A. Sharifi, Zahra Babaalian, M. S. Abaee, M. Moazami, M. Mirzaei
{"title":"Synergistic promoting effect of ball milling and Fe(ii) catalysis for cross-dehydrogenative-coupling of 1,4-benzoxazinones with indoles","authors":"A. Sharifi, Zahra Babaalian, M. S. Abaee, M. Moazami, M. Mirzaei","doi":"10.1515/hc-2020-0123","DOIUrl":"https://doi.org/10.1515/hc-2020-0123","url":null,"abstract":"Abstract In this work, a novel C(sp3)–C(sp2) cross-dehydrogenative-coupling method is developed to react benzoxazin-2-one derivatives with various indoles. As a result, combined use of ball milling and Fe(ii) catalysis leads to rapid coupling of 1,4-benzoxazinones with derivatives of indole. Under the conditions, derivatives of 1 couple with various indoles at room temperature to produce good yields of the desired compounds within 0.5–2 h time period. Thus, derivatives of both starting materials couple smoothly under relatively mild conditions to give good yields of 3.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"27 1","pages":"57 - 62"},"PeriodicalIF":2.3,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2020-0123","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45266134","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}
M. Pirouz, M. Saeed Abaee, P. Harris, M. M. Mojtahedi
{"title":"One-pot synthesis of benzofurans via heteroannulation of benzoquinones","authors":"M. Pirouz, M. Saeed Abaee, P. Harris, M. M. Mojtahedi","doi":"10.1515/hc-2020-0120","DOIUrl":"https://doi.org/10.1515/hc-2020-0120","url":null,"abstract":"Abstract Three different reactions were explored leading to the synthesis of various benzofurans. All reactions took place under AcOH catalysis in a one-pot manner. As a result, benzoquinone derivatives underwent heteroannulation with either itself or cyclohexanones to produce furanylidene-benzofuran or benzofuran structures, respectively.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"27 1","pages":"24 - 31"},"PeriodicalIF":2.3,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2020-0120","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45183184","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":"Design and development of novel thiazole-sulfonamide derivatives as a protective agent against diabetic cataract in Wistar rats via inhibition of aldose reductase","authors":"L. Yin, Mingxue Zhang, Tian-geng He","doi":"10.1515/hc-2020-0124","DOIUrl":"https://doi.org/10.1515/hc-2020-0124","url":null,"abstract":"Abstract In recent years, ALR2 (aldose reductase) inhibitors have attracted attention for their effective ability to reduce the progression of diabetes-associated cataracts. Therefore, in the present article, we intended to develop novel thiazole-sulfonamide hybrids as a potent inhibitor of ALR2. These molecules significantly inhibited the ALR2 level in the rat lenses homogenate, where the most potent compound 7b showed activity comparable to sorbinil as standard. In Wistar rats, compound 7b improved the insulin level and body weight of the experimental animal together with a reduction in the glucose output. Compound 7b showed a significant reduction in the expression of ALR2 in rat lenses in western blot analysis.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"27 1","pages":"63 - 70"},"PeriodicalIF":2.3,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48123442","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}
Martina Bortolami, I. Chiarotto, L. Mattiello, R. Petrucci, D. Rocco, Fabrizio Vetica, M. Feroci
{"title":"Organic electrochemistry: Synthesis and functionalization of β-lactams in the twenty-first century","authors":"Martina Bortolami, I. Chiarotto, L. Mattiello, R. Petrucci, D. Rocco, Fabrizio Vetica, M. Feroci","doi":"10.1515/hc-2020-0121","DOIUrl":"https://doi.org/10.1515/hc-2020-0121","url":null,"abstract":"Abstract Organic electrochemistry is a technique that allows for the heterogeneous redox reactions avoiding both the use of stoichiometric amounts of redox reagents and the resulting formation of stoichiometric by-products. In fact, the redox reagent in these reactions is the electron, which is naturally eco-friendly and produces no side compounds. It is therefore quite obvious that electrochemistry can be classified as a “green” technology. The use of this methodology in the synthesis of β-lactams is not a novelty, but the growing interest in this class of biologically active compounds, due to the discovery of new fields of application (after a moment of decrease in interest due to antibiotic resistance) has been a stimulus for the search for more efficient electrochemical ways to synthesize and transform β-lactams. Thus, this review deals with the twenty-first-century applications of electroorganic technique to the chemistry of β-lactams, by analyzing first the syntheses classified by the type of reactions (cyclization, cycloaddition, etc.) and then by manipulating the β-lactam structure, using it as a synthon. Lastly, the importance of this technique is demonstrated by a study of a pilot plant scale reduction of a cephalosporanic acid derivative to a commercially important antibiotic.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"27 1","pages":"32 - 44"},"PeriodicalIF":2.3,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2020-0121","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45780672","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}
Joseph Tsemeugne, P. K. Nangmo, P. Mkounga, J. Tamokou, Iréne Chinda Kengne, G. Edwards, Emmanuel F Sopbue, A. Nkengfack
{"title":"Synthesis, characteristic fragmentation patterns, and antibacterial activity of new azo compounds from the coupling reaction of diazobenzothiazole ions and acetaminophen","authors":"Joseph Tsemeugne, P. K. Nangmo, P. Mkounga, J. Tamokou, Iréne Chinda Kengne, G. Edwards, Emmanuel F Sopbue, A. Nkengfack","doi":"10.1515/hc-2020-0127","DOIUrl":"https://doi.org/10.1515/hc-2020-0127","url":null,"abstract":"Abstract In this study, a series of azobenzothiazole dyes 4 were synthesized via diazotization of substituted benzothiazole derivatives followed by azo coupling with acetaminophen. The chemical structures of all synthesized compounds were confirmed using analytical data and spectroscopic techniques, including UV-visible, IR, mass spectra, and 1H- and 13C-NMR. The in situ formed diazobenzothiazole ions regiospecifically react with acetaminophen derivatives in the Hollemann-guided electrophilic aromatic substitution mechanism. The regio-orientations were established, on the one hand, by a rigorous interpretation of 1H-NMR spectra and, on the other hand, by the characteristic fragmentation patterns observed on the electrospray mass spectra. In the cases of 4a and 4b, multisubstitutions occurred. The antimicrobial activity of compound 4, along with all the starting materials, was investigated on Pseudomonas aeruginosa PA01, Staphylococcus aureus 18, Escherichia coli 64R, and S. aureus ATCC 25923. The results showed that this skeletal framework exhibited marked potency as antibacterial agents. The most active antibacterial agent against both targeted organisms was compound 4a′.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"27 1","pages":"79 - 89"},"PeriodicalIF":2.3,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43763014","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":"Quantum chemistry study on the promoted reactivity of substituted cyclooctynes in bioorthogonal cycloaddition reactions","authors":"T. Hosseinnejad, Marzieh Omrani-Pachin","doi":"10.1515/hc-2020-0129","DOIUrl":"https://doi.org/10.1515/hc-2020-0129","url":null,"abstract":"Abstract In the present research, we focus on the energetics and electronic aspects of enhanced reactivity in the regioselective bioorthogonal 1,3-dipolar cycloaddition reaction of various substituted cyclooctynes with methyl azide, applying quantum chemistry approaches. In this respect, we assessed the structural and energetic properties of regioisomeric products and their corresponded transition states and calculated the reaction electronic energy changes and energy barriers through the cycloaddition pathways. The obtained results revealed that the trifluoromethyl substitution and fluorination of cyclooctynes lead to improved reactivity, in conjunction with increased exothermicity and decreased activation energy values. On the other hand, quantum theory of atoms in molecules computations were performed on some key bond and ring critical points that demonstrated the stabilizing topological properties of electron density and its derivatives upon trifluoromethyl substitution and fluorination of propargylic carbon of cyclooctynes which can be regarded as the essential origin of enhanced reactivity.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"27 1","pages":"142 - 154"},"PeriodicalIF":2.3,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41710879","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":"Isatin as a simple, highly selective and sensitive colorimetric sensor for fluoride anion","authors":"A. Haider, Mukhtiar Ahmed, M. Faisal, M. Naseer","doi":"10.1515/hc-2020-0003","DOIUrl":"https://doi.org/10.1515/hc-2020-0003","url":null,"abstract":"Abstract Herein, we report the fluoride anion sensing properties of a commercially available and inexpensive organic compound, isatin, which is found to be a highly selective and sensitive sensor. In naked-eye experiments, by addition of fluoride anions, isatin shows a dramatic color change from pale yellow to violet at room temperature, while the addition of other anions, i.e. C l − , $mathrm{Cl}^-,$ B r − , I − , C l O 4 − , H 2 P O 4 − a n d P F 6 − , $mathrm{Br}^-,mathrm I^-,mathrm{ClO}_4^-,{mathrm H}_2mathrm{PO}_4^-,mathrm{and},mathrm{PF}_6^-,$did not induce any colour change. Additionally, recognition and titration studies have also been done through UV/Vis spectroscopy. Isatin displayed a new absorption band at 533 nm after the addition of fluoride anions, which is presumably due to acid-base interaction between isatin and fluoride anions, while other anions did not trigger noticeable spectral changes. The detection limit was observed to be 0.367 ppm. DFT calculations were also performed to further explain the behavior of receptor 1 towards the Fˉ anion. Owing to high sensitivity and selectivity, isatin can be useful in the detection of biologically or environmentally important fluoride anions at very low concentration.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"26 1","pages":"14 - 19"},"PeriodicalIF":2.3,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2020-0003","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45628638","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":"Design, Synthesis and Study of Antibacterial and Antitubercular Activity of Quinoline Hydrazone Hybrids","authors":"Shruthi T G, S. Subramanian, S. Eswaran","doi":"10.1515/hc-2020-0109","DOIUrl":"https://doi.org/10.1515/hc-2020-0109","url":null,"abstract":"Abstract Emerging bacterial resistance is causing widespread problems for the treatment of various infections. Therefore, the search for antimicrobials is a never-ending task. Hydrazones and quinolines possess a wide variety of biological activities. Herewith, eleven quinoline hydrazone derivatives have been designed, synthesized, characterized and evaluated for their antibacterial activity and antitubercular potential against Mtb WT H37Rv. Compounds QH-02, QH-04 and QH-05 were found to be promising compounds with an MIC value of 4 μg/mL against Mtb WT H37Rv. Compounds QH-02, QH-04, QH-05, and QH-11 were also found to be active against bacterial strains including Acinetobacter baumanii, Escherichia coli and Staphylococcus aureus. Further, we have carried out experiments to confirm the cytotoxicity of the active compounds and found them to be non-toxic.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"26 1","pages":"137 - 147"},"PeriodicalIF":2.3,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2020-0109","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49541988","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":"The oxidative coupling between benzaldehyde derivatives and phenylacetylene catalyzed by rhodium complexes via C-H bond activation","authors":"Xinyi Zhao, Hongge Jia, Q. Wang, Heming Song, Yanan Tang, Liqun Ma, Yongqian Shi, Guoxing Yang, Yazhen Wang, Y. Zang, Shuangping Xu","doi":"10.1515/hc-2020-0004","DOIUrl":"https://doi.org/10.1515/hc-2020-0004","url":null,"abstract":"Abstract This paper reports the use of rhodium (Rh) catalysts for the oxidative coupling reaction between phenylacetylene and benzaldehyde derivatives via C-H bond activation. These reactions were catalyzed by Rh(l-amino acid)(cod) (the l-amino acid is l-phenylalanine, l-valine or l-proline; cod is 1,5-cyclooctadiene) to obtain chromones in 12.7–88.3% yield. These new Rh catalysts have excellent activity for the coupling reaction between phenylacetylene and different benzaldehyde derivatives. It was found that the electronic effects of the benzaldehyde derivative substituent affected the reaction yield, which is in accordance with the proposed mechanism.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"26 1","pages":"20 - 25"},"PeriodicalIF":2.3,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2020-0004","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47587294","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}
Ali Irfan, Laila Rubab, Mishbah Ur Rehman, R. Anjum, S. Ullah, Mahwish Marjana, Saba Qadeer, Sadia Sana
{"title":"Coumarin sulfonamide derivatives: An emerging class of therapeutic agents","authors":"Ali Irfan, Laila Rubab, Mishbah Ur Rehman, R. Anjum, S. Ullah, Mahwish Marjana, Saba Qadeer, Sadia Sana","doi":"10.1515/hc-2020-0008","DOIUrl":"https://doi.org/10.1515/hc-2020-0008","url":null,"abstract":"Abstract Coumarin sulfonamide is a heterocyclic pharmacophore and an important structural motif which is a core and integral part of different therapeutic scaffolds and analogues. Coumarin sulfonamides are privileged and pivotal templates which have a broad spectrum of applications in the fields of medicine, pharmacology and pharmaceutics. Coumarin sulfonamide exhibited versatile and myriad biomedical activities such as anti-bacterial, antiviral, antifungal, anti-inflammatory and anti-cancer. This review article focuses on the structural features of coumarin sulfonamide derivatives in the treatment of different lethal diseases on the basis of structure-activity relationships (SAR). The plethora of research cited in this review article summarizes and discusses the various substitutions around the coumarin sulfonamide nucleus which have provided a wide spectrum of biological activities and therapeutic potential that has proved attractive to many researchers looking to exploit the coumarin sulfonamide skeleton for drug discovery and the development of novel therapeutic agents.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"26 1","pages":"46 - 59"},"PeriodicalIF":2.3,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2020-0008","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44260994","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}