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}
Eco-friendly construction of a 3-(3,5-bis(trifluoromethyl)phenyl)-1-((5-phenyl-1,3,4-oxadiazol-2-yl) methyl)-1,8-naphthyridin-2(1H)-one derivatives (10a–j) under microwave method furnished excellent yields in minimal time with maximum selectivity in the presence of PhI(OAc)2. This route aligns with the principles of green chemistry due to its significantly reduced reaction time and enriched energy efficiency, simplicity, and high yields. The synthesized compounds were characterized by spectroscopic techniques IR,1H NMR,13C NMR, Mass spectrometry, and elemental analysis studies. All the synthesized compounds cytotoxicity was tested against four cancer cell lines, MCF-7, Colo-205, A549, and SiHa human Cervix cancer cell lines; all the compounds demonstrated remarkable in vitro anticancer activity, notably, among them, compound 10i exhibited the most potent anti-cancer activity of IC50 valves are 11.21 ± 0.17 μM (MCF-7 breast cancer cell line), 11.62 ± 0.54 μM (Colo-205 colon cancer cell line), 17.85 ± 0.48 μM (A549 lung carcinoma epithelial cells), 19.64 ± 0.46 μM (SiHa human Cervix cancer cell line) compared with clinical standard drug.
{"title":"Green synthesis and anticancer evaluation of novel bis-(trifluoromethyl-5-phenyl-1,3,4-oxadiazol-2-yl) methyl)-1,8-naphthyridine scaffolds","authors":"Mahesh Ellanti (Conceptualization Data curation Validation Writing – review & editing) , Divya A (Software) , Kavati Shireesha (Visualization) , Kumara Swamy Jella (Supervision)","doi":"10.1080/00397911.2025.2501211","DOIUrl":"10.1080/00397911.2025.2501211","url":null,"abstract":"<div><div>Eco-friendly construction of a 3-(3,5-bis(trifluoromethyl)phenyl)-1-((5-phenyl-1,3,4-oxadiazol-2-yl) methyl)-1,8-naphthyridin-2(1H)-one derivatives (<strong>10a–j</strong>) under microwave method furnished excellent yields in minimal time with maximum selectivity in the presence of PhI(OAc)<sub>2</sub>. This route aligns with the principles of green chemistry due to its significantly reduced reaction time and enriched energy efficiency, simplicity, and high yields. The synthesized compounds were characterized by spectroscopic techniques IR,<sup>1</sup>H NMR,<sup>13</sup>C NMR, Mass spectrometry, and elemental analysis studies. All the synthesized compounds cytotoxicity was tested against four cancer cell lines, MCF-7, Colo-205, A549, and SiHa human Cervix cancer cell lines; all the compounds demonstrated remarkable <em>in vitro</em> anticancer activity, notably, among them, compound 10i exhibited the most potent anti-cancer activity of IC<sub>50</sub> valves are 11.21 ± 0.17 μM (MCF-7 breast cancer cell line), 11.62 ± 0.54 μM (Colo-205 colon cancer cell line), 17.85 ± 0.48 μM (A549 lung carcinoma epithelial cells), 19.64 ± 0.46 μM (SiHa human Cervix cancer cell line) compared with clinical standard drug.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 11","pages":"Pages 815-824"},"PeriodicalIF":1.8,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144124340","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 : 2025-05-07DOI: 10.1080/00397911.2025.2500720
Nirmal Singh (Conceptualization Formal analysis Methodology Writing – original draft) , Ankur G Pandey (Writing – review & editing)
Catalysts play an integral role in rationalizing several organic reactions despite suffering major challenges like poor efficiency, high cost and toxicity. In this work, we have reported a green, cost effective and highly efficient squaric acid as an organocatalyst for catalyzing two of the most vital organic reactions, Knoevenagel condensation and 1,6-conjugate addition reactions. Under our optimized conditions, the organocatayst showed excellent yields of up to 94% for both the reactions with an extensive substrate scope and excellent reusability for multiple reaction cycles. In addition, the catalytic efficacy of squaric acid was showcased by employing it in the synthesis of 2-amino-4H-chromene derivatives.
{"title":"Squaric acid as an organocatalyst for Knoevenagel condensation and 1,6-conjugate addition reactions","authors":"Nirmal Singh (Conceptualization Formal analysis Methodology Writing – original draft) , Ankur G Pandey (Writing – review & editing)","doi":"10.1080/00397911.2025.2500720","DOIUrl":"10.1080/00397911.2025.2500720","url":null,"abstract":"<div><div>Catalysts play an integral role in rationalizing several organic reactions despite suffering major challenges like poor efficiency, high cost and toxicity. In this work, we have reported a green, cost effective and highly efficient squaric acid as an organocatalyst for catalyzing two of the most vital organic reactions, Knoevenagel condensation and 1,6-conjugate addition reactions. Under our optimized conditions, the organocatayst showed excellent yields of up to 94% for both the reactions with an extensive substrate scope and excellent reusability for multiple reaction cycles. In addition, the catalytic efficacy of squaric acid was showcased by employing it in the synthesis of 2-amino-<em>4H</em>-chromene derivatives.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 11","pages":"Pages 804-814"},"PeriodicalIF":1.8,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144124369","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 : 2025-05-05DOI: 10.1080/00397911.2025.2500050
Jin Li (Investigation Writing – original draft) , Haotian Cao (Investigation Methodology) , Hongyou Tian (Data curation Investigation) , Huaju Li (Data curation) , Yongke Hu (Funding acquisition Project administration Writing – review & editing)
A practical and efficient methodology for the construction of quinazolinones from readily available alcohols and o-aminobenzamides in the presence of DTBP/Cu(OTf)2 has been developed. This catalytic system exhibits good functional group tolerance and could afford a range of quinazolinones in good to excellent yields. In case of gram-scale reaction, 2-phenylquinazolin-4(3H)-one (3a) was obtained in 86% isolated yield, which indicated this protocol was amenable to scale up and had a potential value in industry. In addition, a plausible reaction mechanism involving a radical process has been proposed, and further applications of this catalytic system are under way in our laboratory.
{"title":"DTBP mediated tandem oxidative reaction of o-aminobenzamides with alcohols for the synthesis of quinazolinones","authors":"Jin Li (Investigation Writing – original draft) , Haotian Cao (Investigation Methodology) , Hongyou Tian (Data curation Investigation) , Huaju Li (Data curation) , Yongke Hu (Funding acquisition Project administration Writing – review & editing)","doi":"10.1080/00397911.2025.2500050","DOIUrl":"10.1080/00397911.2025.2500050","url":null,"abstract":"<div><div>A practical and efficient methodology for the construction of quinazolinones from readily available alcohols and <em>o</em>-aminobenzamides in the presence of DTBP/Cu(OTf)<sub>2</sub> has been developed. This catalytic system exhibits good functional group tolerance and could afford a range of quinazolinones in good to excellent yields. In case of gram-scale reaction, 2-phenylquinazolin-4(3<em>H</em>)-one (<strong>3a</strong>) was obtained in 86% isolated yield, which indicated this protocol was amenable to scale up and had a potential value in industry. In addition, a plausible reaction mechanism involving a radical process has been proposed, and further applications of this catalytic system are under way in our laboratory.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 10","pages":"Pages 774-782"},"PeriodicalIF":1.8,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143948411","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 simple and efficient ligand-assisted iron-catalyzed system for the C-N coupling of 7-azaindole with aryl iodides was developed using water as the sole solvent. Under the optimum conditions, the N-arylated products were obtained in good yields up to 96%.
{"title":"Iron catalyzed N-arylation of 7-azaindole with aryl iodides","authors":"Yong-Chua Teo (Conceptualization Funding acquisition Supervision Writing – original draft Writing – review & editing) , Ying-Rui Tan (Investigation Methodology) , Wei-Zhi Ang (Investigation Methodology) , Anthia Shun-Ai Teo (Investigation Methodology)","doi":"10.1080/00397911.2025.2496968","DOIUrl":"10.1080/00397911.2025.2496968","url":null,"abstract":"<div><div>A simple and efficient ligand-assisted iron-catalyzed system for the C-N coupling of 7-azaindole with aryl iodides was developed using water as the sole solvent. Under the optimum conditions, the N-arylated products were obtained in good yields up to 96%.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 10","pages":"Pages 739-748"},"PeriodicalIF":1.8,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143948427","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}
Tuberculosis (TB) remains a significant global health challenge, with 10 million new cases and 1 million deaths annually. The limited availability of anti-TB drugs, prolonged treatment regimens, and drug resistance underscores the urgent need for new therapeutic agents. Leveraging the pharmacological potential of benzimidazole and thiazolylhydrazone scaffolds, we designed and synthesized a series of novel benzimidazole-thiazolylhydrazone derivatives. These compounds were prepared via reactions of phenacyl bromides with thiosemicarbazide and benzimidazole-containing arylaldehydes in ethanol with catalytic acetic acid. In vitro testing against Mycobacterium tuberculosis (H37Rv) revealed notable activity for 4-fluorophenyl (4b) and 4-bromophenyl (4d) derivatives, with MIC values of 3.125 μg/mL and 6.25 μg/mL, respectively. Molecular docking suggested compound 4b targets DprE1, crucial in mycobacterial cell wall synthesis, with a binding energy of −10.9 kcal/mol. In silico ADME analysis confirmed drug-likeness, and TOPKAT studies indicated non-carcinogenicity. These results position compound 4b as a promising lead for further TB drug development.
{"title":"Design, synthesis and antimycobacterial evaluation of benzimidazole-thiazolylhydrazone derivatives: In silico molecular docking studies, DFT analysis and ADMET predictions","authors":"Arya C. G. (Data curation Formal analysis Methodology Writing – original draft) , Jyothi Kumari (Data curation Formal analysis) , Siddhardha Busi (Data curation Formal analysis Investigation Writing – review & editing) , Simi Asma Salim (Data curation Formal analysis) , Munugala Chandrakanth (Data curation Formal analysis Software) , Dharmarajan Sriram (Data curation Formal analysis Investigation Writing – review & editing) , Ramesh Gondru (Data curation Formal analysis Software Visualization Writing – review & editing) , Janardhan Banothu (Conceptualization Funding acquisition Investigation Project administration Resources Supervision Validation Visualization Writing – review & editing)","doi":"10.1080/00397911.2025.2498535","DOIUrl":"10.1080/00397911.2025.2498535","url":null,"abstract":"<div><div>Tuberculosis (TB) remains a significant global health challenge, with 10 million new cases and 1 million deaths annually. The limited availability of anti-TB drugs, prolonged treatment regimens, and drug resistance underscores the urgent need for new therapeutic agents. Leveraging the pharmacological potential of benzimidazole and thiazolylhydrazone scaffolds, we designed and synthesized a series of novel benzimidazole-thiazolylhydrazone derivatives. These compounds were prepared <em>via</em> reactions of phenacyl bromides with thiosemicarbazide and benzimidazole-containing arylaldehydes in ethanol with catalytic acetic acid. <em>In vitro</em> testing against <em>Mycobacterium tuberculosis</em> (H37Rv) revealed notable activity for 4-fluorophenyl (<strong>4b</strong>) and 4-bromophenyl (<strong>4d</strong>) derivatives, with MIC values of 3.125 μg/mL and 6.25 μg/mL, respectively. Molecular docking suggested compound <strong>4b</strong> targets DprE1, crucial in mycobacterial cell wall synthesis, with a binding energy of −10.9 kcal/mol. <em>In silico</em> ADME analysis confirmed drug-likeness, and TOPKAT studies indicated non-carcinogenicity. These results position compound <strong>4b</strong> as a promising lead for further TB drug development.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 10","pages":"Pages 758-773"},"PeriodicalIF":1.8,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143948410","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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