Pub Date : 2024-10-15DOI: 10.1080/00397911.2024.2408605
Somaiah Nalla , S. Aravind , Sri Charitha Annam , K. V. Padmavathi , Tasqeeruddin Syed , Mannam Subbarao
A new series of 1,2,3-triazole skeleton incorporated pyrrole derivatives (11a–j) were developed and their chemical structures were confirmed by analytical data. Further, the anticancer profile of these newly derived compounds 11a–j was assessed against four types of human cancer cell lines such as human breast cancer (MCF-7), lung cancer (A549), colon cancer (Colo-205) and ovarian cancer (A2780) by employing of the MTT method and was compared with etoposide used as a positive control. Most of the examined derivatives displayed moderate to good activity compared with the positive control. Among them, five compounds 11a, 11b, 11c, 11d, and 11e showed more potent activity. Particularly, compound 11a showed superior activity.
{"title":"Synthesis and biological evaluation of 1, 2, 3-triazole incorporated pyrrole derivatives as anticancer agents","authors":"Somaiah Nalla , S. Aravind , Sri Charitha Annam , K. V. Padmavathi , Tasqeeruddin Syed , Mannam Subbarao","doi":"10.1080/00397911.2024.2408605","DOIUrl":"10.1080/00397911.2024.2408605","url":null,"abstract":"<div><div>A new series of 1,2,3-triazole skeleton incorporated pyrrole derivatives (<strong>11a–j</strong>) were developed and their chemical structures were confirmed by analytical data. Further, the anticancer profile of these newly derived compounds <strong>11a–j</strong> was assessed against four types of human cancer cell lines such as human breast cancer (MCF-7), lung cancer (A549), colon cancer (Colo-205) and ovarian cancer (A2780) by employing of the MTT method and was compared with etoposide used as a positive control. Most of the examined derivatives displayed moderate to good activity compared with the positive control. Among them, five compounds <strong>11a, 11b, 11c, 11d</strong>, and <strong>11e</strong> showed more potent activity. Particularly, compound <strong>11a</strong> showed superior activity.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 21","pages":"Pages 1828-1841"},"PeriodicalIF":1.8,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142528223","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}
Sequential Knoevenagel condensation/cyclization using cyclic active methylene compounds such as Meldrum’s acid have been studied. The reaction of 2-(1-phenylvinyl)benzaldehyde and Meldrum’s acid, dimedone, or 1,3-indandione with piperidine/AcOH or L-proline at room temperature for 17–18 h gave cyclized indene derivatives in 63–80% yield. The reaction of 2-(3,5-dimethoxyphenyl)benzaldehyde and Meldrum’s acid at room temperature for 17 h gave a fluorene derivative in 98% yield. Furthermore, the reaction of 2-(3,5-dimethoxybenzyl)benzaldehyde and Meldrum’s acid with piperidine at room temperature for 18 h gave a dihydroanthracene derivative bearing Meldrum’s acid in 83% yield. The reaction of 2-(3,5-dimethoxybenzyl)benzaldehyde and Meldrum’s acid with piperidine at 110 °C for 2 h gave Meldrum’s acid fragmentated dihydroanthracene derivative in 48% yield. The reaction mechanisms of the cyclization steps and Meldrum’s acid fragmentation have been examined by the DFT calculations.
{"title":"Sequential Knoevenagel condensation/cyclization reaction using Meldrum’s acid","authors":"Shoko Yamazaki , Kohtaro Katayama , Yuta Mouri , Yuki Iwataki , Yuji Mikata , Tsumoru Morimoto","doi":"10.1080/00397911.2024.2413165","DOIUrl":"10.1080/00397911.2024.2413165","url":null,"abstract":"<div><div>Sequential Knoevenagel condensation/cyclization using cyclic active methylene compounds such as Meldrum’s acid have been studied. The reaction of 2-(1-phenylvinyl)benzaldehyde and Meldrum’s acid, dimedone, or 1,3-indandione with piperidine/AcOH or L-proline at room temperature for 17–18 h gave cyclized indene derivatives in 63–80% yield. The reaction of 2-(3,5-dimethoxyphenyl)benzaldehyde and Meldrum’s acid at room temperature for 17 h gave a fluorene derivative in 98% yield. Furthermore, the reaction of 2-(3,5-dimethoxybenzyl)benzaldehyde and Meldrum’s acid with piperidine at room temperature for 18 h gave a dihydroanthracene derivative bearing Meldrum’s acid in 83% yield. The reaction of 2-(3,5-dimethoxybenzyl)benzaldehyde and Meldrum’s acid with piperidine at 110 °C for 2 h gave Meldrum’s acid fragmentated dihydroanthracene derivative in 48% yield. The reaction mechanisms of the cyclization steps and Meldrum’s acid fragmentation have been examined by the DFT calculations.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 21","pages":"Pages 1893-1907"},"PeriodicalIF":1.8,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142528230","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 : 2024-10-10DOI: 10.1080/00397911.2024.2410933
Nadia Hanafy Metwally , Zinab Atwa Saad
Novel 2-imino-6-(aryldiazenyl)-2H-chromene-3-carboxamides 6a–e, 2-amino-4H-cyclopenta or benzo[b]thiophene-3-carboxamides 10a,b, 2,7-diaminopyrazolo[1,5-a]pyrimidine-6-carboxamides 13a–e, pyrimidine-5-carboxamides 14, 15 and 3-amino-1H-pyrazole-4-carboxamide 16 were synthesized from the reaction of 2-cyano-N-(1,3-dihydroxy-2-(hydroxyl-methyl) propan-2-yl) acetamide 2 with 4-arylazosalicylaldehydes 5a-e, cyclopentanone and/or cyclohexanone, guanidine derivatives and hydrazine hydrate, respectively. Some new compounds were evaluated for antibacterial activity in vitro, and exhibited good efficacy compared to gentamicin. Compound 4c showed greater activity against gram negative bacteria (Klebsiella pneumonia and Pseudomonas aeruginosa) than standard antibiotic. Compound 4c with two withdrawing groups also showed the higher activity (38.7 ± 0.6) against fungi (Candida albicans) than the Nystatin (20 ± 0.5). On the other hand, compounds 13a, 13c, and 13e have strong cytotoxic activity among the tested compounds in the three selected cancer cell lines (HePG2, MCF7 and Hela). Physicochemical characterization by Swiss ADME predication was also performed for some synthesized compounds exhibiting better biological and antimicrobial properties.
{"title":"An efficient synthesis, characterization, and in silico studies of novel chromenes, thiophenes, pyrazolo[1,5-a]pyrimidines, and pyrimidines as potential antimicrobial and anticancer agents using the bio-buffer tris(hydroxymethyl)aminomethane (THAM)","authors":"Nadia Hanafy Metwally , Zinab Atwa Saad","doi":"10.1080/00397911.2024.2410933","DOIUrl":"10.1080/00397911.2024.2410933","url":null,"abstract":"<div><div>Novel 2-imino-6-(aryldiazenyl)-2<em>H</em>-chromene-3-carboxamides <strong>6a–e</strong>, 2-amino-4<em>H</em>-cyclopenta or benzo[<em>b</em>]thiophene-3-carboxamides <strong>10a,b</strong>, 2,7-diaminopyrazolo[1,5-<em>a</em>]pyrimidine-6-carboxamides <strong>13a–e</strong>, pyrimidine-5-carboxamides <strong>14</strong>, <strong>15</strong> and 3-amino-1<em>H</em>-pyrazole-4-carboxamide <strong>16</strong> were synthesized from the reaction of 2-cyano-<em>N</em>-(1,3-dihydroxy-2-(hydroxyl-methyl) propan-2-yl) acetamide <strong>2</strong> with 4-arylazosalicylaldehydes <strong>5a-e</strong>, cyclopentanone and/or cyclohexanone, guanidine derivatives and hydrazine hydrate, respectively. Some new compounds were evaluated for antibacterial activity <em>in vitro</em>, and exhibited good efficacy compared to gentamicin. Compound <strong>4c</strong> showed greater activity against gram negative bacteria (<em>Klebsiella pneumonia</em> and <em>Pseudomonas aeruginosa</em>) than standard antibiotic. Compound <strong>4c</strong> with two withdrawing groups also showed the higher activity (38.7 ± 0.6) against fungi (<em>Candida albicans</em>) than the Nystatin (20 ± 0.5). On the other hand, compounds <strong>13a</strong>, <strong>13c,</strong> and <strong>13e</strong> have strong cytotoxic activity among the tested compounds in the three selected cancer cell lines (HePG2, MCF7 and Hela). Physicochemical characterization by Swiss ADME predication was also performed for some synthesized compounds exhibiting better biological and antimicrobial properties.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 21","pages":"Pages 1871-1892"},"PeriodicalIF":1.8,"publicationDate":"2024-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142528228","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 Pummerer rearrangement is extensively utilized for the preparation of various heterocyclic compounds, as well as for the introduction of functional groups such as carbonyl, hydroxyl, and amino groups into organic molecules. The reaction mechanism typically proceeds through an initial electrophilic attack by Lewis acid or another electrophile on the sulfur atom of the sulfoxide, leading to the formation of a sulfonium intermediate. Subsequent rearrangement of this intermediate results in the migration of an alkyl/aryl group from sulfur to a neighboring carbon atom, accompanied by the expulsion of a leaving group. The Pummerer rearrangement of quinoline derivatives has significant synthetic utility and has been employed in the synthesis of various compounds. It has found applications in the synthesis of natural products, agrochemicals, pharmaceuticals, diversity-oriented synthesis, functional group transformations, and other fine chemicals. Overall, The Pummerer rearrangement of quinoline derivatives offers a versatile tool for the synthesis of complex molecules in medicinal chemistry.
{"title":"A review on innovative approaches in quinoline/isoquinoline synthesis: Unveiling the Pummerer reaction strategy","authors":"Tanvi Rajiv Goel , Salahuddin , Kavita Rana , Avijit Mazumder , Rajnish Kumar , Mohamed Jawed Ahsan , Mohammad Shahar Yar , Pankaj Kumar Tyagi , Saurabh Singh","doi":"10.1080/00397911.2024.2411718","DOIUrl":"10.1080/00397911.2024.2411718","url":null,"abstract":"<div><div>The Pummerer rearrangement is extensively utilized for the preparation of various heterocyclic compounds, as well as for the introduction of functional groups such as carbonyl, hydroxyl, and amino groups into organic molecules. The reaction mechanism typically proceeds through an initial electrophilic attack by Lewis acid or another electrophile on the sulfur atom of the sulfoxide, leading to the formation of a sulfonium intermediate. Subsequent rearrangement of this intermediate results in the migration of an alkyl/aryl group from sulfur to a neighboring carbon atom, accompanied by the expulsion of a leaving group. The Pummerer rearrangement of quinoline derivatives has significant synthetic utility and has been employed in the synthesis of various compounds. It has found applications in the synthesis of natural products, agrochemicals, pharmaceuticals, diversity-oriented synthesis, functional group transformations, and other fine chemicals. Overall, The Pummerer rearrangement of quinoline derivatives offers a versatile tool for the synthesis of complex molecules in medicinal chemistry.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 24","pages":"Pages 2089-2114"},"PeriodicalIF":1.8,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142706907","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 : 2024-10-04DOI: 10.1080/00397911.2024.2409872
Abdullah Y. A. Alzahrani , Eman A. E. El-Helw , Sayed K. Ramadan
Cancer affects millions of people worldwide. PDK1 enzyme (co-crystallized with BIM-1) controls the proliferation of breast cancer cells. Aiming to resemble BIM-1’s binding, quinoline-based pyrimidinediones and thiazolidinediones were synthesized starting from 2-chloro-3-formylquinoline. Compared with doxorubicin (reference), in vitro antiproliferative activity against MCF7 and HCT116 cancer cell lines showed the most potency of thiobarbiturate 3 and thiazolidinedione 4. In silico molecular docking, DFT, and pharmacokinetics simulations supported the findings. The docking analysis toward PDK1 enzyme showed that most amino acids interacting with co-crystallized ligand (BIM-1) were successfully bonded to our docked substances, especially thiobarbiturate 3 with highest S-score closer to BIM-1. In DFT calculations, this compound exhibited the lowest energy gap and highest softness leading to more response to radical surface interactions. The compounds with significant antiproliferative activity exhibited high electrophilicity values. ADME analysis showed its desirable drug-likeness and oral bioavailability. This work may contribute to developing new potent antiproliferative agents.
{"title":"Synthesis, antiproliferative activity, and in silico studies of quinoline-based pyrimidinedione and thiazolidinedione derivatives","authors":"Abdullah Y. A. Alzahrani , Eman A. E. El-Helw , Sayed K. Ramadan","doi":"10.1080/00397911.2024.2409872","DOIUrl":"10.1080/00397911.2024.2409872","url":null,"abstract":"<div><div>Cancer affects millions of people worldwide. PDK1 enzyme (co-crystallized with BIM-1) controls the proliferation of breast cancer cells. Aiming to resemble BIM-1’s binding, quinoline-based pyrimidinediones and thiazolidinediones were synthesized starting from 2-chloro-3-formylquinoline. Compared with doxorubicin (reference), in vitro antiproliferative activity against MCF7 and HCT116 cancer cell lines showed the most potency of thiobarbiturate <strong>3</strong> and thiazolidinedione <strong>4</strong>. <em>In silico</em> molecular docking, DFT, and pharmacokinetics simulations supported the findings. The docking analysis toward PDK1 enzyme showed that most amino acids interacting with co-crystallized ligand (BIM-1) were successfully bonded to our docked substances, especially thiobarbiturate <strong>3</strong> with highest S-score closer to BIM-1. In DFT calculations, this compound exhibited the lowest energy gap and highest softness leading to more response to radical surface interactions. The compounds with significant antiproliferative activity exhibited high electrophilicity values. ADME analysis showed its desirable drug-likeness and oral bioavailability. This work may contribute to developing new potent antiproliferative agents.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 21","pages":"Pages 1842-1856"},"PeriodicalIF":1.8,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142528229","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 : 2024-09-28DOI: 10.1080/00397911.2024.2409875
Sherif M. H. Sanad , Ahmed E. M. Mekky
MRSA, a resistant bacteria causing severe infections, is targeted by researchers developing new anti-resistance compounds. The study aimed to investigate the MRSA inhibitory activity of two series of benzofuran-pyrazolo[1,5-a]pyrimidines 1 and 2, attached to arene units via methylene or azo linkage, respectively. The desired products were prepared, in 82–92% yields, by reacting benzofuran-based enaminone 4 with the appropriate 1H-pyrazole-3,5-diamines 5 in pyridine at reflux for 5–6 h. The new hybrids showed a wide spectrum of antibacterial activity against different ATCC strains. Products with azo linkage and para-substituted arene units with electron-releasing groups demonstrated higher antibacterial activity. 3-((4-Methoxyphenyl)diazenyl)-linked pyrazolo[1,5-a]pyrimidine 2e demonstrates activity that exceeded the reference ciprofloxacin with MIC/MBC values of 1.8/3.6 µM against S. aureus and E. coli strains. Also, it demonstrated more effective MRSA inhibitory activity than the reference linezolid, with MIC/MBC values of 3.6/14.4 and 1.8/7.2 µM against MRSA ATCC:33591 and ATCC:43300 strains, respectively.
{"title":"Potential MRSA inhibitory activity of some new benzofuran-pyrazolo[1,5-a]pyrimidine hybrids attached to arene units via methylene or azo linkage","authors":"Sherif M. H. Sanad , Ahmed E. M. Mekky","doi":"10.1080/00397911.2024.2409875","DOIUrl":"10.1080/00397911.2024.2409875","url":null,"abstract":"<div><div>MRSA, a resistant bacteria causing severe infections, is targeted by researchers developing new anti-resistance compounds. The study aimed to investigate the MRSA inhibitory activity of two series of benzofuran-pyrazolo[1,5-<em>a</em>]pyrimidines <strong>1</strong> and <strong>2</strong>, attached to arene units <em>via</em> methylene or azo linkage, respectively. The desired products were prepared, in 82–92% yields, by reacting benzofuran-based enaminone <strong>4</strong> with the appropriate 1<em>H</em>-pyrazole-3,5-diamines <strong>5</strong> in pyridine at reflux for 5–6 h. The new hybrids showed a wide spectrum of antibacterial activity against different ATCC strains. Products with azo linkage and para-substituted arene units with electron-releasing groups demonstrated higher antibacterial activity. 3-((4-Methoxyphenyl)diazenyl)-linked pyrazolo[1,5-<em>a</em>]pyrimidine <strong>2e</strong> demonstrates activity that exceeded the reference ciprofloxacin with MIC/MBC values of 1.8/3.6 µM against <em>S. aureus</em> and <em>E. coli</em> strains. Also, it demonstrated more effective MRSA inhibitory activity than the reference linezolid, with MIC/MBC values of 3.6/14.4 and 1.8/7.2 µM against MRSA ATCC:33591 and ATCC:43300 strains, respectively.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 21","pages":"Pages 1857-1870"},"PeriodicalIF":1.8,"publicationDate":"2024-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142528128","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 syntheses of 3,4-dihydropyrimidin-2(1H)-ones by one-pot, three-component condensation of aldehydes, β-ketoesters and urea or thiourea have been made more simple and efficient by using 20 mol% hydrazine sulfate as catalyst. Aldehydes, β-ketoesters and urea are cyclocondensed in the presence of hydrazine sulfate to produce dihydropyrimidines in ethanol under reflux conditions. The advantages of using hydrazine sulfate as a catalyst over the traditional Biginelli reaction conditions include outstanding yields (80–91%) and a shorter (10–15 hours) reaction time. In order to evaluate the antibacterial efficiencies of the synthesized compounds, we have studied the inhibitions of microbial proliferation of both Gram-positive (Bacillus brevis) and Gram-negative (E. coli) bacterial strains in comparison to a control group. The microbial inhibitions occur in the range of 40–98% by different derivatives of dihydropyrimidinones. Molecular docking studies of the synthesized compounds have also been done using software tools such as SwissADME.
{"title":"Unprecedented one-pot synthesis of 3,4-dihydropyrimidine-2-(1h)-ones catalyzed by hydrazine sulfate through Biginelli reaction, ADMET property, molecular docking studies and their antibacterial activity on Bacillus brevis and E. coli","authors":"Brijesh , Divya Singh , Anjana Pandey , Ashutosh Pandey","doi":"10.1080/00397911.2024.2405931","DOIUrl":"10.1080/00397911.2024.2405931","url":null,"abstract":"<div><div>The syntheses of 3,4-dihydropyrimidin-2(1<em>H</em>)-ones by one-pot, three-component condensation of aldehydes, β-ketoesters and urea or thiourea have been made more simple and efficient by using 20 mol% hydrazine sulfate as catalyst. Aldehydes, β-ketoesters and urea are cyclocondensed in the presence of hydrazine sulfate to produce dihydropyrimidines in ethanol under reflux conditions. The advantages of using hydrazine sulfate as a catalyst over the traditional Biginelli reaction conditions include outstanding yields (80–91%) and a shorter (10–15 hours) reaction time. In order to evaluate the antibacterial efficiencies of the synthesized compounds, we have studied the inhibitions of microbial proliferation of both Gram-positive (<em>Bacillus brevis</em>) and Gram-negative (<em>E. coli</em>) bacterial strains in comparison to a control group. The microbial inhibitions occur in the range of 40–98% by different derivatives of dihydropyrimidinones. Molecular docking studies of the synthesized compounds have also been done using software tools such as SwissADME.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 20","pages":"Pages 1771-1784"},"PeriodicalIF":1.8,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142427565","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 : 2024-09-26DOI: 10.1080/00397911.2024.2407435
Jyoti Yadav , C. P. Kaushik , Munish Ahuja , Anil Kumar , Priyanka Yadav , Archna Yadav
In an endeavor to invent new antimalarial and antimicrobial agents, a series of coumarin bound 1,4-disubstituted 1,2,3-triazoles was synthesized through Cu(I)-promoted click reaction between coumarin bound terminal alkynes, that is, 4/7-(prop-2-yn-1-yloxy)-2H-chromen-2-one and 2-azido-N-arylpropanamides. The synthesized 1,2,3-triazoles were characterized by FTIR,1H NMR,13C NMR, and HRMS techniques and were assessed for in vitro antimalarial activity against Plasmodium falciparum as well as in vitro antimicrobial activity against four bacterial strains (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Klebsiella pneumoniae) and two fungal strains (Candida albicans, Aspergillus niger). Compound 7o [(N-(4-fluorophenyl)-2-(4-(((2-oxo-2H-chromen-7-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)propanamide)] displayed better activity against P. falciparum while compound 7y [(N-(3-nitrophenyl)-2-(4-(((2-oxo-2H-chromen-7-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)propanamide)] displayed excellent activity against all the tested bacterial and fungal strains, amongst the synthesized triazoles. Also, the molecular docking studies of the most potent compounds against DNA gyrase (S. aureus) were also performed to have an insight on binding interactions.
{"title":"Design, synthesis, characterization and biological evaluation of coumarin bound 1,2,3-triazoles using click chemistry","authors":"Jyoti Yadav , C. P. Kaushik , Munish Ahuja , Anil Kumar , Priyanka Yadav , Archna Yadav","doi":"10.1080/00397911.2024.2407435","DOIUrl":"10.1080/00397911.2024.2407435","url":null,"abstract":"<div><div>In an endeavor to invent new antimalarial and antimicrobial agents, a series of coumarin bound 1,4-disubstituted 1,2,3-triazoles was synthesized through Cu(I)-promoted click reaction between coumarin bound terminal alkynes, that is, 4/7-(prop-2-yn-1-yloxy)-2<em>H-</em>chromen-2-one and 2-azido-<em>N</em>-arylpropanamides. The synthesized 1,2,3-triazoles were characterized by FTIR,<sup>1</sup>H NMR,<sup>13</sup>C NMR, and HRMS techniques and were assessed for <em>in vitro</em> antimalarial activity against <em>Plasmodium falciparum</em> as well as <em>in vitro</em> antimicrobial activity against four bacterial strains (<em>Staphylococcus aureus</em>, <em>Bacillus subtilis</em>, <em>Escherichia coli</em>, and <em>Klebsiella pneumoniae</em>) and two fungal strains (<em>Candida albicans</em>, <em>Aspergillus niger</em>). Compound <strong>7o</strong> [(<em>N</em>-(4-fluorophenyl)-2-(4-(((2-oxo-2<em>H</em>-chromen-7-yl)oxy)methyl)-1<em>H</em>-1,2,3-triazol-1-yl)propanamide)] displayed better activity against <em>P. falciparum</em> while compound <strong>7y</strong> [(<em>N</em>-(3-nitrophenyl)-2-(4-(((2-oxo-<em>2H</em>-chromen-7-yl)oxy)methyl)-<em>1H</em>-1,2,3-triazol-1-yl)propanamide)] displayed excellent activity against all the tested bacterial and fungal strains, amongst the synthesized triazoles. Also, the molecular docking studies of the most potent compounds against DNA gyrase (<em>S. aureus</em>) were also performed to have an insight on binding interactions.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 21","pages":"Pages 1808-1827"},"PeriodicalIF":1.8,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142528227","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 : 2024-09-19DOI: 10.1080/00397911.2024.2403141
Kajol Ahmed , Pran Gopal Karmaker , Harendra N. Roy
An operationally simple, cost-effective, and environmentally benign method has been described for the synthesis of various polysubstituted benzoxanthenes via L-proline-catalyzed three-component condensation of β-naphthol, aromatic aldehydes, dimedone, or 2-hydroxy-1,4-naphthoquinone in aqueous medium. This process has additional benefits such as simple product isolation and purification techniques, good to higher yields, and above all, efficient catalyst reusability. The addition of sodium dodecyl sulfate is an extra benefit to speed up this reaction.
{"title":"L-proline catalyzed one-pot synthesis of benzoxanthenes in aqueous medium","authors":"Kajol Ahmed , Pran Gopal Karmaker , Harendra N. Roy","doi":"10.1080/00397911.2024.2403141","DOIUrl":"10.1080/00397911.2024.2403141","url":null,"abstract":"<div><div>An operationally simple, cost-effective, and environmentally benign method has been described for the synthesis of various polysubstituted benzoxanthenes via L-proline-catalyzed three-component condensation of β-naphthol, aromatic aldehydes, dimedone, or 2-hydroxy-1,4-naphthoquinone in aqueous medium. This process has additional benefits such as simple product isolation and purification techniques, good to higher yields, and above all, efficient catalyst reusability. The addition of sodium dodecyl sulfate is an extra benefit to speed up this reaction.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 20","pages":"Pages 1736-1747"},"PeriodicalIF":1.8,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142426878","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 : 2024-09-14DOI: 10.1080/00397911.2024.2399795
Pradip Patil , Kaivalya G. Kulkarni , Sanket Jadhav , Yogesh More , Tushar Khaladkar , Abhijit Roychowdhury , Mukund K. Gurjar , S. R. Patil
A commercially scalable five-step synthetic process starting from cis/trans (7:3) mixture of dimethyl 1,4-cyclohexanedicarboxylate is devised for preparation of tranexamic acid with more than 99.5% purity. All impurities are controlled as per monograph. 47% overall yield over five steps has been achieved based on recovery. Epimerization of a cis-predominant isomeric mixture to trans predominant isomeric mixture under mild conditions followed by exploiting the difference in solubility to obtain trans isomer in very high purity is the key feature of the synthesis. In addition to this, use of readily available and cost efficient raw materials/reagents, recycling of cis isomer, explicit design of downstream processing enabling the retention of the trans-stereochemistry until final API are some of the highlights of this synthesis. This process also circumvents the use of hazardous chemicals and harsh reaction conditions making it greener and safer compared to the previous reports.”
{"title":"Scalable synthesis of tranexamic acid under modest reaction conditions using early stage isomerization of dimethyl 1,4-cyclohexanedicarboxylate as a key step","authors":"Pradip Patil , Kaivalya G. Kulkarni , Sanket Jadhav , Yogesh More , Tushar Khaladkar , Abhijit Roychowdhury , Mukund K. Gurjar , S. R. Patil","doi":"10.1080/00397911.2024.2399795","DOIUrl":"10.1080/00397911.2024.2399795","url":null,"abstract":"<div><p>A commercially scalable five-step synthetic process starting from cis/trans (7:3) mixture of dimethyl 1,4-cyclohexanedicarboxylate is devised for preparation of tranexamic acid with more than 99.5% purity. All impurities are controlled as per monograph. 47% overall yield over five steps has been achieved based on recovery. Epimerization of a cis-predominant isomeric mixture to trans predominant isomeric mixture under mild conditions followed by exploiting the difference in solubility to obtain trans isomer in very high purity is the key feature of the synthesis. In addition to this, use of readily available and cost efficient raw materials/reagents, recycling of cis isomer, explicit design of downstream processing enabling the retention of the trans-stereochemistry until final API are some of the highlights of this synthesis. This process also circumvents the use of hazardous chemicals and harsh reaction conditions making it greener and safer compared to the previous reports.”</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 19","pages":"Pages 1665-1678"},"PeriodicalIF":1.8,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142229238","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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