Synthesis of 2-aryl tetrahydrofurans from 2-aryl-δ-lactones with one-carbon deletion was established by using a catalytic amount (10 mol%) of CuSO4 and two equivalents of sodium persulfate in 5% sulfuric acid. Copper(III) or sulfate radical anion worked as oxidant to generate carboxy radicals and α-aryl carbocations. The aryl group stabilized radicals formed by decarboxylation of the carboxy radicals.
{"title":"Copper-catalyzed persulfate oxidation of δ-lactones to tetrahydrofurans with one-carbon deletion","authors":"So Ohkubo (Investigation Methodology) , Tomoyuki Yoshimura (Supervision Writing – review & editing) , Shohei Hamada (Supervision Writing – review & editing) , Jun-ichi Matsuo (Conceptualization Funding acquisition Supervision Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2609819","DOIUrl":"10.1080/00397911.2025.2609819","url":null,"abstract":"<div><div>Synthesis of 2-aryl tetrahydrofurans from 2-aryl-δ-lactones with one-carbon deletion was established by using a catalytic amount (10 mol%) of CuSO<sub>4</sub> and two equivalents of sodium persulfate in 5% sulfuric acid. Copper(III) or sulfate radical anion worked as oxidant to generate carboxy radicals and α-aryl carbocations. The aryl group stabilized radicals formed by decarboxylation of the carboxy radicals.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 4","pages":"Pages 328-336"},"PeriodicalIF":1.8,"publicationDate":"2026-02-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146135693","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}
This study presents a novel one-pot synthesis of methyl 7-aryl-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate derivatives by reacting equimolar amounts of aromatic aldehydes (5 mmol), methyl acetoacetate (5 mmol), and 3-amino-1,2,4-triazole (5 mmol) in water at room temperature, catalyzed by hyamine (benzethonium chloride). Products were isolated by filtration, purified by recrystallization, and characterized using infrared spectroscopy (IR),1H NMR, 13C NMR, and electrospray ionization mass spectrometry (ESI-MS). The total of 12 synthesized triazolo-fused pyrimidine derivatives were obtained in high yields (up to 95%) with reaction time ranging from 5 to 8 h. The use of hyamine as a cationic surfactant catalyst enhanced the reaction rates through micellar effects, promoting high local substrate concentrations and stabilizing transition states. The hyamine-catalyzed MCR provides a green, efficient, and high-yielding method to synthesize triazolo-fused pyrimidine derivatives using water as a green solvent at room temperature.
{"title":"A facile and green synthesis of methyl 7-aryl-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate derivatives using hyamine in aqueous media at room temperature","authors":"Peeli Kumar Anjali (Formal analysis Investigation Methodology Validation) , Muniyan Ramasamy Kuppusamy (Data curation Formal analysis Validation Writing – original draft Writing – review & editing) , Devendiran Parthiban (Conceptualization Data curation Formal analysis Investigation Methodology Supervision Validation Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2026.2620037","DOIUrl":"10.1080/00397911.2026.2620037","url":null,"abstract":"<div><div>This study presents a novel one-pot synthesis of methyl 7-aryl-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate derivatives by reacting equimolar amounts of aromatic aldehydes (5 mmol), methyl acetoacetate (5 mmol), and 3-amino-1,2,4-triazole (5 mmol) in water at room temperature, catalyzed by hyamine (benzethonium chloride). Products were isolated by filtration, purified by recrystallization, and characterized using infrared spectroscopy (IR),<sup>1</sup>H NMR, <sup>13</sup>C NMR, and electrospray ionization mass spectrometry (ESI-MS). The total of 12 synthesized triazolo-fused pyrimidine derivatives were obtained in high yields (up to 95%) with reaction time ranging from 5 to 8 h. The use of hyamine as a cationic surfactant catalyst enhanced the reaction rates through micellar effects, promoting high local substrate concentrations and stabilizing transition states. The hyamine-catalyzed MCR provides a green, efficient, and high-yielding method to synthesize triazolo-fused pyrimidine derivatives using water as a green solvent at room temperature.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 3","pages":"Pages 235-253"},"PeriodicalIF":1.8,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146098694","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}
An efficient method was established for the synthesis of novel 3-(azidomethyl)-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one. Theoretical calculations for both the synthesized compound and its precursor, 3-(chloromethyl)-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one, were performed using density functional theory (DFT) at the aug-cc-pVDZ level. Furthermore, we established a correlation between the structure, properties, and biological activity of the synthesized compounds, alongside a comprehensive ADME profile. Results from the MTT assay demonstrated that the synthesized 7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one derivatives exhibit promising cytotoxic activity, positioning them as potential candidates for further development as anticancer agents.
{"title":"Discovery of 3-(azidomethyl)-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one with antitumor activity: Structural and biological evaluation","authors":"Mariia Skryl’nikova (Conceptualization) , Andrey Khramchikhin (Formal analysis) , Kirill Timoshchuk (Validation) , Dmitrii Antonenko (Validation) , Natalia Petukhova (Methodology) , Irina Krutetskaia (Resources) , Olga Mikolaichuk (Software) , Oleg Molchanov (Funding acquisition) , Dmitrii Granov (Supervision)","doi":"10.1080/00397911.2026.2615694","DOIUrl":"10.1080/00397911.2026.2615694","url":null,"abstract":"<div><div>An efficient method was established for the synthesis of novel 3-(azidomethyl)-7-methyl-5H-thiazolo[3,2-<em>a</em>]pyrimidin-5-one. Theoretical calculations for both the synthesized compound and its precursor, 3-(chloromethyl)-7-methyl-5<em>H</em>-thiazolo[3,2-<em>a</em>]pyrimidin-5-one, were performed using density functional theory (DFT) at the aug-cc-pVDZ level. Furthermore, we established a correlation between the structure, properties, and biological activity of the synthesized compounds, alongside a comprehensive ADME profile. Results from the MTT assay demonstrated that the synthesized 7-methyl-5<em>H</em>-thiazolo[3,2-<em>a</em>]pyrimidin-5-one derivatives exhibit promising cytotoxic activity, positioning them as potential candidates for further development as anticancer agents.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 3","pages":"Pages 220-225"},"PeriodicalIF":1.8,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146098691","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 : 2026-02-01DOI: 10.1080/00397911.2026.2617872
Ashwini L. Jakkawad (Investigation) , Rameshwar M. More (Investigation Resources) , Archana B. Kadam (Methodology Visualization) , Vivek T. Humne (Resources Supervision Writing – original draft Writing – review & editing) , Subhash B. Junne (Resources Supervision)
A highly efficient and straightforward [3 + 2] annulation reaction between arylisothiocyanate and thioglycolic acid to facilitated a diverse array of N-phenyl rhodanines by using N,N’-dicyclohexylcarbodiimide (DCC) has been explored. The primarily role of DCC is to activate thioglycolic acid which simplify [3 + 2] annulation reaction. Notably, the advantages of the present methodology included availability of starting material, ease of operation, mild reaction condition, and acceptable yield.
{"title":"DCC-mediated [3 + 2] annulation between arylisothiocyanate and thioglycolic acid to access N-phenyl rhodanines","authors":"Ashwini L. Jakkawad (Investigation) , Rameshwar M. More (Investigation Resources) , Archana B. Kadam (Methodology Visualization) , Vivek T. Humne (Resources Supervision Writing – original draft Writing – review & editing) , Subhash B. Junne (Resources Supervision)","doi":"10.1080/00397911.2026.2617872","DOIUrl":"10.1080/00397911.2026.2617872","url":null,"abstract":"<div><div>A highly efficient and straightforward [3 + 2] annulation reaction between arylisothiocyanate and thioglycolic acid to facilitated a diverse array of <em>N</em>-phenyl rhodanines by using <em>N</em>,<em>N</em>’-dicyclohexylcarbodiimide (DCC) has been explored. The primarily role of DCC is to activate thioglycolic acid which simplify [3 + 2] annulation reaction. Notably, the advantages of the present methodology included availability of starting material, ease of operation, mild reaction condition, and acceptable yield.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 3","pages":"Pages 226-234"},"PeriodicalIF":1.8,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146098695","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 : 2026-02-01DOI: 10.1080/00397911.2026.2616386
Tarun P. Patel (Data curation Formal analysis Investigation Validation Writing – original draft) , Megha A. Patel (Conceptualization Writing – review & editing) , Bhargav B. Dave (Data curation Writing – review & editing) , Pratik A. Patel (Data curation Formal analysis) , Vishwa U. Thakor (Software) , Paresh S. Patel (Conceptualization Methodology Resources Supervision Writing – review & editing)
This work the design, and synthesis of thieno[2,3-d]pyrimidine-based isoxazole derivatives (4a–4j) are reported along with characterization with the support of 1H NMR,13C NMR, HRMS spectral techniques. The compounds were investigated for their antibacterial activity against Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), and antifungal activity (Escherichia coli and Pseudomonas aeruginosa). They were also carried out molecular docking and MTT assay against MCF-7 breast cancer cells containing estrogen receptor alpha (ERα) (PDB ID: 3POZ). The compound (4b) exhibited effective docking scores as well as potent microbial activity against Gram-positive bacteria but displayed moderate activity against MCF-7 in the MTT assay. The anti-cancer activity of the synthesized compounds (4b, 4h, and 4j), which revealed good binding affinity in a docking study, was tested against MCF-7 (human Caucasian breast adenocarcinoma) via primary and secondary screening.
{"title":"Design, synthesis, and biological evaluation of thieno[2,3-d]pyrimidine-based isoxazole derivatives as potential antimicrobial and anticancer agents: In vitro and in silico insights","authors":"Tarun P. Patel (Data curation Formal analysis Investigation Validation Writing – original draft) , Megha A. Patel (Conceptualization Writing – review & editing) , Bhargav B. Dave (Data curation Writing – review & editing) , Pratik A. Patel (Data curation Formal analysis) , Vishwa U. Thakor (Software) , Paresh S. Patel (Conceptualization Methodology Resources Supervision Writing – review & editing)","doi":"10.1080/00397911.2026.2616386","DOIUrl":"10.1080/00397911.2026.2616386","url":null,"abstract":"<div><div>This work the design, and synthesis of thieno[2,3<em>-d</em>]pyrimidine-based isoxazole derivatives <strong>(4a–4j)</strong> are reported along with characterization with the support of <sup>1</sup>H NMR,<sup>13</sup>C NMR, HRMS spectral techniques. The compounds were investigated for their antibacterial activity against Gram-positive bacteria (<em>Staphylococcus aureus</em> and <em>Bacillus subtilis</em>), gram-negative bacteria (<em>Escherichia coli</em> and <em>Pseudomonas aeruginosa</em>), and antifungal activity (<em>Escherichia coli</em> and <em>Pseudomonas aeruginosa</em>). They were also carried out molecular docking and MTT assay against MCF-7 breast cancer cells containing estrogen receptor alpha (ERα) (PDB ID: 3POZ). The compound <strong>(4b)</strong> exhibited effective docking scores as well as potent microbial activity against Gram-positive bacteria but displayed moderate activity against MCF-7 in the MTT assay. The anti-cancer activity of the synthesized compounds <strong>(4b, 4h,</strong> and <strong>4j)</strong>, which revealed good binding affinity in a docking study, was tested against MCF-7 (human Caucasian breast adenocarcinoma) via primary and secondary screening.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 3","pages":"Pages 208-219"},"PeriodicalIF":1.8,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146098692","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}
Thiazolidinone is a saturated five-membered heterocyclic system that features sulfur and nitrogen at the 1 and 3 positions, as well as a carbonyl group. There are several derivatives of thiazolidinone which exist with varied positions of carbonyl groups. It is a well-recognized building block in many natural and medicinal compounds. Thiazolidinone derivatives exhibit a wide range of biological activities. The synthesis of thiazolidinone derivatives has gained significant attention in recent years due to the growing demand for heterocycles. Various strategies have been developed for the synthesis of thiazolidinones. In this review, we discuss several recent synthetic approaches, including catalyst-free, metal-based nano-catalyzed, acid-catalyzed, base-catalyzed, ionic liquid-assisted, and other processes employed in multicomponent reactions to form different thiazolidinone derivatives. These studies can help to further develop effective synthetic strategies for functionalized thiazolidinone derivatives.
{"title":"Strategies for the multicomponent reaction facilitating the expedited synthesis of functionalized thiazolidinone scaffolds","authors":"Tanzeela Riaz (Data curation Formal analysis Investigation Methodology Validation Writing – original draft) , Matloob Ahmad (Conceptualization Funding acquisition Resources Supervision Writing – review & editing) , Hafiza Noor Fatima (Data curation Formal analysis Investigation) , Sumayya Akram (Methodology Project administration Validation) , Sana Aslam (Conceptualization Project administration Writing – review & editing)","doi":"10.1080/00397911.2025.2598622","DOIUrl":"10.1080/00397911.2025.2598622","url":null,"abstract":"<div><div>Thiazolidinone is a saturated five-membered heterocyclic system that features sulfur and nitrogen at the 1 and 3 positions, as well as a carbonyl group. There are several derivatives of thiazolidinone which exist with varied positions of carbonyl groups. It is a well-recognized building block in many natural and medicinal compounds. Thiazolidinone derivatives exhibit a wide range of biological activities. The synthesis of thiazolidinone derivatives has gained significant attention in recent years due to the growing demand for heterocycles. Various strategies have been developed for the synthesis of thiazolidinones. In this review, we discuss several recent synthetic approaches, including catalyst-free, metal-based nano-catalyzed, acid-catalyzed, base-catalyzed, ionic liquid-assisted, and other processes employed in multicomponent reactions to form different thiazolidinone derivatives. These studies can help to further develop effective synthetic strategies for functionalized thiazolidinone derivatives.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 3","pages":"Pages 177-207"},"PeriodicalIF":1.8,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146098693","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}
Thiazole derivatives are a significant group of heterocyclic compounds known for their wide range of biological activities and extensive uses in pharmaceuticals, agriculture, and material science. Multicomponent synthetic methods have become powerful tools for the rapid and efficient synthesis of functionalized thiazole derivatives, offering advantages such as operational simplicity, high atom economy, and structural diversity in a single reaction step. This review provides a thorough analysis of one-pot synthetic methodologies reported in the literature from 2014 to 2025 for thiazole derivatives, with a focus on catalytic systems and reaction mechanisms. Furthermore, the review discusses prospects for developing greener, more sustainable, and versatile synthetic protocols to enhance the utility of thiazole derivatives in drug discovery and material innovation. The relevance of this review lies in providing researchers with an in-depth and critical analysis of existing methodologies, thereby enabling them to devise efficient and environmentally friendly approaches to synthesize functionalized thiazole derivatives.
{"title":"Recent advances in multicomponent synthesis of functionalized thiazole derivatives: a critical review","authors":"Maryam Zulfiqar (Data curation Formal analysis Investigation Methodology Visualization Writing – original draft) , Tanzeela Riaz (Formal analysis Methodology Validation Writing – original draft) , Matloob Ahmad (Conceptualization Methodology Project administration Supervision Writing – original draft Writing – review & editing) , Salma Shahid (Data curation Investigation Visualization) , Noshin Afshan (Data curation Investigation Resources Software Validation) , Sana Aslam (Conceptualization Project administration Resources Supervision Writing – review & editing)","doi":"10.1080/00397911.2026.2621788","DOIUrl":"10.1080/00397911.2026.2621788","url":null,"abstract":"<div><div>Thiazole derivatives are a significant group of heterocyclic compounds known for their wide range of biological activities and extensive uses in pharmaceuticals, agriculture, and material science. Multicomponent synthetic methods have become powerful tools for the rapid and efficient synthesis of functionalized thiazole derivatives, offering advantages such as operational simplicity, high atom economy, and structural diversity in a single reaction step. This review provides a thorough analysis of one-pot synthetic methodologies reported in the literature from 2014 to 2025 for thiazole derivatives, with a focus on catalytic systems and reaction mechanisms. Furthermore, the review discusses prospects for developing greener, more sustainable, and versatile synthetic protocols to enhance the utility of thiazole derivatives in drug discovery and material innovation. The relevance of this review lies in providing researchers with an in-depth and critical analysis of existing methodologies, thereby enabling them to devise efficient and environmentally friendly approaches to synthesize functionalized thiazole derivatives.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 4","pages":"Pages 255-287"},"PeriodicalIF":1.8,"publicationDate":"2026-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146135696","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 : 2026-01-29DOI: 10.1080/00397911.2026.2621793
Mohamed A. A. Elneairy (Conceptualization Data curation Formal analysis Resources Software Supervision) , Ahmed E. M. Mekky (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing) , Sherif M. H. Sanad (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing) , Nagwa H. S. Ahmed (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing)
The goal of the current work is to explore the antibacterial potency, especially MRSA inhibitory activity, of new ethyl 4-(2-oxo-2H-chromene-3-carbonyl)-1-aryl-1H-pyrazole-3-carboxylates 1a-1l. The desired products are obtained, in 77–95% yields, by reacting the appropriate chromene-based enaminones with the various hydrazonyl chlorides utilizing a suitable [3 + 2] cycloaddition protocol. The aforementioned protocol was conducted using an equimolar amount of triethylamine in refluxing dioxane for 6–8 h. Some new chromene-pyrazoles showed promising bacterial inhibitory efficacy, especially against Staphylococcus aureus and Enterococcus faecalis. Ethyl 1-(4-nitrophenyl)-1H-pyrazole-3-carboxylate hybrids 1d and 1j, attached to 4-(6-(((4-chlorophenyl)thio)methyl)-2-oxo-2H-chromene-3-carbonyl) or 4-(2-oxo-6-((p-tolylthio)methyl)-2H-chromene-3-carbonyl) units, displayed comparable potency to ciprofloxacin with MIC/MBC of 2.2/4.4 and 2.3/4.6 µM, respectively. Moreover, the previous hybrids demonstrated comparable MRSA inhibitory potency to linezolid with MIC/MBC of 4.4/17.6 and 4.6/18.2 µM, respectively. As shown by the Ames test and in the presence of the S9 mix, 1d and 1j were found not to be mutagenic to Salmonella typhimurium strains.
{"title":"Chromene-based enaminones: Versatile precursors for the synthesis of new 1-phenyl-1H-pyrazole-3-carboxylate hybrids with potential MRSA inhibitory potency","authors":"Mohamed A. A. Elneairy (Conceptualization Data curation Formal analysis Resources Software Supervision) , Ahmed E. M. Mekky (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing) , Sherif M. H. Sanad (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing) , Nagwa H. S. Ahmed (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2026.2621793","DOIUrl":"10.1080/00397911.2026.2621793","url":null,"abstract":"<div><div>The goal of the current work is to explore the antibacterial potency, especially MRSA inhibitory activity, of new ethyl 4-(2-oxo-2<em>H</em>-chromene-3-carbonyl)-1-aryl-1<em>H</em>-pyrazole-3-carboxylates <strong>1a-1l</strong>. The desired products are obtained, in 77–95% yields, by reacting the appropriate chromene-based enaminones with the various hydrazonyl chlorides utilizing a suitable [3 + 2] cycloaddition protocol. The aforementioned protocol was conducted using an equimolar amount of triethylamine in refluxing dioxane for 6–8 h. Some new chromene-pyrazoles showed promising bacterial inhibitory efficacy, especially against <em>Staphylococcus aureus</em> and <em>Enterococcus faecalis</em>. Ethyl 1-(4-nitrophenyl)-1<em>H</em>-pyrazole-3-carboxylate hybrids <strong>1d</strong> and <strong>1j</strong>, attached to 4-(6-(((4-chlorophenyl)thio)methyl)-2-oxo-2<em>H</em>-chromene-3-carbonyl) or 4-(2-oxo-6-((<em>p</em>-tolylthio)methyl)-2<em>H</em>-chromene-3-carbonyl) units, displayed comparable potency to ciprofloxacin with MIC/MBC of 2.2/4.4 and 2.3/4.6 µM, respectively. Moreover, the previous hybrids demonstrated comparable MRSA inhibitory potency to linezolid with MIC/MBC of 4.4/17.6 and 4.6/18.2 µM, respectively. As shown by the Ames test and in the presence of the S9 mix, <strong>1d</strong> and <strong>1j</strong> were found not to be mutagenic to <em>Salmonella typhimurium</em> strains.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 4","pages":"Pages 298-317"},"PeriodicalIF":1.8,"publicationDate":"2026-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146135692","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 : 2026-01-29DOI: 10.1080/00397911.2026.2621827
Guo-Ming Ho (Data curation Investigation Writing – original draft) , Chao-Wen Tseng (Data curation) , Yi-Hung Liu (Data curation) , Yu-Jang Li (Conceptualization Data curation Funding acquisition Methodology Supervision)
A direct synthesis of 5-cycloalkene-substituted γ-butenolides via an tandem [2,3]-Wittig rearrangement/lactonization of γ-allyloxy vinylogous urethane enolates are described. The reaction accommodates diverse cycloalkenyl substrates and affords the corresponding γ-butenolides in good yields with diastereoselectivity that depends on the substrate. The observed stereochemical outcomes, as established by X-ray crystallographic analysis, can be rationalized by simple transition-state models, and the method offers an efficient approach to γ-butenolide frameworks relevant to sesquiterpene lactones.
{"title":"Direct synthesis of 5-cycloalkene-substituted γ-butenolides via [2,3]-Wittig rearrangement of vinylogous urethanes","authors":"Guo-Ming Ho (Data curation Investigation Writing – original draft) , Chao-Wen Tseng (Data curation) , Yi-Hung Liu (Data curation) , Yu-Jang Li (Conceptualization Data curation Funding acquisition Methodology Supervision)","doi":"10.1080/00397911.2026.2621827","DOIUrl":"10.1080/00397911.2026.2621827","url":null,"abstract":"<div><div>A direct synthesis of 5-cycloalkene-substituted γ-butenolides via an tandem [2,3]-Wittig rearrangement/lactonization of γ-allyloxy vinylogous urethane enolates are described. The reaction accommodates diverse cycloalkenyl substrates and affords the corresponding γ-butenolides in good yields with diastereoselectivity that depends on the substrate. The observed stereochemical outcomes, as established by X-ray crystallographic analysis, can be rationalized by simple transition-state models, and the method offers an efficient approach to γ-butenolide frameworks relevant to sesquiterpene lactones.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 4","pages":"Pages 318-327"},"PeriodicalIF":1.8,"publicationDate":"2026-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146135694","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 novel series of 4-arylidene tetrahydrocurcumins was synthesized from tetrahydrocurcumin and various aldehydes via Knoevenagel condensation in 81–90% yield. Aliphatic and aromatic aldehydes substituted with electron-donating and withdrawing groups were found to be effective substrates. The synthesized compounds were characterized using various spectroscopic techniques, and the structure of one of the derivatives was unambiguously established by single-crystal X-ray diffraction. These compounds were designed as a resemblance of combretastatin A4 scaffold integrated with curcumin. Our design and synthesis offer 4-arylidene tetrahydrocurcumin derivatives as a new class of compounds for evaluating bioactivity, with improved bioavailability, stability, and therapeutic efficacy.
{"title":"Design and synthesis of 4-arylidenetetrahydrocurcumins","authors":"Datendra Nath Tripathi (Data curation Formal analysis Investigation Methodology Validation Writing – original draft) , Saravanakumar Rajendran (Conceptualization Formal analysis Supervision Validation Writing – review & editing)","doi":"10.1080/00397911.2026.2613295","DOIUrl":"10.1080/00397911.2026.2613295","url":null,"abstract":"<div><div>A novel series of 4-arylidene tetrahydrocurcumins was synthesized from tetrahydrocurcumin and various aldehydes <em>via</em> Knoevenagel condensation in 81–90% yield. Aliphatic and aromatic aldehydes substituted with electron-donating and withdrawing groups were found to be effective substrates. The synthesized compounds were characterized using various spectroscopic techniques, and the structure of one of the derivatives was unambiguously established by single-crystal X-ray diffraction. These compounds were designed as a resemblance of combretastatin A4 scaffold integrated with curcumin. Our design and synthesis offer 4-arylidene tetrahydrocurcumin derivatives as a new class of compounds for evaluating bioactivity, with improved bioavailability, stability, and therapeutic efficacy.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"56 4","pages":"Pages 288-297"},"PeriodicalIF":1.8,"publicationDate":"2026-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146135695","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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