N. M. Hassanin, T. E. Ali, M. A. Assiri, S. M. Abdel-Kariem
{"title":"Design and Synthesis of Some Novel Phosphorus Heterocycles-Based Coumarin Derivatives as Promising Anticancer Agents","authors":"N. M. Hassanin, T. E. Ali, M. A. Assiri, S. M. Abdel-Kariem","doi":"10.1134/S1070428024130268","DOIUrl":"10.1134/S1070428024130268","url":null,"abstract":"<p>An efficient method was developed for the synthesis of eight novel functionalized 1,2,4,3-triazaphospholes and one 1,3,2-thiazaphosphinine incorporating a coumarin ring. Additionally, two interesting examples of diethyl coumarinyl phosphonate and diethyl chromeno-[3,4-<i>c</i>][1,2,4]triazolo[4,3-<i>a</i>]pyridinyl phosphonate were obtained. The proposed methodology involved the treatment of <i>N'</i>-benzoyl-2-oxo-2<i>H</i>-chromene-3-carbohydrazonamide (<b>2</b>) with various phosphorus agents, including phosphorus halides, phosphorus triamide, phosphorus esters, and phosphorus sulfides. IR, NMR, and mass spectrometric methods were used to confirm the structures of the prepared compounds. The antiproliferative properties of the isolated compounds were screened against HepG-2, MCF-7, and A549 cancer cells. The products <b>5</b>, <b>7</b>, <b>9</b>, and <b>10</b> exhibited excellent cytotoxic properties compared with doxorubicin. These four bioactive compounds have low toxicity in healthy human HFB4 cells.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 1 supplement","pages":"S223 - S235"},"PeriodicalIF":0.8,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142941082","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Solvent-Free Synthesis of Pyrazole Derivatives Mediated by Cobalt-Doped Iron Tartarate","authors":"S. B. Jagtap, A. S. Patki, D. B. Muley","doi":"10.1134/S1070428024130013","DOIUrl":"10.1134/S1070428024130013","url":null,"abstract":"<p>A novel, green, and economically viable method for the one-pot synthesis of 5-amino pyrazole 4-carbonitrile has been established. This approach features the solvent-free reaction between substituted benzaldehyde, malononitrile, and phenyl hydrazine catalyzed by CoFe<sub>2</sub>(C<sub>4</sub>H<sub>4</sub>O<sub>6</sub>)<sub>3</sub>·6H<sub>2</sub>O. The elimination of solvent renders this methodology highly attractive from both cost-effective and environmental perspective. Moreover, the optimized reaction conditions offer operational simplicity, utilize readily available and affordable starting materials, and deliver good to excellent yields (72–92%). The versatility of this protocol is demonstrated by the successful synthesis of ten distinct pyrazole derivatives.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 1 supplement","pages":"S1 - S8"},"PeriodicalIF":0.8,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142941272","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Efficient Synthesis of Bis(indolyl)methane Compounds in the Presence of Recyclable Nickel Oxide/Alumina Nanocatalyst","authors":"Bita Baghernejad, Hamoun Naseri, O. Marvi","doi":"10.1134/S1070428024130190","DOIUrl":"10.1134/S1070428024130190","url":null,"abstract":"<p>Bis(indolyl)methane derivatives, known for anticancer, antimicrobial, and antioxidant properties, have garnered significant research interest. This study reports an efficient and environmentally friendly method for synthesizing bis(indolyl)methanes via a one-pot reaction between indole and aromatic aldehydes using a nickel oxide/alumina nanocatalyst. The catalyst was prepared by co-precipitation of nickel nitrate hexahydrate and urea in the presence of γ-Al<sub>2</sub>O<sub>3</sub>, followed by calcination, and characterized using TEM and SEM techniques to confirm its nanoscale morphology. The reactions were performed in water as a solvent under reflux conditions, giving high product yields (up to 97%) within short reaction times (15 min). All the catalyst is inferior of the known CeO<sub>2</sub> catalyst, it allows the use of water instead of chloroform as a solvent. The catalyst was successfully recycled up to five times without significant loss in efficiency, demonstrating its stability and reusability. Experimental methods included monitoring the reaction progress using thin-layer chromatography and product characterization by IR and NMR spectroscopy. The proposed method for the synthesis of bis(indolyl)methane derivatives offers advantages such as simple product separation, low catalyst consumption, and minimal purification losses, presenting a sustainable and effective approach for the synthesis of bis(indolyl)methanes.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 1 supplement","pages":"S147 - S151"},"PeriodicalIF":0.8,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142940945","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"A Greener and Economical Synthesis of Hexahydroacridine-1,8(2H,5H)-diones Using 2-Aminopyrazine Catalyst Through Mortar-Pestle Grinding Approach with Their Computational Study","authors":"Harish Kumar Edapu, Sathyanarayana Boodida, Ramakanth Pagadala, Thirupathi Damera","doi":"10.1134/S1070428024130128","DOIUrl":"10.1134/S1070428024130128","url":null,"abstract":"<p>A green, simple, and economical protocol was used to synthesize hexahydroacridine-1,8(2<i>H</i>,5<i>H</i>)-dione derivatives. This tandem synthesis uses substituted arylaldehydes, dimedone/cyclohexane-1,3-dione, and NH<sub>4</sub>Cl, and is catalyzed by 2-aminopyrazine (10 mol %) in a three-component, one-pot, and mortar-pestle grinding process. The 2-aminopyrazine acts as an eco-friendly and low-cost organic compound. This unique technique offers additional benefits such as affordability, ease of management of the synthetic procedures, an ambient temperature of the reaction, a reduced reaction time, and a short/easy filtration procedure to achieve an outstanding output percentage. The elimination of hazardous solvents, column-based chromatography, and metal catalysts make the synthesis process more ecologically benign. A computational study of the synthesized compounds was conducted to assess their drug-like characteristics.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 1 supplement","pages":"S85 - S94"},"PeriodicalIF":0.8,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142941080","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Design, Synthesis, and Antioxidant Studies of Newer 4′-(3-Substituted Phenyl-6,6-dimethyl-4-oxo-2,3,5,7-tetrahydrobenzofuran-2-yl)-[1,1′-biphenyl]-2-carbonitriles: Adaptability of Sartans Drug Reactant","authors":"M. Bhatt, J. H. Kamdar, J. Upadhyay","doi":"10.1134/S1070428024130153","DOIUrl":"10.1134/S1070428024130153","url":null,"abstract":"<p>A one-pot reaction of dimedone, 4′-(bromomethyl)-[1,1′-biphenyl] was used to produce a variety of tetrahydrobenzofuran-4(2<i>H</i>)-one derivatives <b>4a</b>–<b>4j</b> in acetonitrile using pyridine and triethylamine as an economic catalyst under mild reaction conditions. The designed approach involves the formation of three bonds: two C–C bonds and one C–O bond. A greater yield and exceptional purity were achieved for all of the compounds. Several techniques were employed to study the benzofurans that were synthesized from sartan series benzyl bromide fragments. These techniques included FTIR, <sup>1</sup>H, <sup>13</sup>C NMR, and MS. The antioxidant capabilities of the synthetic chemicals were evaluated through screening. Substituents in benzaldehyde fragments as dimethoxy (<b>4f</b>), trimethoxy (<b>4g</b>), and nitro (<b>4h</b>) groups exhibited increased efficacy in a controlled laboratory setting utilizing the 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) free radical assay, with IC<sub>50</sub> values of 14, 16, and 15 µM, respectively. In contrast to the standard (ascorbic acid, IC<sub>50</sub> =14.06 µM), compounds containing halogen substituents were discovered to be somewhat effective in the free radical scavenging experiment. They identified a strong correlation between their binding modalities and the antioxidant characteristics in their molecular docking experiment with the myeloperoxidase (PDB: 3MNG) enzyme, which showed high binding affinities (docking score = –19.2 kcal/mol for <b>4f</b>).</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 1 supplement","pages":"S112 - S120"},"PeriodicalIF":0.8,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142941081","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Krishna K. Limbasiya, Jayesh S. Babariya, Vasta A. Modhavadiya
{"title":"Imidazol-1,2,3-triazole Derivatives as Novel and Potent Scaffolds of α-Glucosidase Inhibitors: Synthesis and Biological Evaluations","authors":"Krishna K. Limbasiya, Jayesh S. Babariya, Vasta A. Modhavadiya","doi":"10.1134/S1070428024130244","DOIUrl":"10.1134/S1070428024130244","url":null,"abstract":"<p>A treatment for type 2 diabetes mellitus (T2DM) that has been approved is the inhibition of α-glucosidase. Using a simple and straightforward three-step synthetic route that utilized a Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) click chemistry approach in the last step, a new series of substituted 1<i>H</i>-imidazol-1<i>H</i>-1,2,3-triazoles, specifically <b>5a–5j</b>, were synthesized in an effort to create new anti-α-glucosidase agents. <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy and mass spectrometry were used to characterize these motifs in great detail. The positive control in this investigation was acarbose, which had an IC<sub>50</sub> value of 750.0 µM. The 1<i>H</i>-imidazol-1<i>H</i>-1,2,3-triazoles that were replaced showed inhibitory potencies several times stronger than those of conventional medicines, with IC<sub>50</sub> values ranging from 14.89 to 311.20 μM. In particular, compounds containing fluorine groups as aryl substitutions exhibited anti-α-glucosidase activity with an IC<sub>50</sub> value of 14.89 μM (<b>5f</b> = 4-CF<sub>3</sub>), which was 53 times stronger than the positive control acarbose, while compounds carrying the 2,4-(F)<sub>2</sub> motif had an IC<sub>50</sub> value of 29.50 μM, which was 25 times stronger.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 1 supplement","pages":"S205 - S212"},"PeriodicalIF":0.8,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142941263","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Dharmesh K. Katariya, Amita K. Vyas, Ranjan C. Khunt
{"title":"Exploring Microwave-Assisted Synthesis, Characterization, and Antimicrobial Proficiency of Pyranopyrazole-Based Quinoline Derivatives","authors":"Dharmesh K. Katariya, Amita K. Vyas, Ranjan C. Khunt","doi":"10.1134/S1070428024130098","DOIUrl":"10.1134/S1070428024130098","url":null,"abstract":"<p>The current work describes the green synthesis and antimicrobial screening of pyranopyrazole-based quinoline derivatives (<b>4a</b>–<b>4v</b>). The structures of the synthesized compounds have been confirmed by various spectral analysis. All the synthesized compounds were screened for <i>in vitro</i> antimicrobial activity against some Gram-negative (<i>Pseudomonas aeruginosa, Escherichia coli</i>, and<i> Klebsiella pneumoniae</i>) and Gram-positive (<i>Staphylococcus aureus</i>) bacteria. The pyranopyrazole derivatives of quinoline with a pharmacologically potent group discovered in this article may provide valuable therapeutic involvement in the treatment of microbial diseases, especially against fungal and bacterial infections.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 1 supplement","pages":"S59 - S69"},"PeriodicalIF":0.8,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142940951","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Alim Alsukor, Nurul Alam Inayatsyah, Sharifah Aminah Syed Mohamad, Mohamad Jemain Mohamad Ridhwan, Nurulfazlina Edayah Rasol, Syahrul Imran
{"title":"Synthesis and Biological Evaluation of Coumarin Bearing Thiourea Derivative as Potential Antibacterial Agent","authors":"Alim Alsukor, Nurul Alam Inayatsyah, Sharifah Aminah Syed Mohamad, Mohamad Jemain Mohamad Ridhwan, Nurulfazlina Edayah Rasol, Syahrul Imran","doi":"10.1134/S1070428024130177","DOIUrl":"10.1134/S1070428024130177","url":null,"abstract":"<p>In this study, a series of thiourea-substituted coumarin was synthesized in a four-step reaction from a precursor, 2-oxo-2H-chromene-3-carboxylic acid. The structures of all synthesized compounds were confirmed using NMR and LCMS. All synthesized compounds were screened for their antibacterial activity against gram-negative (<i>Escherichia coli</i>, <i>Salmonella typhimurium</i>, and <i>Enterobacter aerogenes</i>) and gram-positive (<i>Staphylococcus aureus</i> and <i>Bacillus subtilis</i>) bacteria strains using well diffusion method. Most of the synthesized compounds were found to be susceptible to most of the tested bacterial strains. The structure-activity relationship showed that compounds with substituents at the <i>ortho</i> position had lower overall activity as compared to <i>meta</i>-substituted and <i>para</i>-substituted compounds. Compound <b>19</b> was found to be the most effective antibacterial agent against gram-positive <i>S. aureus</i> and <i>B. subtilis</i>, with minimum inhibitory concentration values of 31.25 and 62.50 µg/mL, respectively. Molecular docking performed on potential compounds revealed significant binding site interaction with <i>S. aureus</i> gyrase residue Asp1083 and Met1121.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 1 supplement","pages":"S128 - S139"},"PeriodicalIF":0.8,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142940949","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis and Characterization of Heterocyclic Ligand and Its Metal Complexes","authors":"K. Ramya Charitha, R. Mamatha Rani, P. Kavitha","doi":"10.1134/S1070428024130062","DOIUrl":"10.1134/S1070428024130062","url":null,"abstract":"<p>A ligand has been synthesized from 1-(1-methyl-5-(tosylamino)-1<i>H</i>-1,2,3-triazol-4-yl)ethanone and dimethylpyrimidyl hydrazone, and its copper(II), nickel(II), and zinc(II) complexes have been produced and analyzed. The X-ray diffraction analysis shows that the zinc(II) combination with the N<sub>3</sub>O donor ligand environment has the form of a tetragonal pyramid. The chelate core of the copper(II) complex is structurally identical, as shown by X-ray data. The coordination core of the nickel(II) complex is an octahedron, which is completed by the solvent molecule. Pharmacological evidence of antibacterial activity was obtained for all the substances. The synthetic compounds have been studied and compared to existing antibiotics like chloramphenicol and amphotericin B for their ability to kill bacteria and fungi, respectively.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 1 supplement","pages":"S41 - S45"},"PeriodicalIF":0.8,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142941274","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis, Characterization, and Pharmacokinetic Studies of Novel HydroquinoneBased 1,2,3-Triazole/Amide Derivatives as Anticancer and Antibacterial Agents","authors":"Syed Nazreen","doi":"10.1134/S1070428024130086","DOIUrl":"10.1134/S1070428024130086","url":null,"abstract":"<p>In the present study, new hydroquinone-based 1,2,3-triazole/amide analogues have been prepared and tested for anticancer and antibacterial potential. The structures of final derivatives were established using various analytical techniques. Compound <b>8</b>, containing <i>para-</i>bromo-1,2,3-triazole nucleus, showed promising cytotoxicity with IC<sub>50</sub> of 0.92, 1.72, and 3.56 μM towards MCF-7, HepG2 and SKOV3 cells, respectively, comparable to standard drug doxorubicin. A chloro-bearing hydroquinone derivative (<b>6</b>) exhibited the highest antibacterial potential against <i>S. aureus</i> (MIC 25 μg/mL) and <i>E.coli</i> (MIC 50 μg/mL), which were equipotent to amoxicillin. In terms of <i>in silico</i> ADME properties, all the derivatives followed Lipinski’s rule with zero violations, were flexible and lipophilic, exhibited high gastrointestinal absorption, and could not permeate the blood-brain barrier. In conclusion, these compounds possess good anticancer and antibacterial potential.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 1 supplement","pages":"S50 - S58"},"PeriodicalIF":0.8,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142940952","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}