, such as dialkyl phosphites, alkyl phenyl‐<em>H</em>‐phosphinates (APHPs) and diarylphosphine oxides to make available a new family of compounds with two different P‐functions. Performing the addition of APHPs to DAOEPs in the presence of 40% of the diethylamine catalyst, the primary adducts rearranged to the mixture of the corresponding phosphonoyl‐phosphonate and phosphoryl‐phosphinate. Acylation of the HEBPs led to the formation of the respective acylated derivatives. A part of the new P‐compounds was subjected to cytotoxic screening on myeloma and metastatic cell lines. Among these, two derivatives, dibutyl 1‐(butyl‐phenylphosphinoyl)‐1‐hydroxy‐ethylphosphonate <strong>4a</strong> and tetrabutyl α‐acetyloxy‐ethylidenebisphosphonate <strong>8c</strong>, demonstrated the strongest antiproliferative effects on the A2058 (metastatic melanoma) and U266 (multiple myeloma) cell lines, highlighting their potential as promising candidates for further therapeutic development. The bisphosphonic derivatives <strong>4a</strong> and <strong>8c</strong> reduced the viability of U266 cells by 94% and 91%, respectively</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00596"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145316866","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}
{"title":"Structurally Well‐Resolved Conformational Isomers in Expanded Porphyrinoids: Structures and Photophysical Properties","authors":"Cun Yang , Prof. Dr. Chuanhu Lei","doi":"10.1002/ajoc.202500519","DOIUrl":"10.1002/ajoc.202500519","url":null,"abstract":"<div><div>Conformational isomerism plays a fundamental role in determining molecular properties and has aroused considerable interest across fields of chemistry, biochemistry, and material science. In this context, expanded porphyrinoids represent the most appropriate molecular platforms to study the intricate structure‐properties relationships, since their intrinsic conformational flexibility enables the occurrence of multiple conformers within a single molecular entity. Leveraging these advantages, many efforts have been devoted to identifying distinct conformational isomers and elucidating their attendant electronic features, so that in‐depth insights into conformational modulation, aromaticity, and photophysical behavior can be provided. In this review, we summarize recent advances in the study of structurally well‐resolved conformational isomers of expanded porphyrinoids, along with their basic photophysical properties. It is our hope that this review will serve not only to codify our current understanding of conformational effect in these systems, but also inspire new thoughts for the rational design and synthesis of conformational isomers.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00519"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317573","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}
Dr. Sachin Puri , Shalini , Dr. Kapil Juvale , Dr. Sivapriya Kirubakaran
{"title":"Design and Development of New Benzopyrazole Derivatives as Selective Inhibitors of Helicobacter pylori IMPDH","authors":"Dr. Sachin Puri , Shalini , Dr. Kapil Juvale , Dr. Sivapriya Kirubakaran","doi":"10.1002/ajoc.202500584","DOIUrl":"10.1002/ajoc.202500584","url":null,"abstract":"<div><div><em>Helicobacter pylori</em> (<em>H. pylori</em>) is a Gram‐negative bacterial pathogen responsible for gastritis, peptic ulcers, and gastric cancer. Current treatment regimens involve triple or quadruple antibiotic therapies; however, the rise in antibiotic resistance necessitates the development of alternative therapeutic strategies. This study explores the potential of targeting <em>H. pylori</em> inosine‐5‐monophosphate dehydrogenase (<em>Hp</em>IMPDH), a crucial enzyme in purine nucleotide biosynthesis essential for bacterial proliferation. A novel series of benzopyrazole derivatives was designed and synthesized as potential <em>Hp</em>IMPDH inhibitors. Biochemical assays revealed that the synthesized compounds exhibited potent inhibitory activity, with <strong>SN‐8.1</strong> and <strong>SN‐8.2</strong> displaying IC<sub>50</sub> values of 0.122 and 0.187 µM, respectively. These compounds showed minimal inhibition of human IMPDH2, suggesting selectivity toward the bacterial enzyme. Molecular docking studies further confirmed strong binding affinities at the <em>Hp</em>IMPDH active site. Cytotoxicity assays indicated that the compounds were nontoxic at the tested concentrations. These findings demonstrate that benzopyrazole‐based <em>Hp</em>IMPDH inhibitors offer a promising strategy for the development of new anti‐<em>H. pylori</em> agents.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00584"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317636","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}
Nikolai A. Malashchenko , Dr. Alexander V. Karchava , Dr. Dmitry I. Bugaenko
{"title":"Umpolung C(3)–H Functionalization of Indoles via I(III) Intermediates: Synthesis of Indol‐3‐yl Xanthates","authors":"Nikolai A. Malashchenko , Dr. Alexander V. Karchava , Dr. Dmitry I. Bugaenko","doi":"10.1002/ajoc.202500603","DOIUrl":"10.1002/ajoc.202500603","url":null,"abstract":"<div><div>Herein, we report a transition‐metal‐free strategy for the synthesis of <em>O</em>‐alkyl‐<em>S</em>‐(indol‐3‐yl) xanthates, valuable surrogates for indol‐3‐yl thiols. The method relies on the in situ formation of electrophilic (3,5‐dimethylisoxazol‐4‐yl)(indol‐3‐yl)iodonium salts via highly chemo‐ and regioselective C(3)–H functionalization of indoles with (3,5‐dimethylisoxazol‐4‐yl)–I(OH)OTs, a Koser's type reagent. These electrophilic intermediates readily react with potassium <em>O</em>‐alkyl xanthates, delivering the corresponding <em>O</em>‐alkyl‐<em>S</em>‐(indol‐3‐yl) xanthates in good‐to‐high yields. The protocol exhibits good functional group compatibility and is well‐suited for late‐stage functionalization of complex bioactive molecules, as demonstrated by the derivatization of the antiviral agent CCG‐203926 and estradiol, a steroid hormone. This operationally simple protocol provides an efficient approach to otherwise inaccessible indol‐3‐yl xanthates that are both a class of compounds of considerable interest due to their potential biological activity and valuable precursors for other indole derivatives containing organosulfur functional groups at the C(3) position.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00603"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317793","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}
Lu Wang , Cheng‐Xian Hu , Xue Yang , Yu‐Lu Du , Jian‐Hua Zhang , Ying Fu , Zheng‐Yin Du
{"title":"Pd‐Catalyzed Highly Regioselective N‐Acylation of Indoles with Difluorocarbene as a Carbonyl Source","authors":"Lu Wang , Cheng‐Xian Hu , Xue Yang , Yu‐Lu Du , Jian‐Hua Zhang , Ying Fu , Zheng‐Yin Du","doi":"10.1002/ajoc.202500542","DOIUrl":"10.1002/ajoc.202500542","url":null,"abstract":"<div><div>A novel method has been developed for the exclusively <em>N</em>‐regioselective synthesis of <em>N</em>‐benzoylindoles, utilizing readily available aryl halides, indoles, and sodium difluorochloroacetate. The in situ‐generated carbonyl group produced through difluorocarbene transfer serves as a bridging moiety that facilitates the simultaneous formation of one C─C bond, one C─N bond, and one C═O bond in this transformation.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00542"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317742","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}
{"title":"Regio‐ and Chemo‐Selective Hydration of Terminal Alkynes Catalyzed by Bis(dimethylglyoximato)cobalt(III) Complexes","authors":"Ujala Maddheshiya , Sourav Mandal , Kamlesh Kumar","doi":"10.1002/ajoc.202500426","DOIUrl":"10.1002/ajoc.202500426","url":null,"abstract":"<div><div>The mild reaction conditions, coupled with the cost‐effective and readily available nature of cobaloxime complexes, offer a promising solution to the current challenges in alkyne hydration. These complexes exhibit excellent bench stability and can be easily synthesized in large quantities, making them ideal catalysts for the efficient conversion of alkynes to carbonyl compounds, which have numerous industrial applications. A series of chlorocobaloxime complexes featuring substituted pyridine as an axial ligand have been synthesized and characterized. These complexes have been successfully employed as catalysts for the hydration of terminal alkynes to their corresponding methyl ketones under ambient conditions, affording good to excellent yields. The reaction tolerates a wide range of functional groups, demonstrating broad substrate scope. Notably, the catalyst can be recovered and reused with minimal loss of activity, highlighting its practical utility. The scalability of the approach has been further validated through gram‐scale reactions.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00426"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145316863","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}
Ilya A. Tyumentsev , Igor A. Ushakov , Anton V. Kuzmin , Alexander Yu. Rulev
{"title":"Pull–Pull Halogenated β‐Cyanoacrylates in Aza‐Michael Reaction: Intriguing Problem of Regioselectivity","authors":"Ilya A. Tyumentsev , Igor A. Ushakov , Anton V. Kuzmin , Alexander Yu. Rulev","doi":"10.1002/ajoc.202500414","DOIUrl":"10.1002/ajoc.202500414","url":null,"abstract":"<div><div>The controlled regioselective addition of nitrogen‐centered nucleophiles to the pull–pull halogenated β‐cyanoacrylates is a challenging problem in the chemistry of pull–pull alkenes due to the close electronic properties of the vicinal acceptor groups. The influence of the type of halogen and its position on the double bond, as well as the amine nucleophilicity and the presence of additives on the direction of addition have been studied. The experimental data are in excellent agreement with the density functional theory (DFT) calculations.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00414"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145316654","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}
Zhenlei Zou , Mengmeng Gao , Wenqiang Zhao , Yangyi Liu , Lingyu Kong , Weigang Zhang , Yi Wang
{"title":"Deoxygenation of Alcohols in Organic Electrosynthesis: Basic Strategies and Recent Developments","authors":"Zhenlei Zou , Mengmeng Gao , Wenqiang Zhao , Yangyi Liu , Lingyu Kong , Weigang Zhang , Yi Wang","doi":"10.1002/ajoc.202500568","DOIUrl":"10.1002/ajoc.202500568","url":null,"abstract":"<div><div>Alcohols are among the most prevalent functionalities found in organic molecules and have made deoxyfunctionalization widely used in medicinal chemistry, process manufacturing, and natural product synthesis. However, the excessive use of oxidants and reductants in traditional deoxygenative methods, as well as the resulting stoichiometric by‐products, leads to high process quality intensity and can bring in significant challenges to product purification. The environmental friendliness and sustainability of electrosynthesis have expanded the further application of this remarkable synthetic tool. The primary objective of this review is to provide the reader with the highlights of electrochemically promoted deoxyfunctionalization of alcohols over the past two decades, comprising ionic‐type, radical‐type, and trans‐metal coupling reactions.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00568"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145316726","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}
{"title":"Advancing Sulfono Functionalization: Integrating Classic and Contemporary Approaches to Drive Innovation in Synthetic Chemistry","authors":"Bhaskarjyoti Borah , Sushmita Banerjee , Bharat Kumar Allam","doi":"10.1002/ajoc.202500456","DOIUrl":"10.1002/ajoc.202500456","url":null,"abstract":"<div><div>The growing significance of sulfone‐containing compounds in pharmaceuticals, agrochemicals, and materials science has driven interest in innovative sulfono functionalization strategies. Despite the progress, the diversity of emerging methods, from transition metal catalysis to photoredox and electrochemical approaches, has led to a fragmented understanding across disciplines. This review article aims to consolidate recent advancements, critically analyze current methodologies, and highlight trends shaping the future of sulfono chemistry. By offering a comprehensive overview of established and novel synthetic techniques, this review is a valuable resource for researchers, aiding in the rational design of sulfone‐based molecules and fostering the development of more sustainable, efficient, and selective functionalization protocols. Ultimately, it bridges gaps in literature, stimulates interdisciplinary collaboration, and identifies unexplored avenues for future research.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00456"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317697","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}
Peng‐Yuan Zhang , Shu‐Ji Gao , Li‐Dan Zhang , Li‐Lu Xiao , Ding‐Peng Chen , Prof. Dr. Danhua Ge , Prof. Dr. Xue‐Qiang Chu
{"title":"“On‐Water” Bisphosphorylation of β‐Trifluoromethyl Enones via Successive C(sp3)─F Bonds Functionalization: Synthesis of Multi‐Substituted Furans","authors":"Peng‐Yuan Zhang , Shu‐Ji Gao , Li‐Dan Zhang , Li‐Lu Xiao , Ding‐Peng Chen , Prof. Dr. Danhua Ge , Prof. Dr. Xue‐Qiang Chu","doi":"10.1002/ajoc.202500468","DOIUrl":"10.1002/ajoc.202500468","url":null,"abstract":"<div><div>The selective functionalization of C(sp<sup>3</sup>)─F bonds in accessible trifluoromethyl compounds is challenging but attractive. An “on‐water” defluorinative bisphosphorylation of β‐trifluoromethyl enones and phosphine oxides were developed for the modular synthesis of valuable multi‐substituted furans. This reaction proceeded through the successive functionalization of the trifluoromethyl group on enones, enabling the construction of one <em>O</em>‐heterocycle, the formation of three C─P/C─O bonds, and the cleavage of three C(sp<sup>3</sup>)─F bonds under transition metal‐free reaction conditions. The aqueous solution also plays a unique role in determining the reaction reactivity and selectivity.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00468"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317702","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}