Pub Date : 2025-06-24DOI: 10.1080/00397911.2025.2521830
Wafa A. Bawazir (Investigation Methodology) , Tarik E. Ali (Conceptualization Funding acquisition Supervision Writing – original draft Writing – review & editing) , Mohammed A. Assiri (Formal analysis Software) , Serag E. I. Elbehairi (Methodology Validation) , Mohamed Abdel-Megid (Visualization Writing – review & editing)
An innovative and efficient one-pot approach has been established for the synthesis of 3-{1-([5-amino-7-(arylamino)-6-cyano-7H-[1,4]oxaphosphinino[2,3-d]thiazol-2-yl]hydrazinyl)ethylidene}-2H-chromen-2-one (2a–h) using aromatic amine, phosphorus trichloride, malononitrile, and 3-{[1-(4-oxo-5H-thiazol-2-yl)hydrazinyl]ethylidene}-2H-chromen-2-one with triethylamine. This method is efficient and straightforward, offering high yields, easy product isolation, and minimal waste. The cytotoxic properties against PC3, LS174T, and HepG2 cancer cell lines revealed promising activity for compounds 2d and 2e (fluorine and chlorine substitutions), comparable to Tivozanib. Flow cytometry indicated that these bioactive compounds significantly increased late apoptosis and halted cell cycle progression at S and G2 phases, demonstrating their potential as anticancer agents. Both compounds 2d and 2e were then subjected to a molecular docking experiment to see how they bind with VEGFR-2 receptor.
{"title":"A one-pot route to novel 3-{1-([5-amino-7-(arylamino)-6-cyano-7H-[1,4]oxaphosphinino[2,3-d]thiazol-2-yl]hydrazinyl)ethylidene}-2H-chromen-2-one: Synthesis, cytotoxic activities, apoptosis, and cell cycle studies","authors":"Wafa A. Bawazir (Investigation Methodology) , Tarik E. Ali (Conceptualization Funding acquisition Supervision Writing – original draft Writing – review & editing) , Mohammed A. Assiri (Formal analysis Software) , Serag E. I. Elbehairi (Methodology Validation) , Mohamed Abdel-Megid (Visualization Writing – review & editing)","doi":"10.1080/00397911.2025.2521830","DOIUrl":"10.1080/00397911.2025.2521830","url":null,"abstract":"<div><div>An innovative and efficient one-pot approach has been established for the synthesis of 3-{1-([5-amino-7-(arylamino)-6-cyano-7<em>H</em>-[1,4]oxaphosphinino[2,3-d]thiazol-2-yl]hydrazinyl)ethylidene}-2<em>H</em>-chromen-2-one (<strong>2a–h</strong>) using aromatic amine, phosphorus trichloride, malononitrile, and 3-{[1-(4-oxo-5<em>H</em>-thiazol-2-yl)hydrazinyl]ethylidene}-2<em>H</em>-chromen-2-one with triethylamine. This method is efficient and straightforward, offering high yields, easy product isolation, and minimal waste. The cytotoxic properties against PC3, LS174T, and HepG2 cancer cell lines revealed promising activity for compounds <strong>2d</strong> and <strong>2e</strong> (fluorine and chlorine substitutions), comparable to Tivozanib. Flow cytometry indicated that these bioactive compounds significantly increased late apoptosis and halted cell cycle progression at S and G2 phases, demonstrating their potential as anticancer agents. Both compounds <strong>2d</strong> and <strong>2e</strong> were then subjected to a molecular docking experiment to see how they bind with VEGFR-2 receptor.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 13","pages":"Pages 1007-1028"},"PeriodicalIF":1.8,"publicationDate":"2025-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144510864","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 : 2025-06-21DOI: 10.1080/00397911.2025.2521701
Nikita Shinde (Methodology Project administration Writing – original draft) , Lina Jadhav (Investigation Validation) , Mayuri B. Thorat (Writing – review & editing), Krantisagar More (Resources Supervision) , Yatin U. Gadkari (Conceptualization Methodology Project administration Writing – review & editing)
The present study outlines an efficient and straightforward approach for synthesizing amino-chromenes via multicomponent reaction from aldehyde, dimedone and malononitrile using aqueous sodium hypochlorite (10–13%) (bleach) as a catalyst under neat conditions. Sodium hypochlorite was identified as an effective catalyst, facilitating the reaction with minimal catalyst loading and yielding high product output. The developed protocol demonstrates significant improvements, featuring simplified work-up, reduced energy consumption, shortened reaction times, and an eco-friendly profile with favorable E-factors (3.5), Eco-scale scores (97), and Process mass intensity (6.3).
{"title":"A sustainable approach for one-pot, multicomponent synthesis of 2-amino-4H-chromenes using bleach","authors":"Nikita Shinde (Methodology Project administration Writing – original draft) , Lina Jadhav (Investigation Validation) , Mayuri B. Thorat (Writing – review & editing), Krantisagar More (Resources Supervision) , Yatin U. Gadkari (Conceptualization Methodology Project administration Writing – review & editing)","doi":"10.1080/00397911.2025.2521701","DOIUrl":"10.1080/00397911.2025.2521701","url":null,"abstract":"<div><div>The present study outlines an efficient and straightforward approach for synthesizing amino-chromenes via multicomponent reaction from aldehyde, dimedone and malononitrile using aqueous sodium hypochlorite (10–13%) (bleach) as a catalyst under neat conditions. Sodium hypochlorite was identified as an effective catalyst, facilitating the reaction with minimal catalyst loading and yielding high product output. The developed protocol demonstrates significant improvements, featuring simplified work-up, reduced energy consumption, shortened reaction times, and an eco-friendly profile with favorable E-factors (3.5), Eco-scale scores (97), and Process mass intensity (6.3).</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 13","pages":"Pages 996-1006"},"PeriodicalIF":1.8,"publicationDate":"2025-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144510866","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 method for amide synthesis from aldimines using an aryloyl peroxide/DMSO system has been developed. The acyl groups of the resulting amides are derived from the aryloyl peroxide, while the N-containing motifs originate from the aldimines. Mechanistic investigations reveal that the aryloyl peroxide reacts with DMSO to form an anhydride, which is partially hydrolyzed to produce a carboxylic acid. This acid catalyzes the hydrolysis of aldimines to controllably release amines, which then react with the anhydride to selectively form amides. This approach offers controlled reaction and product selectivity, avoiding byproduct formation from direct arylamine oxidation by BPO. This mild one-pot method not only provides a route for the synthesis of amides from aldimines, but also demonstrates the feasibility of synthesizing amides from amines, thereby expanding the scope of organic synthesis strategies.
{"title":"One-pot synthesis of amides from aryloyl peroxides and aldimines in dimethyl sulfoxide","authors":"Xinyun Zhao (Funding acquisition Writing – review & editing) , Dongli Li (Data curation) , Tsunghsueh Wu (Formal analysis) , Xiaoqiang Hu (Methodology) , Xi Chen (Formal analysis) , Lamei Wu (Formal analysis) , Zhan Zhang (Formal analysis)","doi":"10.1080/00397911.2025.2508211","DOIUrl":"10.1080/00397911.2025.2508211","url":null,"abstract":"<div><div>A novel method for amide synthesis from aldimines using an aryloyl peroxide/DMSO system has been developed. The acyl groups of the resulting amides are derived from the aryloyl peroxide, while the <em>N</em>-containing motifs originate from the aldimines. Mechanistic investigations reveal that the aryloyl peroxide reacts with DMSO to form an anhydride, which is partially hydrolyzed to produce a carboxylic acid. This acid catalyzes the hydrolysis of aldimines to controllably release amines, which then react with the anhydride to selectively form amides. This approach offers controlled reaction and product selectivity, avoiding byproduct formation from direct arylamine oxidation by BPO. This mild one-pot method not only provides a route for the synthesis of amides from aldimines, but also demonstrates the feasibility of synthesizing amides from amines, thereby expanding the scope of organic synthesis strategies.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 12","pages":"Pages 901-915"},"PeriodicalIF":1.8,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144510959","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 : 2025-06-18DOI: 10.1080/00397911.2025.2505905
L. Boughani (Conceptualization Investigation Methodology Validation Visualization Writing – original draft Writing – review & editing) , D. Bouchouk (Methodology Visualization) , T. Abbaz (Methodology Visualization) , A. Bendjeddou (Methodology Visualization) , Z. Regainia (Conceptualization Methodology Supervision)
A new series of C2-symmetric bisoxazolidines containing a sulfonamide moiety has been prepared. The synthesis started by reducing the bisaminoester sulfonamides derived from natural amino acids by lithium aluminum hydride (LiAlH4). The bisaminoalcohol sulfonamides resulting from the reduction react with aliphatic and aromatic aldehydes in an acidic medium to form heterocyclic compounds. The obtained N,N’-sulfonyl-bisoxazolidines are isolated in good yields. Bisoxazolidines derived from paraformaldehyde crystallize in ether, yielding their bridged [4.4.1] bicyclic isomers. The structures of synthesized compounds have been explored and validated using standard spectroscopic techniques, such as NMR, IR, and mass spectrometry.
{"title":"Convenient synthesis of novel C2-symmetric bisoxazolidine derivatives containing a sulfonamide moiety","authors":"L. Boughani (Conceptualization Investigation Methodology Validation Visualization Writing – original draft Writing – review & editing) , D. Bouchouk (Methodology Visualization) , T. Abbaz (Methodology Visualization) , A. Bendjeddou (Methodology Visualization) , Z. Regainia (Conceptualization Methodology Supervision)","doi":"10.1080/00397911.2025.2505905","DOIUrl":"10.1080/00397911.2025.2505905","url":null,"abstract":"<div><div>A new series of C<sub>2</sub>-symmetric bisoxazolidines containing a sulfonamide moiety has been prepared. The synthesis started by reducing the bisaminoester sulfonamides derived from natural amino acids by lithium aluminum hydride (LiAlH<sub>4</sub>). The bisaminoalcohol sulfonamides resulting from the reduction react with aliphatic and aromatic aldehydes in an acidic medium to form heterocyclic compounds. The obtained <em>N,N’-</em>sulfonyl-bisoxazolidines are isolated in good yields. Bisoxazolidines derived from paraformaldehyde crystallize in ether, yielding their bridged [4.4.1] bicyclic isomers. The structures of synthesized compounds have been explored and validated using standard spectroscopic techniques, such as NMR, IR, and mass spectrometry.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 12","pages":"Pages 892-900"},"PeriodicalIF":1.8,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144510962","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 : 2025-06-18DOI: 10.1080/00397911.2025.2511819
Sayed K. Ramadan (Conceptualization Data curation Investigation Methodology Validation Visualization Writing – original draft Writing – review & editing) , Amira T. Ali (Investigation Methodology Writing – original draft Writing – review & editing) , Sobhi M. Gomha (Data curation Investigation Supervision Writing – review & editing) , Eman A. E. El-Helw (Conceptualization Investigation Methodology Writing – original draft Writing – review & editing)
Breast and liver cancers are the most common causes of cancer death and finding new anticancer agents is critical. Inspired by their antitumor potential, thiazole and thiazolidinone derivatives bearing a pyrazole core were prepared from thiosemicarbazone unit through reactions with carbon electrophiles. Compared to doxorubicin and roscovitine, in vitro, antiproliferative activity against MCF7 and HepG2 cancer cell panels implied the most potency of 2,4-dihydroxybenzylidene- and 4-dimethylaminobenzylidene-thiazolidinone, being capable of powerful interactions with protein receptors. In density functional theory simulation, the dimethylaminobenzylidine-thiazolidine exhibited the lowest energy gap and highest softness values. Consistently, the superlative docking score toward CDK2 protein (PDB ID: 2A4L) was shown by later compound through hydrogen bonding, arene-hydrogen, and arene-cation interactions with key nucleobases and amino acids of CDK2 protein which might be potential CDK2 inhibitor. According to ADME study, these compounds showed good lipophilicity and oral bioavailability. This work may contribute to the advancing of new potent antiproliferative agents.
{"title":"Design, synthesis, and in silico studies of pyrazolyl-thiazole and thiazolidinone hybrids as potential antiproliferative agents","authors":"Sayed K. Ramadan (Conceptualization Data curation Investigation Methodology Validation Visualization Writing – original draft Writing – review & editing) , Amira T. Ali (Investigation Methodology Writing – original draft Writing – review & editing) , Sobhi M. Gomha (Data curation Investigation Supervision Writing – review & editing) , Eman A. E. El-Helw (Conceptualization Investigation Methodology Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2511819","DOIUrl":"10.1080/00397911.2025.2511819","url":null,"abstract":"<div><div>Breast and liver cancers are the most common causes of cancer death and finding new anticancer agents is critical. Inspired by their antitumor potential, thiazole and thiazolidinone derivatives bearing a pyrazole core were prepared from thiosemicarbazone unit through reactions with carbon electrophiles. Compared to doxorubicin and roscovitine, <em>in vitro</em>, antiproliferative activity against MCF7 and HepG2 cancer cell panels implied the most potency of 2,4-dihydroxybenzylidene- and 4-dimethylaminobenzylidene-thiazolidinone, being capable of powerful interactions with protein receptors. In density functional theory simulation, the dimethylaminobenzylidine-thiazolidine exhibited the lowest energy gap and highest softness values. Consistently, the superlative docking score toward CDK2 protein (PDB ID: 2A4L) was shown by later compound through hydrogen bonding, arene-hydrogen, and arene-cation interactions with key nucleobases and amino acids of CDK2 protein which might be potential CDK2 inhibitor. According to ADME study, these compounds showed good lipophilicity and oral bioavailability. This work may contribute to the advancing of new potent antiproliferative agents.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 12","pages":"Pages 931-951"},"PeriodicalIF":1.8,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144510960","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 face index is a topological descriptor that provides insights into the molecular architecture of PAHs, which are significant due to their environmental persistence and potential health impacts. By analyzing the graphical representations of these compounds, we derive mathematical expressions for their face indices, highlighting the relationships between their structural features and chemical properties. Our findings contribute to a deeper understanding of how molecular structure influences the behavior of PAHs, paving the way for further research in both theoretical and applied chemistry contexts. This study not only enhances the characterization of complex PAH structures but also serves as a foundation for future investigations into their environmental and toxicological implications. We focus on Hexa-cata-hexa-benzocoronene and Dodeca-benzo-circumcoronene and derive analytical expressions for their face index based on their molecular graphs.
{"title":"Face index computation of certain polycyclic aromatic hydrocarbons","authors":"Shriya Negi (Conceptualization Investigation Validation Writing – original draft Writing – review & editing) , Jai Parkash (Investigation Methodology Writing – review & editing) , Vijay Kumar Bhat (Conceptualization Investigation Supervision Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2509114","DOIUrl":"10.1080/00397911.2025.2509114","url":null,"abstract":"<div><div>The face index is a topological descriptor that provides insights into the molecular architecture of PAHs, which are significant due to their environmental persistence and potential health impacts. By analyzing the graphical representations of these compounds, we derive mathematical expressions for their face indices, highlighting the relationships between their structural features and chemical properties. Our findings contribute to a deeper understanding of how molecular structure influences the behavior of PAHs, paving the way for further research in both theoretical and applied chemistry contexts. This study not only enhances the characterization of complex PAH structures but also serves as a foundation for future investigations into their environmental and toxicological implications. We focus on Hexa-cata-hexa-benzocoronene and Dodeca-benzo-circumcoronene and derive analytical expressions for their face index based on their molecular graphs.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 12","pages":"Pages 916-930"},"PeriodicalIF":1.8,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144510958","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 : 2025-06-18DOI: 10.1080/00397911.2025.2487080
Glanish Jude Martis (Software Writing – original draft) , Sneha O (Writing – original draft) , Rajkumar Bhat D (Writing – review & editing) , Praveen S. Mugali (Writing – review & editing)
Pyrimidine-containing organic compounds have been widely studied and are highly important. With this intent, a genuine attempt has been made to reflect the various synthetic developments and biological perspectives of pyrimidine-containing analogues leading to drug design and discovery. The synthetic strategies give the in-depth route of generating pyrimidines. The biology includes antiviral, antioxidant, anti-inflammatory, and anticancer, activities. By going in depth with all the studies made by various researchers, the scope of pyrimidine is vast. The extensive properties exhibited by various compounds reveal the ability of pyrimidines to act as potent drugs in future. Most of the compounds showed better performance than the standard drugs available. Therefore, the need for reviewing all the recent advances in pyrimidine-related chemistry was necessary and it will aid to boost the research both in academic and pharma sector.
{"title":"Recent advancements of pyrimidine chemistry thriving deeper into drug discovery","authors":"Glanish Jude Martis (Software Writing – original draft) , Sneha O (Writing – original draft) , Rajkumar Bhat D (Writing – review & editing) , Praveen S. Mugali (Writing – review & editing)","doi":"10.1080/00397911.2025.2487080","DOIUrl":"10.1080/00397911.2025.2487080","url":null,"abstract":"<div><div>Pyrimidine-containing organic compounds have been widely studied and are highly important. With this intent, a genuine attempt has been made to reflect the various synthetic developments and biological perspectives of pyrimidine-containing analogues leading to drug design and discovery. The synthetic strategies give the in-depth route of generating pyrimidines. The biology includes antiviral, antioxidant, anti-inflammatory, and anticancer, activities. By going in depth with all the studies made by various researchers, the scope of pyrimidine is vast. The extensive properties exhibited by various compounds reveal the ability of pyrimidines to act as potent drugs in future. Most of the compounds showed better performance than the standard drugs available. Therefore, the need for reviewing all the recent advances in pyrimidine-related chemistry was necessary and it will aid to boost the research both in academic and pharma sector.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 12","pages":"Pages 863-891"},"PeriodicalIF":1.8,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144510961","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 research, the facile pyrazole-sulfone hybridization via Ag2CO3-catalyzed aza-Michael addition of pyrazoles to vinyl sulfones has been developed. The methodology offers an efficient and regioselective synthesis of N-sulfonylethylated pyrazoles as an important subset of pyrazole-sulfone hybrids and it featured mild reaction conditions, excellent yields and high regioselectivity (reaching the highest N1/N2 ratio of 25:1).
{"title":"Pyrazole-Sulfone hybridization via silver-catalyzed regioselective aza-Michael addition of pyrazoles to vinyl sulfones: Synthesis of N-sulfonylethylated pyrazoles","authors":"Xue Zhang (Conceptualization Writing – original draft Writing – review & editing) , Yang Song (Data curation Formal analysis) , Yutong Peng (Investigation) , Dakang Zhu (Methodology) , Wanxin Zhang (Investigation) , Haifeng Yu (Conceptualization) , Xiaobo Zhao (Project administration)","doi":"10.1080/00397911.2025.2518387","DOIUrl":"10.1080/00397911.2025.2518387","url":null,"abstract":"<div><div>In this research, the facile pyrazole-sulfone hybridization via Ag<sub>2</sub>CO<sub>3</sub>-catalyzed aza-Michael addition of pyrazoles to vinyl sulfones has been developed. The methodology offers an efficient and regioselective synthesis of <em>N</em>-sulfonylethylated pyrazoles as an important subset of pyrazole-sulfone hybrids and it featured mild reaction conditions, excellent yields and high regioselectivity (reaching the highest <em>N</em><sup>1</sup>/<em>N</em><sup>2</sup> ratio of 25:1).</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 13","pages":"Pages 985-995"},"PeriodicalIF":1.8,"publicationDate":"2025-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144510867","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 : 2025-05-16DOI: 10.1080/00397911.2025.2505903
Wenpei Zhang (Data curation Investigation Methodology Writing – original draft Writing – review & editing) , Xinyue Pan (Investigation) , Jie He (Supervision) , Yirong Lin (Visualization) , Fengyang Zhang (Validation) , Li Guo (Validation) , Jieqing Liu (Conceptualization Funding acquisition Project administration Resources)
Erianin, a natural biphenyl compound found in Dendrobium, exhibits significant pharmacological effects, including anti-tumor and anti-inflammatory properties. Here, we report a novel and efficient three-step synthetic route for Erianin, utilizing homovanillic acid and 3,4,5-trimethoxybenzaldehyde as starting materials. Our method integrates hydroxyaldehyde condensation, microwave-assisted decarboxylation, and mild double bond reduction, achieving a total yield of 45.3%—a 47.7% improvement over prior approaches. The developed protocol provides a cost-effective and scalable approach to access Erianin, offering significant potential for therapeutic research and drug development.
{"title":"A novel strategy for the efficient synthesis of Erianin","authors":"Wenpei Zhang (Data curation Investigation Methodology Writing – original draft Writing – review & editing) , Xinyue Pan (Investigation) , Jie He (Supervision) , Yirong Lin (Visualization) , Fengyang Zhang (Validation) , Li Guo (Validation) , Jieqing Liu (Conceptualization Funding acquisition Project administration Resources)","doi":"10.1080/00397911.2025.2505903","DOIUrl":"10.1080/00397911.2025.2505903","url":null,"abstract":"<div><div>Erianin, a natural biphenyl compound found in Dendrobium, exhibits significant pharmacological effects, including anti-tumor and anti-inflammatory properties. Here, we report a novel and efficient three-step synthetic route for Erianin, utilizing homovanillic acid and 3,4,5-trimethoxybenzaldehyde as starting materials. Our method integrates hydroxyaldehyde condensation, microwave-assisted decarboxylation, and mild double bond reduction, achieving a total yield of 45.3%—a 47.7% improvement over prior approaches. The developed protocol provides a cost-effective and scalable approach to access Erianin, offering significant potential for therapeutic research and drug development.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 11","pages":"Pages 852-861"},"PeriodicalIF":1.8,"publicationDate":"2025-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144124337","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 : 2025-05-14DOI: 10.1080/00397911.2025.2501761
Keerthana L. (Formal analysis Methodology Writing – original draft) , Sharulatha V. (Supervision Writing – review & editing) , Rajan V. K. (Formal analysis Software)
The synthesis and characterization of Schiff bases based on 3, 4, 5-trimethoxy benzaldehyde and 2-aminopyridine derivatives 3a to 3i were done using FT-IR, 1H NMR and 13CNMR and Mass spectral studies. The antibacterial properties of the compounds were assessed with two gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus, and two gram-negative bacteria, Pseudomonas aeruginosa and Escherichia coli. Compounds 3h and 3j exhibited greater activity than standard against S. aureus and E. coli. Molecular docking, cited several type interactions among the target proteins and Schiff base compounds including H-bond, Alkyl, Van der Waals and π–alkyl interactions. DFT calculations confirmed that the cis form of all the synthesized compounds were stable more than the trans form. Global reactive descriptors calculation indicated that the maximum reactivity of compound 3f present in IV quadrant while all the other compounds were present in I and III quadrant indicated the good reactivity rate compared to reference.
{"title":"2-Aminopyridine schiff base compounds: Synthesis, characterization, anti-bacterial properties, molecular docking and computational studies","authors":"Keerthana L. (Formal analysis Methodology Writing – original draft) , Sharulatha V. (Supervision Writing – review & editing) , Rajan V. K. (Formal analysis Software)","doi":"10.1080/00397911.2025.2501761","DOIUrl":"10.1080/00397911.2025.2501761","url":null,"abstract":"<div><div>The synthesis and characterization of Schiff bases based on 3, 4, 5-trimethoxy benzaldehyde and 2-aminopyridine derivatives 3a to 3i were done using FT-IR, <sup>1</sup>H NMR and <sup>13</sup>CNMR and Mass spectral studies. The antibacterial properties of the compounds were assessed with two gram-positive bacteria, <em>Bacillus subtilis</em> and <em>Staphylococcus aureus</em>, and two gram-negative bacteria, <em>Pseudomonas aeruginosa</em> and <em>Escherichia coli.</em> Compounds <strong>3h</strong> and <strong>3j</strong> exhibited greater activity than standard against <em>S. aureus</em> and <em>E. coli.</em> Molecular docking, cited several type interactions among the target proteins and Schiff base compounds including H-bond, Alkyl, Van der Waals and π–alkyl interactions. DFT calculations confirmed that the <em>cis</em> form of all the synthesized compounds were stable more than the <em>trans</em> form. Global reactive descriptors calculation indicated that the maximum reactivity of compound <strong>3f</strong> present in IV quadrant while all the other compounds were present in I and III quadrant indicated the good reactivity rate compared to reference.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 11","pages":"Pages 825-851"},"PeriodicalIF":1.8,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144124338","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}
扫码关注我们
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号