Kübra Uysal , Muhammet Yıldırım , Hamza Karakuş , Arzu Yıldırım
{"title":"A simple, facile and greener route to thiazolo[3,2-c]pyrimidinones in semi-aqueous medium and their antibacterial properties","authors":"Kübra Uysal , Muhammet Yıldırım , Hamza Karakuş , Arzu Yıldırım","doi":"10.1080/00397911.2024.2314597","DOIUrl":"https://doi.org/10.1080/00397911.2024.2314597","url":null,"abstract":"<div><p>By using easily accessible heterocyclic enamines, acetaldehyde (or formaldehyde) and primary amines as suitable precursors, a water-assisted three-component synthesis of new 3-oxothiazolo[3,2-<em>c</em>]pyridimines has been efficiently achieved in mild and semi-aqueous medium. All the cyclization reactions under optimized and catalyst-free conditions furnish the target compounds in 40–100% yields. Although cyclizations with arylamines in the presence of formaldehyde yield moderate to good yields, certain cyclizations involving aryl amines in the presence of acetaldehyde do not result in any product formation. Structural characterization of all the products were performed by means of FT-IR,<sup>1</sup>H and <sup>13</sup>C NMR and HRMS analyses. Besides, some of the products demonstrated bacteriostatic effects in the antibacterial study conducted against S. <em>aureus</em> and S. <em>epidermidis</em> bacteria.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-02-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139749674","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}
Constantine V. Milyutin , Andrey N. Komogortsev , Boris V. Lichitsky , Valeriya G. Melekhina
{"title":"Synthesis of allomaltol containing terarylenes with imidazole N-oxides bridge fragment","authors":"Constantine V. Milyutin , Andrey N. Komogortsev , Boris V. Lichitsky , Valeriya G. Melekhina","doi":"10.1080/00397911.2024.2310522","DOIUrl":"https://doi.org/10.1080/00397911.2024.2310522","url":null,"abstract":"<div><p>Method for the synthesis of previously unknown imidazole <em>N</em>-oxides bearing allomaltol unit has been elaborated. The presented approach is based on multicomponent condensation of corresponding oximes containing aroyl and 3-hydroxypyran-4-one fragments with various aldehydes and amines. The advantages of considered method are easily available starting compounds, atom economy, simple experimental procedure including isolation of the final products without column chromatography. The synthetic utility of prepared <em>N</em>-oxides was demonstrated by its further conversion to corresponding 2-chloroimidazole and 2-phenylaminoimidazole derivatives.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139749673","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}
{"title":"Novel organic–inorganic hybrid dimethyltin(IV) complexes of heterocyclic carboxylic acid and N-phthaloyl amino acids: Design, synthesis, spectroscopic characterization, DFT calculations and their anti-oxidant potential","authors":"Ankur M. Kumar , Suchitra Budania , Asha Jain","doi":"10.1080/00397911.2024.2306641","DOIUrl":"https://doi.org/10.1080/00397911.2024.2306641","url":null,"abstract":"<div><p>Four new organic–inorganic hybrid dimethyltin(IV) complexes (<strong>1–4</strong>) having general formula Me<sub>2</sub>SnAL which were generated by the reaction of dimethyltin(IV) dichloride with sodium salts of indole-3-acetic acid (AH) and flexible N-phthaloyl amino acids (LH) in 1:1:1 molar ratio in refluxing dry THF. The plausible structure of newly generated complexes has been elucidated on the basis of spectroscopic [IR, NMR (<sup>1</sup>H,<sup>13</sup>C,<sup>119</sup>Sn), HRMS] studies. The suggested five coordinated geometry of the hybrid dimethyltin(IV) complexes have been further supported by computational calculations using density functional theory (DFT). DFT calculations were carried out using B3LYP/6-31G* functional basis set. DFT calculations furnish an insight into the optimized geometry, optimized energy, stability, global reactivity descriptors and frontier molecular orbital (FMO) analysis of newly synthesized organic–inorganic hybrid dimethyltin(IV) complexes. These newly synthesized complexes were also evaluated for their anti-radical activity by DPPH free radical scavenging assay. All the dimethyltin(IV) complexes acted as efficient radical scavengers.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139738715","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}
{"title":"P4O10/TfOH-mediated metal-free synthesis of 4-hydroxycoumarins and a one-pot strategy to build their hybrids","authors":"G. D. Kotkar , S. G. Tilve","doi":"10.1080/00397911.2024.2306610","DOIUrl":"https://doi.org/10.1080/00397911.2024.2306610","url":null,"abstract":"<div><p>4-Hydroxycoumarins are among the most versatile heterocyclic scaffolds, and they are extensively used in the synthesis of a wide range of chemical molecules. Because of their biological and pharmacological effects, 4-hydroxycoumarin-based compounds are important among heterocyclic structures. In this study, a new method is developed to synthesize 4-hydroxycoumarins using a phosphoric anhydride and trifluromethanesulfonic acid (P<sub>4</sub>O<sub>10</sub>/TfOH) reagent system without the employment of either a catalyst or solvent. The direct condensation of phenols with malonic acid at ambient conditions provided 4-hydroxycoumrins in 85–90% yield. In medicinal chemistry, the 4-hydroxycoumarin motif is often used to make new hybrid heterocyclic scaffolds that can be used to find new molecules. The method was then successfully extended to synthesize hybrids of 4-hydroxycoumarin, such as biscoumarylphenylmethane, dioxinocoumarin, and tetracoumarylpehylenebismethane, in a one-pot method from phenol, avoiding the intermediate step of isolating and purifying 4-hydroxycoumarin.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139738714","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}
{"title":"Friedländer reactions for novel annulated pyridotriazolothiazolopyridines: Synthetic approaches and antimicrobial evaluation","authors":"Youssef A Alnamer , Magdy A Ibrahim","doi":"10.1080/00397911.2024.2306926","DOIUrl":"10.1080/00397911.2024.2306926","url":null,"abstract":"<div><p><em>o</em>-Aminoaldehyde <strong>1</strong> was employed as starting precursor for construction of some linear heterocyclic compounds. <em>o</em>-Aminoaldehyde <strong>1</strong> was permitted to undergo Friedländer reaction with some acyclic and cyclic methylene ketones giving the novel annulated heterocyclic systems <strong>2</strong>-<strong>10</strong>. Moreover, the reactivity of <em>o</em>-aminoaldehyde <strong>1</strong> was examined toward some cyclic enamines and enols producing the corresponding annulated heterocyclic systems. The prepared compounds were investigated for their antimicrobial efficiency displaying different inhibition action toward the tested microorganisms. Based on analytical spectral and results, structures of the produced compounds were established.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139560465","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}
{"title":"Asymmetric aza-Henry reaction of BOC-protected imines with zinc-FAM catalyst","authors":"Nurzhan Beksultanova , Özdemir Doğan","doi":"10.1080/00397911.2024.2303054","DOIUrl":"10.1080/00397911.2024.2303054","url":null,"abstract":"<div><p>Derivatives of ferrocenyl-substituted aziridinyl methanol (<strong>FAM</strong>) ligands were used with zinc metal for asymmetric aza-Henry (nitro-aldol) reaction of <em>N</em>-Boc protected imines with nitroalkanes. At optimized reaction conditions Zn-<strong>PFAM1</strong> catalyst system with a variety of aromatic imines provided products in up to 77% ee and 88% yield. In addition, the reaction of <em>N</em>-Boc substituted imines with nitroethane also proceeded smoothly with moderate enantioselectivities and diastereoselectivities.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139476818","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}
{"title":"Design, synthesis, anticancer evaluation and molecular docking studies of 1,2,4-oxadiazole incorporated indazole-isoxazole derivatives","authors":"Jesse Lingam , Bijaya Ketan Sahoo , Bala Divya Mallavarapu , Reddymasu Sreenivasulu","doi":"10.1080/00397911.2023.2282599","DOIUrl":"10.1080/00397911.2023.2282599","url":null,"abstract":"<div><p>A new series of 1,2,4-oxadiazole incorporated indazole-isoxazole (<strong>12a–j</strong>) derivatives were designed, synthesized and confirmed their structures by <sup>1</sup>HNMR, <sup>13</sup>CNMR and mass spectral analysis. Further, all compounds were evaluated for their anticancer activity against a panel of human cell lines like breast cancer (MCF-7), lung cancer (A549), prostate cancer (DU-145) and breast cancer (MDA MB-231) by using MTT assay. The etoposide used as a reference drug and the results were expressed with IC<sub>50</sub> (µM). Most of the compounds were showed good to moderate activity with respective cell lines. Among them, compounds <strong>12b, 12e, 12 g, 12h</strong> and <strong>12i</strong> have exhibited more potent activity as compared with the reference drug etoposide. In which one of the compound <strong>12i</strong> has showed most significant activity. Molecular docking studies were carried out using PyRx tool and visualized through Chimera and Pymol visualization tools, revealed that the interactions between the active site of the tubulin with the selected compound <strong>12i</strong> exhibited good interactions with the active site amino acids. These findings suggested that the <strong>12i</strong> compound acts as a potential binder to the tubulin complex. These results revealed that the selected synthesized compounds were used in anticancer therapies.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138496820","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}
Sivagami Mathavan , Subburethinam Ramesh , Rajesh B. R. D. Yamajala
{"title":"Base promoted coupling of α-ketoacids and 2-substituted aromatic amines: Green synthesis of diverse benzoxazoles, benzothiazoles, quinoxalinones and benzoxazinones and its practical application","authors":"Sivagami Mathavan , Subburethinam Ramesh , Rajesh B. R. D. Yamajala","doi":"10.1080/00397911.2023.2280599","DOIUrl":"10.1080/00397911.2023.2280599","url":null,"abstract":"<div><p>Synthesis of 2-aryl substituted benzoxazoles, benzothiazoles, and quinoxalinones <em>via</em> decarboxylative coupling of α-keto acids with 2-aminophenol, 2-aminothiophenol, and OPD (<em>o</em>-phenylenediamine), using K<sub>2</sub>CO<sub>3</sub> as a base in water at room temperature, and as well as solvent-free grinding and the synthesis of benzoxazinones from the reaction of α-keto acids with 2-aminophenol at 60 °C have been reported. Both the protocols afforded a wide range of desired products with excellent functional group tolerance in yields of 87–99%. The major advantages of these approaches are catalyst-free protocol, short reaction times, straightforward workup, and chromatography-free processing of the products. Additionally, to test the translational demand of this methodology, the synthesis of 2-(3,5-dichlorophenyl)-6-methylbenzo[<em>d</em>]oxazole was carried out which is a key structure of tafamidis, a commercially available drug.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138496821","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}
Wen Luo , Xinqiang Cheng , Xinyuan Zhu , Yong Li , Yongjia Liu , Wenqian Huang , Yan Li , Guilong Zhao
{"title":"An efficient, concise synthetic approach to γ-aminobutyric acid (GABA) derivatives bearing bicyclo[2.2.2]octane and bicyclo[2.2.1]heptane rings","authors":"Wen Luo , Xinqiang Cheng , Xinyuan Zhu , Yong Li , Yongjia Liu , Wenqian Huang , Yan Li , Guilong Zhao","doi":"10.1080/00397911.2023.2284348","DOIUrl":"10.1080/00397911.2023.2284348","url":null,"abstract":"<div><p>An efficient, concise 5-step synthetic approach to γ-aminobutyric acid (GABA) derivatives bearing bridged bicyclo[2.2.2]octane and bicyclo[2.2.1]heptane rings was developed, which consists of Diels-Alder cycloaddition to construct the bridged bicyclic rings with a nitrile functionality, hydrogenation, LDA-mediated S<sub>N</sub>2 alkylation to introduce acetate moiety at the α-position of nitrile, reduction of the nitrile functionality to amino group followed by intramolecular formation of lactam and finally acidic hydrolysis of lactam to give the desired GABA derivatives (<strong>1</strong> and <strong>19</strong> as HBr salts). The reaction conditions of Diels-Alder cycloaddition and LDA-mediated S<sub>N</sub>2 alkylation were intensively optimized to improve the yields. The stereochemistry of the S<sub>N</sub>2 reaction involved in the bicyclo[2.2.1]heptane ring system was unambiguously elucidated by single-crystal X-ray diffraction. This synthetic approach possesses advantages of less reaction steps, high overall yields and avoidance of toxic reagents, and may find wide applications in the synthesis of other GABA derivatives with similar bicyclic or polycyclic rings.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138496819","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}
{"title":"Recent insights into synthesis, biological activities, structure activity relationship and molecular interactions of thiazolidinone hybrids: A systematic review","authors":"Sabnam Parveen , Ritchu Babbar , Vishnu Nayak Badavath , Suman Kumar Nath , Sourabh Kumar , Ravi Rawat , Sridevi Chigurupati , Rohini Karunakaran , Pranay Wal , Monica Gulati , Tapan Behl","doi":"10.1080/00397911.2023.2269582","DOIUrl":"10.1080/00397911.2023.2269582","url":null,"abstract":"<div><p>The thiazolidinone component is a specialized frame exhibiting various biological reactions comprising analgesic, hypnotic, antiviral, anticancer, antitubercular, and many more. As the target scaffold for biological investigations, current category of heterocycles has been created by researchers using a number of fundamental techniques, as well as sophisticated routes. Recent research has focused heavily on 1,3-thiazolidin-4-one heterocyclic nuclei, which contain electron configurations at the tetrahedral site and at positions 1 and 3, sulfur and nitrogen atoms, respectively. The goal of the current review is to summarize the published work concerning the chemistry and pharmacological properties of thiazolidinone derivatives over the past few years. This is executed by characterizing thiazolidinone derivatives with various pharmacological activities using structural substitution patterns around the thiazolidinone moiety as the basis for the SAR study and their interactions with various proteins. This review also summarizes current developments in the chemical, molecular and biological activities of thiazolidinones.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136263566","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}