Pub Date : 2025-12-17DOI: 10.1080/00397911.2025.2602773
Irina A. Doroshenko (Conceptualization Writing – original draft) , Nazar V. Shmychkov (Investigation Visualization) , Anna V. Shik (Investigation) , Irina I. Levina (Investigation) , Mikhail K. Beklemishev (Conceptualization Writing – review & editing) , Tatyana A. Podrugina (Conceptualization Writing – review & editing)
For sensing small organic molecules, the tricarbocyanine derivatives are particularly efficient if contain at least two binding sites. As a step toward such ditopic structures, we synthesized the tricarbocyanines bearing ionogenic functional groups in the meso-position and studied their complexes with transition metals. New compounds exhibited a differential colorimetric response to individual pharmaceutical compounds tentatively due to the formation of mixed-ligand complexes.
{"title":"Synthesis of tricarbocyanines with ionogenic functional groups: Toward the development of efficient synthetic sensors","authors":"Irina A. Doroshenko (Conceptualization Writing – original draft) , Nazar V. Shmychkov (Investigation Visualization) , Anna V. Shik (Investigation) , Irina I. Levina (Investigation) , Mikhail K. Beklemishev (Conceptualization Writing – review & editing) , Tatyana A. Podrugina (Conceptualization Writing – review & editing)","doi":"10.1080/00397911.2025.2602773","DOIUrl":"10.1080/00397911.2025.2602773","url":null,"abstract":"<div><div>For sensing small organic molecules, the tricarbocyanine derivatives are particularly efficient if contain at least two binding sites. As a step toward such ditopic structures, we synthesized the tricarbocyanines bearing ionogenic functional groups in the <em>meso</em>-position and studied their complexes with transition metals. New compounds exhibited a differential colorimetric response to individual pharmaceutical compounds tentatively due to the formation of mixed-ligand complexes.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 24","pages":"Pages 1909-1919"},"PeriodicalIF":1.8,"publicationDate":"2025-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145842316","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 : 2025-12-17DOI: 10.1080/00397911.2025.2578795
Glanish Jude Martis (Software Writing – original draft) , Praveen S. Mugali (Supervision Writing – review & editing) , Santosh L. Gaonkar (Supervision Writing – review & editing)
Nitrogen-containing heterocycles have created their own hallmark in the field of organic synthesis, chemical sciences and biological sciences. From the past five years, the recent advances observed in the synthesis of N-containing heterocycles via conventional methods by making use of different reagents, bases and appropriate solvent-systems is a salient prospective of this review. The chemistry behind such syntheses is more impactful when employed with cycloadditions, multicomponent reactions, named-reactions and sustainability approaches will aid for in-depth research in heterocyclic chemistry. The use of microwave and ultrasound techniques also play a key role in making chemistry quick. The C-H activation and direct functionalization of nitrogen-containing heterocycles discussed here is among the hot areas of discussion that provide insights of the heterocyclic molecules. Electrochemical oxidative reactions and biocatalytic utility provide the new methods of synthesis. Altogether, the better understanding of the synthesis of biologically active molecules is more impactful and requisite.
{"title":"Synthetic exploration of nitrogen-containing 5- and 6-membered heterocycles and their fused derivatives","authors":"Glanish Jude Martis (Software Writing – original draft) , Praveen S. Mugali (Supervision Writing – review & editing) , Santosh L. Gaonkar (Supervision Writing – review & editing)","doi":"10.1080/00397911.2025.2578795","DOIUrl":"10.1080/00397911.2025.2578795","url":null,"abstract":"<div><div>Nitrogen-containing heterocycles have created their own hallmark in the field of organic synthesis, chemical sciences and biological sciences. From the past five years, the recent advances observed in the synthesis of N-containing heterocycles via conventional methods by making use of different reagents, bases and appropriate solvent-systems is a salient prospective of this review. The chemistry behind such syntheses is more impactful when employed with cycloadditions, multicomponent reactions, named-reactions and sustainability approaches will aid for in-depth research in heterocyclic chemistry. The use of microwave and ultrasound techniques also play a key role in making chemistry quick. The C-H activation and direct functionalization of nitrogen-containing heterocycles discussed here is among the hot areas of discussion that provide insights of the heterocyclic molecules. Electrochemical oxidative reactions and biocatalytic utility provide the new methods of synthesis. Altogether, the better understanding of the synthesis of biologically active molecules is more impactful and requisite.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 24","pages":"Pages 1823-1856"},"PeriodicalIF":1.8,"publicationDate":"2025-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145842314","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 : 2025-12-17DOI: 10.1080/00397911.2025.2601666
Shyam V. Londhe (Data curation Formal analysis Methodology Validation Writing – original draft) , Pornima N. Gund (Formal analysis Investigation Validation) , Abhishek K. Khanzode (Data curation Formal analysis Validation) , Shubham M. Sulakhe (Formal analysis Investigation Software Visualization) , Kavita S. Chavan (Data curation Methodology Visualization) , Prafulla B. Choudhari (Conceptualization Resources Software Supervision Writing – original draft) , Atish T. Paul (Conceptualization Project administration Resources Supervision Writing – review & editing) , Kishan P. Haval (Conceptualization Funding acquisition Project administration Resources Supervision Writing – review & editing)
A new series of quinazolinone–triazole hybrids (5a–q) was synthesized via Cu(I)-catalyzed azide–alkyne cycloaddition. O-Propargylation of compound 1 afforded intermediate 2, which underwent CuAAC with azidobenzenes (3a–q), followed by condensation with anthranilamide to yield the target molecules in good yields. Structures were confirmed by standard spectroscopic techniques. Anticancer evaluation against MCF-7 cells (MTT assay) identified 5a, 5n, and 5o as the most active derivatives, with IC50 values of 17.21, 20.23, and 14.92 μM, respectively. Docking studies showed strong binding affinities toward CDK2, supported by key hydrogen-bonding and hydrophobic interactions. A 100 ns molecular dynamics simulation further validated the stable binding of the 5o–CDK2 complex. Overall, the study introduces a novel class of quinazolinone–triazole derivatives with promising CDK2-targeted anticancer potential, highlighting 5o as a lead candidate for further optimization.
{"title":"Synthesis, in silico and in vitro assessment of new quinazolinone tethered triazole derivatives as anticancer agents","authors":"Shyam V. Londhe (Data curation Formal analysis Methodology Validation Writing – original draft) , Pornima N. Gund (Formal analysis Investigation Validation) , Abhishek K. Khanzode (Data curation Formal analysis Validation) , Shubham M. Sulakhe (Formal analysis Investigation Software Visualization) , Kavita S. Chavan (Data curation Methodology Visualization) , Prafulla B. Choudhari (Conceptualization Resources Software Supervision Writing – original draft) , Atish T. Paul (Conceptualization Project administration Resources Supervision Writing – review & editing) , Kishan P. Haval (Conceptualization Funding acquisition Project administration Resources Supervision Writing – review & editing)","doi":"10.1080/00397911.2025.2601666","DOIUrl":"10.1080/00397911.2025.2601666","url":null,"abstract":"<div><div>A new series of quinazolinone–triazole hybrids (5a–q) was synthesized via Cu(I)-catalyzed azide–alkyne cycloaddition. O-Propargylation of compound 1 afforded intermediate 2, which underwent CuAAC with azidobenzenes (3a–q), followed by condensation with anthranilamide to yield the target molecules in good yields. Structures were confirmed by standard spectroscopic techniques. Anticancer evaluation against MCF-7 cells (MTT assay) identified 5a, 5n, and 5o as the most active derivatives, with IC<sub>50</sub> values of 17.21, 20.23, and 14.92 μM, respectively. Docking studies showed strong binding affinities toward CDK2, supported by key hydrogen-bonding and hydrophobic interactions. A 100 ns molecular dynamics simulation further validated the stable binding of the 5o–CDK2 complex. Overall, the study introduces a novel class of quinazolinone–triazole derivatives with promising CDK2-targeted anticancer potential, highlighting 5o as a lead candidate for further optimization.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 24","pages":"Pages 1857-1877"},"PeriodicalIF":1.8,"publicationDate":"2025-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145842315","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 versatile protocol for the regioselective Csp2–H chalcogenation of indolo[1,2-a]quinoxaline derivatives through I2/DMSO-catalyzed cross-dehydrogenative coupling (CDC) utilizing arylthiols/arylselenols at 80 °C has been established. This C–H functionalization proceeds selectively at the C3-position of indole fragment embedded in indolo[1,2-a]quinoxaline hybrids integrated with various pharmacologically active units, namely aryl, benzoyl, benzoyl ester and phthalazinones. This robust iodine-catalyzed metal-free technique where DMSO acts as oxidant as well as solvent exhibited broad functional group tolerance and enabled the synthesis of diversely decorated sulfenylated/selenylated indolo[1,2-a]quinoxalines under mild reaction conditions within a short reaction time. Interestingly, these chalcogenated indoloquinoxaline hybrids can be achieved via a regioselective cascade C-H activation through two possible reaction pathways, one involving C-insertion followed by chalcogenation (direct) and the other one involving chalcogenation followed by C-insertion (indirect).
{"title":"General and efficient I2/DMSO mediated synthesis of chalcogenated indolo[1,2-a]quinoxalines through direct and indirect methodologies","authors":"Sayanwita Panja (Conceptualization Data curation Formal analysis Investigation Methodology Resources Software Visualization Writing – review & editing) , Arun Dhurey (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Validation Visualization Writing – original draft Writing – review & editing) , Animesh Pramanik (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2602765","DOIUrl":"10.1080/00397911.2025.2602765","url":null,"abstract":"<div><div>A versatile protocol for the regioselective Csp<sup>2</sup>–H chalcogenation of indolo[1,2-<em>a</em>]quinoxaline derivatives through I<sub>2</sub>/DMSO-catalyzed cross-dehydrogenative coupling (CDC) utilizing arylthiols/arylselenols at 80 °C has been established. This C–H functionalization proceeds selectively at the C3-position of indole fragment embedded in indolo[1,2-<em>a</em>]quinoxaline hybrids integrated with various pharmacologically active units, namely aryl, benzoyl, benzoyl ester and phthalazinones. This robust iodine-catalyzed metal-free technique where DMSO acts as oxidant as well as solvent exhibited broad functional group tolerance and enabled the synthesis of diversely decorated sulfenylated/selenylated indolo[1,2-<em>a</em>]quinoxalines under mild reaction conditions within a short reaction time. Interestingly, these chalcogenated indoloquinoxaline hybrids can be achieved via a regioselective cascade C-H activation through two possible reaction pathways, one involving C-insertion followed by chalcogenation (direct) and the other one involving chalcogenation followed by C-insertion (indirect).</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 24","pages":"Pages 1891-1908"},"PeriodicalIF":1.8,"publicationDate":"2025-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145842313","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 study, magnetic deep eutectic solvents with Lewis acid catalytic properties were synthesized for the solvent-free condensation of 1,8-dioxooctahydroxanthene (xanthene) derivatives. The originality of this study is that magnetic deep eutectic solvents based on choline chloride and Lewis acids were investigated for the first time in the condensation reaction of xanthene derivatives. Research results indicated that ferric (III) chloride worked as an efficient catalyst, but nickel (II) chloride and cobalt (II) chloride just yielded intermediate products, and the hydrogen bond donor, choline chloride, improved the catalytic efficiency of Fe3+. The catalyst composed of choline chloride and ferric (III) chloride exhibited the most notable enhancement in the reaction, yielding corresponding xanthene derivatives in high yields and within a short reaction time. The formation of the catalysts was evaluated by FTIR, TGA, VSM, and Raman methods, and their stability and reusability were examined. The catalyst showed stability after five cycles. The research also demonstrated that a 1:2 ratio of choline chloride to ferric (III) chloride supported effective intermolecular hydrogen bonding, consequently boosting the catalytic effectiveness of Fe³+ ions in the procedure.
{"title":"An efficient synthesis of xanthene derivatives enhanced by magnetic deep eutectic solvent from choline chloride and ferric (III) chloride","authors":"Vinh Hoang-Phu Nguyen (Investigation) , Dung Duc Pham (Investigation)","doi":"10.1080/00397911.2025.2599467","DOIUrl":"10.1080/00397911.2025.2599467","url":null,"abstract":"<div><div>In this study, magnetic deep eutectic solvents with Lewis acid catalytic properties were synthesized for the solvent-free condensation of 1,8-dioxooctahydroxanthene (xanthene) derivatives. The originality of this study is that magnetic deep eutectic solvents based on choline chloride and Lewis acids were investigated for the first time in the condensation reaction of xanthene derivatives. Research results indicated that ferric (III) chloride worked as an efficient catalyst, but nickel (II) chloride and cobalt (II) chloride just yielded intermediate products, and the hydrogen bond donor, choline chloride, improved the catalytic efficiency of Fe<sup>3+</sup>. The catalyst composed of choline chloride and ferric (III) chloride exhibited the most notable enhancement in the reaction, yielding corresponding xanthene derivatives in high yields and within a short reaction time. The formation of the catalysts was evaluated by FTIR, TGA, VSM, and Raman methods, and their stability and reusability were examined. The catalyst showed stability after five cycles. The research also demonstrated that a 1:2 ratio of choline chloride to ferric (III) chloride supported effective intermolecular hydrogen bonding, consequently boosting the catalytic effectiveness of Fe³<sup>+</sup> ions in the procedure.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 24","pages":"Pages 1878-1890"},"PeriodicalIF":1.8,"publicationDate":"2025-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145842312","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}
Catalytic protocols have developed as an effective paradigm in synthetic chemistry, providing a simplified approach to the fast synthesis of complex compounds with Atom economy (AE). This review focuses on catalytic approaches to synthesize new quinoline analogs, which are of great interest due to their diverse pharmaceutical and biological activities, such as anticancer, antibacterial, and anti-inflammatory effects. By emphasizing recent review in this decade, the article highlights how catalysts can speed up the development of quinoline derivatives with varied functional groups, allowing for fine-tuning of their characteristics for specific pharmacological applications, also covers the positive aspects of catalytic reactions, which include faster reaction times, greater yields, the selectivity and functional groups, possibilities of utilizing green chemistry concepts and innovative catalytic systems in one-pot quinoline synthesis are discussed. This review emphasizes the importance of catalytic innovations in facilitating the development of novel quinoline-based drug candidates with potential therapeutic applications.
{"title":"Catalyzed protocol in the development of new quinoline derivatives: Recent updates","authors":"Mohd Arham Siddiqui (Writing – original draft Writing – review & editing) , Salahuddin (Conceptualization Methodology) , Rajnish Kumar (Conceptualization Methodology) , Avijit Mazumder (Data curation Methodology) , Mohamed Jawed Ahsan (Formal analysis Validation) , Mohammad Shahar Yar (Data curation Methodology)","doi":"10.1080/00397911.2025.2576717","DOIUrl":"10.1080/00397911.2025.2576717","url":null,"abstract":"<div><div>Catalytic protocols have developed as an effective paradigm in synthetic chemistry, providing a simplified approach to the fast synthesis of complex compounds with Atom economy (AE). This review focuses on catalytic approaches to synthesize new quinoline analogs, which are of great interest due to their diverse pharmaceutical and biological activities, such as anticancer, antibacterial, and anti-inflammatory effects. By emphasizing recent review in this decade, the article highlights how catalysts can speed up the development of quinoline derivatives with varied functional groups, allowing for fine-tuning of their characteristics for specific pharmacological applications, also covers the positive aspects of catalytic reactions, which include faster reaction times, greater yields, the selectivity and functional groups, possibilities of utilizing green chemistry concepts and innovative catalytic systems in one-pot quinoline synthesis are discussed. This review emphasizes the importance of catalytic innovations in facilitating the development of novel quinoline-based drug candidates with potential therapeutic applications.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 23","pages":"Pages 1743-1773"},"PeriodicalIF":1.8,"publicationDate":"2025-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145760554","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 series of new pyrazol-3-one-derived spiro compounds 4 containing dihydro-quinazolinone moiety were synthesized by the reaction of pyrazole-4,5-diones 1 and 2-aminobenzamides 2. Thermal treatment of 1 with 2 in boiling toluene in the presence of a catalytic amount of p-toluenesulfonic acid (p-TsOH) caused a nucleophilic addition/dehydration/intramolecular cyclization sequence to give the corresponding pyrazol-3-one-derived spiro compounds 4 in moderate to good yields. All the synthesized compounds 4 were characterized by spectroscopic analysis.
{"title":"An efficient synthesis of novel pyrazol-3-one-derived spiro compounds containing dihydro-quinazolinone moiety","authors":"Takafumi Fujita (Investigation Methodology Writing – review & editing) , Fumi Okabe-Nakahara (Investigation Methodology Writing – review & editing) , Hiroshi Maruoka (Investigation Methodology Writing – review & editing) , Eiichi Masumoto (Investigation Methodology Writing – review & editing)","doi":"10.1080/00397911.2025.2597379","DOIUrl":"10.1080/00397911.2025.2597379","url":null,"abstract":"<div><div>A series of new pyrazol-3-one-derived spiro compounds <strong>4</strong> containing dihydro-quinazolinone moiety were synthesized by the reaction of pyrazole-4,5-diones <strong>1</strong> and 2-aminobenzamides <strong>2</strong>. Thermal treatment of <strong>1</strong> with <strong>2</strong> in boiling toluene in the presence of a catalytic amount of <em>p</em>-toluenesulfonic acid (<em>p</em>-TsOH) caused a nucleophilic addition/dehydration/intramolecular cyclization sequence to give the corresponding pyrazol-3-one-derived spiro compounds <strong>4</strong> in moderate to good yields. All the synthesized compounds <strong>4</strong> were characterized by spectroscopic analysis.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 23","pages":"Pages 1782-1790"},"PeriodicalIF":1.8,"publicationDate":"2025-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145760553","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The synthetic sequence involves the preparation of key Aminolactone 1 via four novel intermediates, which is common key intermediate for the synthesis of anticancer drugs: Trabectedin 2 and Lurbinectedin 3. The novelty of this route initiates with Knoevenagel condensation, furnishing 20, which is subsequently coupled with (1,3-dioxolan-2-yl)methanol 21 to yield 22, with predominantly desired isomer (9:1) which is more advantageous when the reported conditions. 22 is then undergoes Curtius rearrangement, generating 23 via an isocyanate intermediate, that is further treated with Rh-based chiral catalyst. This Rh-catalyzed asymmetric transformation affords the target compound 24 with exceptional enantioselectivity (ee > 99.8%), by utilizing minimal catalyst loading. The optimized conditions result in a significant enhancement in overall yield and cost efficiency of the synthetic process for the preparation of the key amino lactone (1) intermediate of Trabectedin and Lurbinectedin.
{"title":"A new, efficient, and improved process for the synthesis of key aminolactone intermediate for preparation of anticancer drugs: Trabectedin and Lurbinectedin","authors":"Chandrasekhar Byravakunta (Data curation Investigation Methodology Validation Writing – original draft) , Ramesh Kola (Conceptualization Supervision Writing – review & editing) , Nareshkumar Reddy Kondampally (Formal analysis) , Subba Narasimhulu Porala (Resources) , Naresh Reddy Kanakanola (Validation Visualization) , Pavankumar Reddy Bandla (Software Visualization)","doi":"10.1080/00397911.2025.2596114","DOIUrl":"10.1080/00397911.2025.2596114","url":null,"abstract":"<div><div>The synthetic sequence involves the preparation of key Aminolactone <strong>1</strong> via four novel intermediates, which is common key intermediate for the synthesis of anticancer drugs: Trabectedin <strong>2</strong> and Lurbinectedin <strong>3</strong>. The novelty of this route initiates with Knoevenagel condensation, furnishing <strong>20</strong>, which is subsequently coupled with (1,3-dioxolan-2-yl)methanol <strong>21</strong> to yield <strong>22</strong>, with predominantly desired isomer (9:1) which is more advantageous when the reported conditions. <strong>22</strong> is then undergoes Curtius rearrangement, generating <strong>23</strong> via an isocyanate intermediate, that is further treated with Rh-based chiral catalyst. This Rh-catalyzed asymmetric transformation affords the target compound <strong>24</strong> with exceptional enantioselectivity (ee > 99.8%), by utilizing minimal catalyst loading. The optimized conditions result in a significant enhancement in overall yield and cost efficiency of the synthetic process for the preparation of the key amino lactone (<strong>1</strong>) intermediate of Trabectedin and Lurbinectedin.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 23","pages":"Pages 1774-1781"},"PeriodicalIF":1.8,"publicationDate":"2025-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145760552","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 : 2025-12-02DOI: 10.1080/00397911.2025.2599470
Ahmed E. M. Mekky (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing) , Ahmed A. M. Ahmed (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing) , Sherif M. H. Sanad (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing)
The goal of this study is to investigate the antibacterial activity of pyrazolo[1,5-a]pyrimidine-fused chromeno[2,3-b]pyridine hybrids 1a-1n linked to 4,6-diarylnicotinonitrile units. The desired hybrids are prepared, in 77-88% yields, by reacting the appropriate 4,6-diarylnicotinonitrile-based salicylaldehydes 2a-2j with 3-cyanopyrazolo[1,5-a]pyrimidine-linked acetonitriles 3a,b. The reaction was mediated in refluxing ethanolic sodium ethoxide solution for 6–8 h. The new pentacyclic hybrids displayed a diverse antibacterial activity. A structure-activity relationship study was adopted to explore the influence of the electronic nature of the aryl units attached to the nicotinonitrile-C4 and C6 on the obtained activity. The hybrids linked to 4-(4-methoxyphenyl)-6-(p-tolyl)nicotinonitrile 1i and 1 m, or 4,6-bis(4-methoxyphenyl)nicotinonitrile 1j and 1n, demonstrated comparable in vitro MIC/MBC values to ciprofloxacin. The MIC and MBC values varied from 4.5-3.0 and 4.9–5.9 µM, respectively.
{"title":"New pyrazolo[1,5-a]pyrimidine-fused chromeno[2,3-b]pyridine hybrids linked to 4,6-diarylnicotinonitrile units: Synthesis, antibacterial screening and SAR study","authors":"Ahmed E. M. Mekky (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing) , Ahmed A. M. Ahmed (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing) , Sherif M. H. Sanad (Conceptualization Data curation Formal analysis Investigation Methodology Project administration Resources Software Supervision Validation Visualization Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2599470","DOIUrl":"10.1080/00397911.2025.2599470","url":null,"abstract":"<div><div>The goal of this study is to investigate the antibacterial activity of pyrazolo[1,5-<em>a</em>]pyrimidine-fused chromeno[2,3-<em>b</em>]pyridine hybrids <strong>1a-1n</strong> linked to 4,6-diarylnicotinonitrile units. The desired hybrids are prepared, in 77-88% yields, by reacting the appropriate 4,6-diarylnicotinonitrile-based salicylaldehydes <strong>2a-2j</strong> with 3-cyanopyrazolo[1,5-<em>a</em>]pyrimidine-linked acetonitriles <strong>3a,b</strong>. The reaction was mediated in refluxing ethanolic sodium ethoxide solution for 6–8 h. The new pentacyclic hybrids displayed a diverse antibacterial activity. A structure-activity relationship study was adopted to explore the influence of the electronic nature of the aryl units attached to the nicotinonitrile-C4 and C6 on the obtained activity. The hybrids linked to 4-(4-methoxyphenyl)-6-(<em>p</em>-tolyl)nicotinonitrile <strong>1i</strong> and <strong>1 m</strong>, or 4,6-bis(4-methoxyphenyl)nicotinonitrile <strong>1j</strong> and <strong>1n</strong>, demonstrated comparable in vitro MIC/MBC values to ciprofloxacin. The MIC and MBC values varied from 4.5-3.0 and 4.9–5.9 µM, respectively.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 23","pages":"Pages 1791-1805"},"PeriodicalIF":1.8,"publicationDate":"2025-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145760555","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 : 2025-12-02DOI: 10.1080/00397911.2025.2597372
Yucheng Cui (Data curation Formal analysis Investigation Writing – original draft) , Chengfei Li (Investigation Writing – review & editing) , Wengui Duan (Funding acquisition Methodology Supervision Writing – review & editing) , Qijin Mo (Supervision) , Bo Cen (Investigation Supervision) , Xianli Ma (Funding acquisition Resources Supervision Writing – review & editing) , Guishan Lin (Methodology Software)
In an attempt to discover natural product-derived novel green herbicides, eighteen novel cinnamaldehyde-derived 1,3,4-oxadiazole-amide compounds were synthesized by multi-step reaction, among them the key intermediate cinnamaldehyde-derived 2-amino-1,3,4-oxadiazole (3) was prepared under ultrasound irradiation. Their herbicidal activities were evaluated, and it was found that the target compounds exhibited good inhibition activity against the dicotyledon plant rape (Brassica campestris). A reasonable and effective 3-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) model was established to investigate the effect of different substituent groups in the benzene ring of the target compounds on their herbicidal activity. Meanwhile, the influence of the frontier molecular orbitals and electrostatic potentials of the cinnamaldehyde skeleton and 1,3,4-oxadiazole-amide moiety in the target compounds 4f, 4l, 4r, and 4b on their herbicidal activity was also explored employing Density Functional Theory (DFT) calculation. Besides, the action mechanism of the target compounds was preliminarily investigated by molecular docking and concise molecular dynamics simulation.
{"title":"Synthesis, herbicidal activity, and structure-activity relationship study of cinnamaldehyde-derived 1,3,4-oxadiazole-amide compounds","authors":"Yucheng Cui (Data curation Formal analysis Investigation Writing – original draft) , Chengfei Li (Investigation Writing – review & editing) , Wengui Duan (Funding acquisition Methodology Supervision Writing – review & editing) , Qijin Mo (Supervision) , Bo Cen (Investigation Supervision) , Xianli Ma (Funding acquisition Resources Supervision Writing – review & editing) , Guishan Lin (Methodology Software)","doi":"10.1080/00397911.2025.2597372","DOIUrl":"10.1080/00397911.2025.2597372","url":null,"abstract":"<div><div>In an attempt to discover natural product-derived novel green herbicides, eighteen novel cinnamaldehyde-derived 1,3,4-oxadiazole-amide compounds were synthesized by multi-step reaction, among them the key intermediate cinnamaldehyde-derived 2-amino-1,3,4-oxadiazole (<strong>3</strong>) was prepared under ultrasound irradiation. Their herbicidal activities were evaluated, and it was found that the target compounds exhibited good inhibition activity against the dicotyledon plant rape (<em>Brassica campestris</em>). A reasonable and effective 3-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) model was established to investigate the effect of different substituent groups in the benzene ring of the target compounds on their herbicidal activity. Meanwhile, the influence of the frontier molecular orbitals and electrostatic potentials of the cinnamaldehyde skeleton and 1,3,4-oxadiazole-amide moiety in the target compounds <strong>4f</strong>, <strong>4l</strong>, <strong>4r</strong>, and <strong>4b</strong> on their herbicidal activity was also explored employing Density Functional Theory (DFT) calculation. Besides, the action mechanism of the target compounds was preliminarily investigated by molecular docking and concise molecular dynamics simulation.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 23","pages":"Pages 1806-1821"},"PeriodicalIF":1.8,"publicationDate":"2025-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145760872","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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