Pub Date : 2025-11-17DOI: 10.1080/00397911.2025.2589481
Milena R. Garbuzova (Investigation Methodology) , Constantine V. Milyutin (Formal analysis Project administration Software Visualization Writing – review & editing) , Andrey N. Komogortsev (Conceptualization Resources Supervision Writing – original draft Writing – review & editing)
In present study, we report efficient and straightforward method of the synthesis of pyrano[2,3-f]pyrazolo[3,4-d][1,3]oxazepine-4,6-dione derivatives, representing a completely new class of heterocycles. The presented approach employs readily available allomaltol-containing pyrazoles and proceeds via CDI-mediated cyclization as the key step. This strategy offers several advantages, including mild reaction conditions, operational simplicity, and facile isolation of the target heterocycles. The scope of the developed methodology was demonstrated through the synthesis of 21 products with yields reaching 80%. UV–vis absorption and fluorescence studies were carried out for the obtained compound. The structures of several target compounds were unambiguously established by X-ray analysis.
{"title":"Efficient method for the synthesis of novel pyrano[2,3-f]pyrazolo[3,4-d][1,3]oxazepines from allomaltol containing pyrazoles","authors":"Milena R. Garbuzova (Investigation Methodology) , Constantine V. Milyutin (Formal analysis Project administration Software Visualization Writing – review & editing) , Andrey N. Komogortsev (Conceptualization Resources Supervision Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2589481","DOIUrl":"10.1080/00397911.2025.2589481","url":null,"abstract":"<div><div>In present study, we report efficient and straightforward method of the synthesis of pyrano[2,3-<em>f</em>]pyrazolo[3,4-<em>d</em>][1,3]oxazepine-4,6-dione derivatives, representing a completely new class of heterocycles. The presented approach employs readily available allomaltol-containing pyrazoles and proceeds <em>via</em> CDI-mediated cyclization as the key step. This strategy offers several advantages, including mild reaction conditions, operational simplicity, and facile isolation of the target heterocycles. The scope of the developed methodology was demonstrated through the synthesis of 21 products with yields reaching 80%. UV–vis absorption and fluorescence studies were carried out for the obtained compound. The structures of several target compounds were unambiguously established by X-ray analysis.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 22","pages":"Pages 1680-1691"},"PeriodicalIF":1.8,"publicationDate":"2025-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145705457","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-11-17DOI: 10.1080/00397911.2025.2597375
Baojie Qiu (Investigation Writing – original draft) , Chun He (Funding acquisition Project administration) , Yaorong Liu (Investigation Methodology) , Siyu Liang (Formal analysis Investigation) , Xingxian Zhang (Conceptualization Project administration Supervision Writing – review & editing)
A novel and practical seven-step synthesis of relebactam has been developed, starting from (2 R,5S)-5-((benzyloxy)amino)piperidine-2-carboxylic acid, achieving an overall yield of 42.27% with high HPLC purity (99.27%). This approach offers an efficient synthesis of the key diazabicyclooctane (DBO) core, while also demonstrating cost-effectiveness and improved operational simplicity.
{"title":"An efficient and practical approach to synthesis of relebactam","authors":"Baojie Qiu (Investigation Writing – original draft) , Chun He (Funding acquisition Project administration) , Yaorong Liu (Investigation Methodology) , Siyu Liang (Formal analysis Investigation) , Xingxian Zhang (Conceptualization Project administration Supervision Writing – review & editing)","doi":"10.1080/00397911.2025.2597375","DOIUrl":"10.1080/00397911.2025.2597375","url":null,"abstract":"<div><div>A novel and practical seven-step synthesis of relebactam has been developed, starting from (2 <em>R</em>,5<em>S</em>)-5-((benzyloxy)amino)piperidine-2-carboxylic acid, achieving an overall yield of 42.27% with high HPLC purity (99.27%). This approach offers an efficient synthesis of the key diazabicyclooctane (DBO) core, while also demonstrating cost-effectiveness and improved operational simplicity.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 22","pages":"Pages 1736-1741"},"PeriodicalIF":1.8,"publicationDate":"2025-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145705454","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Click synthesis of ether-ester linked 1,4-disubstituted 1,2,3-triazoles (7a–j) was carried out through reaction of Benzyl/phenethyl 2-bromoacetates (6a–e) and 1-(4-(prop-2-yn-1-yloxy)phenyl)ethanone (3a)/phenyl(4-(prop-2-yn-1-yloxy)phenyl)methanone (3b) and sodium azide. Further, 1,4-disubstituted 1,2,3-triazoles containing hydrazone functionality (9a–o) were synthesized from ether-ester linked 1,4-disubstituted 1,2,3-triazoles (7a–e) through condensation with phenylhydrazine derivatives (8a–c). The structural characterization of the synthesized 1,2,3-triazoles were accomplished by FTIR,1H NMR,13C NMR, HRMS techniques. The structure of compound 7e (CCDC 2130838) was also confirmed by X-ray crystallography. All the synthesized compounds were screened for antimicrobial activity against Staphylococcus aureus, Bacillus subtilis, Salmonella enterica, Escherichia coli, Candida albicans and Rhizopus oryzae. The substituted 1,2,3-triazoles reflected moderate activity against tested bacterial/fungal strains. Docking studies of the compound 9 l were also undertaken in the binding site of E. coli DNA gyrase and C. albicans Lanosterol 14-α-demethylase to have an insight into mode of action.
{"title":"Synthesis, crystal structure and antimicrobial evaluation of 1,4-disubstituted 1,2,3-triazole enriched with varied functionality","authors":"Manisha Chahal (Investigation Methodology Writing – original draft) , C. P. Kaushik (Conceptualization Resources Supervision) , Sonika Asija (Formal analysis Validation) , Mahavir Parshad (Formal analysis Validation) , Mukesh Kumar (Formal analysis Software) , Raj Luxmi (Data curation Formal analysis) , Jyoti Sangwan (Formal analysis Writing – review & editing) , Jyoti Yadav (Formal analysis Writing – review & editing)","doi":"10.1080/00397911.2025.2591086","DOIUrl":"10.1080/00397911.2025.2591086","url":null,"abstract":"<div><div>Click synthesis of ether-ester linked 1,4-disubstituted 1,2,3-triazoles <strong>(7a–j)</strong> was carried out through reaction of Benzyl/phenethyl 2-bromoacetates <strong>(6a–e)</strong> and 1-(4-(prop-2-yn-1-yloxy)phenyl)ethanone <strong>(3a)</strong>/phenyl(4-(prop-2-yn-1-yloxy)phenyl)methanone <strong>(3b)</strong> and sodium azide. Further, 1,4-disubstituted 1,2,3-triazoles containing hydrazone functionality <strong>(9a–o)</strong> were synthesized from ether-ester linked 1,4-disubstituted 1,2,3-triazoles <strong>(7a–e)</strong> through condensation with phenylhydrazine derivatives <strong>(8a–c).</strong> The structural characterization of the synthesized 1,2,3-triazoles were accomplished by FTIR,<sup>1</sup>H NMR,<sup>13</sup>C NMR, HRMS techniques. The structure of compound <strong>7e</strong> (CCDC 2130838) was also confirmed by X-ray crystallography. All the synthesized compounds were screened for antimicrobial activity against <em>Staphylococcus aureus, Bacillus subtilis, Salmonella enterica, Escherichia coli, Candida albicans</em> and <em>Rhizopus oryzae</em>. The substituted 1,2,3-triazoles reflected moderate activity against tested bacterial/fungal strains. Docking studies of the compound <strong>9 l</strong> were also undertaken in the binding site of <em>E. coli</em> DNA gyrase and <em>C. albicans</em> Lanosterol 14-α-demethylase to have an insight into mode of action.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 22","pages":"Pages 1692-1711"},"PeriodicalIF":1.8,"publicationDate":"2025-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145705455","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-11-17DOI: 10.1080/00397911.2025.2592258
Manjula K. (Investigation Methodology Validation Visualization Writing – original draft) , Raja Rajeswari T. (Investigation Methodology Project administration Supervision Writing – review & editing) , Ch. Subramanyam (Data curation Investigation Software Writing – review & editing)
A new library of α-aminophosphonate derivatives (9a–j) was developed utilizing a Kabachnik–Fields multicomponent method with microwave assistance. Prior to synthesis, their pharmacokinetic characteristics and inhibitory interactions with the enzymes α-amylase and α-glucosidase were predicted using molecular docking simulations and in silico ADMET evaluation. Spectroscopy was used to check the structural integrity. The synthesized compounds were examined in vitro for inhibitory effects against two enzymes associated with type 2 diabetes. Compound 9e inhibited α-glucosidase the most (IC50 = 88.89 μg/mL), while compound 9b inhibited both enzymes (IC50 = 2.6 μg/mL for α-glucosidase and 102.36 μg/mL for α-amylase), similar to acarbose. SAR analysis found that electron-donating and heterocyclic groups increased activity, whereas bulky or electron-withdrawing substituents reduced efficacy. Statistical validation with ANOVA and Tukey’s HSD test revealed significant variations in enzyme inhibition across the compound set. These findings suggest that the synthesized compounds serve as promising candidates for the development of dual-action anti-diabetic agents.
{"title":"Microwave-driven synthesis of α-aminophosphonates targeting diabetes: in silico and in vitro assessment of α-amylase and α-glucosidase inhibition","authors":"Manjula K. (Investigation Methodology Validation Visualization Writing – original draft) , Raja Rajeswari T. (Investigation Methodology Project administration Supervision Writing – review & editing) , Ch. Subramanyam (Data curation Investigation Software Writing – review & editing)","doi":"10.1080/00397911.2025.2592258","DOIUrl":"10.1080/00397911.2025.2592258","url":null,"abstract":"<div><div>A new library of α-aminophosphonate derivatives (<strong>9a</strong>–<strong>j</strong>) was developed utilizing a Kabachnik–Fields multicomponent method with microwave assistance. Prior to synthesis, their pharmacokinetic characteristics and inhibitory interactions with the enzymes α-amylase and α-glucosidase were predicted using molecular docking simulations and in silico ADMET evaluation. Spectroscopy was used to check the structural integrity. The synthesized compounds were examined in vitro for inhibitory effects against two enzymes associated with type 2 diabetes. Compound <strong>9e</strong> inhibited α-glucosidase the most (IC<sub>50</sub> = 88.89 μg/mL), while compound <strong>9b</strong> inhibited both enzymes (IC<sub>50</sub> = 2.6 μg/mL for α-glucosidase and 102.36 μg/mL for α-amylase), similar to acarbose. SAR analysis found that electron-donating and heterocyclic groups increased activity, whereas bulky or electron-withdrawing substituents reduced efficacy. Statistical validation with ANOVA and Tukey’s HSD test revealed significant variations in enzyme inhibition across the compound set. These findings suggest that the synthesized compounds serve as promising candidates for the development of dual-action anti-diabetic agents.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 22","pages":"Pages 1712-1735"},"PeriodicalIF":1.8,"publicationDate":"2025-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145705456","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-11-17DOI: 10.1080/00397911.2025.2554673
Hafiza Noor Fatima (Data curation Formal analysis Investigation Methodology Writing – original draft) , Matloob Ahmad (Conceptualization Investigation Project administration Supervision Writing – review & editing) , Tanzeela Riaz (Data curation Formal analysis Investigation) , Muhammad Shahid Nazir (Data curation Formal analysis Validation) , Sana Aslam (Conceptualization Investigation Project administration Writing – review & editing)
Heterocycles are considered a versatile pharmacophore in the medical field due to their immense biological applications in pharmaceutical chemistry. Thiadiazine is a six-membered ring heterocyclic moiety that contains one sulfur and two nitrogen atoms in its structure. It has numerous isomeric forms that are formed by the rearrangement of sulfur and nitrogen atoms in the cyclic structure. The derivatives of thiadiazine have been studied for their unique potential biological activities, including anti-inflammatory, anti-convulsant, anti-hypertensive, anti-cancer, anti-diabetic, anti-tuberculosis, anti-malarial, and anti-fungal properties. Due to the growing demand for bioactive heterocyclic compounds, organic researchers have developed synthetic methodologies for the synthesis of thiadiazine compounds. This review highlights the synthesis of thiadiazine isomers that have been produced through multicomponent processes by using catalyst-based reactions, solvent-free reactions, catalyst-free reactions, Mannich reactions, and condensation reactions during the years 2011–2025.
{"title":"Recent advances in the synthesis of thiadiazine derivatives through multicomponent reactions","authors":"Hafiza Noor Fatima (Data curation Formal analysis Investigation Methodology Writing – original draft) , Matloob Ahmad (Conceptualization Investigation Project administration Supervision Writing – review & editing) , Tanzeela Riaz (Data curation Formal analysis Investigation) , Muhammad Shahid Nazir (Data curation Formal analysis Validation) , Sana Aslam (Conceptualization Investigation Project administration Writing – review & editing)","doi":"10.1080/00397911.2025.2554673","DOIUrl":"10.1080/00397911.2025.2554673","url":null,"abstract":"<div><div>Heterocycles are considered a versatile pharmacophore in the medical field due to their immense biological applications in pharmaceutical chemistry. Thiadiazine is a six-membered ring heterocyclic moiety that contains one sulfur and two nitrogen atoms in its structure. It has numerous isomeric forms that are formed by the rearrangement of sulfur and nitrogen atoms in the cyclic structure. The derivatives of thiadiazine have been studied for their unique potential biological activities, including anti-inflammatory, anti-convulsant, anti-hypertensive, anti-cancer, anti-diabetic, anti-tuberculosis, anti-malarial, and anti-fungal properties. Due to the growing demand for bioactive heterocyclic compounds, organic researchers have developed synthetic methodologies for the synthesis of thiadiazine compounds. This review highlights the synthesis of thiadiazine isomers that have been produced through multicomponent processes by using catalyst-based reactions, solvent-free reactions, catalyst-free reactions, Mannich reactions, and condensation reactions during the years 2011–2025.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 22","pages":"Pages 1655-1679"},"PeriodicalIF":1.8,"publicationDate":"2025-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145705458","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In cutting-edge organic synthesis, the creation of sustainable catalytic systems occupies center stage, especially in light of the growing need for environmentally friendly and energy-efficient procedures. FeVO4 is a triclinic, n-type semiconductor that has been studied for a variety of uses, such as photocatalytic hydrogen generation, zinc batteries, photodegradation, and catalytic reactions. FeVO4 is a pertinent semiconductor since it is stable, chemically unreactive, nontoxic, and attainable. FeVO4 has attracted the attention of researchers due to its stable chemical properties, reduced band gap, and lower cost compared to InVO4 and BiVO4. As a result, an increasing number of metal vanadates with strong catalytic and photocatalytic activities have been discovered and described. We primarily focused on the catalytic organic transformations in the presence of FeVO4 and its nanocomposites. The review presents a thorough grasp of the ways that FeVO4 nanocomposites might aid in the creation of more environmentally friendly and effective catalytic systems for organic synthesis, while also addressing the field’s challenges, obstacles and future prospects. Our current evaluation efforts are expected to shed light on the future path of FeVO4 nano catalysts.
{"title":"FeVO4 based nanocomposites: Versatile heterogeneous catalysts for organic transformations","authors":"Mohamed Sulthan Hasan Fathima Afridha (Data curation Formal analysis Investigation Writing – original draft) , Selvaraj Mohana Roopan (Methodology Project administration Supervision Validation Writing – review & editing)","doi":"10.1080/00397911.2025.2546605","DOIUrl":"10.1080/00397911.2025.2546605","url":null,"abstract":"<div><div>In cutting-edge organic synthesis, the creation of sustainable catalytic systems occupies center stage, especially in light of the growing need for environmentally friendly and energy-efficient procedures. FeVO<sub>4</sub> is a triclinic, n-type semiconductor that has been studied for a variety of uses, such as photocatalytic hydrogen generation, zinc batteries, photodegradation, and catalytic reactions. FeVO<sub>4</sub> is a pertinent semiconductor since it is stable, chemically unreactive, nontoxic, and attainable. FeVO<sub>4</sub> has attracted the attention of researchers due to its stable chemical properties, reduced band gap, and lower cost compared to InVO<sub>4</sub> and BiVO<sub>4</sub>. As a result, an increasing number of metal vanadates with strong catalytic and photocatalytic activities have been discovered and described. We primarily focused on the catalytic organic transformations in the presence of FeVO<sub>4</sub> and its nanocomposites. The review presents a thorough grasp of the ways that FeVO<sub>4</sub> nanocomposites might aid in the creation of more environmentally friendly and effective catalytic systems for organic synthesis, while also addressing the field’s challenges, obstacles and future prospects. Our current evaluation efforts are expected to shed light on the future path of FeVO<sub>4</sub> nano catalysts.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 21","pages":"Pages 1577-1595"},"PeriodicalIF":1.8,"publicationDate":"2025-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145760868","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-11-02DOI: 10.1080/00397911.2025.2588715
Pallavi D. Vedpathak (Investigation Methodology Validation) , Sarika U. Kesgire (Investigation Methodology) , Shobha A. Waghmode (Conceptualization Data curation Funding acquisition Project administration Resources Supervision Validation Writing – review & editing) , Suresh Iyer (Conceptualization Data curation Formal analysis Methodology Supervision Writing – original draft Writing – review & editing)
Bimetallic Pd-Ni and Pd-Cu nanoparticles anchored on rGO (reduced graphene oxide) catalyzed the thermal and sunlight and visible light-powered Suzuki-Miyaura coupling. The reactions were completed in short times with high yields. The Pd-Ni-rGO catalyst could be recycled without much deterioration of activity. Comparative reactions with monometallic Pd or Ni on rGO and commercial Pd(OAc)2 were slower and with lower yield indicating the beneficiary effects of rGO as nanoalloy support.
{"title":"Photothermal, bimetallic synergistic heterogeneous catalysis: Solar energy-driven ligand-free Pd-Ni and Pd-Cu on rGO catalyzed Suzuki-Miyaura coupling","authors":"Pallavi D. Vedpathak (Investigation Methodology Validation) , Sarika U. Kesgire (Investigation Methodology) , Shobha A. Waghmode (Conceptualization Data curation Funding acquisition Project administration Resources Supervision Validation Writing – review & editing) , Suresh Iyer (Conceptualization Data curation Formal analysis Methodology Supervision Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2588715","DOIUrl":"10.1080/00397911.2025.2588715","url":null,"abstract":"<div><div>Bimetallic Pd-Ni and Pd-Cu nanoparticles anchored on rGO (reduced graphene oxide) catalyzed the thermal and sunlight and visible light-powered Suzuki-Miyaura coupling. The reactions were completed in short times with high yields. The Pd-Ni-rGO catalyst could be recycled without much deterioration of activity. Comparative reactions with monometallic Pd or Ni on rGO and commercial Pd(OAc)2 were slower and with lower yield indicating the beneficiary effects of rGO as nanoalloy support.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 21","pages":"Pages 1633-1640"},"PeriodicalIF":1.8,"publicationDate":"2025-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145760870","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A new and efficient metal-free method for the visible-light-driven oxidative cyclodesulfurization of phenolic thioureas to 2-aminobenzoxazoles is reported using tetrabutylammonium tribromide (TBATB) as the sustainable promoter. This approach eliminates the need of additional metallic or nonmetallic bases. It overcomes the limitations of existing methods that rely on organic photocatalysts requiring multi-step synthesis or on costly and potentially hazardous polypyridyl organometallic complexes. The reaction proceeds at room temperature employing visible light and TBATB without external oxidants, or inert atmospheres. This study highlights another synthetic utility of TBATB-mediated visible-light-driven organic transformations, demonstrating its potential as an efficient promoter for visible-light-driven reactions in organic synthesis. Thus, this work may open new avenues for developing TBATB-mediated green synthesis methodologies.
{"title":"Visible-light-driven, metal-free oxidative cyclodesulfurization of thioureas to 2-aminobenzoxazoles using tetrabutylammonium tribromide","authors":"Babita Yadav (Methodology Writing – original draft Writing – review & editing) , Arvind Kumar Yadav (Methodology Supervision Writing – review & editing) , Garima (Methodology Writing – review & editing) , Vishnu Prabhakar Srivastava (Conceptualization Methodology Writing – review & editing) , Santosh Kumar Srivastava (Methodology Supervision Writing – original draft)","doi":"10.1080/00397911.2025.2589474","DOIUrl":"10.1080/00397911.2025.2589474","url":null,"abstract":"<div><div>A new and efficient metal-free method for the visible-light-driven oxidative cyclodesulfurization of phenolic thioureas to 2-aminobenzoxazoles is reported using tetrabutylammonium tribromide (TBATB) as the sustainable promoter. This approach eliminates the need of additional metallic or nonmetallic bases. It overcomes the limitations of existing methods that rely on organic photocatalysts requiring multi-step synthesis or on costly and potentially hazardous polypyridyl organometallic complexes. The reaction proceeds at room temperature employing visible light and TBATB without external oxidants, or inert atmospheres. This study highlights another synthetic utility of TBATB-mediated visible-light-driven organic transformations, demonstrating its potential as an efficient promoter for visible-light-driven reactions in organic synthesis. Thus, this work may open new avenues for developing TBATB-mediated green synthesis methodologies.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 21","pages":"Pages 1641-1654"},"PeriodicalIF":1.8,"publicationDate":"2025-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145760833","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-11-02DOI: 10.1080/00397911.2025.2588178
Sara Shawkat (Writing – original draft Writing – review & editing) , Mohamed Abass (Data curation Investigation) , Hany Mohamed Hassanin (Supervision) , Dalia Abdel-Kader (Conceptualization Data curation Formal analysis Methodology Project administration Supervision Writing – review & editing)
A novel 4-chloro-2,5-dioxo-6-phenyl-5,6-dihydro-2H-pyrano[3,2-c]quinoline-3-carbaldehyde was synthesized via the Vilsmeier reaction and served as a key intermediate for constructing a series of heterocyclic quinoline derivatives. Modification of the pyranoquinoline-3-carbaldehyde scaffold through subsequent reactions with hydrazines, o-phenylenediamine, and barbituric acid led to quinoline derivatives bearing pyrazole, diazepine, and pyrimidine moieties. These structural variations significantly influenced the compounds’ biological profiles. Spectroscopic techniques and elemental analysis were used to confirm the structures. Favorable binding affinities were demonstrated by molecular docking tests against human thymidylate synthase (HT-hTS, PDB: 6QXG), with docking scores (−8.4 to −10.7 kcal/mol) higher than those of the reference ligand 5-fluorodeoxyuridinemonophosphate FdUMP (−7.8 kcal/mol). Cytotoxicity was evaluated against HepG-2 and HCT-116 cell lines using the MTT assay. Compound 14 showed the most potent antiproliferative activity, with IC50 values of 33.61 µM (HepG-2) and 50.73 µM (HCT-116), comparable to that of 5-fluorouracil (5-FL). These results highlight quinoline derivatives as promising anticancer agents and HT-hTS inhibitors.
{"title":"Synthetic utility of 4-chloro-2,5-dioxo-6-phenyl-5,6-dihydro-2H-pyrano[3,2-c]quinoline-3-carbaldehyde and molecular docking and cytotoxicity of its derivatives","authors":"Sara Shawkat (Writing – original draft Writing – review & editing) , Mohamed Abass (Data curation Investigation) , Hany Mohamed Hassanin (Supervision) , Dalia Abdel-Kader (Conceptualization Data curation Formal analysis Methodology Project administration Supervision Writing – review & editing)","doi":"10.1080/00397911.2025.2588178","DOIUrl":"10.1080/00397911.2025.2588178","url":null,"abstract":"<div><div>A novel 4-chloro-2,5-dioxo-6-phenyl-5,6-dihydro-2H-pyrano[3,2-<em>c</em>]quinoline-3-carbaldehyde was synthesized via the Vilsmeier reaction and served as a key intermediate for constructing a series of heterocyclic quinoline derivatives. Modification of the pyranoquinoline-3-carbaldehyde scaffold through subsequent reactions with hydrazines, o-phenylenediamine, and barbituric acid led to quinoline derivatives bearing pyrazole, diazepine, and pyrimidine moieties. These structural variations significantly influenced the compounds’ biological profiles. Spectroscopic techniques and elemental analysis were used to confirm the structures. Favorable binding affinities were demonstrated by molecular docking tests against human thymidylate synthase (HT-hTS, PDB: 6QXG), with docking scores (−8.4 to −10.7 kcal/mol) higher than those of the reference ligand 5-fluorodeoxyuridinemonophosphate FdUMP (−7.8 kcal/mol). Cytotoxicity was evaluated against HepG-2 and HCT-116 cell lines using the MTT assay. Compound <strong>14</strong> showed the most potent antiproliferative activity, with IC<sub>50</sub> values of 33.61 µM (HepG-2) and 50.73 µM (HCT-116), comparable to that of 5-fluorouracil (5-FL). These results highlight quinoline derivatives as promising anticancer agents and HT-hTS inhibitors.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 21","pages":"Pages 1612-1632"},"PeriodicalIF":1.8,"publicationDate":"2025-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145760871","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-11-02DOI: 10.1080/00397911.2025.2584278
Mintu Maan Dutta (Conceptualization Data curation Formal analysis Funding acquisition Investigation Methodology Resources Supervision Writing – original draft Writing – review & editing) , Jimi Saud (Formal analysis Investigation Methodology Writing – original draft) , Nikhil Basistha (Formal analysis Methodology Writing – original draft Writing – review & editing) , Rofiqul Hussain (Formal analysis Investigation Methodology Writing – original draft)
Copper chromite nanoparticles were synthesized by co-precipitation method. The synthesized nanoparticles were characterized using various analytical techniques such as X-ray Diffraction (XRD), Infrared spectroscopy (IR), Scanning Electron Microscopy (SEM) and Energy Dispersive X-ray Spectroscopy (EDX), Dynamic Light Scattering (DLS), Thermogravimetric Analysis (TGA). Upon successful characterization of synthesized material, Copper chromite nanoparticles were utilized as a catalyst for the synthesis of N-containing heterocycles using o-phenylenediamine and aldehydes under mild reaction conditions. N-containing heterocycles obtained have numerous therapeutic applications.
{"title":"Synthesis of Copper chromite nanoparticles (CuCr2O4) and exploring its potential application toward synthesis of N-containing heterocycles","authors":"Mintu Maan Dutta (Conceptualization Data curation Formal analysis Funding acquisition Investigation Methodology Resources Supervision Writing – original draft Writing – review & editing) , Jimi Saud (Formal analysis Investigation Methodology Writing – original draft) , Nikhil Basistha (Formal analysis Methodology Writing – original draft Writing – review & editing) , Rofiqul Hussain (Formal analysis Investigation Methodology Writing – original draft)","doi":"10.1080/00397911.2025.2584278","DOIUrl":"10.1080/00397911.2025.2584278","url":null,"abstract":"<div><div>Copper chromite nanoparticles were synthesized by co-precipitation method. The synthesized nanoparticles were characterized using various analytical techniques such as X-ray Diffraction (XRD), Infrared spectroscopy (IR), Scanning Electron Microscopy (SEM) and Energy Dispersive X-ray Spectroscopy (EDX), Dynamic Light Scattering (DLS), Thermogravimetric Analysis (TGA). Upon successful characterization of synthesized material, Copper chromite nanoparticles were utilized as a catalyst for the synthesis of <em>N</em>-containing heterocycles using <em>o</em>-phenylenediamine and aldehydes under mild reaction conditions. <em>N</em>-containing heterocycles obtained have numerous therapeutic applications.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 21","pages":"Pages 1596-1611"},"PeriodicalIF":1.8,"publicationDate":"2025-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145760869","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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