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Journal of Carbohydrate Chemistry Volume 24, 2005 - Issue 3
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Original Articles

Bioactive Pseudo‐C‐nucleosides Containing Thiazole, Thiazolidinone, and Tetrazole Rings

Amélia P. Rauter Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade de Lisboa, Campo Grande, Lisboa, PortugalCorrespondence[email protected]
,
Mária Padilha Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade de Lisboa, Campo Grande, Lisboa, Portugal
,
José A. Figueiredo Departamento de Química da Universidade da Beira Interior, Unidade I&D de Materiais Têxteis e Papeleiros, Covilhã, Portugal
,
Maria I. Ismael Departamento de Química da Universidade da Beira Interior, Unidade I&D de Materiais Têxteis e Papeleiros, Covilhã, Portugal
,
Jorge Justino Escola Superior Agrária—Instituto Politécnico de Santarém, Santarém, Portugal
,
Humberto Ferreira Centro de Química Estrutural do Instituto Superior Técnico, Lisboa, Portugal
,
Maria J. Ferreira Centro de Química Estrutural do Instituto Superior Técnico, Lisboa, Portugal
,
Candasamy Rajendran School of Biology, University of Newcastle, Newcastle upon Tyne, UK
,
Richard Wilkins School of Biology, University of Newcastle, Newcastle upon Tyne, UK
,
Pedro D. Vaz Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade de Lisboa, Campo Grande, Lisboa, Portugal; ITQB, UNL, Oeiras, Portugal
&
M. J. Calhorda Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade de Lisboa, Campo Grande, Lisboa, Portugal; ITQB, UNL, Oeiras, Portugal
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Pages 275-296 | Received 09 Sep 2004, Accepted 16 Mar 2005, Published online: 16 Aug 2006

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Ahmed I. Khodair, Fatimah M. Alzahrani, Mohamed K. Awad, Siham A. Al-Issa, Ghaferah H. Al-Hazmi & Mohamed S. Nafie. (2023) Design, synthesis, molecular modelling and antitumor evaluation of S-glucosylated rhodanines through topo II inhibition and DNA intercalation. Journal of Enzyme Inhibition and Medicinal Chemistry 38:1.
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Nadia Hanafy Metwally & Ibrahim Adel El-Doseky. (2015) Facile Synthesis of Some New Pyrazole-Based 2-Thioxo-4-thiazolidinone. Synthetic Communications 45:23, pages 2683-2690.
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Xingchen Yan, Yuhua Fan, Caifeng Bi, Xia Zhang, Jian Zuo, Pengfei Zhang & Zhongyu Zhang. (2014) Synthesis, Crystal Structure, and Theoretical Calculation of the Cd(II) Complex with 2-Aminobenzothiazole. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry 44:4, pages 603-610.
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NadiaH. Metwally, NoraM. Rateb & HusseinF. Zohdi. (2011) A simple and green procedure for the synthesis of 5-arylidene-4-thiazolidinones by grinding. Green Chemistry Letters and Reviews 4:3, pages 225-228.
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Articles from other publishers (22)

Catarina Maria & Amélia P. Rauter. (2023) Nucleoside analogues: N-glycosylation methodologies, synthesis of antiviral and antitumor drugs and potential against drug-resistant bacteria and Alzheimer's disease. Carbohydrate Research 532, pages 108889.
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Rita Gonçalves-Pereira, Jose A. Figueiredo, Susana D. Lucas, Maria I. García-Moreno, Carmen O. Mellet, Amelia P. Rauter & Maria I. Ismael. (2023) Synthesis, Biological Evaluation, and Docking Studies of Open-Chain Carbohydrate Amides as Acetylcholinesterase Inhibitors. Medicinal Chemistry 19:6, pages 570-577.
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Ahmed I. Khodair, Fatimah M. Alzahrani, Mohamed K. Awad, Siham A. Al-Issa, Ghaferah H. Al-Hazmi & Mohamed S. Nafie. (2023) Design, Synthesis, Computational Investigations, and Antitumor Evaluation of N -Rhodanine Glycosides Derivatives as Potent DNA Intercalation and Topo II Inhibition against Cancer Cells . ACS Omega 8:14, pages 13300-13314.
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Mariam Azzam Alanazi, Wael A.A. Arafa, Ibrahim O. Althobaiti, Hamud A. Altaleb, Rania B. Bakr & Nadia A. A. Elkanzi. (2022) Green Design, Synthesis, and Molecular Docking Study of Novel Quinoxaline Derivatives with Insecticidal Potential against Aphis craccivora . ACS Omega 7:31, pages 27674-27689.
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Sachin P. Gadekar, Sudarshan S. Dipake, Suresh T. Gaikwad & Machhindra K. Lande. (2018) Solid acid TS-1 catalyst: an efficient catalyst in Knoevenagel condensation for the synthesis of 5-arylidene-2,4-thiazolidinediones/Rhodanines in aqueous medium. Research on Chemical Intermediates 44:12, pages 7509-7518.
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Mamdouh A. Abu-Zaied & Galal H. Elgemeie. (2017) Thiazoles in glycosylation reactions: Novel synthesis of thiazole thioglycosides. Heteroatom Chemistry 28:6, pages e21404.
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Joana Darc Souza Chaves, Jaqueline Lopes Damasceno, Marcela Cristina Ferreira Paula, Pollyanna Francielli de Oliveira, Gustavo Chevitarese Azevedo, Renato Camargo Matos, Maria Cristina S. Lourenço, Denise Crispim Tavares, Heveline Silva, Ana Paula Soares Fontes & Mauro Vieira de Almeida. (2015) Synthesis, characterization, cytotoxic and antitubercular activities of new gold(I) and gold(III) complexes containing ligands derived from carbohydrates. BioMetals 28:5, pages 845-860.
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Éva Bokor, Attila Fekete, Gergely Varga, Béla Szőcs, Katalin Czifrák, István Komáromi & László Somsák. (2013) C-(β-d-Glucopyranosyl)formamidrazones, formic acid hydrazides and their transformations into 3-(β-d-glucopyranosyl)-5-substituted-1,2,4-triazoles: a synthetic and computational study. Tetrahedron 69:48, pages 10391-10404.
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Chang-Ji Zheng, Ming-Xia Song, Liang-Peng Sun, Yan Wu, Lan Hong & Hu-Ri Piao. (2012) Synthesis and biological evaluation of 5-aryloxypyrazole derivatives bearing a rhodanine-3-aromatic acid as potential antimicrobial agents. Bioorganic & Medicinal Chemistry Letters 22:23, pages 7024-7028.
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Ming-Xia Song, Chang-Ji Zheng, Xian-Qing Deng, Qing Wang, Shao-Pu Hou, Ting-Ting Liu, Xiao-Lan Xing & Hu-Ri Piao. (2012) Synthesis and bioactivity evaluation of rhodanine derivatives as potential anti-bacterial agents. European Journal of Medicinal Chemistry 54, pages 403-412.
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V. A. Ostrovskii, R. E. Trifonov & E. A. Popova. (2013) Medicinal chemistry of tetrazoles. Russian Chemical Bulletin 61:4, pages 768-780.
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J.A. Figueiredo, M.I. Ismael, J.M. Pinheiro, A.M.S. Silva, J. Justino, F.V.M. Silva, M. Goulart, D. Mira, M.E.M. Araújo, R. Campoy & A.P. Rauter. (2012) Facile synthesis of oxo-/thioxopyrimidines and tetrazoles C–C linked to sugars as novel non-toxic antioxidant acetylcholinesterase inhibitors. Carbohydrate Research 347:1, pages 47-54.
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Hua Chen, Qingmei Yin, Chunxiao Li, Enkai Wang, Fang Gao, Xiaobo Zhang, Zhi Yin, Sinan Wei, Xiaoliu Li, Ming Meng, Pingzhu Zhang, Na Li & Jinchao Zhang. (2011) Synthesis of C -Pseudonucleosides Bearing Thiazolidin-4-one as a Novel Potential Immunostimulating Agent . ACS Medicinal Chemistry Letters 2:11, pages 845-848.
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Ahmed I. Khodair & Jean-Pierre Gesson. (2011) A new approach for the N- and S-galactosylation of 5-arylidene-2-thioxo-4-thiazolidinones. Carbohydrate Research.
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Nadia Hanafy Metwally & Sabry El-Taher. (2011) Synthesis, Theoretical Study, and Antimicrobial Activity of Novel Polysubstituted Thiazoles. HETEROCYCLES 83:5, pages 1029.
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Nadia Hanafy Metwally, Magda Ahmed Abdalla, Mosselhi Abdel Nabi Mosselhi & Ebrahim Adel El-Desoky. (2010) Synthesis and antimicrobial activity of some new N-glycosides of 2-thioxo-4-thiazolidinone derivatives. Carbohydrate Research 345:9, pages 1135-1141.
Crossref
Hua Chen, Hongzhi Zhang, Junna Feng, Xiaoliu Li, Lingling Jiao, Zhanbin Qin, Qingmei Yin & Jinchao Zhang. (2009) A Convenient Synthesis and Biological Evaluation of Novel Pseudonucleosides Bearing a Thiazolidin-4-one Moiety by Tandem Staudinger/Aza-Wittig/Cyclization. European Journal of Organic Chemistry 2009:35, pages 6100-6103.
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Hua Chen, Lingling Jiao, Zaihong Guo, Xiaoliu Li, Cuilan Ba & Jinchao Zhang. (2008) Synthesis and biological activity of novel thiazolidin-4-ones with a carbohydrate moiety. Carbohydrate Research 343:18, pages 3015-3020.
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Elena Gómez-Sánchez, Elena Soriano & José Marco-Contelles. (2008) Synthesis of Heterocyclic Analogues of Epibatidine via 7-Azabicyclo[2.2.1]hept-2-yl Radical Intermediates. 1. Intermolecular Reactions. The Journal of Organic Chemistry 73:17, pages 6784-6792.
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V.A. Ostrovskii, G.I. Koldobskii & R.E. Trifonov. 2008. Comprehensive Heterocyclic Chemistry III. Comprehensive Heterocyclic Chemistry III 257 423 .
Mamdouh M. Ali & Sohair A. Hassan. (2007) Role of Some Newly Synthesized Tetrahydronaphthalenthiazol Derivatives as Anticancer Compounds. International Journal of Cancer Research 3:2, pages 103-110.
Crossref
E. S. H. El Ashry, Y. El Kilany & N. M. Nahas. 2007. Heterocycles from Carbohydrate Precursors. Heterocycles from Carbohydrate Precursors 1 30 .

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