Pub Date : 2024-11-05DOI: 10.1080/00397911.2024.2423897
Shuang Wang , Nanxin Peng , Liping Yin , Wei Wang , Yue Wu , Di Zhang , Zongjie Gan
A facile and practical synthetic route for erdafitinib has been developed. In this route, the key intermediate N1-(3,5-dimethoxyphenyl)-N2-isopropylethane-1,2-diamine (12) was prepared from readily available staring materials, 3,5-dimethoxyaniline (5) and 2-bromoethylamine hydrobromide (16), through a novel two-step process with an overall yield of 70%. Erdafitinib was subsequently synthesized from compound 12 and 7-bromo-2-(1-methyl-1H-pyrazol-4-yl)quinoxaline (4) in 80% yield and 99% purity. This alternative procedure offers an economical and efficient route to produce erdafitinib.
{"title":"Development of an improved and facile synthesis route of the FGFR inhibitor erdafitinib","authors":"Shuang Wang , Nanxin Peng , Liping Yin , Wei Wang , Yue Wu , Di Zhang , Zongjie Gan","doi":"10.1080/00397911.2024.2423897","DOIUrl":"10.1080/00397911.2024.2423897","url":null,"abstract":"<div><div>A facile and practical synthetic route for erdafitinib has been developed. In this route, the key intermediate <em>N<sup>1</sup></em>-(3,5-dimethoxyphenyl)-<em>N<sup>2</sup></em>-isopropylethane-1,2-diamine (<strong>12</strong>) was prepared from readily available staring materials, 3,5-dimethoxyaniline (<strong>5</strong>) and 2-bromoethylamine hydrobromide (<strong>16</strong>), through a novel two-step process with an overall yield of 70%. Erdafitinib was subsequently synthesized from compound <strong>12</strong> and 7-bromo-2-(1-methyl-1H-pyrazol-4-yl)quinoxaline (<strong>4</strong>) in 80% yield and 99% purity. This alternative procedure offers an economical and efficient route to produce erdafitinib.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 24","pages":"Pages 2120-2129"},"PeriodicalIF":1.8,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142707129","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}
Erastin, a classic ferroptosis inducer, mediates ferroptosis through various molecular pathways. A highly efficient and convenient synthesis of erastin has been developed, starting from 2-nitrobenzoic acid through 7 steps in an overall yield of 21.6%. This synthesis approach features the efficient construction of the key quinazolinone core and highly selective bromination.
{"title":"An efficient and practical synthesis of ferroptosis inducer erastin","authors":"Xinxin Cui , Chenghan Zhuang , Siyu Liang , Xingxian Zhang","doi":"10.1080/00397911.2024.2423363","DOIUrl":"10.1080/00397911.2024.2423363","url":null,"abstract":"<div><div>Erastin, a classic ferroptosis inducer, mediates ferroptosis through various molecular pathways. A highly efficient and convenient synthesis of erastin has been developed, starting from 2-nitrobenzoic acid through 7 steps in an overall yield of 21.6%. This synthesis approach features the efficient construction of the key quinazolinone core and highly selective bromination.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 24","pages":"Pages 2115-2119"},"PeriodicalIF":1.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142706256","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 : 2024-10-24DOI: 10.1080/00397911.2024.2417362
Ahmed Younis , Asmaa F Kassem , Wael M Aboulthana , Ashraf A Sediek
Ultrasonic waves were used for synthesis of novel hydrazones, bishydrazones, pyrazoles, 1,2,4-triazole and 1,3,4-oxadiazole. The structural formulae of the synthesized compounds were elucidated in terms of elemental and spectroscopic analyses. All synthesized compounds were estimated by testing total antioxidant capacity, iron‐reducing power, the scavenging activity against ABTS and DPPH radicals in addition to testing anti‐diabetic, anti‐Alzheimer and anti‐arthritic activities. All compounds displayed good to potent bioactivity. Compounds 6, 10 exhibit the highest antioxidant and free radicals scavenging activities. Furthermore, compounds 6, 10 demonstrate the strongest inhibition of α‐amylase and α-glucosidase. Compound 12 exhibit strongest acetylcholinesterase inhibition among prepared compounds. However, compounds 18a,b, 19 show a significantly higher inhibition percentage for protein denaturation and proteinase. The most bioactive prepared compounds 6, 10 and 12 were investigated toward docking methodology against appropriate protein.
{"title":"Green synthesis, molecular docking and in vitro biological evaluation of novel hydrazones, pyrazoles, 1,2,4-triazoles and 1,3,4-oxadiazoles","authors":"Ahmed Younis , Asmaa F Kassem , Wael M Aboulthana , Ashraf A Sediek","doi":"10.1080/00397911.2024.2417362","DOIUrl":"10.1080/00397911.2024.2417362","url":null,"abstract":"<div><div>Ultrasonic waves were used for synthesis of novel hydrazones, bishydrazones, pyrazoles, 1,2,4-triazole and 1,3,4-oxadiazole. The structural formulae of the synthesized compounds were elucidated in terms of elemental and spectroscopic analyses. All synthesized compounds were estimated by testing total antioxidant capacity, iron‐reducing power, the scavenging activity against ABTS and DPPH radicals in addition to testing anti‐diabetic, anti‐Alzheimer and anti‐arthritic activities. All compounds displayed good to potent bioactivity. Compounds <strong>6, 10</strong> exhibit the highest antioxidant and free radicals scavenging activities. Furthermore, compounds <strong>6, 10</strong> demonstrate the strongest inhibition of α‐amylase and α-glucosidase. Compound <strong>12</strong> exhibit strongest acetylcholinesterase inhibition among prepared compounds. However, compounds <strong>18a,b, 19</strong> show a significantly higher inhibition percentage for protein denaturation and proteinase. The most bioactive prepared compounds <strong>6</strong>, <strong>10</strong> and <strong>12</strong> were investigated toward docking methodology against appropriate protein.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 22","pages":"Pages 1984-2002"},"PeriodicalIF":1.8,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142586756","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 : 2024-10-18DOI: 10.1080/00397911.2024.2415435
Zhen-zhong Wei , Xing-bao Chi
The synthesis of a novel large type double-layered cyclophanes has been successfully accomplished by free radical coupling reaction with the bis(N-alkylene benzothiazolium) dibromide salts as their important synthetic intermediates. The structures of the two-layered cyclophanes and the synthetic intermediates have been elucidated based on the NMR data and X-ray structural analysis, respectively. The two-layered cyclophanes consist of two different geometries, anti-two cyclic lactam amide rings inside and two bridges of disulfide bonds outside, which are unique and novel structures. Their physical properties were investigated by UV–Vis and redox potential, too.
以双（N-亚烷基苯并噻唑）二溴化盐为重要合成中间体，通过自由基偶联反应成功合成了一种新型的大型双层环烷。根据核磁共振数据和 X 射线结构分析，分别阐明了二层环烷和合成中间体的结构。双层环烷由两种不同的几何结构组成，内含两个反双环内酰胺酰胺环，外含两个二硫键桥，结构独特新颖。此外，还通过紫外可见光和氧化还原电位研究了它们的物理性质。
{"title":"Synthesis and structural characterization of a novel large type double-layered cyclophanes based on the reaction of bis(N-alkylene benzothiazolium) dibromide and triethylamine","authors":"Zhen-zhong Wei , Xing-bao Chi","doi":"10.1080/00397911.2024.2415435","DOIUrl":"10.1080/00397911.2024.2415435","url":null,"abstract":"<div><div>The synthesis of a novel large type double-layered cyclophanes has been successfully accomplished by free radical coupling reaction with the bis(<em>N</em>-alkylene benzothiazolium) dibromide salts as their important synthetic intermediates. The structures of the two-layered cyclophanes and the synthetic intermediates have been elucidated based on the NMR data and X-ray structural analysis, respectively. The two-layered cyclophanes consist of two different geometries, <em>anti</em>-two cyclic lactam amide rings inside and two bridges of disulfide bonds outside, which are unique and novel structures. Their physical properties were investigated by UV–Vis and redox potential, too.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 22","pages":"Pages 1940-1949"},"PeriodicalIF":1.8,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142586757","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 : 2024-10-16DOI: 10.1080/00397911.2024.2416529
Pradeepruban Joseph , Pintu K. Kundu
The copper (II)-incorporated iminophenol containing porous polymer (Cu-TAzo-TAPB), which was reported to be a recyclable catalyst for click reactions, is now exploited as an efficient catalyst in the solvent-free one-pot process to make 3,4-dihydropyrimidinone derivatives (DHPMs) by a three-component condensation reaction of urea/thiourea, aldehydes, and active methylene compounds. Usually, these reactions are complicated to carry out in a neutral medium. We describe here an eco-friendly method to produce Biginelli products with 5 mol% catalyst loading with a simple isolation technique. The high product yields show the effective Biginelli reaction technique. The catalyst is highly stable and easily recoverable for reuse without significant loss of catalytic efficiency.
铜 (II) 嵌合含亚胺苯酚的多孔聚合物（Cu-TAzo-TAPB）曾被报道为点击反应的可循环催化剂，现在被用作一种高效催化剂，通过脲/硫脲、醛和活性亚甲基化合物的三组分缩合反应，在无溶剂一锅工艺中制造 3,4-二氢嘧啶酮衍生物 (DHPM)。通常，这些反应在中性介质中进行比较复杂。我们在此介绍一种生态友好型方法，利用简单的分离技术，在催化剂负载量为 5 摩尔% 的情况下生产 Biginelli 产品。产品的高产率显示了比吉奈利反应技术的有效性。催化剂高度稳定，易于回收再利用，且不会明显降低催化效率。
{"title":"Solvent-free and efficient heterogeneous Biginelli reactions catalyzed by copper (II)-incorporated iminophenol-based porous organic polymer","authors":"Pradeepruban Joseph , Pintu K. Kundu","doi":"10.1080/00397911.2024.2416529","DOIUrl":"10.1080/00397911.2024.2416529","url":null,"abstract":"<div><div>The copper (II)-incorporated iminophenol containing porous polymer (<strong>Cu-TAzo-TAPB</strong>), which was reported to be a recyclable catalyst for click reactions, is now exploited as an efficient catalyst in the solvent-free one-pot process to make 3,4-dihydropyrimidinone derivatives (DHPMs) by a three-component condensation reaction of urea/thiourea, aldehydes, and active methylene compounds. Usually, these reactions are complicated to carry out in a neutral medium. We describe here an eco-friendly method to produce Biginelli products with 5 mol% catalyst loading with a simple isolation technique. The high product yields show the effective Biginelli reaction technique. The catalyst is highly stable and easily recoverable for reuse without significant loss of catalytic efficiency.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 22","pages":"Pages 1974-1983"},"PeriodicalIF":1.8,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142586759","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 : 2024-10-16DOI: 10.1080/00397911.2024.2414410
Rajagopal Rajesh , Joseph Prince Devassy , Rasheed Nihala , Rajesh Kunjanpillai
The aza-Michael addition reaction of primary and secondary amines to α,β-unsaturated olefins viz; acrylonitrile, phenyl vinyl sulfone and dimethyl maleate has been carried out using 5–10 mol% Co(NO3)2.6H2O as a catalyst in t-BuOMe at 80–100 °C, giving rise to the desired β-aminocarbonyl compounds or sulfones in moderate to good yields. A wide range of aromatic amines, even those bearing electron withdrawing groups could be added to activated olefins via this strategy. Addition of (hetero)aromatic amines were also feasible, while in case of 2-aminopyridine the reaction was found to be effective only when AgOTf was added along with the catalyst. The aliphatic amines; benzylamine, dibenzylamine, di-n-butylamine were also smoothly added to acrylonitrile and phenyl vinyl sulfone. The methodology describes cobalt(II) nitrate as an eco-friendly, cheap and shelf available catalyst suitable for performing the Michael-type hydroamination reactions.
{"title":"Cobalt(II) catalyzed Michael-type hydroamination of activated olefins","authors":"Rajagopal Rajesh , Joseph Prince Devassy , Rasheed Nihala , Rajesh Kunjanpillai","doi":"10.1080/00397911.2024.2414410","DOIUrl":"10.1080/00397911.2024.2414410","url":null,"abstract":"<div><div>The aza-Michael addition reaction of primary and secondary amines to <em>α</em>,<em>β</em>-unsaturated olefins viz; acrylonitrile, phenyl vinyl sulfone and dimethyl maleate has been carried out using 5–10 mol% Co(NO<sub>3</sub>)<sub>2</sub>.6H<sub>2</sub>O as a catalyst in <em>t</em>-BuOMe at 80–100 °C, giving rise to the desired <em>β</em>-aminocarbonyl compounds or sulfones in moderate to good yields. A wide range of aromatic amines, even those bearing electron withdrawing groups could be added to activated olefins via this strategy. Addition of (hetero)aromatic amines were also feasible, while in case of 2-aminopyridine the reaction was found to be effective only when AgOTf was added along with the catalyst. The aliphatic amines; benzylamine, dibenzylamine, di-<em>n</em>-butylamine were also smoothly added to acrylonitrile and phenyl vinyl sulfone. The methodology describes cobalt(II) nitrate as an eco-friendly, cheap and shelf available catalyst suitable for performing the Michael-type hydroamination reactions.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 22","pages":"Pages 1959-1973"},"PeriodicalIF":1.8,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142586760","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 : 2024-10-15DOI: 10.1080/00397911.2024.2415442
Xiaoyun Ma , Xiaoyan Wan , Jun Zhao
A method for the preparation of nitriles from primary amides using trichloroacetonitrile and a catalytic amount of cupric acetate is described. Using this method, amides including aromatic amides, aromatic heterocyclic amides and aliphatic amides were converted into the corresponding nitriles in moderate to good yields. Trichloroacetonitrile reacted with amide in the presence of cupric acetate to form trichloroacetamide, which has been isolated and confirmed.
{"title":"Copper(II)-catalyzed dehydration of primary amides to nitriles with the aid of trichloroacetonitrile","authors":"Xiaoyun Ma , Xiaoyan Wan , Jun Zhao","doi":"10.1080/00397911.2024.2415442","DOIUrl":"10.1080/00397911.2024.2415442","url":null,"abstract":"<div><div>A method for the preparation of nitriles from primary amides using trichloroacetonitrile and a catalytic amount of cupric acetate is described. Using this method, amides including aromatic amides, aromatic heterocyclic amides and aliphatic amides were converted into the corresponding nitriles in moderate to good yields. Trichloroacetonitrile reacted with amide in the presence of cupric acetate to form trichloroacetamide, which has been isolated and confirmed.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 22","pages":"Pages 1950-1958"},"PeriodicalIF":1.8,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142586758","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 : 2024-10-15DOI: 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}
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