Abraão Pinheiro de Sousa , Helivaldo Diógenes da Silva Souza , Alexandre Almeida-Júnior , Marcelo Felipe Rodrigues da Silva , Laísa Vilar Cordeiro , Edeltrudes de Oliveira Lima , Gabriela Fehn Fiss , Petrônio Filgueiras de Athayde-Filho
{"title":"Novel esters derived from 4-hydroxychalcones as potential sunscreens with antimicrobial action","authors":"Abraão Pinheiro de Sousa , Helivaldo Diógenes da Silva Souza , Alexandre Almeida-Júnior , Marcelo Felipe Rodrigues da Silva , Laísa Vilar Cordeiro , Edeltrudes de Oliveira Lima , Gabriela Fehn Fiss , Petrônio Filgueiras de Athayde-Filho","doi":"10.1080/00397911.2024.2356641","DOIUrl":"10.1080/00397911.2024.2356641","url":null,"abstract":"<div><p>Ten novel 4-esterchalcones, licochalcone analogues, were strategically synthesized to study the effect of electro-donating or electro-withdrawing substituents in the aryl enone moiety on their pharmacological and photoprotective properties. 4-Esterchalcones had their drug-like character evaluated, which demonstrated positive characteristics for the development of novel drug candidates. In the <em>in vitro</em> antimicrobial evaluation, isovaleryl 4-esterchalcones showed activity against strains of <em>Staphylococcus aureus</em>, <em>Candida albicans</em> and <em>C. tropicalis</em> with minimum inhibitory concentration (MIC) in the range of 2.64-3.32 µmol mL<sup>−1</sup>, and the isobutyryl 4-esterchalcone <strong>5d</strong> (4’-Br) presented antimicrobial activity against all strains tested, with a MIC of 2.74 µmol mL<sup>−1</sup>. In the UV-Vis study, <em>λ</em><sub>max</sub> were observed at 312-327 nm, the UVB range, mainly. The best SPF-UVB results ranged from 18.04 to 21.06, with high <em>ε</em><sub>max</sub> values, indicating that 4-esterchalcones have the potential to act as sunscreens. Furthermore, along with the environmental concern, halogenated compounds demonstrated slightly toxic on <em>Artemia salina</em>.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 12","pages":"Pages 973-991"},"PeriodicalIF":2.1,"publicationDate":"2024-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141122380","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}
{"title":"Synthesis and antimicrobial evaluation of 6-hydroxy-4,7-dimethoxybenzofuranylcarbonyl tethered annulated pyridines","authors":"Najla A. Alshaye , Magdy A. Ibrahim","doi":"10.1080/00397911.2024.2342358","DOIUrl":"10.1080/00397911.2024.2342358","url":null,"abstract":"<div><p>2-Chloro-5-[(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)carbonyl]pyridine-3-carbonitrile (<strong>3</strong>) was synthesized and its chemical reactivity was investigated toward a diversity of binucleophiles. Treatment of compound <strong>3</strong> hydrazine hydrate and phenylhydrazine produced pyrazolo[3,4-<em>b</em>]pyridines while isoxazolo[5,4-<em>b</em>]pyridine was obtained from reacting compound <strong>3</strong> with hydroxylamine. A diversity of pyrido[2,3-<em>d</em>]pyrimidines was synthesized from treatment of staring substrate <strong>3</strong> with some 1,3-<em>N</em>,<em>N</em>-binucleophiles. Treating compound <strong>3</strong> with some 1,4-binucleophiles including ethylenediamine, <em>o</em>-phenylenediamine, 2-aminophenol and 2-aminothiophenol furnished pyrido[2,3-<em>e</em>][1,4]diazepine <strong>12</strong> and pyrido[2,3-<em>b</em>][1,5] benzodiazepine <strong>13</strong>, pyrido[2,3-<em>b</em>][1,5]benzoxazepine <strong>14</strong> and pyrido[2,3-<em>b</em>][1,5] benzothiazepine <strong>15</strong>, respectively. The synthesize compounds shown remarkable effect against yeast and fungus, while compounds <strong>4</strong> and <strong>7</strong>–<strong>11</strong> exhibit excellent efficacy against all types of Gram + and Gram - bacteria. Structures of the produced compounds were established using analytical and spectroscopic tools.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 10","pages":"Pages 815-825"},"PeriodicalIF":2.1,"publicationDate":"2024-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140613462","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}
{"title":"Synthesis and biological evaluation of tetrazole ring incorporated oxazole-pyrimidine derivatives as anticancer agents","authors":"Yahya I. Asiri , Tasqeeruddin Syed , Thirumala Chary Maringanti , Laxminarayana Eppakayala , Venkat Swamy Puli","doi":"10.1080/00397911.2024.2331922","DOIUrl":"10.1080/00397911.2024.2331922","url":null,"abstract":"<div><p>A new library of tetrazole rings with oxazole-pyrimidine derivatives (<strong>9a–j</strong>) has been developed and synthesized. All of the compounds were characterized using spectral data. These were then tested for in vitro anticancer activity against four human cancer cell lines: prostate cancer (PC3 & DU-145), lung cancer (A549), and breast cancer (MCF-7) using an MTT assay. Etoposide was chosen as the positive control. Most of the compounds demonstrated moderate to good activity. These compounds (<strong>9a, 9b, 9d, 9g, and 9h</strong>) demonstrated the most powerful action. Particularly, one chemical 9h had exceptional antitumor efficacy.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 10","pages":"Pages 802-814"},"PeriodicalIF":2.1,"publicationDate":"2024-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140568694","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}
Abouelhaoul El Alami , Amine El Maraghi , Hamid Sdassi
{"title":"Review of synthesis process of benzoxazole and benzothiazole derivatives","authors":"Abouelhaoul El Alami , Amine El Maraghi , Hamid Sdassi","doi":"10.1080/00397911.2024.2337089","DOIUrl":"10.1080/00397911.2024.2337089","url":null,"abstract":"<div><p>Benzoxazoles and benzothiazoles are a class of aromatic heterocyclic compounds having similar ring structures, in which a benzene ring is fused to the 4 and 5 positions of the 1,3-oxazole and 1,3-thiazole rings respectively. They constitute an interesting class of organic compounds due to their powerful and significant biological, agrochemical, pharmaceutical and physicochemical activities. Indeed, benzoxazole and benzothiazole derivatives possess a wide range of applications, such as: anticancer, anti-inflammatory, antioxidant, anticonvulsant, antitubercular, antifungal, pesticidal, anticorrosive, complexing properties and so on. The synthesis of benzoxazole and benzothiazole derivatives has attracted much attention from several researchers across the world and numerous synthetic methods have been developed to access these compounds over the past decades. In this review, we present new and recent synthetic strategies, as well as some biological properties of benzoxazole and benzothiazole derivatives.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 10","pages":"Pages 769-801"},"PeriodicalIF":2.1,"publicationDate":"2024-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140568843","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}
Shital B. Sukale , Dipak S. Aher , Laxmikant D. Chavan , Kiran R. Khillare , Sunil G. Shankarwar
{"title":"Synthesis and characterization of alumina supported molybdosilicic acid (SiMo12/Al2O3): Efficient solid acid catalyst for the synthesis of pyranopyrazole derivatives","authors":"Shital B. Sukale , Dipak S. Aher , Laxmikant D. Chavan , Kiran R. Khillare , Sunil G. Shankarwar","doi":"10.1080/00397911.2024.2345380","DOIUrl":"10.1080/00397911.2024.2345380","url":null,"abstract":"<div><p>A series of highly reusable heterogeneous catalysts (10-40 wt.% SiMo<sub>12</sub>/Al<sub>2</sub>O<sub>3</sub>), consisting of molybdosilicic acid (SiMo<sub>12</sub>) impregnated on alumina (Al<sub>2</sub>O<sub>3</sub>) support was synthesized by the wetness impregnation method. The physicochemical properties of synthesized catalyst were studied using FT-IR, XRD, SEM, EDX, TEM, BET and TG-DTA analysis techniques. The study proves that the synthesized SiMo<sub>12</sub> catalyst efficiently incorporated on the surface of Al<sub>2</sub>O<sub>3.</sub> The catalytic activity of prepared catalyst was investigated for the synthesis of pyranopyrazole(6-amino-4-phenyl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5carbonitrile) via cyclocondensation reaction of aldehydes, malononitrile, hydrazine hydrate and ethyl-acetoacetate under solvent-free conditions. Among different catalysts, 30% SiMo<sub>12</sub> supported on to Al<sub>2</sub>O<sub>3</sub> showed the highest catalytic activity. High yield, shorter reaction time, operational simplicity, solvent-free conditions and reusability of the catalyst are the distinct features of this protocol.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 10","pages":"Pages 826-842"},"PeriodicalIF":2.1,"publicationDate":"2024-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140988661","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}
F. M. Alshareef , Zahra M. Alamshany , Sami A. Al-Harbi , Esam S. Allehyani , Magdy A. Ibrahim
{"title":"Novel annulated chromeno[3',2':5,6]pyrido[2,3-d][1,3,4]thiadiazolo[3,2-a] pyrimidines and chromeno[3'',2'':5',6']pyrido[2',3':4,5]pyrimido[2,1-b][1,3,4] thiadiazines: Synthetic approaches and antimicrobial efficiency","authors":"F. M. Alshareef , Zahra M. Alamshany , Sami A. Al-Harbi , Esam S. Allehyani , Magdy A. Ibrahim","doi":"10.1080/00397911.2024.2346565","DOIUrl":"10.1080/00397911.2024.2346565","url":null,"abstract":"<div><p>The current study includes synthetic approaches for some linear heterocyclic compounds containing chromone moiety. Chromenopyridopyrimidine bearing amino-thione functions <strong>4</strong> was efficiently synthesized starting from 6,8-dimethylchromone-3-carbonitrile (<strong>1</strong>). The novel chromenopyridothiadiazolopyrimidines were synthesized through condensation of the key precursor <strong>4</strong> with some mono-electrophilic reagents. In addition, heteroannulated chromenopyridopyrimidothiadiazines were synthesized through condensation of compound <strong>4</strong> with some α-halogenated carbonyl reagents. The synthesized products were examined for their antimicrobial efficiency appearing remarkable activity against the inspected microorganisms especially compounds <strong>7</strong>, <strong>12</strong> and <strong>14</strong>. The synthesized products were inferred using analytical and spectral data.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 10","pages":"Pages 843-852"},"PeriodicalIF":2.1,"publicationDate":"2024-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141050554","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}
Urvi J. Khengar , Dharti R. Bhandari , Rajesh H. Vekariya , Jinal A. Gajjar
{"title":"An overall development on catalytic applications of potassium phthalimide (PPI) and potassium phthalimide-N-oxyl (POPINO) in organic synthesis","authors":"Urvi J. Khengar , Dharti R. Bhandari , Rajesh H. Vekariya , Jinal A. Gajjar","doi":"10.1080/00397911.2024.2342316","DOIUrl":"10.1080/00397911.2024.2342316","url":null,"abstract":"<div><p>Potassium phthalimide (PPI) and Potassium phthalimide<em>-N-</em>oxyl (POPINO) have emerged as a versatile and efficient catalyst in various organic synthesis reactions, playing a crucial role in the development of sustainable and environmentally friendly synthetic methodologies. This review highlights the catalytic applications of PPI and POPINO in diverse transformations, showcasing its potential as a valuable tool in modern organic synthesis. The multifaceted reactivity of PPI and POPINO has been explored in reactions such as nucleophilic substitutions, condensations, cycloadditions, and oxidation processes, making it an attractive catalyst for the synthesis of complex organic molecules.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 12","pages":"Pages 935-952"},"PeriodicalIF":2.1,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140659028","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}
Chun Keng Thy , Yean Kee Lee , Iskandar Abdullah , Noorsaadah Abd Rahman , Chin Fei Chee
{"title":"Asymmetric Diels–Alder reaction of chalcone and isoprene mediated by titanium-based complexes","authors":"Chun Keng Thy , Yean Kee Lee , Iskandar Abdullah , Noorsaadah Abd Rahman , Chin Fei Chee","doi":"10.1080/00397911.2024.2324002","DOIUrl":"10.1080/00397911.2024.2324002","url":null,"abstract":"<div><p>The asymmetric Diels–Alder reaction of chalcone and isoprene has been accomplished by use of chiral titanium complexes. Notably, an enantiomeric excess as high as 61% and a regioselectivity of 95% have been achieved. The preparation of the chiral titanium complexes is simple and does not require the pre-installation of a chiral auxiliary. This study represents the first example of asymmetric Diels–Alder reaction between chalcone and isoprene.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 8","pages":"Pages 636-644"},"PeriodicalIF":2.1,"publicationDate":"2024-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140072732","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}
{"title":"Polyethyleneimine-immobilized CoCl2 nanoparticles: Synthesis, characterization, application as a new efficient and reusable nanocomposite catalyst for one-step transesterification reaction","authors":"Tahereh Darvishi , Sedigheh Azadi , Nooredin Goudarzian","doi":"10.1080/00397911.2024.2328287","DOIUrl":"10.1080/00397911.2024.2328287","url":null,"abstract":"<div><p>Polyethyleneimine-supported cobalt (II) chloride as a novel polymeric nanocomposite acidic catalyst for the one-stage transesterification reaction of ethyl acetate with various alcohols is reported. The catalyst was characterized by Fourier transform infrared spectroscopy, X-ray powder diffraction, transmission electron microscopy, scanning electron microscopy, dynamic light scattering technique, and thermal gravimetric analysis. Furthermore, inductively coupled plasma and atomic absorption spectroscopy were used to determine the quantity of Cobalt nanoparticles in the catalyst. By adding the catalyst (0.10 g, 0.20 mol%) and n-hexane/chloroform (5.0 cm<sup>3</sup>) as solvent under reflux conditions, the studies demonstrated successful transesterification reactions with excellent yields (80–98%) and short reaction times (0.50–1.30 h) using various substrates on the scale of 1.0 mmol. Seven consecutive reactions could be performed on the catalyst without significantly decreasing its activity. The most noteworthy aspects of this process are its low cost, safety, and environmental friendliness due to the catalyst’s non-toxicity, straightforward operation, and effective outcomes.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 8","pages":"Pages 672-693"},"PeriodicalIF":2.1,"publicationDate":"2024-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140199332","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}
Wenjuan Li , Xiao Li , Hailong Hong , Ruijun Xie , Ning Zhu
{"title":"Synthesis of 1H-benzimidazoles via the condensation of o-phenylenediamines with DMF promoted by organic acid under microwave irradiation","authors":"Wenjuan Li , Xiao Li , Hailong Hong , Ruijun Xie , Ning Zhu","doi":"10.1080/00397911.2024.2324456","DOIUrl":"10.1080/00397911.2024.2324456","url":null,"abstract":"<div><p>An effective, green and eco-friendly method was developed to synthesize 1<em>H</em>-benzimidazole under microwave irradiation. The reactions of substituted <em>o</em>-phenylenediamine with DMF were efficiently promoted by butanoic acid, and the desired product 1<em>H</em>-benzimidazole derivatives were obtained in good to excellent yields. Compared with the conventional heating method, microwave irradiation significantly reduced the reaction time and improved the yields of the target products.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 8","pages":"Pages 645-654"},"PeriodicalIF":2.1,"publicationDate":"2024-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140044284","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}