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Keywords = imino Diels–Alder reaction

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18 pages, 4520 KiB  
Article
Design, Synthesis, and Cytotoxicity and Topoisomerase I/IIα Inhibition Activity of Pyrazolo[4,3-f]quinoline Derivatives
by Chhabi Lal Chaudhary, Seungyun Ko, Chaerim Lee, Yerin Kim, Chanhyun Jung, Soonsil Hyun, Youngjoo Kwon, Jong-Soon Kang, Jae-Kyung Jung and Heesoon Lee
Pharmaceuticals 2022, 15(4), 399; https://doi.org/10.3390/ph15040399 - 24 Mar 2022
Cited by 4 | Viewed by 3957
Abstract
With the several targets of cancer treatment, inhibition of DNA topoisomerase activity is one of the well-known focuses in cancer chemotherapy. Here, we describe the design and synthesis of a novel series of pyrazolo[4,3-f]quinolines with potential anticancer/topoisomerase inhibition activity. Forty newly [...] Read more.
With the several targets of cancer treatment, inhibition of DNA topoisomerase activity is one of the well-known focuses in cancer chemotherapy. Here, we describe the design and synthesis of a novel series of pyrazolo[4,3-f]quinolines with potential anticancer/topoisomerase inhibition activity. Forty newly designed pyrazolo[4,3-f]quinoline derivatives were synthesized via inverse imino Diels–Alder reaction. The antiproliferative activity of the synthesized derivatives was initially measured in the human NUGC-3 cancer cell line. Then, the selected compounds 1B, 1C, 1M, 2A, 2D, 2E, 2F, and 2R with higher activity among tested compounds were screened against six cancer cell lines, including ACHN, HCT-15, MM231, NCI-H23, NUGC-3, and PC-3. The results demonstrated that the compounds 1M, 2E, and 2P were most effective in all cancer cell lines exhibiting GI50 below 8 µM. Among them, 2E showed an equivalent inhibition pattern of topoisomerase IIα activity to that of etoposide, positive control at a 100 µM dose. Full article
(This article belongs to the Special Issue Heterocyclic Compounds and Their Application in Therapy)
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10 pages, 3491 KiB  
Article
Brønsted and Lewis Solid Acid Catalysts in the Valorization of Citronellal
by Federica Zaccheria, Federica Santoro, Elvina Dhiaul Iftitah and Nicoletta Ravasio
Catalysts 2018, 8(10), 410; https://doi.org/10.3390/catal8100410 - 22 Sep 2018
Cited by 18 | Viewed by 5373
Abstract
Terpenes are valuable starting materials for the synthesis of molecules that are of interest to the flavor, fragrance, and pharmaceutical industries. However, most processes involve the use of mineral acids or homogeneous Lewis acid catalysts. Here, we report results obtained in the liquid-phase [...] Read more.
Terpenes are valuable starting materials for the synthesis of molecules that are of interest to the flavor, fragrance, and pharmaceutical industries. However, most processes involve the use of mineral acids or homogeneous Lewis acid catalysts. Here, we report results obtained in the liquid-phase reaction of citronellal with anilines under heterogeneous catalysis conditions to give tricyclic compounds with interesting pharmacological activity. The terpenic aldehyde could be converted into octahydroacridines with a 92% yield through an intramolecular imino Diels–Alder reaction of the imine initially formed in the presence of an acidic clay such as Montmorillonite KSF. Selectivity to the desired product strongly depended on the acid sites distribution, with Brønsted acids favoring selectivity to octahydroacridine and formation of the cis isomer. Pure Lewis acids such as silica–alumina with a very low amount of alumina gave excellent results with electron-rich anilines like toluidine and p-anisidine. This protocol can be applied starting directly from essential oils such as kaffir lime oil, which has a high citronellal content. Full article
(This article belongs to the Special Issue Solid Catalysts for the Upgrading of Renewable Sources)
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15 pages, 619 KiB  
Article
Synthesis of Bistetrahydroquinolines as Potential Anticholinesterasic Agents by Double Diels-Alder Reactions
by Yorley Duarte, Margarita Gutiérrez, Luis Astudillo, Jans Alzate-Morales and Natalia Valdés
Molecules 2013, 18(10), 12951-12965; https://doi.org/10.3390/molecules181012951 - 17 Oct 2013
Cited by 8 | Viewed by 6179
Abstract
The tetrahydroquinoline ring system is a unit found in many biologically active natural products and pharmacologically relevant therapeutic agents. A new series of bistetrahydroquinolines (bis-THQs) was synthesized using imino Diels-Alder reactions between dialdehydes, anilines and N-vinyl-2-pyrrolidone (NVP). The notable features [...] Read more.
The tetrahydroquinoline ring system is a unit found in many biologically active natural products and pharmacologically relevant therapeutic agents. A new series of bistetrahydroquinolines (bis-THQs) was synthesized using imino Diels-Alder reactions between dialdehydes, anilines and N-vinyl-2-pyrrolidone (NVP). The notable features of this procedure are mild reaction conditions, greater selectivity and good yields of products. In addition, the inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) of some selected derivatives is reported. The feasible binding modes of these active compounds, within AChE and BuChE binding sites, were predicted by molecular docking experiments and their binding affinity was estimated by means of free energy calculations through the MM-GBSA approximation. Full article
(This article belongs to the Section Organic Chemistry)
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