- Design, synthesis and cytotoxic activity of novel sulfonylurea derivatives of podophyllotoxin
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Three series of novel sulfonylurea podophyllotoxin derivatives were designed, synthesized, and evaluated for in vitro cytotoxicity against four tumor cell lines (A-549, DU-145, KB and KBvin). Compounds 14c (IC50: 1.41-1.76 μM) and 14e (IC5
- Zhang, Zhi-Jun,Tian, Jing,Wang, Li-Ting,Wang, Mei-Juan,Nan, Xiang,Yang, Liu,Liu, Ying-Qian,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung
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- Gold(i)-catalyzed Nicholas reaction with aromatic molecules utilizing a bifunctional propargyl dicobalt hexacarbonyl complex
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A benchtop-stable reagent for the catalytic Nicholas reaction was developed. By combining a propargyl dicobalt hexacarbonyl cluster with an ortho-alkynylbenzoate unit and a fluorous tag, introduction of a propargyl hexacarbonyl complex on various aromatic compounds having acid- or base-sensitive functional groups becomes possible by using a gold(i) catalyst. In addition, the presence of a fluorous tag facilitates convenient separation of the target products from byproducts.
- Okamura, Toshitaka,Fujiki, Shogo,Iwabuchi, Yoshiharu,Kanoh, Naoki
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supporting information
p. 8522 - 8526
(2019/10/02)
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- Catalytic Enantioselective Synthesis of (-)-Podophyllotoxin
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The first catalytic enantioselective total synthesis of (-)-podophyllotoxin is accomplished by a challenging organocatalytic cross-aldol Heck cyclization and distal stereocontrolled transfer hydrogenation in five steps from three aldehydes. Reversal of se
- Hajra, Saumen,Garai, Sujay,Hazra, Sunit
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supporting information
p. 6530 - 6533
(2017/12/26)
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- Antitumor agents. Part 232: Synthesis of cyclosulfite podophyllotoxin analogues as novel prototype antitumor agents
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An 11,13-O,O′-cyclosulfite GL-331 analogue (7) was synthesized in six steps from podophyllotoxin and evaluated as a potential antitumor agent. Compound 7 was significantly cytotoxic against human tumor cell lines, but showed no inhibition against human DN
- Xiao, Zhiyan,Han, Shiqing,Bastow, Kenneth F.,Lee, Kuo-Hsiung
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p. 1581 - 1584
(2007/10/03)
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- Antitumor agents. 207. Design, synthesis, and biological testing of 4β-anilino-2-fluoro-4′-demethylpodophyllotoxin analogues as cytotoxic and antiviral agents
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2-Fluoropodophyllotoxin (11) and several 4β-anilino-2-fluoro-4′-O-demethyl analogues were synthesized and evaluated in both antineoplastic and antiviral assays. These compounds were moderately active against some cancer cell lines, but they were less acti
- VanVliet,Tachibana,Bastow,Huang,Lee
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p. 1422 - 1428
(2007/10/03)
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- Synthesis of picropodophyllin homolactone
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Based on a Wittig olefination strategy, the first synthesis of picropodophyllin homolactone 2 is described in nine steps and 30% overall yield from podophyllotoxine 1. The relative configuration of 2 was unambiguously determined using 2D NOESY NMR and a Monte Carlo search protocol. This work corrects the literature on the synthesis of 2. (C) 2000 Elsevier Science Ltd.
- Roulland, Emmanuel,Bertounesque, Emmanuel,Huel, Christiane,Monneret, Claude
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p. 6769 - 6773
(2007/10/03)
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- A high yield preparation of 2-fluoropodophyllotoxin
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The high yield synthesis of 2-fluoropodophyllotoxin is presented. This preparation represents the first example of a 100% diastereospecific electrophilic fluorination.
- VanVliet, David S.,Lee, Kuo-Hsiung
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p. 2259 - 2262
(2007/10/03)
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- Synthesis of sterically fixed podophyllotoxins
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Podophyllotoxin and epi-podophyllotoxin derivatives (1/2) with an unsaturated side chain at C-5a were obtained by C-alkylation of protected derivatives of 1. The azide 3a afforded 4 in quantitative yield at 80°C. With pyridine/acetyl chloride, the latter yielded the rigid epi-podophyllotoxin derivative 7, whose structure was established by crystal structure analysis. All reported podophyllotoxin derivatives are less cytotoxic than podophyllotoxin (1a) itself. VCH Verlagsgesellschaft mbH, 1996.
- Laatsch, Hartmut,Ernst, Bernd Peter,Noltemeyer, Mathias
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p. 731 - 737
(2007/10/03)
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- Asymmetric Total Synthesis of (-)-Podophyllotoxin
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Using a diastereoselective addition of the appropriate aryllithium to a naphtalene-containing chiral oxazoline leads to advanced intermadiate 11 in the podophyllotoxin series.The latter is obtained in a 92:8 de.Transformation of the oxazoline moiety to the requisite lactone 18 followed by invoking the Kende route to the target gave natural (-)-podophyllotoxin in 94 percent ee.The overall yield of the sequence, accomplished in 24 steps, was 5 percent.
- Andrews, Robert C.,Teague, Simon J.,Meyers, A. I.
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p. 7854 - 7858
(2007/10/02)
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- Studies on the Constituents of the Seeds of Hernandia ovigera L. VI. Isolation and Structural Determination of Three Lignans
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Three kinds of lignans, including a new lignan, named hernolactone, were isolated from the seeds of Hernandia ovigera L. besides six previously reported lignans, desoxypodophyllotoxin (DPT), desoxypicropodophyllin, bursehernin, podorhizol, hernandin and d
- Tanoguchi, Mariko,Arimoto, Masao,Saika, Hideyuki,Yamaguchi, Hideo
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p. 4162 - 4168
(2007/10/02)
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