Manar Kh. Mohamed , Dr. Ahmed A. K. Mohammed , Prof. Dr. Morsy M. M. Aly , Prof. Dr. Abdel‐Aal M. Gaber , Dr. Abdelreheem A. Saddik
{"title":"Synthesis, DFT Calculations, and Molecular Docking Study of New Aggregation‐Induced Emission Lumiogens Based on Thieno[2,3‐d]pyrimidine Moiety","authors":"Manar Kh. Mohamed , Dr. Ahmed A. K. Mohammed , Prof. Dr. Morsy M. M. Aly , Prof. Dr. Abdel‐Aal M. Gaber , Dr. Abdelreheem A. Saddik","doi":"10.1002/ajoc.202400670","DOIUrl":"10.1002/ajoc.202400670","url":null,"abstract":"<div><div>The discovery of novel Aggregation‐Induced Emission (AIE) systems based on heterocyclic compounds holds significant potential. In this study, a series of new AIE systems based on thieno[2,3‐<em>d</em>]pyrimidine moiety synthesized and characterized by spectroscopic analyses. These compounds exhibited weak emission in DMSO solution but displayed strong solid‐state fluorescence at λ<sub>max</sub>=556, 527, 527, and 515 nm for compounds <strong>7 a</strong>, <strong>7 b</strong>, <strong>7 c</strong>, and <strong>7 e</strong> respectively. Additionally, compound <strong>10</strong> exhibited emission at 480 nm in DMSO, which was red‐shifted to 490 nm in the solid state. Furthermore, the AIE behavior for these compounds was investigated in different DMSO/H<sub>2</sub>O fractions. Compounds <strong>7 a</strong>–<strong>c</strong>, <strong>7 e</strong>, and <strong>10</strong> exhibits a typical AIE behavior since these compounds showed weak fluorescence intensity in pure DMSO but sharply increased while the water content reached 80 % in the case of compounds <strong>7 a</strong>–<strong>c</strong>, and <strong>7 e</strong>, and 90 % in compound <strong>10</strong>. Moreover, Density Functional Theory (DFT) calculations supported the role of molecular packing and intermolecular interactions in modulating the luminescence properties. Molecular docking studies suggested the potential of these AIE compounds as anticancer agents. Compound <strong>7 a</strong> exhibits a strong binding affinity of −9.6 kcal/mol for CDK‐2 compared with abemaciclib, palbociclib, and ribociclib drugs, indicating its potential as a potent CDK‐2 inhibitor.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400670"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622362","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":"Synthesis and Properties of Covalently Linked Terpyridine‐BODIPY and Terpyridine‐3‐Pyrrolyl BODIPY Conjugates","authors":"Kanhu Charan Behera , Mangalampalli Ravikanth","doi":"10.1002/ajoc.202400693","DOIUrl":"10.1002/ajoc.202400693","url":null,"abstract":"<div><div>A series of covalently linked terpyridine‐BODIPY and terpyridine‐3‐pyrrolyl BODIPY conjugates were synthesized by strategically tuning the position of the terpyridine moiety at the <em>α</em> and/or <em>meso</em> positions of the BODIPY (<strong>3</strong>–<strong>4</strong>) and 3‐pyrrolyl BODIPY cores (<strong>5</strong>–<strong>7</strong>). These compounds were synthesized over a sequence of synthetic steps and their identities were confirmed by HR‐MS, 1D, 2D NMR, and X‐ray crystallography of one of the conjugates and studied by various spectroscopic, electrochemical, and theoretical techniques. The presence of terpyridine moieties on BODIPY and 3‐pyrrolyl BODIPY cores significantly alters their electronic properties and these conjugates absorb strongly in the 505–640 nm region. Furthermore, the <em>α</em>‐terpyridinyl 3‐pyrrolyl BODIPY conjugate was used as a ligand to form heteroleptic ruthenium(II/III) complexes. The Ru(II)/Ru(III) complexes exhibit weak fluorescence with significantly reduced quantum yield and single‐state lifetime due to the presence of a heavy Ru(II)/Ru(III) ion, which enhances spin‐orbit coupling and increases the rate of intersystem crossing (ISC), leading to non‐radiative relaxation. DFT and TD‐DFT studies corroborated our experimental findings, providing deeper insights into the structural, photophysical, and electronic properties of these conjugates.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400693"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622658","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":"Synthesis of Tetraaryl Diazachrysenes by the Povarov Reaction and π Extension To Construct a Condensed Azaperylene Motif","authors":"Yuanrong Shan , Takeshi Yasuda , Takaki Kanbara , Junpei Kuwabara","doi":"10.1002/ajoc.202400625","DOIUrl":"10.1002/ajoc.202400625","url":null,"abstract":"<div><div>Incorporating nitrogen into carbon‐based materials can significantly modify their electronic properties. A comprehensive understanding of the structural and physical characteristics of aza‐polycyclic aromatic hydrocarbons (aza‐PAHs) is crucial for developing innovative materials. In this study, four aza‐PAHs were synthesized using a combination of the Povarov reaction and intramolecular cyclization reaction by direct C−H arylation. The synthesized compounds were evaluated in terms of the crystal structure, photophysical properties, frontier energy levels, and hole‐blocking properties in organic light‐emitting diode (OLED). The intramolecular cyclization by direct C−H arylation afforded a condensed azaperylene molecule that exhibited long‐wavelength absorption and emission, attributed to the high HOMO level resulting from π‐extension.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400625"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202400625","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622458","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Recent Advances in Copper‐Catalyzed Oxidative Cyclization Reactions","authors":"Cai Zhang","doi":"10.1002/ajoc.202400529","DOIUrl":"10.1002/ajoc.202400529","url":null,"abstract":"<div><div>In this review, we have presented an overview on the copper‐catalyzed oxidative cyclization reactions over the period from 2020 to the present. In general, both Cu(II) and Cu(I) can be used as starting catalysts, but the reaction mechanisms were different. For example, from the perspective of reaction mechanism, as a starting catalyst, Cu(II) was often directly combined with oxidants to participate in the catalytic oxidation of intermediates or substrates. When Cu(I) served as the starting catalyst, it directly promoted the cleavage of N−O bonds or coordinated with alkyne bonds, while oxidants were used for the subsequent oxidation of intermediates. The experimental results showed that most of the copper‐catalyzed oxidative cyclization strategies have achieved satisfactory results.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400529"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622657","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}
Oj Shikhar Srivastava , Ruchir Kant , Dr. Namrata Rastogi
{"title":"Photocatalytic Csp2−H Amination of Hydrazones with N‐aminopyridinium Salts","authors":"Oj Shikhar Srivastava , Ruchir Kant , Dr. Namrata Rastogi","doi":"10.1002/ajoc.202400757","DOIUrl":"10.1002/ajoc.202400757","url":null,"abstract":"<div><div>The current approach describes Csp<sup>2</sup>−H amination of aldehyde‐derived hydrazones via nitrogen centred radical generation from <em>N‐</em>aminopyridinium salts under photocatalytic conditions. The scope of reaction is wide in terms of both the substrates and most of the products were isolated in good yields furnishing <em>Z</em>‐isomer exclusively. Further, aminated hydrazones were hydrolyzed to give amides resulting into indirect Csp<sup>2</sup>−H amination of aldehydes.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400757"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622367","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}
Anis Ur Rahman , Nighat Zarshad , Sai Zhang , Farooq Ahmad , Guigen Li , Asad Ali
{"title":"3D Multilayer Folding of Chiral and Achiral Targets Cotaining Aryl‐Aryl‐Alkynyl Motifs Enabled by π‐π Stacking","authors":"Anis Ur Rahman , Nighat Zarshad , Sai Zhang , Farooq Ahmad , Guigen Li , Asad Ali","doi":"10.1002/ajoc.202400704","DOIUrl":"10.1002/ajoc.202400704","url":null,"abstract":"<div><div>3D multi‐layered achiral and chiral compounds containing aryl‐aryl‐alkenyl motifs are considered crucial for achieving planarity via π.π stacking, enhanced stability by conjugation, improved optoelectronic properties and receptor binding capabilities. By taking advantage of palladium (0) catalyzed Suzuki‐Miyaura and Sonogashira cross coupling reactions, newly designed atropisomerically 3D multi‐layered achiral and chiral compounds have been synthesized successfully synthesized that leverage center‐to‐multilayer chirality. These compounds were obtained in overall yields of 27 % to 89 % through flash column chromatography, and comprehensively characterized with their absolute configurations confirmed using X‐ray structural analysis. Utilizing readily available commercial starting materials, fourteen distinct diastereomers with multilayer chirality were successfully synthesized in a seven‐step process, along with fifteen achiral multilayered targets achieved in five steps. This research will open new avenues in the fields of atropisomeric drug designing, bio‐sensing and circularly polarised luminescence materials.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400704"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622555","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}
Tianqi Wang , Fangyao Su , Shuting Yin , Boxiao Zhang , Yongguo Liu , Prof. Baoguo Sun , Prof. Hongyu Tian , Dr. Sen Liang
{"title":"Aromatizaiton of 2‐Carbonyl‐1‐Tetralones and Analogues via Aerobic Oxidation under Basic Conditions","authors":"Tianqi Wang , Fangyao Su , Shuting Yin , Boxiao Zhang , Yongguo Liu , Prof. Baoguo Sun , Prof. Hongyu Tian , Dr. Sen Liang","doi":"10.1002/ajoc.202400458","DOIUrl":"10.1002/ajoc.202400458","url":null,"abstract":"<div><div>1‐Tetralone‐2‐carboxylates have been shown to undergo aromatization in the presence of sodium hydride under blue light irradiation in DMSO, yielding 1‐hydroxy‐2‐naphthoates with yields ranging from 30 % to 92 %. This method is also effective for the aromatization of 2‐acyl‐1‐tetralones, 1‐tetralone‐2‐carboxamides, and related structures containing heteroarenes. Thus, it serves as a valuable synthetic approach for the preparation of 2‐carbonyl substituted 1‐naphthols. The proposed mechanism involves aerobic oxidation under light irradiation, leading to the formation of <em>α</em>,<em>β</em>‐unsaturated hydroperoxide intermediates, which subsequently produce the aromatized products.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400458"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622609","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":"One‐pot Synthesis and Antitubercular Activity of Imidazo[2,1‐b]thiazol‐1H‐pyrazolylphosphonates","authors":"Nagaraju Chirra , Varshitha Shanigarapu , Balasubramanian Sridhar , Srinivas Kantevari","doi":"10.1002/ajoc.202400724","DOIUrl":"10.1002/ajoc.202400724","url":null,"abstract":"<div><div>Herein, we present an effective one‐pot method for the synthesis of imidazo[2,1‐<em>b</em>]thiazole‐pyrazole phosphonates from 5‐imidazo[2,1‐<em>b</em>] thiazole carboxaldehydes. The reaction involves a 1,3‐dipolar cycloaddition between <em>in situ</em> generated <em>α</em>,<em>β</em>‐unsaturated ketones and the Bestmann–Ohira reagent (BOR), facilitated by a base, leading to the formation of pyrazole phosphonates as the sole regioisomer with excellent yields. The <em>in vitro</em> evaluation of the newly synthesized compounds <strong>4(a</strong>–<strong>x)</strong> against <em>Mycobacterium tuberculosis</em> H37Rv (<em>Mtb</em>) identified compound <strong>4</strong> <strong>o</strong> as the most effective analogue (MIC: 6.25 μg/mL; 10.40 μM).</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400724"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622310","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":"Recent Total Syntheses of Cephalotaxine‐Type Alkaloids and Their Structural Diversification (2021–2024): An Update","authors":"Yeju Oh , Anagha Reneesh , Hongjun Jeon","doi":"10.1002/ajoc.202400652","DOIUrl":"10.1002/ajoc.202400652","url":null,"abstract":"<div><div>Cephalotaxine‐type alkaloids present a challenging yet rewarding target for synthetic chemists due to their intricate polycyclic structures and significant biological activity. This review consolidates recent reports (2021–2024) on the total synthesis of cephalotaxine‐type alkaloids, emphasizing innovative catalytic approaches and key transformations that enable efficient construction of the core tetracyclic framework. Advances in techniques such as asymmetric polycyclization, dual catalysis, and rearrangement strategies have streamlined synthetic routes, reducing the number of steps and enhancing stereocontrol. Additionally, structural diversification on the cephalotaxine scaffold during this period has offered valuable insights into structural modifications in medicinal chemistry and potential biosynthetic pathways. This review proposes a new structural classification of cephalotaxine‐type alkaloids. It covers ten recent total syntheses, providing detailed descriptions of the synthetic methodologies employed and comparative analyses with previous syntheses. Four reports on the structural diversification of cephalotaxines are also included.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400652"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622327","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}
Deepika , Dr. Ravindresh Chhabra , Prof. Ajay Bansal , Prof. Virender Singh
{"title":"Transition Metal‐Free Synthesis of β‐Carboline Substituted 1,2,3‐Thiadiazoloyl Derivatives Using Elemental Sulfur as a Sulfur Source","authors":"Deepika , Dr. Ravindresh Chhabra , Prof. Ajay Bansal , Prof. Virender Singh","doi":"10.1002/ajoc.202400485","DOIUrl":"10.1002/ajoc.202400485","url":null,"abstract":"<div><div>A transition metal‐free, I<sub>2</sub>‐catalyzed C−S cross‐coupling reaction has been developed for the synthesis of β‐carboline substituted 1,2,3‐thiadiazoloyl derivatives using β‐carboline‐based enaminones, tosyl hydrazide, and elemental sulfur. The highlighted features of this methodology include the formation of C−S, S−N, and C−N bonds, the use of inexpensive and nontoxic catalyst, high efficiency, easy procedures, short reaction time, and generation of natural product inspired scaffolds with good to excellent yields (upto 89 %). All the synthesized β‐carboline substituted 1,2,3‐thiadiazoloyl derivatives (<strong>1</strong>–<strong>25</strong> <strong>B</strong>) were investigated for <em>in vitro</em> cytotoxicity against HeLa cell line. The compound <strong>4</strong> <strong>B</strong> emerged as the most potent anticancer agent with IC<sub>50</sub> values of 25.9 μM.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400485"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622348","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}