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Synthetic Communications最新文献

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Synthesis and antioxidant activity of 14-Aryl-14H-dibenzo[a,j] xanthene’s and bis(3-hydroxy-5,5′-dimethyl-2-cyclohexene-1-ones) derivatives using silica-tungstosulfonic acid catalyst 使用二氧化硅-钨磺酸催化剂合成 14-芳基-14H-二苯并[a,j]氧杂蒽和双(3-羟基-5,5′-二甲基-2-环己烯-1-酮)衍生物并提高其抗氧化活性
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-11-21 DOI: 10.1080/00397911.2024.2424487
Reddi Mohan Naidu Kalla , Swetha Kumari Koduru , Sivarama Krishna Lakkboyana , Jaewoong Lee
{"title":"Synthesis and antioxidant activity of 14-Aryl-14H-dibenzo[a,j] xanthene’s and bis(3-hydroxy-5,5′-dimethyl-2-cyclohexene-1-ones) derivatives using silica-tungstosulfonic acid catalyst","authors":"Reddi Mohan Naidu Kalla ,&nbsp;Swetha Kumari Koduru ,&nbsp;Sivarama Krishna Lakkboyana ,&nbsp;Jaewoong Lee","doi":"10.1080/00397911.2024.2424487","DOIUrl":"10.1080/00397911.2024.2424487","url":null,"abstract":"<div><div>The synthesis of biologically active benzoxanthene, and bis(3-hydroxy-5,5’-dimethyl-2-cyclohexene-1-ones) derivatives has been conducted under an environmentally benign method by using an efficient catalyst, silica-tungstosulphonic acid. The benefits of this catalyst include being safe for the environment, low-cost, and simple to construct. It produces good yields and high purity in a short time and facilitates easy cleansing, products are obtained by straightforward recrystallization without the need for column chromatography. The reagent retained its catalytic activity for at least five consecutive cycles of reuse. The catalyst is described by IR, XRD, and SEM-EDX, which clearly shows that sulfonation happens in silica tungstic acid. In addition, the targeted derivatives were studied for anti-oxidant properties such as DPPH, reducing power assay, and H<sub>2</sub>O<sub>2</sub> scavenging activity. The synthesized products such as <strong>3e, 5k, 5 m, 5o,</strong> and <strong>5p</strong> showed good anti-oxidant properties. Among all of these compounds, <strong>5p</strong> showed good activity due to the nitro substitution on the benzene ring.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 24","pages":"Pages 2143-2158"},"PeriodicalIF":1.8,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142706906","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}
引用次数: 0
Novel and efficient process for the synthesis of 1,3,4-oxadiazole containing MBX-4132 as antimicrobial agent in Neisseria gonorrhoeae 合成含 MBX-4132 的 1,3,4-oxadiazole 的新型高效工艺，作为淋病奈瑟菌的抗菌剂
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-11-11 DOI: 10.1080/00397911.2024.2424995
Prachi Ramteke , M.S. Gill
{"title":"Novel and efficient process for the synthesis of 1,3,4-oxadiazole containing MBX-4132 as antimicrobial agent in Neisseria gonorrhoeae","authors":"Prachi Ramteke ,&nbsp;M.S. Gill","doi":"10.1080/00397911.2024.2424995","DOIUrl":"10.1080/00397911.2024.2424995","url":null,"abstract":"<div><div>A novel and efficient approach to the synthesis of MBX-4132 has been reported. Having 1,3,4-oxadiazole-containing compound that inhibits trans translation process by binding to the bacterial ribosome and act as an antimicrobial agent. It involved the reaction of 5-(4-fluorophenyl)-1,3,4-oxadiazol-2-amine, with diphenyl carbonate to yield the corresponding carbamates, which <em>in situ</em> reacted with 1,2,3,4-tetrahydroisoquinoline to produce MBX-4132 with a comparatively higher yield (65%). The above process involves mild reaction conditions and uses nontoxic, non-hazardous, and cheaper reagents such as diphenyl carbonate as a carbonyl source thereby making the process economical and environment friendly.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 24","pages":"Pages 2159-2168"},"PeriodicalIF":1.8,"publicationDate":"2024-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142706860","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}
引用次数: 0
Novel Schiff bases of quinolin-4(1h)-one: Synthesis, antiproliferative evaluation, apoptosis, cell cycle, autophagy and molecular docking studies in human colon cancer cells 喹啉-4(1h)-酮的新型希夫碱：在人类结肠癌细胞中进行合成、抗增殖评估、细胞凋亡、细胞周期、自噬和分子对接研究
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-11-06 DOI: 10.1080/00397911.2024.2424486
Tarik E. Ali , Mohammed A. Assiri , Mohamed Hussien , Ali A. Shati , Mohammad Y. Alfaifi , Serag E. I. Elbehairi
{"title":"Novel Schiff bases of quinolin-4(1h)-one: Synthesis, antiproliferative evaluation, apoptosis, cell cycle, autophagy and molecular docking studies in human colon cancer cells","authors":"Tarik E. Ali ,&nbsp;Mohammed A. Assiri ,&nbsp;Mohamed Hussien ,&nbsp;Ali A. Shati ,&nbsp;Mohammad Y. Alfaifi ,&nbsp;Serag E. I. Elbehairi","doi":"10.1080/00397911.2024.2424486","DOIUrl":"10.1080/00397911.2024.2424486","url":null,"abstract":"<div><div>A green and efficient ultrasound-mediated protocol was developed for the synthesis of a series of novel Schiff bases derived from quinoline-4-one. The synthetic strategy involved the condensation of 4-oxo-1,4-dihydro-quinoline-3-carboxaldehyde with diverse anilines and heteroaryl amines. The synthesized compounds were characterized using spectroscopic techniques. A comprehensive in <em>vitro</em> cytotoxicity evaluation against HCT116 and HT-29 human colon cancer cell lines revealed that several compounds exhibited potent anticancer activity. Notably, compounds <strong>3c</strong> and <strong>3e</strong> demonstrated superior cytotoxicity compared to the clinical standard doxorubicin. Mechanistic studies indicated that these lead compounds induced apoptosis, necrosis, and cell cycle arrest at G1 and G2 phases. Furthermore, autophagy induction was observed. <em>In silico</em> ADMET predictions support the potential of compounds <strong>3c</strong> and <strong>3e</strong> as promising anticancer drug candidates. The molecular docking studies revealed that the Schiff bases <strong>3c</strong> and <strong>3e</strong> displayed good interaction with VEGFR-2 receptor. These findings underscore the quinoline-4-one scaffold as a valuable template for the development of novel antitumor agents.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 24","pages":"Pages 2130-2142"},"PeriodicalIF":1.8,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142707128","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}
引用次数: 0
Development of an improved and facile synthesis route of the FGFR inhibitor erdafitinib 开发表皮生长因子受体抑制剂厄达非替尼的改进型简易合成路线
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-11-05 DOI: 10.1080/00397911.2024.2423897
Shuang Wang , Nanxin Peng , Liping Yin , Wei Wang , Yue Wu , Di Zhang , Zongjie Gan
{"title":"Development of an improved and facile synthesis route of the FGFR inhibitor erdafitinib","authors":"Shuang Wang ,&nbsp;Nanxin Peng ,&nbsp;Liping Yin ,&nbsp;Wei Wang ,&nbsp;Yue Wu ,&nbsp;Di Zhang ,&nbsp;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}
引用次数: 0
An efficient and practical synthesis of ferroptosis inducer erastin 一种高效实用的铁色素沉着诱导剂麦拉宁合成方法
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-11-01 DOI: 10.1080/00397911.2024.2423363
Xinxin Cui , Chenghan Zhuang , Siyu Liang , Xingxian Zhang
{"title":"An efficient and practical synthesis of ferroptosis inducer erastin","authors":"Xinxin Cui ,&nbsp;Chenghan Zhuang ,&nbsp;Siyu Liang ,&nbsp;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}
引用次数: 0
Green synthesis, molecular docking and in vitro biological evaluation of novel hydrazones, pyrazoles, 1,2,4-triazoles and 1,3,4-oxadiazoles 新型肼、吡唑、1,2,4-三唑和 1,3,4-恶二唑的绿色合成、分子对接和体外生物学评价
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-10-24 DOI: 10.1080/00397911.2024.2417362
Ahmed Younis , Asmaa F Kassem , Wael M Aboulthana , Ashraf A Sediek
{"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 ,&nbsp;Asmaa F Kassem ,&nbsp;Wael M Aboulthana ,&nbsp;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}
引用次数: 0
Synthesis and structural characterization of a novel large type double-layered cyclophanes based on the reaction of bis(N-alkylene benzothiazolium) dibromide and triethylamine 基于双（N-亚烷基苯并噻唑）二溴化物和三乙胺反应的新型大型双层环烷的合成及其结构特征
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-10-18 DOI: 10.1080/00397911.2024.2415435
Zhen-zhong Wei , Xing-bao Chi
{"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 ,&nbsp;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}
引用次数: 0
Solvent-free and efficient heterogeneous Biginelli reactions catalyzed by copper (II)-incorporated iminophenol-based porous organic polymer 铜(II)掺杂亚氨基苯酚基多孔有机聚合物催化的无溶剂高效异相比吉内利反应
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-10-16 DOI: 10.1080/00397911.2024.2416529
Pradeepruban Joseph , Pintu K. Kundu
{"title":"Solvent-free and efficient heterogeneous Biginelli reactions catalyzed by copper (II)-incorporated iminophenol-based porous organic polymer","authors":"Pradeepruban Joseph ,&nbsp;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}
引用次数: 0
Cobalt(II) catalyzed Michael-type hydroamination of activated olefins 钴（II）催化活化烯烃的迈克尔型加氢反应
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-10-16 DOI: 10.1080/00397911.2024.2414410
Rajagopal Rajesh , Joseph Prince Devassy , Rasheed Nihala , Rajesh Kunjanpillai
{"title":"Cobalt(II) catalyzed Michael-type hydroamination of activated olefins","authors":"Rajagopal Rajesh ,&nbsp;Joseph Prince Devassy ,&nbsp;Rasheed Nihala ,&nbsp;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}
引用次数: 0
Copper(II)-catalyzed dehydration of primary amides to nitriles with the aid of trichloroacetonitrile 铜(II)催化伯胺在三氯乙腈帮助下脱水成腈纶
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-10-15 DOI: 10.1080/00397911.2024.2415442
Xiaoyun Ma , Xiaoyan Wan , Jun Zhao
{"title":"Copper(II)-catalyzed dehydration of primary amides to nitriles with the aid of trichloroacetonitrile","authors":"Xiaoyun Ma ,&nbsp;Xiaoyan Wan ,&nbsp;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}
引用次数: 0
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