Journal of the Iranian Chemical Society最新文献

{"title":"One-pot synthesis of novel 5-(azidomethyl)-2-aryloxazole derivatives from propargylamide through Cu-catalyzed C–N bond formation","authors":"Saeed Yazdanseta,&nbsp;Mohammad Ghanbari","doi":"10.1007/s13738-024-03167-8","DOIUrl":"10.1007/s13738-024-03167-8","url":null,"abstract":"<div><p>A series of <i>N</i>-propargylarylamide derivatives were successfully transformed into novel 5-(azidomethyl)-2-aryloxazole systems bearing a single azide group. The transformation involved a two-step process: (1) synthesis of 5-(iodomethylene)-2-aryl-4,5-dihydrooxazoles, followed by (2) azide coupling with sodium azide (NaN₃). Additionally, a one-pot protocol was developed for the synthesis of triazole-methylene-oxazole derivatives, integrating <i>N</i>-iodosuccinimide (NIS)-mediated oxazole formation, azide coupling, and a subsequent click reaction. This streamlined approach demonstrated excellent overall efficiency, yielding products in 68–82% yield across a broad substrate scope. Notably, the entire reaction sequence could be conducted using a single precatalyst, significantly reducing reaction waste and enhancing both economic and environmental sustainability.</p><h3>Graphical abstract</h3><p>A series of <i>N</i>-propargylarylamide derivatives were transformed into the corresponding novel 5-(azidomethyl)-2-aryloxazole systems that bear one azide group. The two-step procedure consisted of a 5-(iodomethylene)-2-aryl-4,5-dihydrooxazole synthesis and a subsequent azide coupling with NaN₃.</p>\u0000<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":"22 3","pages":"535 - 544"},"PeriodicalIF":2.2,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143581065","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 advances in the synthesis, reactivity, and applications of symmetrical and asymmetrical cross-conjugated dienones","authors":"Ayoub Mouhib,&nbsp;Bouchra Es-Sounni,&nbsp;Abdelkrim Mouzdahir,&nbsp;Noureddine Mazoir,&nbsp;Mohamed El Yazidi,&nbsp;Mohamed Bakhouch","doi":"10.1007/s13738-024-03150-3","DOIUrl":"10.1007/s13738-024-03150-3","url":null,"abstract":"<div><p>Cross-conjugated dienones are a family of organic compounds endowed with important chemical and biological properties. Their high reactivity especially as Michael acceptors, and also their interesting biological properties are highly related to their structures. This review covers the recent advances made in the synthesis methods, reactivity, and biological properties of cross-conjugated dienones and their hetero-analogs. The review summarizes the works published since 2000.</p></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":"22 2","pages":"243 - 262"},"PeriodicalIF":2.2,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143184867","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":"A simple fluorescent assay for thiocyanate based on Cu2+-triggered oxidation of o-phenylenediamine","authors":"Yan Tan,&nbsp;Jing Hu,&nbsp;Dongjin Tang,&nbsp;Peng Yu","doi":"10.1007/s13738-025-03175-2","DOIUrl":"10.1007/s13738-025-03175-2","url":null,"abstract":"<div><p>Thiocyanate (SCN⁻) is an anionic contaminant and is a biomarker of environmental cyanide exposure. Therefore, it is particularly necessary to develop a simple, fast and sensitive method for SCN⁻ assay. Herein, a fluorescent assay method was developed to determine SCN⁻ based on Cu²⁺-triggered oxidation of o-phenylenediamine (OPD). Without SCN⁻, OPD was oxidized by Cu²⁺ and the resultant product (i.e., OPD oxide) exhibited a high fluorescence. However, in the presence of SCN⁻, Cu²⁺ reacted with SCN⁻; and thus, the oxidation ability of Cu²⁺ toward OPD was reduced, resulting in a weak fluorescence. Several important parameters such as the concentrations of Cu²⁺ and OPD, pH and the reaction time were optimized. Under the optimized conditions, the linear range was 5–80 μM and the limit of detection was 5 μM for SCN⁻ assay. In addition, the high selectivity and the satisfactory recoveries in tap water and artificial saliva were achieved for SCN⁻ detection due to the strong chelation between SCN⁻ and Cu²⁺. The whole detection process was simple and fast without using complex nanoparticles. More importantly, the developed assay method will have promising applications in monitoring of SCN⁻ for the assessment of water safety and human health.</p><h3>Graphical abstract</h3><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":"22 3","pages":"631 - 639"},"PeriodicalIF":2.2,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s13738-025-03175-2.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143581060","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":"CuS/Nitrogen-biomass derived carbon composites for heterogeneous Fenton-like degradation of dyes: C-, N- and S-mediated electron transfer mechanism for redox cycling of Cu(I)/Cu (II) couple","authors":"Priyanga Manjuri Bhuyan,&nbsp;Chiranjita Goswami,&nbsp;Deepak Jyoti Deuri,&nbsp;Kula Kamal Senapati,&nbsp;Parikshit Gogoi","doi":"10.1007/s13738-025-03178-z","DOIUrl":"10.1007/s13738-025-03178-z","url":null,"abstract":"<div><p>Wastewater treatment is a critical environmental issue, and Fenton-like catalysts have emerged as effective solutions for degrading persistent organic pollutants. One promising group of catalysts introduced for hydrogen peroxide activation in Fenton and Fenton-like reactions are transition metal sulfides. However, their applications are limited due to the insufficient number of active sites on the surfaces of these catalysts. CuS functions as a photo-Fenton catalyst only in the presence of light. Therefore, making the catalyst to retain its catalytic ability even in the absence of light is a fundamental objective of the present study. The anchoring of the CuS matrix to carbonaceous materials enhances active site exposure and catalyst stability. In this study, a CuS/nitrogen-biomass-derived carbon (CuS/N-BMC) nanocomposite catalyst was synthesized to enhance catalytic activity and stability. The composite showed high degradation efficiency of methylene blue (MB) without light irradiation, achieving 93% degradation within 60 min at pH 4.1 with a rate constant of 0.0367 min⁻¹. It demonstrated its efficiency in degrading mixed dyes. The catalyst demonstrated effectiveness over a wide pH range (3.3–8.6) showcasing its potential in waste water treatment. The mechanism involved H₂O₂ activation, electron donation by the active functional groups, i.e., sp²C = C/C–C present in the carbon, pyridinic-N of nitrogen, and reduced state of S-species and regeneration of Cu⁺ species. The CuS/N-BMC composite demonstrated excellent stability and could be reused for five cycles, retaining 83% degradation efficiency. This study contributes to the development of efficient catalysts for environmental applications.</p></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":"22 4","pages":"699 - 716"},"PeriodicalIF":2.2,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143769861","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":"Design, molecular modelling, synthesis, characterization studies of novel N-(7-(substituted benzylidene)-4-phenyl-4,5,6,7-tetrahydro-3H-cyclopenta[d]pyrimidin-2-yl)-1-(substituted phenyl)methanimine against breast cancer","authors":"Arunkumar Manoharan,&nbsp;Panneerselvam Theivendren,&nbsp;Maya Sharma,&nbsp;Selvaraj Kunjiappan,&nbsp;Saravanan Govindaraj,&nbsp;Parasuraman Pavadai","doi":"10.1007/s13738-024-03169-6","DOIUrl":"10.1007/s13738-024-03169-6","url":null,"abstract":"<div><p>A designed seventy-five distinct group of compounds namely N-(7-(substituted benzylidene)-4-phenyl-4,5,6,7-tetrahydro-3H-cyclopenta[d]pyrimidin-2-yl)-1-(substitutedphenyl) methanimine underwent evaluation for their potential against breast cancer utilizing various methods such as computational docking and dynamics, synthetic processes, structural characterization, and in vitro testing. The compound known as 2a3 was pinpointed through several analyses including elemental, HR-MS, FT-IR, ¹H NMR, and ¹³C NMR. The online platform SwissADME predicted its physicochemical, drug-like, and pharmacokinetic profiles. Identification of drug targets was achieved using a network pharmacology technique, and extensive molecular docking tests were conducted to analyse how well the ligand and its complexes interacted with 23 specific breast cancer targets. These experiments revealed that the 2a3 complex demonstrated superior binding energy and interaction capabilities. Remarkably, 3LFF (Human p38 kinase), 5EW8 (Fibroblast growth factor receptor), 6E2N (MAPK), 6WW8 (CDK4/6 receptor), 7PCD (HER2), 7WT0 (human glyoxalase 1 receptor) and 8EXL (PI3K-alpha) showed outstanding binding energy and an amino acid interaction profile that stood out from the rest. The anticancer abilities of the synthesized compounds were assessed using the MTT assay, which showed that the compound 4-((2-((3-nitrobenzylidene)amino)-4-phenyl-3,4,5,6-tetrahydro-7H-cyclopenta [d]pyrimidin-7-ylidene) methyl) aniline 2a3 exhibited significant cytotoxic properties against MCF-7 cell lines. Given their highly effective performance in cellular environments, the compound 2a3, hold IC₅₀ value of 14.03 µM/mL against MCF-7 cells and it’s a potential in the advancement of more effective treatments against cancer cell proliferation.</p><h3>Graphical abstract</h3>\u0000<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":"22 3","pages":"561 - 573"},"PeriodicalIF":2.2,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s13738-024-03169-6.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143581263","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":"MOF-5 derived magnetic CuFe2O4@SiO2 nanocomposite for highly efficient and sustainable carboxylative cyclization of CO2 to α‑alkylidene cyclic carbonates","authors":"Yulin Hu,&nbsp;Qinyan Shen","doi":"10.1007/s13738-025-03173-4","DOIUrl":"10.1007/s13738-025-03173-4","url":null,"abstract":"<div><p>Carbon dioxide as a C1 building block to synthesize α-alkylidene cyclic carbonates is an environmental and sustainable approach. In this work, we designed and synthesized a multifunctional magnetic MOF nanocatalyst CuFe₂O₄@SiO₂@MOF-5, which could realize the carboxylic cyclization of CO₂ and propargylic alcohols into α-alkylidene cyclic carbonates in high to excellent yields under mild reaction conditions. More importantly, the nanocatalyst CuFe₂O₄@SiO₂@MOF-5 exhibited excellent reusability and could be recycled at least six times retaining its excellent catalytic activity as well as chemical stability. These findings may be useful for the rational design of heterogeneous and recyclable routes for the catalytic conversion of CO₂ to valuable chemicals.</p><h3>Graphical Abstract</h3>\u0000<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":"22 3","pages":"657 - 666"},"PeriodicalIF":2.2,"publicationDate":"2025-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143581198","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":"Rapid, simple and highly selective determination of Chromium(III) in aqueous samples by a microfluidic cell coupled to a smartphone-based colorimetric-sensing detector","authors":"Bahareh Moradifar,&nbsp;Abbas Afkhami,&nbsp;Tayyebeh Madrakian,&nbsp;Mohammad Reza Jalali Sarvestani,&nbsp;Sina Khalili","doi":"10.1007/s13738-025-03172-5","DOIUrl":"10.1007/s13738-025-03172-5","url":null,"abstract":"<div><p>In this study, citrate-modified Ag (AgNPs@Cit) plasmonic nanoparticles were synthesized and characterized using UV–visible spectrophotometry and transmission electron microscopy (TEM). Subsequently, a microfluidic kit was developed for the colorimetric point of care (POC) detection of Cr³⁺ based on the color change of AgNPs@Cit solution from yellow to red in the presence of Cr³⁺ ions. The experimental parameters were optimized using a central composite experimental design, and the interactions between operational factors were thoroughly examined. Under optimum conditions (flow rate: 0.04 mL/min, flow path length: 9.65 cm, and pH = 7.6), a linear relationship was established between the red component of RGB pixels of the analyzed images captured by a smartphone and the concentration of Cr³⁺ within the range of 1.00–35.00 µmol L⁻¹. The proposed method exhibited a detection limit of 0.33 µmol L⁻¹. The selectivity of the developed microfluidic kit was evaluated, and no significant interference was observed. Furthermore, the applicability of the suggested microfluidic kit for the determination of Cr³⁺ in five different drinking water samples was successfully demonstrated, with calculated recovery values falling within the range of 96.2–106.4%.</p></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":"22 3","pages":"605 - 613"},"PeriodicalIF":2.2,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s13738-025-03172-5.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143581150","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":"A novel catalyst for the synthesis of 3–5-disubstituted isoxazole derivatives from aldoximes","authors":"Nesimi Uludag,&nbsp;Alper Sanlı","doi":"10.1007/s13738-024-03164-x","DOIUrl":"10.1007/s13738-024-03164-x","url":null,"abstract":"<div><p>An efficient new approach has been described for the synthesis of substituted isoxazole derivatives 3a-l from substituted aldoximes and diethyl acetylenedicarboxylate using NaNO₂ and AlCl₃ in one step in moderate to excellent yields (55–94%). The key nitrile <i>N-</i>oxide intermediates that are required for the synthesis of isoxazole derivatives are formed by treatment of substituted aldoxime with assisted discovery of its newer applications by successive treatment with NaNO₂. The generated nitrile oxides underwent [3 + 2] dipolar cycloaddition of alkynes over AlCl₃ as a Lewis acid. Moreover, this approach has considerably assisted in the discovery of its significant advantages. This strategy is creating a five-membered ring with an oxygen and nitrogen atom adjacent to each other as either catalyst or reagent. The structures of the synthesized compounds were confirmed by spectroscopic methods, and a mechanism was proposed.</p><h3>Graphical abstract</h3>\u0000<div><figure><div><div><picture><img></picture></div></div></figure></div></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":"22 3","pages":"509 - 515"},"PeriodicalIF":2.2,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s13738-024-03164-x.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143581151","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":"Spectrophotometric trace determination of Fe(II) with 5,7-dibromo-8-hydroxyquinoline and investigating the spectral, antimicrobial, anticancer properties and DFT study of iron complexes","authors":"Kusum,&nbsp;Amita Garg,&nbsp; Sumit,&nbsp;Pawan Kumar,&nbsp;Jai Kumar","doi":"10.1007/s13738-024-03171-y","DOIUrl":"10.1007/s13738-024-03171-y","url":null,"abstract":"<div><p>A simple, selective and versatile spectrophotometric technique has been developed for determination of iron in novel complex of iron with 5,7-Dibromo-8-hydroxyquinoline in a basic medium. The green-colored complex was extractable in chloroform within the pH range of 8.95–8.99 with maximum intensity of color in the wavelength range of 429–439 nm. Analytical techniques confirmed the complex stoichiometry of 1:2 [Fe(II)-DBHQ]. Several parameters were also calculated like Sandell^’s sensitivity (0.001953 µg cm⁻²), molar absorptivity coefficient (2.849 × 10⁴ L mol⁻¹ cm⁻²), standard deviation of reproducibility (± 0.001048/0.205%), detection limit (0.14 µg/ml) and regression coefficient (0.9497). These parametric values showed higher adaptability, cost-effectiveness and higher sensitivity of the proposed method of complex determination as compared to already reported methods. Computational chemistry calculations were studied using DFT, and global reactivity descriptors such as electronegativity, softness, hardness, electron affinity, ionization potential and electrophilicity were estimated with HOMO and LUMO energies. Using MEP analysis possible targets for nucleophilic or electrophilic attacks on the chemical structures of the complex were identified. In vitro anticancer and antimicrobial activity of the complex was further determined, and the complex showed antineoplastic as well as antimicrobial potency, hence showed the novel complex compatibility in antimicrobial and anticancer applications like therapeutic agents and metal-based drugs.</p></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":"22 3","pages":"589 - 603"},"PeriodicalIF":2.2,"publicationDate":"2025-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s13738-024-03171-y.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143581229","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":"Synthesis, characterization and biological evaluation, determination of physico chemical parameters at three different temperatures and ADME studies of some 4-thiazolidinone containing furan and pyrimidine moiety","authors":"Umang P. Mehta,&nbsp;Dinesh R. Godhani,&nbsp;Anwar H. Saiyad,&nbsp;Kuldip P. Parmar,&nbsp;Jignasu P. Mehta","doi":"10.1007/s13738-024-03162-z","DOIUrl":"10.1007/s13738-024-03162-z","url":null,"abstract":"<div><p>We created a novel family of 5-benzylidene-2-(furan-2-yl)-3-(pyrimidin-2-yl)thiazolidin-4-one (5a-o) to successfully decrease viral diseases linked to antimicrobial resistance (AMR), which is a major public health problem worldwide. Using spectral approaches, the structures of the pertinent chemicals have been identified and confirmed. Compounds with chloro substituents in both the <i>p</i>-position and the <i>m</i>-position showed good activity against the fungi, products with the nitro group at the ring's <i>m</i>-position and methyl, bromo, and nitro substituents in the benzene ring's <i>p</i>-position showed very good activity against bacterial strains. <i>Aspergillus Niger</i> and <i>Fusarium Javanicum</i> In a binary liquid mixture containing 4-thiazolidinone derivatives containing furan and pyrimidine moiety over the whole molality range at temperatures T = (303.15, 308.15, 313.15 and 318.15) K and different solvents DMSO and DMF, density (<i>ρ</i>), ultrasonic velocity (<i>U</i>), and viscosity (<i>η</i>) have been measured.</p><h3>Graphical abstract</h3><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":676,"journal":{"name":"Journal of the Iranian Chemical Society","volume":"22 3","pages":"475 - 497"},"PeriodicalIF":2.2,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s13738-024-03162-z.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143581138","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}