A Stereospecific Route for the Preparation of Trans-Combretastatin Analogs: Synthesis and Cytotoxicity

Pati, Hari N.; Taherbhai, Zarmeen T.; Forrest, Lori; Wicks, Martha; Bailey, Suzanna; Staples, Andrew M.; Stewart, Michelle; Pennington, William T.; Harris, Jeffery L.; Lee, Moses

doi:10.2174/1570180043398821

Cited by 5 publications

(3 citation statements)

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“…This outcome is interesting given the varied potencies observed in cis and trans analogues of medicinally important stilbenes such as resveratrol 25 and combretastatin. 26 …”

Section: Biological Results and Discussionmentioning

confidence: 99%

Structural analogues of schweinfurthin F: Probing the steric, electronic, and hydrophobic properties of the D-ring substructure

Ulrich

Kodet

Mente

et al. 2010

Bioorganic & Medicinal Chemistry

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The natural tetracyclic schweinfurthins are potent and selective inhibitors of cell growth in the National Cancer Institute’s 60-cell line screen. An interest in determination of their cellular or molecular target has inspired our efforts to prepare both the natural products and analogues. In this paper, chemical synthesis of analogues modified in different olefinic positions, and preliminary results from studies of their biological activity, are reported.

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“…This outcome is interesting given the varied potencies observed in cis and trans analogues of medicinally important stilbenes such as resveratrol 25 and combretastatin. 26 …”

Section: Biological Results and Discussionmentioning

confidence: 99%

Structural analogues of schweinfurthin F: Probing the steric, electronic, and hydrophobic properties of the D-ring substructure

Ulrich

Kodet

Mente

et al. 2010

Bioorganic & Medicinal Chemistry

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“…6 Its anticancer effects have been noted in a wide variety of tumor cells. 2,3,[7][8][9][10][11][12] The in vitro antineoplastic potency of MR-4 was found to be higher than that of resveratrol. 3,7,10,11 Interestingly, the antiproliferative activity of MR-4 was more specific to transformed cells than to normal cells.…”

Section: ' Introductionmentioning

confidence: 94%

“…trans -3,4,5,4′-Tetramethoxystilbene (MR-4, also reported as DMU-212) , ( 2 , Figure ) is a resveratrol analogue present in the leaves of Piper caninum . Its anticancer effects have been noted in a wide variety of tumor cells. ,,− The in vitro antineoplastic potency of MR-4 was found to be higher than that of resveratrol. ,,, Interestingly, the antiproliferative activity of MR-4 was more specific to transformed cells than to normal cells. ,, Besides its anticancer effects, MR-4 also displayed anti-inflammatory potential. , It suppressed tumor necrosis factor-α-induced activation of transcription factor nuclear factor-κB and inhibited both cyclooxygenases-1 and -2 . Clearly, MR-4 has emerged as a promising candidate for further therapeutic exploration.…”

Section: Introductionmentioning

confidence: 99%

Quantification of trans-3,4,5,4′-Tetramethoxystilbene in Rat Plasma by HPLC: Application to Pharmacokinetic Study

Lin

Zhang

et al. 2011

J. Agric. Food Chem.

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A simple HPLC method was established to quantify trans-3,4,5,4'-tetramethoxystilbene (MR-4 or DMU-212) in rat plasma. Chromatographic separation was obtained with a reversed-phase HPLC column through an 11 min gradient delivery of a mixture of acetonitrile and water at a flow rate of 1.5 mL/min at 50 °C. The limit of quantification was 15 ng/mL. The intra- and interday precisions in terms of relative standard deviation were <9% at all concentrations. Similarly, the accuracy was good, and the bias rates ranged within ±7%. The pharmacokinetic profiles of MR-4 were subsequently assessed in rats using 2-hydroxypropyl-β-cyclodextrin as a dosing vehicle. Upon intravenous administration, MR-4 displayed moderate clearance (46.5 ± 7.6 mL/min/kg) and terminal elimination half-life (154 ± 80 min). However, the absolute oral bioavailability of MR-4 was low (6.31 ± 3.30%). Future investigation on MR-4 as a chemotherapeutic agent should be focused on colorectal cancers.

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Nickel-catalyzed Suzuki–Miyaura type cross-coupling reactions of (2,2-difluorovinyl)benzene derivatives with arylboronic acids

Xiong

Huang

et al. 2015

Org. Biomol. Chem.

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A Stereospecific Route for the Preparation of Trans-Combretastatin Analogs: Synthesis and Cytotoxicity

Cited by 5 publications

References 0 publications

Structural analogues of schweinfurthin F: Probing the steric, electronic, and hydrophobic properties of the D-ring substructure

Structural analogues of schweinfurthin F: Probing the steric, electronic, and hydrophobic properties of the D-ring substructure

Quantification of trans-3,4,5,4′-Tetramethoxystilbene in Rat Plasma by HPLC: Application to Pharmacokinetic Study

Nickel-catalyzed Suzuki–Miyaura type cross-coupling reactions of (2,2-difluorovinyl)benzene derivatives with arylboronic acids

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