Pub Date : 2024-04-17DOI: 10.1080/00397911.2024.2327047
David S. A. Haneen , Mohamed H. Hekal , Wael S. I. Abou-Elmagd , Wael M. El-Sayed
The poor selectivity, significant toxicity, high cost, and emergence of resistance of conventional chemotherapies are driving motive for the ongoing search for novel anticancer agents. New pyrano[2,3-c]pyrazolopyrimidines were synthesized and examined as antiproliferative agents, and the possible molecular mechanism(s) of action were explored. The mass and elemental analyses, alongside the IR,1H, and 13C NMR spectra, confirmed the proposed structures of the obtained compounds. Derivatives 4 and 7 demonstrated the best antiproliferative profile against HepG2 cancer cells at 4 µM, with a high selectivity index of ∼7–9 folds. They increased the S phase cell population by 51% and 40% and caused a 5- and 11-fold increase in the p21 protein. Compound 7 was superior in inhibiting HepG2 cell migration and delayed wound healing, reducing migration rates by 55% and 90%, respectively. Future studies on the pharmacokinetics, pharmacodynamics, antimetastatic, and antitumor activities in animal models would be a robust advance.
{"title":"Novel pyrano[2,3-c]pyrazolopyrimidines as promising anticancer agents: Design, synthesis, and cell cycle arrest of HepG2 cells at S phase","authors":"David S. A. Haneen , Mohamed H. Hekal , Wael S. I. Abou-Elmagd , Wael M. El-Sayed","doi":"10.1080/00397911.2024.2327047","DOIUrl":"10.1080/00397911.2024.2327047","url":null,"abstract":"<div><p>The poor selectivity, significant toxicity, high cost, and emergence of resistance of conventional chemotherapies are driving motive for the ongoing search for novel anticancer agents. New pyrano[2,3-<em>c</em>]pyrazolopyrimidines were synthesized and examined as antiproliferative agents, and the possible molecular mechanism(s) of action were explored. The mass and elemental analyses, alongside the IR,<sup>1</sup>H, and <sup>13</sup>C NMR spectra, confirmed the proposed structures of the obtained compounds. Derivatives <strong>4</strong> and <strong>7</strong> demonstrated the best antiproliferative profile against HepG2 cancer cells at 4 µM, with a high selectivity index of ∼7–9 folds. They increased the S phase cell population by 51% and 40% and caused a 5- and 11-fold increase in the p21 protein. Compound <strong>7</strong> was superior in inhibiting HepG2 cell migration and delayed wound healing, reducing migration rates by 55% and 90%, respectively. Future studies on the pharmacokinetics, pharmacodynamics, antimetastatic, and antitumor activities in animal models would be a robust advance.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140125388","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 : 2024-04-17DOI: 10.1080/00397911.2024.2316718
Abouelhaoul El Alami , Hamid Sdassi , Said Bouzikri
Over the last few years, benzimidazole-heterocycle hybrid compounds have received considerable attention due to the wide spectrum of their biological property and many important chemical and pharmacological applications. These compounds have revealed antibacterial, antimicrobial, anticoagulant, antidiabetic and other activities, and they have been used as drugs in the market to treat several diseases. Furthermore, hybrid heterocyclic compounds possessing a benzimidazole skeleton exhibit significant complexing and anticorrosive properties. All of these applications have favored the development of a large number of synthetic strategies to prepare these heterocyclic systems in different reaction conditions. Many research articles on the synthesis of benzimidazole-heterocycle hybrid compounds have been reported in the literature. In this review, we present and discuss the synthetic routes of several benzimidazole-heterocycle hybrid compounds.
在过去几年中,苯并咪唑-杂环杂化化合物因其广泛的生物特性和许多重要的化学和医药用途而受到广泛关注。
{"title":"Review of synthesis process of benzimidazole-heterocycle hybrid compounds","authors":"Abouelhaoul El Alami , Hamid Sdassi , Said Bouzikri","doi":"10.1080/00397911.2024.2316718","DOIUrl":"10.1080/00397911.2024.2316718","url":null,"abstract":"<div><p>Over the last few years, benzimidazole-heterocycle hybrid compounds have received considerable attention due to the wide spectrum of their biological property and many important chemical and pharmacological applications. These compounds have revealed antibacterial, antimicrobial, anticoagulant, antidiabetic and other activities, and they have been used as drugs in the market to treat several diseases. Furthermore, hybrid heterocyclic compounds possessing a benzimidazole skeleton exhibit significant complexing and anticorrosive properties. All of these applications have favored the development of a large number of synthetic strategies to prepare these heterocyclic systems in different reaction conditions. Many research articles on the synthesis of benzimidazole-heterocycle hybrid compounds have been reported in the literature. In this review, we present and discuss the synthetic routes of several benzimidazole-heterocycle hybrid compounds.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139756854","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 : 2024-04-17DOI: 10.1080/00397911.2024.2329245
Vikas S. Patil , Gayathri Chunduri , Balaram Kiran Avasarala , Gangaiah L , Pasham Yoganand , Kola Srinivas , Murali Koparala , Nagaraju Devunuri
A catalyst free oxone mediated synthesizing N-alkyl 1, 4-dihydroquinoxaline-2,3-dione has been developed by oxidation of the N-alkyl quinoxalin-2(1H)-one. The developed method is a novel, safest, cost-effective, industrially viable method and applicable for N-substituted and without substitution of 1,4-dihydroquinoxaline-2,3-dione. Consequently, the process is applicable to a broad spectrum of functionality. The reaction can be performed in all organic solvents without any further heating with an extended time and without generating side products. This novel synthetic methodology using Oxone is believed to be the shortest and most efficient to prepare various key intermediates which can be used for further derivatization to make the different biologically active molecules, the key feature of this methodology is not solvent specific, all organic solvents giving the optimum purity and quality using the same reaction condition.
{"title":"The Lacunae identified in processing, analyzing and finding means of catalyst free Oxone mediated through C-3 oxidation of N-alkyl quinoxalin-2(1h)-one","authors":"Vikas S. Patil , Gayathri Chunduri , Balaram Kiran Avasarala , Gangaiah L , Pasham Yoganand , Kola Srinivas , Murali Koparala , Nagaraju Devunuri","doi":"10.1080/00397911.2024.2329245","DOIUrl":"10.1080/00397911.2024.2329245","url":null,"abstract":"<div><p>A catalyst free oxone mediated synthesizing N-alkyl 1, 4-dihydroquinoxaline-2,3-dione has been developed by oxidation of the N-alkyl quinoxalin-2(1<em>H</em>)-one. The developed method is a novel, safest, cost-effective, industrially viable method and applicable for N-substituted and without substitution of 1,4-dihydroquinoxaline-2,3-dione. Consequently, the process is applicable to a broad spectrum of functionality. The reaction can be performed in all organic solvents without any further heating with an extended time and without generating side products. This novel synthetic methodology using Oxone is believed to be the shortest and most efficient to prepare various key intermediates which can be used for further derivatization to make the different biologically active molecules, the key feature of this methodology is not solvent specific, all organic solvents giving the optimum purity and quality using the same reaction condition.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140147791","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 : 2024-04-04DOI: 10.1080/00397911.2024.2335638
Jiecheng Zheng , Feng Gong , Wei Wang , Yue Wu , Dezhang Zhao , Tianyuan Zhang , WenWen Yang , Zongjie Gan
A broad scope of quinazolin-4(3H)-ones or benzothiadiazine 1,1-dioxides was obtained via a transition-metal free and convenient method. This approach involving KHSO4 promoted cyclization and dehydration between diverse functionalized 2-aminobenzamides or 2-aminobenzenesulfonamides and N, N-dimethylformamide derivatives. The protocol offers moderate to excellent yields (45%-93%) under mild condition in a short of reaction time of 6 hours. The use of an environment-friendly and less expensive catalyst KHSO4 also makes this protocol more attractive.
{"title":"KHSO4 promoted practical synthesis of quinazolin-4(3H)-ones and benzothiadiazine 1,1-dioxides","authors":"Jiecheng Zheng , Feng Gong , Wei Wang , Yue Wu , Dezhang Zhao , Tianyuan Zhang , WenWen Yang , Zongjie Gan","doi":"10.1080/00397911.2024.2335638","DOIUrl":"https://doi.org/10.1080/00397911.2024.2335638","url":null,"abstract":"<div><p>A broad scope of quinazolin-4(<em>3H</em>)-ones or benzothiadiazine 1,1-dioxides was obtained via a transition-metal free and convenient method. This approach involving KHSO<sub>4</sub> promoted cyclization and dehydration between diverse functionalized 2-aminobenzamides or 2-aminobenzenesulfonamides and <em>N, N</em>-dimethylformamide derivatives. The protocol offers moderate to excellent yields (45%-93%) under mild condition in a short of reaction time of 6 hours. The use of an environment-friendly and less expensive catalyst KHSO<sub>4</sub> also makes this protocol more attractive.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140548080","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 main objective of the present work is to synthesize and identify the potential breast cancer medication of 2-aryl quinoxaline derivatives via in silico investigations. Synthesis of 2-aryl quinoxaline derivatives have been achieved via the reaction of 3-aroylmethylene-2H-indol-2-ones 1 with various 1,2-diamines. Good yields were obtained at 60 °C in methanol by using graphene oxide (GO) as catalyst, however, the regio selectivity in case of unsymmetrically substituted diamines were low to moderated. This is the first report of the oxidative cleavage of C = C bond during the course of the reaction. Molecular docking study of these synthesized compounds were employed to calculate the binding affinity with human epidermal growth factor receptor 2 (HER2). 6-Bromo-3-phenylpyrido[2,3-b]pyrazine 3k showed highest binding energy of −7.70 kcal/mol depicting the potential inhibitor of HER2 receptor protein. However, this study needs to be supported by in vitro and in vivo studies.
{"title":"Synthesis of 2-aryl quinoxaline derivatives and their in silico investigation for breast cancer medication","authors":"Barkha Darra Wadhwani , Deepak Mali , Lokesh Kumar Agarwal , Pooja Kumawat , Pooja Vyas , Rashmy Nair , Tarun Kumar , Poonam Khandelwal","doi":"10.1080/00397911.2024.2333014","DOIUrl":"https://doi.org/10.1080/00397911.2024.2333014","url":null,"abstract":"<div><p>The main objective of the present work is to synthesize and identify the potential breast cancer medication of 2-aryl quinoxaline derivatives via <em>in silico</em> investigations. Synthesis of 2-aryl quinoxaline derivatives have been achieved <em>via</em> the reaction of 3-aroylmethylene-2H-indol-2-ones <strong>1</strong> with various 1,2-diamines. Good yields were obtained at 60 °C in methanol by using graphene oxide (GO) as catalyst, however, the regio selectivity in case of unsymmetrically substituted diamines were low to moderated. This is the first report of the oxidative cleavage of C = C bond during the course of the reaction. Molecular docking study of these synthesized compounds were employed to calculate the binding affinity with human epidermal growth factor receptor 2 (HER2). 6-Bromo-3-phenylpyrido[2,3-b]pyrazine <strong>3k</strong> showed highest binding energy of −7.70 kcal/mol depicting the potential inhibitor of HER2 receptor protein. However, this study needs to be supported by <em>in vitro</em> and <em>in vivo</em> studies.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140548079","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 : 2024-03-28DOI: 10.1080/00397911.2024.2325786
Khalid Mujasam Batoo , Mohammed Kadhem Abid , Abdul-Hameed M. Hamoody , Ola Kamal A. Alkadir , Sajjad Hussain , Ahmed Alawadi , Ali Alsalamy
Research on benzimidazole derivatives is always an attractive challenge among synthetic chemists because benzimidazole derivatives are very key and important components in the structure of many drugs, biological active molecules, and natural products. Benzimidazole derivatives are very interesting because of their valuable biological and medicinal activities, such as anti-bacterial, anti-cancer, anti-tuberculosis, anti-fungal, pain killer, and anti-HIV activities. During the last decade, most reports in the field of catalysts have been related to magnetic nanocatalysts, which shows the high popularity and remarkable efficiency of this type of catalyst in performing chemical reactions. Magnetic nanocatalysts are ideal catalysts both from the point of view of green chemistry and economically because they are easily separated from the reaction mixture and have significant catalytic activity. In this review article, we have summarized the methods presented on the synthesis of various benzimidazole derivatives based on the use of magnetic nanomaterials as green recoverable catalysts.
{"title":"Magnetic nanomaterials as green and recoverable nanocatalysts: Research on synthesis of benzimidazole derivatives","authors":"Khalid Mujasam Batoo , Mohammed Kadhem Abid , Abdul-Hameed M. Hamoody , Ola Kamal A. Alkadir , Sajjad Hussain , Ahmed Alawadi , Ali Alsalamy","doi":"10.1080/00397911.2024.2325786","DOIUrl":"10.1080/00397911.2024.2325786","url":null,"abstract":"<div><p>Research on benzimidazole derivatives is always an attractive challenge among synthetic chemists because benzimidazole derivatives are very key and important components in the structure of many drugs, biological active molecules, and natural products. Benzimidazole derivatives are very interesting because of their valuable biological and medicinal activities, such as anti-bacterial, anti-cancer, anti-tuberculosis, anti-fungal, pain killer, and anti-HIV activities. During the last decade, most reports in the field of catalysts have been related to magnetic nanocatalysts, which shows the high popularity and remarkable efficiency of this type of catalyst in performing chemical reactions. Magnetic nanocatalysts are ideal catalysts both from the point of view of green chemistry and economically because they are easily separated from the reaction mixture and have significant catalytic activity. In this review article, we have summarized the methods presented on the synthesis of various benzimidazole derivatives based on the use of magnetic nanomaterials as green recoverable catalysts.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140372909","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 : 2024-03-16DOI: 10.1080/00397911.2024.2330617
Najla A. Alshaye , Magdy A. Ibrahim
The novel chromonyltriazolo[3,4-b][1,3,4]thiadiazole derivative 5 was efficiently synthesized and utilized as key intermediate for construction of a diversity of heterocyclic rings; through reactions with binucleophilic reagents. Treating electron deficient substrate 5 with hydrazine hydrate, phenylhydrazine and hydroxylamine furnished pyrazolyl/isoxazolyltriazolo[3,4-b][1,3,4]thiadiazoles 6-8. Also, reacting substrate 5 with guanidine, cyanoguanidine and thiourea provided pyrimidinyltriazolo[3,4-b][1,3,4]thiadiazoles 9-11. Reaction of substrate 5 with ethylenediamine and o-phenylenediamine afforded diazepine derivatives 12 and 13. Reaction of substrate 5 with malononitrile, ethyl cyanoacetate and cyanoacetamide afforded pyrans 14, 15 and pyridine 16 linked triazolo[3,4-b][1,3,4]thiadiazolyl chromeno[2,3-b]pyridines. The anticancer efficiency of the current compounds presented diverse inhibitory action against certain cancer cell lines. On the basis of analytical and spectral findings, the structures of the synthesized products were confirmed.
{"title":"Synthetic strategies and anticancer evaluation for the novel 3-(6-heteroaryltriazolo[3,4-b][1,3,4]thiadiazol-3-yl)chromeno [2,3-b]pyridines","authors":"Najla A. Alshaye , Magdy A. Ibrahim","doi":"10.1080/00397911.2024.2330617","DOIUrl":"10.1080/00397911.2024.2330617","url":null,"abstract":"<div><p>The novel chromonyltriazolo[3,4-<em>b</em>][1,3,4]thiadiazole derivative <strong>5</strong> was efficiently synthesized and utilized as key intermediate for construction of a diversity of heterocyclic rings; through reactions with binucleophilic reagents. Treating electron deficient substrate <strong>5</strong> with hydrazine hydrate, phenylhydrazine and hydroxylamine furnished pyrazolyl/isoxazolyltriazolo[3,4-<em>b</em>][1,3,4]thiadiazoles <strong>6</strong>-<strong>8</strong>. Also, reacting substrate <strong>5</strong> with guanidine, cyanoguanidine and thiourea provided pyrimidinyltriazolo[3,4-<em>b</em>][1,3,4]thiadiazoles <strong>9-11</strong>. Reaction of substrate <strong>5</strong> with ethylenediamine and <em>o</em>-phenylenediamine afforded diazepine derivatives <strong>12</strong> and <strong>13</strong>. Reaction of substrate <strong>5</strong> with malononitrile, ethyl cyanoacetate and cyanoacetamide afforded pyrans <strong>14</strong>, <strong>15</strong> and pyridine <strong>16</strong> linked triazolo[3,4-<em>b</em>][1,3,4]thiadiazolyl chromeno[2,3-<em>b</em>]pyridines. The anticancer efficiency of the current compounds presented diverse inhibitory action against certain cancer cell lines. On the basis of analytical and spectral findings, the structures of the synthesized products were confirmed.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140148041","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 : 2024-03-07DOI: 10.1080/00397911.2024.2323999
Flavia Martins da Silva , Joel Jones Junior , July A. Hernández Muñoz , Priscila Nogueira de Azevedo
A highly substituted family of imidazoles is effectively obtained through the Debus-Japp-Radziszewski reaction. In this process, benzil, ammonium acetate, and various benzaldehydes react in a particularly notable solvent: ethyl lactate (EL). This bio-based solvent, derived from biomass fermentation, stands out not only for its sustainable origin but also for its remarkable properties. Ethyl lactate is biodegradable, health-risk-free, is easily recyclable, and is non-corrosive, categorizing it as an exemplary green solvent. The multicomponent reaction, carried out under these conditions, eliminates the need for a catalyst, resulting in products with good yields. The isolation of the products is very simple, requiring only filtration, as they are insoluble in the solvent. In this way, this methodology aligns with various principles of green chemistry, emphasizing the strategic choice of ethyl lactate. This choice has a positive impact on the synthesis of imidazoles, well-known for their pharmacological properties.
{"title":"Sustainable synthesis of imidazoles using a catalyst-free approach and ethyl lactate as a bio-based green solvent in the Debus-Japp-Radziszewski reaction","authors":"Flavia Martins da Silva , Joel Jones Junior , July A. Hernández Muñoz , Priscila Nogueira de Azevedo","doi":"10.1080/00397911.2024.2323999","DOIUrl":"10.1080/00397911.2024.2323999","url":null,"abstract":"<div><p>A highly substituted family of imidazoles is effectively obtained through the Debus-Japp-Radziszewski reaction. In this process, benzil, ammonium acetate, and various benzaldehydes react in a particularly notable solvent: ethyl lactate (EL). This bio-based solvent, derived from biomass fermentation, stands out not only for its sustainable origin but also for its remarkable properties. Ethyl lactate is biodegradable, health-risk-free, is easily recyclable, and is non-corrosive, categorizing it as an exemplary green solvent. The multicomponent reaction, carried out under these conditions, eliminates the need for a catalyst, resulting in products with good yields. The isolation of the products is very simple, requiring only filtration, as they are insoluble in the solvent. In this way, this methodology aligns with various principles of green chemistry, emphasizing the strategic choice of ethyl lactate. This choice has a positive impact on the synthesis of imidazoles, well-known for their pharmacological properties.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140072714","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 : 2024-02-29DOI: 10.1080/00397911.2024.2324009
Safaa S. M. Shaban , David S. A. Haneen , Mohsen M. Abou-El-Regal , Souad A. El-Metwally
The significant medicinal and pharmacological facts about chromenes (benzopyran) nucleus prompted us to focus on constructing unique chromenes with biological value. New chromene derivatives 2–15 were synthesized, and their antibacterial effectiveness was studied. The reaction of the 2-amino-4H-chromene derivative 1 with a variety of reagents such as acetic anhydride, formic acid, chloroacetyl chloride, cyclopentanone, ethyl acetoacetate, diethyl malonate, aldehydes, and isatin produced derivatives 2–13. Compound 1 was also treated with aromatic amines such as p-toluidine and/or benzene-1,4-diamine with formaldehyde, yielding derivatives 14 and 15, respectively; spectral techniques were used to confirm the predicted structures of all compounds. The antibacterial activity of the recently synthesized compounds was assessed against two types of bacteria, Bacillus subtilis and Escherichia coli. There is encouraging antibacterial activity in compounds 5 and 7.
{"title":"Design, synthesis and antibacterial assessment of novel 4H-chromene analogues","authors":"Safaa S. M. Shaban , David S. A. Haneen , Mohsen M. Abou-El-Regal , Souad A. El-Metwally","doi":"10.1080/00397911.2024.2324009","DOIUrl":"10.1080/00397911.2024.2324009","url":null,"abstract":"<div><p>The significant medicinal and pharmacological facts about chromenes (benzopyran) nucleus prompted us to focus on constructing unique chromenes with biological value. New chromene derivatives <strong>2–15</strong> were synthesized, and their antibacterial effectiveness was studied. The reaction of the 2-amino-4<em>H</em>-chromene derivative <strong>1</strong> with a variety of reagents such as acetic anhydride, formic acid, chloroacetyl chloride, cyclopentanone, ethyl acetoacetate, diethyl malonate, aldehydes, and isatin produced derivatives <strong>2</strong>–<strong>13</strong>. Compound <strong>1</strong> was also treated with aromatic amines such as <em>p</em>-toluidine and/or benzene-1,4-diamine with formaldehyde, yielding derivatives <strong>14</strong> and <strong>15</strong>, respectively; spectral techniques were used to confirm the predicted structures of all compounds. The antibacterial activity of the recently synthesized compounds was assessed against two types of bacteria, <em>Bacillus subtilis</em> and <em>Escherichia coli</em>. There is encouraging antibacterial activity in compounds <strong>5</strong> and <strong>7</strong>.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-02-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140007450","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 : 2024-02-28DOI: 10.1080/00397911.2024.2320398
V. N. Chandra Sekhar , Gorle Simhachalam , L. Vaikunta Rao , A. V. Dhanunjaya Rao , Madhavaram Shankar , Akula Raghunadh
A four-component protocol for the development of poly-substituted pyridines derivatives by using SiO2 as a recycle catalyst. The protocol offers good to excellent yields (85%-95%) under milder conditions in a short reaction time of 2-3 hours. The use of a less expensive catalyst makes this protocol more convenient. SiO2 has been identified as a convenient catalyst for the synthesis and can be reused for up to three cycles.
{"title":"An efficient four-component protocol for synthesis of poly-substituted pyridines with SiO2 as a robust recyclable catalyst","authors":"V. N. Chandra Sekhar , Gorle Simhachalam , L. Vaikunta Rao , A. V. Dhanunjaya Rao , Madhavaram Shankar , Akula Raghunadh","doi":"10.1080/00397911.2024.2320398","DOIUrl":"10.1080/00397911.2024.2320398","url":null,"abstract":"<div><p>A four-component protocol for the development of poly-substituted pyridines derivatives by using SiO<sub>2</sub> as a recycle catalyst. The protocol offers good to excellent yields (85%-95%) under milder conditions in a short reaction time of 2-3 hours. The use of a less expensive catalyst makes this protocol more convenient. SiO<sub>2</sub> has been identified as a convenient catalyst for the synthesis and can be reused for up to three cycles.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":2.1,"publicationDate":"2024-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140007239","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}