Pub Date : 2025-11-02DOI: 10.1080/17415993.2025.2551759
Ilyas Nizamov , Vladimir Yu. Yakimov , Ivan I. Kalekulin , Ilnar D. Nizamov , Ramazan Salikhov , Kamil A. Ivshin , Olga N. Kataeva , Guzel G. Garifzianova , Denis Yu. Grishaev , Marina Shulaeva , Andrey A. Parfenov , Alexandra B. Vyshtakalyuk
Dithiophosphonic acids were prepared by the reactions of Lawesson’s reagent with racemic 2-butanol, 2-ethylhexanol and diethyl malate reacted with ammonia and hexadecylamine to form ammonium and hexadecylammonium dithiophosphonates. The molecular structure of ammonium O-(2-butyl)-4-methoxyphenyldithiophosphonate derivative was established by X-ray single crystal analysis. The dithiophosphonic acids obtained and their ammonium salts possessed high hydrolytic stability, antimicrobial activity and low cytotoxicity. The chemical behavior of dithiophosphonic acids and their salts in water and the Mueller-Hinton nutrient broth was established. The electrical conductivity dithiophosphonic acids and their salts in water and in a water–ethanol mixture was studied.
{"title":"Racemic 2-butanol, 2-ethylhexanol and malic ester in the synthesis of ammonium and hexadecylammonium dithiophosphonates with antimicrobial and cytotoxic activity","authors":"Ilyas Nizamov , Vladimir Yu. Yakimov , Ivan I. Kalekulin , Ilnar D. Nizamov , Ramazan Salikhov , Kamil A. Ivshin , Olga N. Kataeva , Guzel G. Garifzianova , Denis Yu. Grishaev , Marina Shulaeva , Andrey A. Parfenov , Alexandra B. Vyshtakalyuk","doi":"10.1080/17415993.2025.2551759","DOIUrl":"10.1080/17415993.2025.2551759","url":null,"abstract":"<div><div>Dithiophosphonic acids were prepared by the reactions of Lawesson’s reagent with racemic 2-butanol, 2-ethylhexanol and diethyl malate reacted with ammonia and hexadecylamine to form ammonium and hexadecylammonium dithiophosphonates. The molecular structure of ammonium <em>O</em>-(2-butyl)-4-methoxyphenyldithiophosphonate derivative was established by X-ray single crystal analysis. The dithiophosphonic acids obtained and their ammonium salts possessed high hydrolytic stability, antimicrobial activity and low cytotoxicity. The chemical behavior of dithiophosphonic acids and their salts in water and the Mueller-Hinton nutrient broth was established. The electrical conductivity dithiophosphonic acids and their salts in water and in a water–ethanol mixture was studied.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 6","pages":"Pages 1103-1121"},"PeriodicalIF":1.6,"publicationDate":"2025-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145493266","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 : 2025-11-02DOI: 10.1080/17415993.2025.2555480
Kübra Yildirim , Ali Ihsan Karaçolak , Emine Kutlu , Fatih Mehmet Emen , Muhammad Asim Ali , Ece Şimşek , Ahmet Yılmaz Çoban , Cemilenur Ataş , Tuncay Yesilkaynak
This study aimed to synthesize and evaluate the anti-tuberculosis potential of a series of novel thiourea derivatives (1–4) containing halogenated pyridine and chlorobenzamide scaffolds. The compounds were synthesized via the reaction of appropriate pyridine derivatives with 2-chlorobenzoyl isothiocyanate and characterized by the FT-IR, 1H-NMR, 13C-NMR and ESI-MS techniques. 6–311++G (d,p) mode and B3LYP method were used in the DFT analysis to calculate the HOMO–LUMO energies of ligands 3 and 4. The calculated HOMO–LUMO transition energies indicated that 3 and 4 have low chemical hardness and may have high chemical activity. The anti-tuberculosis activity of the synthesized thioureas was investigated via the microplate nitrate reductase test method (MNRA). The 1 and 2 show less antituberculosis effect. The 3 was found to have MIC values of 16 and 32 µg/ml against the ATCC35822 (INH-R) and the ATCC35837 (EMB-R) strains, respectively. The highest value was observed with the 4 (MIC 8–128 µg/ml). The meaningful decrease in the MIC values against all the bacteria strains including the MDR isolates, which have been chosen for their clinical aspects, indicating that compound 4 may serve as a promising lead compound for the development of new anti-tuberculosis agents.
{"title":"Synthesis and biological evaluation of novel thioureas containing pyridine derivatives against Mycobacterium tuberculosis","authors":"Kübra Yildirim , Ali Ihsan Karaçolak , Emine Kutlu , Fatih Mehmet Emen , Muhammad Asim Ali , Ece Şimşek , Ahmet Yılmaz Çoban , Cemilenur Ataş , Tuncay Yesilkaynak","doi":"10.1080/17415993.2025.2555480","DOIUrl":"10.1080/17415993.2025.2555480","url":null,"abstract":"<div><div>This study aimed to synthesize and evaluate the anti-tuberculosis potential of a series of novel thiourea derivatives (<strong>1–4</strong>) containing halogenated pyridine and chlorobenzamide scaffolds. The compounds were synthesized via the reaction of appropriate pyridine derivatives with 2-chlorobenzoyl isothiocyanate and characterized by the FT-IR, <sup>1</sup>H-NMR, <sup>13</sup>C-NMR and ESI-MS techniques. 6–311++G (d,p) mode and B3LYP method were used in the DFT analysis to calculate the HOMO–LUMO energies of ligands 3 and 4. The calculated HOMO–LUMO transition energies indicated that <strong>3</strong> and <strong>4</strong> have low chemical hardness and may have high chemical activity. The anti-tuberculosis activity of the synthesized thioureas was investigated via the microplate nitrate reductase test method (MNRA). The <strong>1</strong> and <strong>2</strong> show less antituberculosis effect. The <strong>3</strong> was found to have MIC values of 16 and 32 µg/ml against the ATCC35822 (INH-R) and the ATCC35837 (EMB-R) strains, respectively. The highest value was observed with the <strong>4</strong> (MIC 8–128 µg/ml). The meaningful decrease in the MIC values against all the bacteria strains including the MDR isolates, which have been chosen for their clinical aspects, indicating that compound 4 may serve as a promising lead compound for the development of new anti-tuberculosis agents.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 6","pages":"Pages 1142-1160"},"PeriodicalIF":1.6,"publicationDate":"2025-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145493267","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 rapid and environmentally benign method for the synthesis of pyrazole derivatives via cyclocondensation reaction between α-oxoketene S,S/N,S-acetals and hydrazine hydrate under ultrasound irradiation in an aqueous medium has been reported. This green and versatile synthetic protocol avoids the use of toxic organic solvents and additional catalysts/ligands, generates no waste, and affords twenty diversely substituted regioselective products with isolated yields ranging from 82 to 93%. The positive impact of sonication led to drastically reduced reaction times (15–45 min), as compared to known conventional methods (10–18 h), which clearly indicated the importance of ultrasound-promoted synthesis in organic transformations. Most of the synthesized compounds possessed –SCH3 as a good leaving group, which is readily accessible for further transformation to generate libraries of biologically important compounds.
{"title":"Ultrasound-promoted, catalyst-free, greener synthesis of pyrazoles in aqueous medium","authors":"Khandelwal Keertika , Sunita Bhagat , Nutan Sharma","doi":"10.1080/17415993.2025.2567698","DOIUrl":"10.1080/17415993.2025.2567698","url":null,"abstract":"<div><div>A rapid and environmentally benign method for the synthesis of pyrazole derivatives <em>via</em> cyclocondensation reaction between <em>α</em>-oxoketene <em>S,S/N,S-</em>acetals and hydrazine hydrate under ultrasound irradiation in an aqueous medium has been reported. This green and versatile synthetic protocol avoids the use of toxic organic solvents and additional catalysts/ligands, generates no waste, and affords twenty diversely substituted regioselective products with isolated yields ranging from 82 to 93%. The positive impact of sonication led to drastically reduced reaction times (15–45 min), as compared to known conventional methods (10–18 h), which clearly indicated the importance of ultrasound-promoted synthesis in organic transformations. Most of the synthesized compounds possessed –SCH<sub>3</sub> as a good leaving group, which is readily accessible for further transformation to generate libraries of biologically important compounds.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 6","pages":"Pages 1161-1171"},"PeriodicalIF":1.6,"publicationDate":"2025-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145493120","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 : 2025-11-02DOI: 10.1080/17415993.2025.2536599
Tarik E. Ali , Mohammed A. Assiri , Ali A. Shati , Mohammad Y. Alfaifi , Serag E. Elbehairi
A novel class of 3-Substituted-5-[(4-oxo-4H-chromen-3-yl)methylene]−2-(2-phenylhydrazineylidene)thiazolidin-4-one (3a-g and 5) was efficiently synthesized via a one-pot three components involving 1-phenyl-4-substituted-thiosemicarbazide, ethyl bromoacetate and 3-formylchromone in absolute ethanol and freshly fused sodium acetate under the effect of ultrasound irradiation at 50 °C. The target compounds were obtained in excellent yields within a short time. The synthesized compounds were evaluated for their cytotoxic potential against human breast cancer cell lines MCF-7 and MDA-MB-231 using the sulforhodamine B (SRB) assay. Both compounds 3a and 3f exhibited markedly enhanced cytotoxic activity in comparison to the reference drugs doxorubicin and tamoxifen. These bioactive molecules significantly promoted late-stage apoptosis and necrosis across all tested tumor cell lines. Furthermore, compounds 3a and 3f demonstrated a strong capacity to cause cell-cycle arrest at the G1 and S phases. Additionally, compounds 3a and 3f had potential autophagic induction. ADMET analysis revealed that compound 3a displayed superior oral absorption, a more favorable pharmacokinetic profile, lower toxicity, and no mutagenic risk. Molecular docking studies indicated that both 3a and 3f interact effectively with the VEGFR-2 receptor. These findings suggested that these compounds possess a valuable skeletal structure for the development of novel antitumor agents.
{"title":"Synthesis, in silico ADMET, and molecular docking studies of novel 3-substituted- 5-[(4-oxo-4H-chromen-3-yl)methylene]−2-(2-phenylhydrazineylidene)thiazolidin-4-ones inducing apoptosis, autophagy, and cell cycle arrest in breast cancer cell lines","authors":"Tarik E. Ali , Mohammed A. Assiri , Ali A. Shati , Mohammad Y. Alfaifi , Serag E. Elbehairi","doi":"10.1080/17415993.2025.2536599","DOIUrl":"10.1080/17415993.2025.2536599","url":null,"abstract":"<div><div>A novel class of 3-Substituted-5-[(4-oxo-4<em>H</em>-chromen-3-yl)methylene]−2-(2-phenylhydrazineylidene)thiazolidin-4-one (3a-g and 5) was efficiently synthesized via a one-pot three components involving 1-phenyl-4-substituted-thiosemicarbazide, ethyl bromoacetate and 3-formylchromone in absolute ethanol and freshly fused sodium acetate under the effect of ultrasound irradiation at 50 °C. The target compounds were obtained in excellent yields within a short time. The synthesized compounds were evaluated for their cytotoxic potential against human breast cancer cell lines MCF-7 and MDA-MB-231 using the sulforhodamine B (SRB) assay. Both compounds 3a and 3f exhibited markedly enhanced cytotoxic activity in comparison to the reference drugs doxorubicin and tamoxifen. These bioactive molecules significantly promoted late-stage apoptosis and necrosis across all tested tumor cell lines. Furthermore, compounds 3a and 3f demonstrated a strong capacity to cause cell-cycle arrest at the G1 and S phases. Additionally, compounds 3a and 3f had potential autophagic induction. ADMET analysis revealed that compound 3a displayed superior oral absorption, a more favorable pharmacokinetic profile, lower toxicity, and no mutagenic risk. Molecular docking studies indicated that both 3a and 3f interact effectively with the VEGFR-2 receptor. These findings suggested that these compounds possess a valuable skeletal structure for the development of novel antitumor agents.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 6","pages":"Pages 1055-1076"},"PeriodicalIF":1.6,"publicationDate":"2025-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145493264","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 : 2025-09-03DOI: 10.1080/17415993.2025.2507054
Song Bai , Lijun Chen , Miao Li , Suran Wan , Fang Wang , Shouyin Tang , Xian Wei , Rong Wu
Through active splicing techniques and chemical synthesis methods, we have successfully synthesized a series of novel abietic acid derivatives that combine abietic acid backbone with a sulfonamide group. In vitro tests, these derivatives exhibited remarkable antibacterial activities, especially compound C3. Using three-dimensional quantitative structure–activity relationship (3D-QSAR) analysis, we found that the introduction of electron-absorbing groups at the R1 position, as well as the introduction of larger groups at the R2 position, may enhance the antibacterial activity of the target compounds. In addition, studies on the antibacterial mechanism of action of compound C3 showed that it could increase the permeability of bacterial membranes, disrupt the cell membrane of Xanthomonas oryzae pv. oryzicola (Xoc), and effectively inhibit bacterial growth. These findings not only elucidate the antibacterial mechanism of C3, but also provide an important scientific basis for the design and development of new antibacterial agents.
{"title":"Design and synthesis of abietic acid derivatives containing sulfonamide structure, biological activity and mechanism of action studies","authors":"Song Bai , Lijun Chen , Miao Li , Suran Wan , Fang Wang , Shouyin Tang , Xian Wei , Rong Wu","doi":"10.1080/17415993.2025.2507054","DOIUrl":"10.1080/17415993.2025.2507054","url":null,"abstract":"<div><div>Through active splicing techniques and chemical synthesis methods, we have successfully synthesized a series of novel abietic acid derivatives that combine abietic acid backbone with a sulfonamide group. <em>In vitro</em> tests, these derivatives exhibited remarkable antibacterial activities, especially compound <strong>C3</strong>. Using three-dimensional quantitative structure–activity relationship (3D-QSAR) analysis, we found that the introduction of electron-absorbing groups at the R<sup>1</sup> position, as well as the introduction of larger groups at the R<sup>2</sup> position, may enhance the antibacterial activity of the target compounds. In addition, studies on the antibacterial mechanism of action of compound <strong>C3</strong> showed that it could increase the permeability of bacterial membranes, disrupt the cell membrane of <em>Xanthomonas oryzae</em> pv. <em>oryzicola</em> (<em>Xoc</em>), and effectively inhibit bacterial growth. These findings not only elucidate the antibacterial mechanism of <strong>C3</strong>, but also provide an important scientific basis for the design and development of new antibacterial agents.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 5","pages":"Pages 818-834"},"PeriodicalIF":1.6,"publicationDate":"2025-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048672","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 : 2025-09-03DOI: 10.1080/17415993.2025.2497317
Babli Roy
The chemically and medicinally versatile dithiocarbamates play a significant role in advancing various fields, including agriculture, chemical synthesis, and environmental remediation. However, dithiocarbamates have primarily been utilised as pesticides and fungicides for crop protection since the 1930s. Recently, the revival of dithiocarbamates from agrochemicals to repurposed drugs for treating life-threatening diseases like cancer and microbial infections has stimulated medicinal chemists to reinvestigate their unmet potential. Furthermore, dithiocarbamates containing diversified organic functionalities have shown promising antifungal activity against fungal-resistant phytopathogens, offering a solution to addressing the global threat of fungal resistance. Consequently, the synthesis of multifaceted S and N-functionalized organic dithiocarbamates using diverse organic substrates has resurfaced in synthetic and medicinal chemistry research. There is also a growing trend to develop more convenient synthetic approaches for synthesising organic dithiocarbamates featuring various green chemistry aspects, including alternative or renewable energy resources, green solvents, solvent-free reaction conditions, and cost-effectiveness. These greener approaches are also associated with high efficiency, better selectivity, broad substrate scope, outstanding yields, operational simplicity, and viability. This review provides an in-depth overview of the recent developments in the diverse synthetic routes for preparing novel organic dithiocarbamates, including multi-component approaches involving the reaction of amines, carbon disulfide, and a wide range of organic substrates. The emerging methodologies for directly synthesising S-alkyl and S-aryl dithiocarbamates using commercially available and non-hazardous tetraalkylthiuram disulfides or monosulfides as organic precursors are also comprehensively discussed in this article. This review also highlights recently developed unconventional greener protocols using alternative reactants instead of carbon disulfide or thiuram disulfides.
{"title":"Recent advances in synthetic approaches for biologically active organic dithiocarbamates","authors":"Babli Roy","doi":"10.1080/17415993.2025.2497317","DOIUrl":"10.1080/17415993.2025.2497317","url":null,"abstract":"<div><div>The chemically and medicinally versatile dithiocarbamates play a significant role in advancing various fields, including agriculture, chemical synthesis, and environmental remediation. However, dithiocarbamates have primarily been utilised as pesticides and fungicides for crop protection since the 1930s. Recently, the revival of dithiocarbamates from agrochemicals to repurposed drugs for treating life-threatening diseases like cancer and microbial infections has stimulated medicinal chemists to reinvestigate their unmet potential. Furthermore, dithiocarbamates containing diversified organic functionalities have shown promising antifungal activity against fungal-resistant phytopathogens, offering a solution to addressing the global threat of fungal resistance. Consequently, the synthesis of multifaceted S and N-functionalized organic dithiocarbamates using diverse organic substrates has resurfaced in synthetic and medicinal chemistry research. There is also a growing trend to develop more convenient synthetic approaches for synthesising organic dithiocarbamates featuring various green chemistry aspects, including alternative or renewable energy resources, green solvents, solvent-free reaction conditions, and cost-effectiveness. These greener approaches are also associated with high efficiency, better selectivity, broad substrate scope, outstanding yields, operational simplicity, and viability. This review provides an in-depth overview of the recent developments in the diverse synthetic routes for preparing novel organic dithiocarbamates, including multi-component approaches involving the reaction of amines, carbon disulfide, and a wide range of organic substrates. The emerging methodologies for directly synthesising S-alkyl and S-aryl dithiocarbamates using commercially available and non-hazardous tetraalkylthiuram disulfides or monosulfides as organic precursors are also comprehensively discussed in this article. This review also highlights recently developed unconventional greener protocols using alternative reactants instead of carbon disulfide or thiuram disulfides.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 5","pages":"Pages 922-974"},"PeriodicalIF":1.6,"publicationDate":"2025-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048667","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 : 2025-09-03DOI: 10.1080/17415993.2025.2510420
Zhilong Li , Yan Xia , Dongfeng Li , Ruibin Hou
To create multi-stimulus responsive organogels, a novel low-molecular-weight organic gelator (LMMG) 1 was synthesized by linking two photoresponsive azobenzene groups with two hydrophobic chains containing amide functionalities to a central electroactive tetrathiafulvalene (TTF) unit. The gelation properties of compound 1 were comprehensively evaluated, revealing its ability to immobilize 1,2-dichloroethane and n-butanol, while other solvents tested did not form gels. A series of analyses, including SEM, FTIR, 1H NMR, and UV/Vis absorption spectroscopy, were conducted to investigate the characteristics of the resulting organogels. The findings indicated that the gelator self-assembled into a three-dimensional supramolecular network, driven by intermolecular hydrogen bonding. As anticipated, the organogels displayed multiple stimuli-responsive sol–gel transitions in response to changes in chemical redox conditions, heating, and the presence of anions due to the dynamic and reversible nature of the non-covalent interactions. Notably, the gelators interacted with various electron acceptor molecules, resulting in the formation of charge transfer (CT) complexes and binary organogels, accompanied by noticeable color changes. Additionally, the gels proved to be effective absorbents, suggesting potential applications for the removal of Rhodamine B cationic dyes from water.
{"title":"A novel tetrathiafulvalene-based organogelator with multi-stimuli responsiveness and dye adsorption","authors":"Zhilong Li , Yan Xia , Dongfeng Li , Ruibin Hou","doi":"10.1080/17415993.2025.2510420","DOIUrl":"10.1080/17415993.2025.2510420","url":null,"abstract":"<div><div>To create multi-stimulus responsive organogels, a novel low-molecular-weight organic gelator (LMMG) 1 was synthesized by linking two photoresponsive azobenzene groups with two hydrophobic chains containing amide functionalities to a central electroactive tetrathiafulvalene (TTF) unit. The gelation properties of compound 1 were comprehensively evaluated, revealing its ability to immobilize 1,2-dichloroethane and n-butanol, while other solvents tested did not form gels. A series of analyses, including SEM, FTIR, <sup>1</sup>H NMR, and UV/Vis absorption spectroscopy, were conducted to investigate the characteristics of the resulting organogels. The findings indicated that the gelator self-assembled into a three-dimensional supramolecular network, driven by intermolecular hydrogen bonding. As anticipated, the organogels displayed multiple stimuli-responsive sol–gel transitions in response to changes in chemical redox conditions, heating, and the presence of anions due to the dynamic and reversible nature of the non-covalent interactions. Notably, the gelators interacted with various electron acceptor molecules, resulting in the formation of charge transfer (CT) complexes and binary organogels, accompanied by noticeable color changes. Additionally, the gels proved to be effective absorbents, suggesting potential applications for the removal of Rhodamine B cationic dyes from water.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 5","pages":"Pages 887-903"},"PeriodicalIF":1.6,"publicationDate":"2025-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048670","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 the pursuit of pharmacologically important compounds, platinum(II) complexes were synthesized using both green microwave-assisted and thermal methods with the bidentate NS Schiff base ligand benzyl-2-(1-(pyridine-2-yl)ethylidene)hydrazine-1-carbodithioate (HL). This ligand was synthesized through the reaction between benzyl hydrazinecarbodithioate and 1-(pyridine-2-yl)ethan-1-one. The results from both methods were summarized and compared. Microwave-assisted reactions were completed in a shorter time and yielded higher amounts of product compared to thermal methods. The structural characterization of both the ligand and metal complexes was performed using various physicochemical methods. A square planar geometry was inferred for the platinum(II) complexes based on spectral and analytical data. Both the ligand (HL) and the platinum complex, [Pt(L)2] were evaluated for antituberculosis, DNA cleavage, and antimicrobial activities. Additionally, the [Pt(HL)2]Cl2 complex was also investigated for antimicrobial activity. The platinum complex, [Pt(L)2] was found to effectively inhibit the growth of Mycobacterium tuberculosis. DNA cleavage studies suggested that both the ligand and the metal complex, [Pt(L)2] were able to completely cleave Staphylococcus aureus DNA. Antimicrobial testing showed that both the ligand and the metal complexes exhibited activity against two bacteria (Escherichia coli and Bacillus subtilis) and two fungi (Aspergillus niger and Penicillium chrysogenum), demonstrating antibacterial and antifungal effects.
{"title":"Green microwave-assisted synthesis, characterization, and PXRD studies of nitrogen- and sulfur-containing Schiff base platinum (II) complexes: evaluation of antituberculosis, DNA cleavage, and antimicrobial activities","authors":"Akshita Jain , Shivansh Bhatnagar , Anita Kumari , Saurabh Dave , Nighat Fahmi","doi":"10.1080/17415993.2025.2535433","DOIUrl":"10.1080/17415993.2025.2535433","url":null,"abstract":"<div><div>In the pursuit of pharmacologically important compounds, platinum(II) complexes were synthesized using both green microwave-assisted and thermal methods with the bidentate NS Schiff base ligand benzyl-2-(1-(pyridine-2-yl)ethylidene)hydrazine-1-carbodithioate (HL). This ligand was synthesized through the reaction between benzyl hydrazinecarbodithioate and 1-(pyridine-2-yl)ethan-1-one. The results from both methods were summarized and compared. Microwave-assisted reactions were completed in a shorter time and yielded higher amounts of product compared to thermal methods. The structural characterization of both the ligand and metal complexes was performed using various physicochemical methods. A square planar geometry was inferred for the platinum(II) complexes based on spectral and analytical data. Both the ligand (HL) and the platinum complex, [Pt(L)<sub>2</sub>] were evaluated for antituberculosis, DNA cleavage, and antimicrobial activities. Additionally, the [Pt(HL)<sub>2</sub>]Cl<sub>2</sub> complex was also investigated for antimicrobial activity. The platinum complex, [Pt(L)<sub>2</sub>] was found to effectively inhibit the growth of <em>Mycobacterium tuberculosis</em>. DNA cleavage studies suggested that both the ligand and the metal complex, [Pt(L)<sub>2</sub>] were able to completely cleave <em>Staphylococcus aureus</em> DNA. Antimicrobial testing showed that both the ligand and the metal complexes exhibited activity against two bacteria (<em>Escherichia coli</em> and <em>Bacillus subtilis</em>) and two fungi (<em>Aspergillus niger</em> and <em>Penicillium chrysogenum</em>), demonstrating antibacterial and antifungal effects.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 5","pages":"Pages 904-921"},"PeriodicalIF":1.6,"publicationDate":"2025-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048666","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 : 2025-09-03DOI: 10.1080/17415993.2025.2508810
Harbi Tomah Al-Masri , Akram Ali Almejled , Ziad Moussa
N-methyl-P,P-diphenyl-N-(2-pyridinyl)phosphinous amide was oxidized with elemental sulfur in refluxing toluene to produce the corresponding sulfide C6H3N-2-N(CH3)(P(S)Ph2) (1) ligand. The reaction of 1 with an equimolar quantity of HgX2 (X = Cl, I) produced cis-[HgX2{1-κ2S,Npy }] (X = Cl(2), I(3)) complexes. In addition, the side product Ph2P(S2).C6H4N(CH3)(H) (4) was identified while ligand 1 was being prepared. 1–4 were characterized using multinuclear NMR (1H, 13C, and 31P) and IR spectroscopy. The molecular structures of 1–4 were determined using a single X-ray crystallography. 2 and 3 are structurally characterized novel κ2S,Npy-bidentate ligands with Hg(II) metal complexes.
{"title":"N-methyl-P,P-diphenyl-N-(2-pyridinyl)phosphinothioic amide chelating ligand: synthesis, characterization, and X-ray structures of novel Hg(II) metal complexes","authors":"Harbi Tomah Al-Masri , Akram Ali Almejled , Ziad Moussa","doi":"10.1080/17415993.2025.2508810","DOIUrl":"10.1080/17415993.2025.2508810","url":null,"abstract":"<div><div><em>N</em>-methyl-<em>P</em>,<em>P</em>-diphenyl-<em>N</em>-(2-pyridinyl)phosphinous amide was oxidized with elemental sulfur in refluxing toluene to produce the corresponding sulfide C<sub>6</sub>H<sub>3</sub>N-2-N(CH<sub>3</sub>)(P(S)Ph<sub>2</sub>) (<strong>1</strong>) ligand. The reaction of <strong>1</strong> with an equimolar quantity of HgX<sub>2</sub> (X = Cl, I) produced <em>cis</em>-[HgX<sub>2</sub>{<strong>1</strong>-κ<sup>2</sup><em>S,N<sup>py</sup></em> }] (X = Cl(<strong>2</strong>), I(<strong>3</strong>)) complexes. In addition, the side product Ph<sub>2</sub>P(S<sub>2</sub>).C<sub>6</sub>H<sub>4</sub>N(CH<sub>3</sub>)(H) (<strong>4</strong>) was identified while ligand <strong>1</strong> was being prepared. <strong>1</strong>–<strong>4</strong> were characterized using multinuclear NMR (<sup>1</sup>H, <sup>13</sup>C, and <sup>31</sup>P) and IR spectroscopy. The molecular structures of <strong>1</strong>–<strong>4</strong> were determined using a single X-ray crystallography. <strong>2</strong> and <strong>3</strong> are structurally characterized novel κ<sup>2</sup><em>S,N<sup>py</sup></em>-bidentate ligands with Hg(II) metal complexes.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 5","pages":"Pages 806-817"},"PeriodicalIF":1.6,"publicationDate":"2025-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048669","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 : 2025-09-03DOI: 10.1080/17415993.2025.2516552
Sydney S. Lahm , Ryan D. McCulla
Computational analysis was conducted to determine the bond dissociation enthalpies (BDEs) of S–O bonds in eight molecules, which were subsequently compared to their experimentally derived BDEs. Computational BDEs were determined utilizing various combinations of density functional theory (DFT) functionals with an assortment of basis sets. Specifically, DFT methods including M06-2X, mPW1LYP, ωB97X-D3, PBE0, and B3P86 were paired with basis sets def2-TZVP/J, def2-TZVP, aug-cc-pV(T + d)Z, 6-311 + G(2df,2p), and def2-QZVP. The comparison between computational and experimental BDEs was evaluated through graphical representation, yielding slope, coefficient of determination (R2), and root mean square error (RMSE) metrics. Additionally, comparative analyses were expanded to include complete basis set methods (CBS-QB3 and CBS-4M), which exhibited comparatively lower accuracy in predicting experimentally determined S–O BDEs than the DFT methods. Among all methods tested, the B3P86/aug-cc-pV(T + d)Z and B3P86/def2-QZVP methods are recommended for computational prediction of BDEs for sulfoxides.
{"title":"Sulfoxide bond dissociation enthalpies predicted by DFT paired with Pople, Dunning, and Karlsruhe basis sets","authors":"Sydney S. Lahm , Ryan D. McCulla","doi":"10.1080/17415993.2025.2516552","DOIUrl":"10.1080/17415993.2025.2516552","url":null,"abstract":"<div><div>Computational analysis was conducted to determine the bond dissociation enthalpies (BDEs) of S–O bonds in eight molecules, which were subsequently compared to their experimentally derived BDEs. Computational BDEs were determined utilizing various combinations of density functional theory (DFT) functionals with an assortment of basis sets. Specifically, DFT methods including M06-2X, mPW1LYP, ωB97X-D3, PBE0, and B3P86 were paired with basis sets def2-TZVP/J, def2-TZVP, aug-<em>cc</em>-pV(T + d)Z, 6-311 + G(2df,2p), and def2-QZVP. The comparison between computational and experimental BDEs was evaluated through graphical representation, yielding slope, coefficient of determination (R<sup>2</sup>), and root mean square error (RMSE) metrics. Additionally, comparative analyses were expanded to include complete basis set methods (CBS-QB3 and CBS-4M), which exhibited comparatively lower accuracy in predicting experimentally determined S–O BDEs than the DFT methods. Among all methods tested, the B3P86/aug-<em>cc</em>-pV(T + d)Z and B3P86/def2-QZVP methods are recommended for computational prediction of BDEs for sulfoxides.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"46 5","pages":"Pages 853-864"},"PeriodicalIF":1.6,"publicationDate":"2025-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048673","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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