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Heterocyclic Communications最新文献

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Synthesis, characterization, and antibacterial activity of a new poly azo compound containing N-arylsuccinimid and dibenzobarrelene moieties 含N-芳基琥珀酰亚胺和二苯并巴龙烯部分的新型聚偶氮化合物的合成、表征及其抗菌活性
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2023-01-01 DOI: 10.1515/hc-2022-0157
Njoya Abdou Salamou, Tamokou Jean-de-Dieu, Sopbué Fondjo Emmanuel, Matsuete Takongmo Germaine, Bitchagno Mbahbou T. Gabin, Peter F. W. Simon, A. Tsopmo, Kuiate Jules-Roger
{"title":"Synthesis, characterization, and antibacterial activity of a new poly azo compound containing N-arylsuccinimid and dibenzobarrelene moieties","authors":"Njoya Abdou Salamou, Tamokou Jean-de-Dieu, Sopbué Fondjo Emmanuel, Matsuete Takongmo Germaine, Bitchagno Mbahbou T. Gabin, Peter F. W. Simon, A. Tsopmo, Kuiate Jules-Roger","doi":"10.1515/hc-2022-0157","DOIUrl":"https://doi.org/10.1515/hc-2022-0157","url":null,"abstract":"Abstract The present work describes the synthesis, characterization, and evaluation of the antibacterial activity of a new poly azo compound resulting from the coupling of a previously reported N-arylsuccinimid precursor 5 with the diazonium ion of aniline. This azo compound was characterized using its physical, elemental, and 1D and 2D spectroscopic data. The novel azo compound 7 (minimum inhibitory concentration [MIC] = 16–32 μg/mL) showed higher antibacterial activity than its precursor 5 (MIC = 32–64 μg/mL), although it was low compared to the reference drug ciprofloxacin (MIC = 0.5–4 μg/mL). Graphical abstract","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"29 1","pages":""},"PeriodicalIF":2.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41963595","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
Syntheses, crystal structure, thermal behavior, and anti-tumor activity of three ternary metal complexes with 2-chloro-5-nitrobenzoic acid and heterocyclic compounds 2-氯-5-硝基苯甲酸及杂环化合物三元金属配合物的合成、晶体结构、热行为及抗肿瘤活性
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2022-01-01 DOI: 10.1515/hc-2022-0011
Zhongyu Zhang, Meng Chen, M. Tong, Wan Sun, P. Dong, Xinfeng Song, Xiaoyue Wang
{"title":"Syntheses, crystal structure, thermal behavior, and anti-tumor activity of three ternary metal complexes with 2-chloro-5-nitrobenzoic acid and heterocyclic compounds","authors":"Zhongyu Zhang, Meng Chen, M. Tong, Wan Sun, P. Dong, Xinfeng Song, Xiaoyue Wang","doi":"10.1515/hc-2022-0011","DOIUrl":"https://doi.org/10.1515/hc-2022-0011","url":null,"abstract":"Abstract Three complexes, namely complex (1), complex (2), and complex (3), were synthesized and characterized by X-ray diffraction, thermogravimetric study, and elemental study. Complex (1) comprises discrete binuclear clusters, where two oxygen atoms of 2-chloro-5-nitrobenzoic acid bridge the two copper atoms. Complex (2) is a six-coordination structure consisting of four nitrogen atoms and two oxygen atoms in 2-chloro-5-nitrobenzoic acid and 1,10-phenanthroline to furnish a twisted octahedron. Complex (3) is a six-coordination structure consisting of four oxygen atoms and two nitrogen atoms from the 2-chloro-5-nitrobenzoic acid, methanol, and 2,2′-dipyridyl to furnish a distorted octahedral geometry. Metal complexes’ anti-tumor activity was also investigated by the MTT assay. Of the complexes tested, complex (1) could induce apoptosis in these A549 lung cancer and Caco-2 colon adenocarcinoma cells and complex (2) could induce apoptosis in Caco-2 colon adenocarcinoma cells. CCDC for complex (1) was 1543354, CCDC for complex (2) was 1546991, and CCDC for complex (3) was 1543417.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"28 1","pages":"84 - 94"},"PeriodicalIF":2.3,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46909406","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: 2
Synthesis of newer substituted chalcone linked 1,2,3-triazole analogs and evaluation of their cytotoxic activities 新取代查尔酮连接1,2,3-三唑类似物的合成及其细胞毒活性评价
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2022-01-01 DOI: 10.1515/hc-2022-0147
M. Raghavender, B. Shankar, Nalla Umapathi, P. Jalapathi
{"title":"Synthesis of newer substituted chalcone linked 1,2,3-triazole analogs and evaluation of their cytotoxic activities","authors":"M. Raghavender, B. Shankar, Nalla Umapathi, P. Jalapathi","doi":"10.1515/hc-2022-0147","DOIUrl":"https://doi.org/10.1515/hc-2022-0147","url":null,"abstract":"Abstract An innovative heterocyclic biologically active chalcone 1,2,3-triazole analogs (6a–j) were prepared to extract excellent yields by coupling the substituted aryl azides (5a–5j) and 5-ethynyl-1,2,3-trimethoxybenzene, by using the method of Huisgen azide–alkyne cycloaddition. The typically synthesized analogs were elucidated by IR, 1H-nuclear magnetic resonance (NMR), 13C-NMR, and Electron spray ionization (ESI)-mass spectroscopy and tested for their cytotoxicity effectiveness in MTT assays against the A549 lung cancer cells. The cytotoxic studies suggested that a few analogs showed moderate to good activities. The compounds 6i and 6c showed low cytotoxicity against the A549 cell line among 12 analogs, the values of IC50 were displayed in the range of 65.05 ± 1.12 and 71.56 ± 1.29 µM, respectively. The compound 6j showed slightly less cytotoxicity but showed good selectivity against A549 cell lines.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"28 1","pages":"130 - 138"},"PeriodicalIF":2.3,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41373545","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
DABCO-based ionic liquid-promoted synthesis of indeno-benzofurans derivatives: Investigation of antioxidant and antidiabetic activities 基于dabco的离子液体促进吲哚-苯并呋喃衍生物的合成:抗氧化和抗糖尿病活性的研究
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2022-01-01 DOI: 10.1515/hc-2022-0153
Narges Alipour Saqa, Shiva Khalil-Moghaddam, A. Shahvelayati
{"title":"DABCO-based ionic liquid-promoted synthesis of indeno-benzofurans derivatives: Investigation of antioxidant and antidiabetic activities","authors":"Narges Alipour Saqa, Shiva Khalil-Moghaddam, A. Shahvelayati","doi":"10.1515/hc-2022-0153","DOIUrl":"https://doi.org/10.1515/hc-2022-0153","url":null,"abstract":"Abstract A simple and effective method for synthesis of indeno-benzofurans derivatives using polyphenols and ninhydrins is explored using an acidic catalyst based on DABCO (1,4-diaza bicycle [2.2.2] octane)-based ionic liquid. The products of these types of reactions have very low yields without catalysts, but with DABCO-AIL, the yields are excellent, reaction times are reduced, and the media are cleaner. Using infrared (IR), proton nuclear magnetic resonance (1H NMR), Carbon-13 nuclear magnetic resonance (13C NMR), and mass spectrometry, the structures of products can be confirmed. There is evidence that oxidative stress plays a role in the pathophysiology of numerous diseases, including diabetes. Therapeutic antioxidants are promising candidates for the prevention and treatment of such diseases. To investigate the antioxidant properties of all synthesized derivatives, the 2,2-diphenyl-1-picrylhydrazylhydrazyl-hydrate (DPPH) assay was used. Derivatives 3d and 4 with the highest antioxidant effect (with IC50 value of 0.015 µmol/mL) were selected to evaluate the anti-diabetic effect using the Bernfeld method. The best result was seen at 0.8 mg/mL of 4 derivative and results of the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) test revealed that 4 at this concentration lacked cellular toxicity, too.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"28 1","pages":"164 - 173"},"PeriodicalIF":2.3,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45748948","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
Study on effective synthesis of 7-hydroxy-4-substituted coumarins 7-羟基-4-取代香豆素的有效合成研究
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2022-01-01 DOI: 10.1515/hc-2022-0154
Dejun Zhou, Youchao Zhuang, Zuntian Sheng
{"title":"Study on effective synthesis of 7-hydroxy-4-substituted coumarins","authors":"Dejun Zhou, Youchao Zhuang, Zuntian Sheng","doi":"10.1515/hc-2022-0154","DOIUrl":"https://doi.org/10.1515/hc-2022-0154","url":null,"abstract":"Abstract Many coumarin derivatives have good biological activity and application value in fluorescent probes. Therefore, synthetic routes to coumarin derivatives have also attracted the attention of many research groups. In this work, based on the Pechmann coumarin synthesis method, the influence of various Lewis acids on the reaction was discussed, and the optimal synthesis conditions of 7-hydroxy-4-substituted coumarins were explored. Based on the experimental results, a possible mechanism was proposed, which provides a reference for future industrialized production of coumarins.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"28 1","pages":"181 - 187"},"PeriodicalIF":2.3,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44072986","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
Two independent and consecutive Michael addition of 1,3-dimethylbarbituric acid to (2,6-diarylidene)cyclohexanone: Flying-bird-shaped 2D-polymeric structure 1,3-二甲基巴比妥酸对(2,6-二芳二烯)环己酮的两个独立和连续的Michael加成:飞鸟形状的2d聚合物结构
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2022-01-01 DOI: 10.1515/hc-2022-0009
N. Pesyan, Saman Mousavi, E. Şahin
{"title":"Two independent and consecutive Michael addition of 1,3-dimethylbarbituric acid to (2,6-diarylidene)cyclohexanone: Flying-bird-shaped 2D-polymeric structure","authors":"N. Pesyan, Saman Mousavi, E. Şahin","doi":"10.1515/hc-2022-0009","DOIUrl":"https://doi.org/10.1515/hc-2022-0009","url":null,"abstract":"Abstract Two independent and consecutive intermolecular Michael addition of 1,3-dimethylbarbituric acid to 2,6-diarylidenecyclohexanone as an α,β-unsaturated ketone leads to synthesis of a new type of meso form 5,5′-((2-oxocyclohexane-1,3-diyl)bis(arylmethylene))bis(1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione) in good yield. These compounds showed a 2D-polymeric structure via intermolecular H-bonds. Structure elucidation is carried out by 1H NMR, 13C NMR, FT-IR, and X-ray diffraction analyses. A plausible reaction mechanism is discussed. Graphical abstract","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"28 1","pages":"44 - 50"},"PeriodicalIF":2.3,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42692212","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: 1
Eelectrosynthesis of benzothiazole derivatives via C–H thiolation 巯基化法电合成苯并噻唑衍生物
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2022-01-01 DOI: 10.1515/hc-2022-0008
Reza Ahdenov, A. Mohammadi, S. Makarem, S. Taheri, Hoda Mollabagher
{"title":"Eelectrosynthesis of benzothiazole derivatives via C–H thiolation","authors":"Reza Ahdenov, A. Mohammadi, S. Makarem, S. Taheri, Hoda Mollabagher","doi":"10.1515/hc-2022-0008","DOIUrl":"https://doi.org/10.1515/hc-2022-0008","url":null,"abstract":"Abstract Benzothiazole derivatives are essential intermediates in synthesizing a wide variety of medical and pharmaceutical compounds, and there is a great demand for a simple and efficient method to synthesize benzothiazoles under mild reaction conditions. Organic electrosynthesis as an energy-efficient process represents an environmentally benign and safer method than traditional methods for organic synthesis. Herein, we present bromine-free and straightforward synthesis of 2-amino benzothiazole derivatives via the reaction of aniline derivatives and ammonium thiocyanate using electrosynthesis in the presence of sodium bromide both as an electrolyte and as a brominating agent at room temperature in isopropyl alcohol (i-PrOH) as a solvent. The reaction of ammonium thiocyanate via C–H thiolation routes, using various aniline derivatives, resulted in a simple, green, and bromine-free synthesis of 2-amino benzothiazole in moderate to good yields under mild reaction conditions. Riluzole drug can be produced using the same procedure in moderate yields. Graphical abstract","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"28 1","pages":"67 - 74"},"PeriodicalIF":2.3,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47802764","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: 4
Synthesis of rhodium catalysts with amino acid or triazine as a ligand, as well as its polymerization property of phenylacetylene 以氨基酸或三嗪为配体的铑催化剂的合成，以及其对苯乙炔的聚合性能
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2022-01-01 DOI: 10.1515/hc-2022-0014
R. Xu, Mingyu Zhang, Yuyan Zhang, Hongge Jia
{"title":"Synthesis of rhodium catalysts with amino acid or triazine as a ligand, as well as its polymerization property of phenylacetylene","authors":"R. Xu, Mingyu Zhang, Yuyan Zhang, Hongge Jia","doi":"10.1515/hc-2022-0014","DOIUrl":"https://doi.org/10.1515/hc-2022-0014","url":null,"abstract":"Abstract Three novel rhodium complexes, with l-tyrosine (l-Tyr), l-arginine (l-Arg), or 2,4-diamino-6-phenyl-1,3,5-triazine (Dpt) as a ligand, named as [Rh(cod)(l-Tyr)], [Rh(cod)(l-Arg)], and [Rh(cod)(Dpt)2], respectively, had been synthesized for catalyzing the polymerization of phenylacetylene. Their yields were 62.34, 54.87, and 58.21%, respectively, by the most suitable synthesis conditions at 25°C for 4 h. The structures and purity of these complexes were proved by 1H NMR, element analysis, and scanning electron microscope (SEM). It has been examined that phenylacetylene could be polymerized by the three complexes as catalysts with high degrees of polymerization (n = 368, 385, and 664, respectively) and yields (about 87.62, 88.39, and 59.67%, respectively). In conclusion, compared with traditional [Rh–N] type catalysts, the novel [N–Rh–N] type catalyst ([Rh(cod)(Dpt)2]) gained better catalytic performance. By comparing the yield, Mw, and degree of their polymerization, the polymerization mechanism was found under the [N–Rh–N] type rhodium catalyst system.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"28 1","pages":"149 - 156"},"PeriodicalIF":2.3,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42029281","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 of novel triiodide ionic liquid based on quaternary ammonium cation and its use as a solvent reagent under mild and solvent-free conditions 基于季铵阳离子的新型三碘离子液体的合成及其在温和无溶剂条件下用作溶剂试剂的研究
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2022-01-01 DOI: 10.1515/hc-2022-0006
Mahnaz Sakhdari, Nadiya Koukabi, M. Zolfigol
{"title":"Synthesis of novel triiodide ionic liquid based on quaternary ammonium cation and its use as a solvent reagent under mild and solvent-free conditions","authors":"Mahnaz Sakhdari, Nadiya Koukabi, M. Zolfigol","doi":"10.1515/hc-2022-0006","DOIUrl":"https://doi.org/10.1515/hc-2022-0006","url":null,"abstract":"Abstract In this article, for the first time, N,N,N-triethyl-3-iodopropan-1-aminium triiodide [N2223I] [I3] was synthesized and utilized as both a reagent and a solvent in combination with H2O2 (35%) to convert aromatic compounds into their corresponding iodo derivatives. The iodination was accomplished in the absence of organic solvents, and in most instances, water was the sole extraction solvent used. The consumed reagent N,N,N-triethyl-3-iodopropan-1-aminium iodide was comfortably recycled. Graphical abstract","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"28 1","pages":"58 - 66"},"PeriodicalIF":2.3,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46330691","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
Ionic liquid-catalyzed synthesis of (1,4-benzoxazin-3-yl) malonate derivatives via cross-dehydrogenative-coupling reactions 离子液体催化交叉脱氢偶联反应合成（1,4-苯并恶嗪-3-基）丙二酸衍生物
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2022-01-01 DOI: 10.1515/hc-2022-0007
A. Sharifi, M. Moazami, M. Saeed Abaee, M. Mirzaei
{"title":"Ionic liquid-catalyzed synthesis of (1,4-benzoxazin-3-yl) malonate derivatives via cross-dehydrogenative-coupling reactions","authors":"A. Sharifi, M. Moazami, M. Saeed Abaee, M. Mirzaei","doi":"10.1515/hc-2022-0007","DOIUrl":"https://doi.org/10.1515/hc-2022-0007","url":null,"abstract":"Abstract A convenient C(sp3)–C(sp3) oxidative dehydrogenative coupling reaction of 1,4-benzoxazin-2-ones with malonate esters was developed under mild conditions to obtain the respective ester malonates in high yields. Reactions take place in [omim]FeCl4, acting as both the solvent and the catalyst. Under [omim]Cl/FeCl3-DDQ conditions, derivatives of 1 coupled with malonate 2 to give the target molecules within 1–2 h time periods. The ionic liquid was recovered and reused in the next reactions without losing its efficiency. Graphical abstract","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"28 1","pages":"51 - 57"},"PeriodicalIF":2.3,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42580527","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: 3
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