Pub Date : 2025-09-02Epub Date: 2025-08-18DOI: 10.1080/00397911.2025.2547391
Zhila Zharf Zaki (Conceptualization Investigation Methodology Writing – original draft) , Abbas Ali Esmaeili (Conceptualization Investigation Project administration Supervision Writing – review & editing)
A novel and efficient one-pot, three-component reaction was developed for the synthesis of 2-phenyl-4-((arylamino)methylene)-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one derivatives. The reaction proceeds via the condensation of 1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one, aniline derivatives, and trimethyl orthoformate under solvent-free conditions at 110 °C. This green protocol integrates multiple pharmacophores, offering potential for biological applications. Key advantages include operational simplicity, high yields (80%–92%), and the absence of catalysts and solvents. IR,1H,1³C, 19F NMR, mass spectrometry, and elemental analysis confirmed product structures.
{"title":"Efficient solvent- and catalyst-free one-pot synthesis of novel trifluoromethylated pyrazole derivatives","authors":"Zhila Zharf Zaki (Conceptualization Investigation Methodology Writing – original draft) , Abbas Ali Esmaeili (Conceptualization Investigation Project administration Supervision Writing – review & editing)","doi":"10.1080/00397911.2025.2547391","DOIUrl":"10.1080/00397911.2025.2547391","url":null,"abstract":"<div><div>A novel and efficient one-pot, three-component reaction was developed for the synthesis of 2-phenyl-4-((arylamino)methylene)-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one derivatives. The reaction proceeds via the condensation of 1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one, aniline derivatives, and trimethyl orthoformate under solvent-free conditions at 110 °C. This green protocol integrates multiple pharmacophores, offering potential for biological applications. Key advantages include operational simplicity, high yields (80%–92%), and the absence of catalysts and solvents. IR,<sup>1</sup>H,<sup>1</sup>³C, <sup>19</sup>F NMR, mass spectrometry, and elemental analysis confirmed product structures.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 17","pages":"Pages 1306-1314"},"PeriodicalIF":1.8,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048720","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 direct α‑iodination of α,β‑unsaturated aldehydes and ketones carried out without metal bases at room temperature in water, utilizing 1–7 equivalents of pyridine, is reported herein. High yields are obtained in the iodination of enals. Liquid and solid enones give good to moderate yields of the iodo products. Pyridine was the most effective catalyst among the secondary and tertiary amines studied. An absence of water reduces yields, while yields of (Z)-α-iodo-α,β-unsaturated aldehydes and ketones improved significantly with water as the solvent. The reactivities of the enals and, to a certain extent, enones such as (E)-4-phenylbut-3-en-2-one and mesityl oxide could be accounted for by the Mayr electrophilicity parameter (E). However, the lower reactivities of (E)-hex-4-en-3-one and chalcone were the outliers of their E parameter values prediction.
{"title":"The impact of water and pyridine on the α-iodination of α,β-unsaturated aldehydes and ketones","authors":"Phutawan Kittithanaluk (Investigation Methodology Visualization) , Pakorn Bovonsombat (Conceptualization Formal analysis Investigation Methodology Project administration Supervision Writing – original draft Writing – review & editing) , Eaint Thu Thu Mon (Investigation) , Fahsai Ploymanee (Investigation) , Nattawadee Srikamhom (Investigation) , Jing Ting We (Investigation) , Sirirat Choosakoonkriang (Investigation Resources) , Amber Hocks (Investigation)","doi":"10.1080/00397911.2025.2548310","DOIUrl":"10.1080/00397911.2025.2548310","url":null,"abstract":"<div><div>A direct α‑iodination of α,β‑unsaturated aldehydes and ketones carried out without metal bases at room temperature in water, utilizing 1–7 equivalents of pyridine, is reported herein. High yields are obtained in the iodination of enals. Liquid and solid enones give good to moderate yields of the iodo products. Pyridine was the most effective catalyst among the secondary and tertiary amines studied. An absence of water reduces yields, while yields of (<em>Z</em>)-α-iodo-α,β-unsaturated aldehydes and ketones improved significantly with water as the solvent. The reactivities of the enals and, to a certain extent, enones such as (<em>E</em>)-4-phenylbut-3-en-2-one and mesityl oxide could be accounted for by the Mayr electrophilicity parameter (<em>E</em>). However, the lower reactivities of (<em>E</em>)-hex-4-en-3-one and chalcone were the outliers of their <em>E</em> parameter values prediction.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 17","pages":"Pages 1315-1327"},"PeriodicalIF":1.8,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048722","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}
The catalyst plays an important role while the organic transformations are taking place. They enhance the reaction process by reducing the reaction time and provide highly efficient yields. Imidazole is one of the most common heterocyclic rings with several pharmaceutical and other significances. Trisubstituted imidazoles have various scientific and biological applications among the different types of imidazole rings. This review compiles the list of catalysts used in the synthesis of trisubstituted imidazoles using benzil, aldehydes and ammonium sources like ammonium acetate or urea. Hence, the study evaluates the efficiency of different catalytic systems in promoting the above-mentioned multicomponent reaction, leading to enhanced yields and reduced reaction times.
{"title":"Significant advances in catalytic strategies for the synthesis of trisubstituted imidazoles: a review","authors":"Saloni Mangal (Writing – original draft) , Salahuddin (Methodology Writing – review & editing) , Avijit Mazumder (Supervision) , Rajnish Kumar (Validation Visualization) , Sapna Rani (Data curation) , Mohamed Jawed Ahsan (Investigation) , Mohammad Shahar Yar (Conceptualization Formal analysis)","doi":"10.1080/00397911.2025.2505901","DOIUrl":"10.1080/00397911.2025.2505901","url":null,"abstract":"<div><div>The catalyst plays an important role while the organic transformations are taking place. They enhance the reaction process by reducing the reaction time and provide highly efficient yields. Imidazole is one of the most common heterocyclic rings with several pharmaceutical and other significances. Trisubstituted imidazoles have various scientific and biological applications among the different types of imidazole rings. This review compiles the list of catalysts used in the synthesis of trisubstituted imidazoles using benzil, aldehydes and ammonium sources like ammonium acetate or urea. Hence, the study evaluates the efficiency of different catalytic systems in promoting the above-mentioned multicomponent reaction, leading to enhanced yields and reduced reaction times.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 17","pages":"Pages 1281-1305"},"PeriodicalIF":1.8,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048719","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 : 2025-09-02Epub Date: 2025-08-19DOI: 10.1080/00397911.2025.2548309
Austin Carter (Data curation Methodology Writing – review & editing) , Daniel Wright (Data curation Methodology) , Giavanna Alongi (Data curation) , Christopher G. Hamaker (Data curation) , Shawn R. Hitchcock (Conceptualization Funding acquisition Methodology Project administration Supervision Writing – original draft) , Desmond H. Murray (Conceptualization Data curation Methodology Writing – review & editing)
The drug ataluren has been prepared using a one-pot synthesis of 1,2,4-oxadiazoles from amidoximes. This one-pot approach involves the in situ formation of O-acylamidoximes via the DMAP catalyzed O-acylation of amidoximes followed by cyclization in the presence of potassium hydroxide in DMSO. Using this methodology, a series of 17 examples of 1,2,4-oxadiazoles were formed in isolated yields up to 94% and the synthesis of ataluren was completed.
{"title":"Synthetic preparation of Ataluren via a one-pot synthesis of 1,2,4-oxadiazoles employing a DMAP catalyzed amidoxime O-acylation/cyclization pathway","authors":"Austin Carter (Data curation Methodology Writing – review & editing) , Daniel Wright (Data curation Methodology) , Giavanna Alongi (Data curation) , Christopher G. Hamaker (Data curation) , Shawn R. Hitchcock (Conceptualization Funding acquisition Methodology Project administration Supervision Writing – original draft) , Desmond H. Murray (Conceptualization Data curation Methodology Writing – review & editing)","doi":"10.1080/00397911.2025.2548309","DOIUrl":"10.1080/00397911.2025.2548309","url":null,"abstract":"<div><div>The drug ataluren has been prepared using a one-pot synthesis of 1,2,4-oxadiazoles from amidoximes. This one-pot approach involves the <em>in situ</em> formation of <em>O</em>-acylamidoximes via the DMAP catalyzed <em>O</em>-acylation of amidoximes followed by cyclization in the presence of potassium hydroxide in DMSO. Using this methodology, a series of 17 examples of 1,2,4-oxadiazoles were formed in isolated yields up to 94% and the synthesis of ataluren was completed.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 17","pages":"Pages 1328-1339"},"PeriodicalIF":1.8,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048721","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 : 2025-08-18Epub Date: 2025-07-24DOI: 10.1080/00397911.2025.2535655
Ajay J. Jani (Conceptualization Data curation Formal analysis Investigation Methodology Software Visualization Writing – original draft Writing – review & editing) , Jignesh H. Kamdar (Methodology Software Validation Visualization Writing – original draft) , Satishkumar D. Tala (Conceptualization Investigation Methodology Project administration Resources Supervision Writing – original draft Writing – review & editing)
A series of benzoxazole-piperazine hybrids (9a–n) has been synthesized via a multistep approach incorporating the Mitsunobu reaction. These compounds were obtained in good yields using cost-effective and readily available starting materials under mild reaction conditions. Structural characterization was performed using 1H NMR,13C NMR, LCMS, elemental analysis, and FTIR spectroscopy. The antimicrobial potential of 9a–n was assessed against bacterial strains Bacillus subtilis, Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli and fungal strains Aspergillus niger, and Candida albicans. Notably, compounds 9b, 9c and 9f exhibited potent antibacterial activity, comparable to chloramphenicol and gentamicin, and antifungal activity similar to nystatin. Molecular docking and dynamics simulations suggested that 9f inhibits E. coli DNA gyrase, forming a stable protein-ligand complex with strong binding interactions and low docking scores. Furthermore, in silico ADMET analysis indicated favorable pharmacokinetic properties with no significant toxicity concerns, highlighting their potential as promising antimicrobial agents.
{"title":"Design, synthesis, antimicrobial evaluation, in-silico molecular docking, and ADME-T evaluation of novel benzoxazole-piperazine hybrids with amide linkage","authors":"Ajay J. Jani (Conceptualization Data curation Formal analysis Investigation Methodology Software Visualization Writing – original draft Writing – review & editing) , Jignesh H. Kamdar (Methodology Software Validation Visualization Writing – original draft) , Satishkumar D. Tala (Conceptualization Investigation Methodology Project administration Resources Supervision Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2535655","DOIUrl":"10.1080/00397911.2025.2535655","url":null,"abstract":"<div><div>A series of benzoxazole-piperazine hybrids (<strong>9a–n</strong>) has been synthesized via a multistep approach incorporating the Mitsunobu reaction. These compounds were obtained in good yields using cost-effective and readily available starting materials under mild reaction conditions. Structural characterization was performed using <sup>1</sup>H NMR,<sup>13</sup>C NMR, LCMS, elemental analysis, and FTIR spectroscopy. The antimicrobial potential of <strong>9a–n</strong> was assessed against bacterial strains <em>Bacillus subtilis, Staphylococcus aureus, Pseudomonas aeruginosa,</em> and <em>Escherichia coli</em> and fungal strains <em>Aspergillus niger,</em> and <em>Candida albicans</em>. Notably, compounds <strong>9b</strong>, <strong>9c</strong> and <strong>9f</strong> exhibited potent antibacterial activity, comparable to chloramphenicol and gentamicin, and antifungal activity similar to nystatin. Molecular docking and dynamics simulations suggested that <strong>9f</strong> inhibits <em>E. coli</em> DNA gyrase, forming a stable protein-ligand complex with strong binding interactions and low docking scores. Furthermore, in silico ADMET analysis indicated favorable pharmacokinetic properties with no significant toxicity concerns, highlighting their potential as promising antimicrobial agents.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 16","pages":"Pages 1228-1246"},"PeriodicalIF":1.8,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144908835","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 : 2025-08-18Epub Date: 2025-08-21DOI: 10.1080/00397911.2025.2546610
Nkwane D. Thobejane (Writing – original draft) , Comfort M. Nkambule (Supervision Writing – review & editing)
An efficient synthesis of N-benzyl-3-hydroxypyrrolidines was achieved by the cyclodehydration of 4-amino-1,2-butanediols using thionyl chloride (SOCl2). The 4-amino-1,2-butanediols are readily accessible from aldehydes and ketones via homoallylic amines. While the cyclodehydration is non-stereoselective, the diastereomers are easily separated by column chromatography and the N-benzyl-3-pyrrolidinol enantiomers obtainable via Aspergillus Oryzae catalyzed transesterification.
{"title":"A simple synthesis of substituted N-benzyl-3-pyrrolidinols","authors":"Nkwane D. Thobejane (Writing – original draft) , Comfort M. Nkambule (Supervision Writing – review & editing)","doi":"10.1080/00397911.2025.2546610","DOIUrl":"10.1080/00397911.2025.2546610","url":null,"abstract":"<div><div>An efficient synthesis of <em>N</em>-benzyl-3-hydroxypyrrolidines was achieved by the cyclodehydration of 4-amino-1,2-butanediols using thionyl chloride (SOCl<sub>2</sub>). The 4-amino-1,2-butanediols are readily accessible from aldehydes and ketones via homoallylic amines. While the cyclodehydration is non-stereoselective, the diastereomers are easily separated by column chromatography and the <em>N</em>-benzyl-3-pyrrolidinol enantiomers obtainable via <em>Aspergillus Oryzae</em> catalyzed transesterification.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 16","pages":"Pages 1265-1279"},"PeriodicalIF":1.8,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144908836","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 : 2025-08-18Epub Date: 2025-05-14DOI: 10.1080/00397911.2025.2503341
Hafiza Noor Fatima (Data curation Investigation Software Writing – original draft) , Matloob Ahmad (Conceptualization Resources Supervision Writing – review & editing) , Muhammad Shahid Nazir (Data curation Methodology Visualization) , Sumayya Akram (Formal analysis Investigation Visualization) , Sana Aslam (Conceptualization Writing – original draft Writing – review & editing)
Heterocyclic chemistry has appeared as a significant part of organic chemistry due to their distinct physiological characteristics. Many biologically active nitrogen-containing heterocyclic compounds are found as a main backbone in structures of the complex compounds. Pyrrolidine is a saturated five-membered heterocyclic moiety containing secondary amine in its ring structure. Pyrrolidine derivatives occur in many plants as natural alkaloids. Pyrrolidine derivatives exhibit diverse biological activities, including anti-bacterial, anti-cancer, anti-diabetic, anti-fungal, and acetylcholinesterase (AChE) inhibitory activities. Over the past years many bioactive compounds bearing pyrrolidine moiety have been synthesized through cycloaddition reactions by using azomethine ylide and isatin as the primary reactants. Because of its multiple uses, many researchers are in efforts to produce pyrrolidine derivatives via different ways, which are helpful in therapeutics. The aim of this review is to critically discuss the synthesis of pyrrolidine and their derivatives via multicomponent approach by using different processes like ultrasound irradiation, microwave heating, catalyst-based reactions, catalyst-free, salts and azomethine ylide formation during the years 2018–2024.
{"title":"Recent synthetic methodologies for pyrrolidine derivatives through multicomponent reactions","authors":"Hafiza Noor Fatima (Data curation Investigation Software Writing – original draft) , Matloob Ahmad (Conceptualization Resources Supervision Writing – review & editing) , Muhammad Shahid Nazir (Data curation Methodology Visualization) , Sumayya Akram (Formal analysis Investigation Visualization) , Sana Aslam (Conceptualization Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2503341","DOIUrl":"10.1080/00397911.2025.2503341","url":null,"abstract":"<div><div>Heterocyclic chemistry has appeared as a significant part of organic chemistry due to their distinct physiological characteristics. Many biologically active nitrogen-containing heterocyclic compounds are found as a main backbone in structures of the complex compounds. Pyrrolidine is a saturated five-membered heterocyclic moiety containing secondary amine in its ring structure. Pyrrolidine derivatives occur in many plants as natural alkaloids. Pyrrolidine derivatives exhibit diverse biological activities, including anti-bacterial, anti-cancer, anti-diabetic, anti-fungal, and acetylcholinesterase (AChE) inhibitory activities. Over the past years many bioactive compounds bearing pyrrolidine moiety have been synthesized through cycloaddition reactions by using azomethine ylide and isatin as the primary reactants. Because of its multiple uses, many researchers are in efforts to produce pyrrolidine derivatives <em>via</em> different ways, which are helpful in therapeutics. The aim of this review is to critically discuss the synthesis of pyrrolidine and their derivatives <em>via</em> multicomponent approach by using different processes like ultrasound irradiation, microwave heating, catalyst-based reactions, catalyst-free, salts and azomethine ylide formation during the years 2018–2024.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 16","pages":"Pages 1201-1227"},"PeriodicalIF":1.8,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144908837","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 : 2025-08-18Epub Date: 2025-07-31DOI: 10.1080/00397911.2025.2541185
Amol R. Shelar (Methodology) , Kisan M. Gadave (Resources Supervision Validation) , Ramdas A. Pawar (Supervision Validation) , Madhuri S. Pansare (Methodology) , Ajit P. Ingale (Investigation Methodology Supervision Writing – original draft Writing – review & editing)
A straightforward, one-pot, solvent-free, and environmentally friendly method for synthesizing 4,6-Diarylpyrimidin-2(1H)-ones through a Biginelli-type reaction is presented, utilizing sulfated tungstate as a catalyst. This approach offers enhanced product yields while employing a cost-effective and easily accessible catalyst. The simplicity of the experimental setup makes it an effective and stress-free strategy for producing 4,6-diarylpyrimidin-2-(1H)-ones. The catalyst demonstrates remarkable activity and can be reused, further contributing to the method’s efficiency.
{"title":"Sulfated tungstate: an eco-friendly and reusable catalyst for efficient one-pot synthesis of 4,6-diarylpyrimidin-2(1H)-ones in solvent-free conditions","authors":"Amol R. Shelar (Methodology) , Kisan M. Gadave (Resources Supervision Validation) , Ramdas A. Pawar (Supervision Validation) , Madhuri S. Pansare (Methodology) , Ajit P. Ingale (Investigation Methodology Supervision Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2541185","DOIUrl":"10.1080/00397911.2025.2541185","url":null,"abstract":"<div><div>A straightforward, one-pot, solvent-free, and environmentally friendly method for synthesizing 4,6-Diarylpyrimidin-2(1<em>H</em>)-ones through a Biginelli-type reaction is presented, utilizing sulfated tungstate as a catalyst. This approach offers enhanced product yields while employing a cost-effective and easily accessible catalyst. The simplicity of the experimental setup makes it an effective and stress-free strategy for producing 4,6-diarylpyrimidin-2-(1<em>H</em>)-ones. The catalyst demonstrates remarkable activity and can be reused, further contributing to the method’s efficiency.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 16","pages":"Pages 1247-1256"},"PeriodicalIF":1.8,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144908838","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 this study, 2-amino-5-(4-chlorophenyl)furan/thiophene were synthesized via Paal-Knorr and Gewald cyclization strategies. A series of novel furan/thiophene selenocyanate derivatives were constructed by introducing selenocyanate groups with varying chain lengths through amide bonds. All compounds were structurally characterized using NMR and HR-MS analyses. MTT assay for antitumor activity revealed that several compounds exhibited superior efficacy compared to cisplatin. Notably, furan selenocyanate 5c showed significant inhibitory activity against HepG-2 cells (IC50 = 8.64 ± 0.94 μM), while thiophene selenocyanate 11d demonstrated remarkable inhibition against HeLa and MCF-7 cells with IC50 values of 6.39 and 6.77 μM, respectively. Structure-activity relationship (SAR) analysis indicated that the carbon chain length significantly influenced antitumor activity, with the C8-chain thiophene selenocyanate derivative 11d exhibiting optimal selectivity for HeLa and MCF-7 cells. This study provides important references for development of novel selenium-containing antitumor drugs.
{"title":"Synthesis and antitumor activity of selenocyanate derivatives based on 2-amino-5-(4-chlorophenyl)furan/thiophene scaffolds","authors":"Maixia Liu (Data curation Formal analysis Investigation Methodology) , Lijie Che (Methodology Resources Validation) , Xiyan Tang (Investigation Supervision) , Chunfang Gan (Data curation Software) , Yanmin Huang (Funding acquisition Project administration Writing – review & editing) , Zhiping Liu (Investigation Supervision Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2545850","DOIUrl":"10.1080/00397911.2025.2545850","url":null,"abstract":"<div><div>In this study, 2-amino-5-(4-chlorophenyl)furan/thiophene were synthesized <em>via</em> Paal-Knorr and Gewald cyclization strategies. A series of novel furan/thiophene selenocyanate derivatives were constructed by introducing selenocyanate groups with varying chain lengths through amide bonds. All compounds were structurally characterized using NMR and HR-MS analyses. MTT assay for antitumor activity revealed that several compounds exhibited superior efficacy compared to cisplatin. Notably, furan selenocyanate <strong>5c</strong> showed significant inhibitory activity against HepG-2 cells (IC<sub>50</sub> = 8.64 ± 0.94 μM), while thiophene selenocyanate <strong>11d</strong> demonstrated remarkable inhibition against HeLa and MCF-7 cells with IC<sub>50</sub> values of 6.39 and 6.77 μM, respectively. Structure-activity relationship (SAR) analysis indicated that the carbon chain length significantly influenced antitumor activity, with the C<sub>8</sub>-chain thiophene selenocyanate derivative <strong>11d</strong> exhibiting optimal selectivity for HeLa and MCF-7 cells. This study provides important references for development of novel selenium-containing antitumor drugs.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 16","pages":"Pages 1257-1264"},"PeriodicalIF":1.8,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144908834","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}
Striatal Enriched protein tyrosine Phosphatase (STEP61) plays a crucial role in motor reflexes, cognition, and Alzheimer’s pathology. Despite its significance, STEP61’s exploration via in silico methods has been limited.
Method
We identified STEP61’s binding site using induced fit docking, screened a peptidomimetic library of 32,800 compounds for potential inhibitors, and synthesized top hits. Docking studies emphasized binding requirements within STEP61’s catalytic domain and WPD loop. Molecular dynamics simulations highlighted the importance of hydrophobic contacts and hydrogen bonding in complex stability.
Results
High Throughput Screening yielded promising docking scores (-11.4 to −3.8), with XP docking showing scores ranging from −6.6 to −7.6, indicating potential interaction and activity. Cα residues maintained RMSD values below 2 Å throughout simulations, ensuring structural stability. These findings lay the groundwork for developing novel STEP61 inhibitors, offering promising avenues for Alzheimer’s disease therapeutics.
{"title":"Design of peptidomimetic library: In-silico screening, molecular docking, synthesis and characterization of hits for STEP61","authors":"Pritam V. Bagwe (Conceptualization Data curation Methodology Software Writing – original draft Writing – review & editing) , Radni D. Deshpande (Data curation Visualization) , Gabor Juhasz (Supervision Visualization) , Sadhana Sathaye (Funding acquisition Investigation Visualization) , Shreerang V. Joshi (Project administration Resources Supervision Validation Visualization Writing – review & editing)","doi":"10.1080/00397911.2025.2526018","DOIUrl":"10.1080/00397911.2025.2526018","url":null,"abstract":"<div><h3>Introduction</h3><div>Striatal Enriched protein tyrosine Phosphatase (STEP61) plays a crucial role in motor reflexes, cognition, and Alzheimer’s pathology. Despite its significance, STEP61’s exploration via in silico methods has been limited.</div></div><div><h3>Method</h3><div>We identified STEP61’s binding site using induced fit docking, screened a peptidomimetic library of 32,800 compounds for potential inhibitors, and synthesized top hits. Docking studies emphasized binding requirements within STEP61’s catalytic domain and WPD loop. Molecular dynamics simulations highlighted the importance of hydrophobic contacts and hydrogen bonding in complex stability.</div></div><div><h3>Results</h3><div>High Throughput Screening yielded promising docking scores (-11.4 to −3.8), with XP docking showing scores ranging from −6.6 to −7.6, indicating potential interaction and activity. Cα residues maintained RMSD values below 2 Å throughout simulations, ensuring structural stability. These findings lay the groundwork for developing novel STEP61 inhibitors, offering promising avenues for Alzheimer’s disease therapeutics.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 14","pages":"Pages 1072-1088"},"PeriodicalIF":1.8,"publicationDate":"2025-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144655333","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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