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Relevant bibliographies by topics / Rocaglamide synthesis

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Academic literature on the topic 'Rocaglamide synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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Journal articles on the topic "Rocaglamide synthesis"

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Cai, Xiao-hua, Bing Xie, and Hui Guo. "Progress in the Total Synthesis of Rocaglamide." ISRN Organic Chemistry 2011 (April 4, 2011): 1–7. http://dx.doi.org/10.5402/2011/239817.

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The first cyclopenta[b]benzofuran derivative, rocaglamide, from Aglaia elliptifolia, was found to exhibit considerable insecticidal activities and excellent potential as a therapeutic agent candidate in cancer chemotherapy; the genus Aglaia has been subjected to further investigation. Both the structural complexity of rocaglamide and its significant activity make it an attractive synthetic target. Stereoselective synthesis of the dense substitution pattern of these targets is a formidable synthetic challenge: the molecules bear five contiguous stereocenters and cis aryl groups on adjacent carbons. In past years of effort, only a handful of completed total syntheses have been reported, evidence of the difficulties associated with the synthesis of rocaglate natural products. The advance on total synthesis of rocaglamide was mainly reviewed from intramolecular cyclization and biomimetic cycloaddition approach.

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Callahan, Kevin P., Cheryl Corbett, Steven Jacob, Mohammad Minhajuddin, Eleni D. Lagadinou, Randall M. Rossi, Valerie Gross, et al. "Rocaglamide Selectively Eradicates Human Leukemia Stem Cells and Synergizes with Multiple Agents to Target AML Cells." Blood 120, no. 21 (November 16, 2012): 1338. http://dx.doi.org/10.1182/blood.v120.21.1338.1338.

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Abstract Abstract 1338 Recent evidence suggests that myeloid leukemia is initiated and maintained by Leukemia Stem Cells (LSCs). Standard chemotherapy however, does not efficiently ablate LSCs. Consequently, even for leukemia patients who attain a clinical remission, LSCs are generally not destroyed and are thought to be responsible for subsequent relapse of the disease. Therefore, new treatment regimens are necessary to improve therapeutic outcomes. Nearly half of the agents used in cancer therapy today are either natural products or derivatives of natural products. The present studies demonstrate that rocaglamide, a compound derived from the traditional Chinese medicinal plants Aglaia induces robust apoptosis in primary human AML cells while sparing normal hematopoietic cells. Further analysis of progenitor cells using in vitro colony assays, as well as stem cells using the NOD Scid Gamma (NSG) xenograft model, show that rocaglamide also preferentially targets AML progenitor and stem cell populations. Methionine metabolic labeling experiments show that rocaglamide inhibits the translation of nascent protein synthesis within twenty-four hours and this inhibition results in the rapid loss of short-lived survival proteins such as c-myc, Mcl-1, and Bcl-xl. These results are consistent with previous work showing rocaglamide, and members of the rocaglamide family of compounds, inhibit translation. To investigate further the molecular mechanism of LSC-specific cell death induced by rocaglamide we performed next generation sequencing on 5 AML specimens treated with rocaglamide. Bioinformatic analysis and subsequent experiments showed that rocagalmide leads to P53 activation, NFkB inhibition, cell cycle inhibition as well as defects in mitochondrial integrity and energy metabolism. In addition to efficacy as a single agent, pre-treatment of leukemia cells with rocaglamide significantly sensitizes the cells to several anti-cancer compounds, including cytarabine and daunorubicin two of the front-line chemotherapuetic drugs for AML patients. Importantly, we show that many of the mechanistic features of rocaglamide as a single agent play a role in its ability to synergize. In comparison with translational inhibitors that are used clinically to treat AML patients, temsirolimus and ribovarin, rocaglamide is significantly more toxic to leukemia cells. Interestingly, this increased cytotoxicity does not directly correlate with ability of the compounds to inhibit translational inhibition. Temsirolimus, inhibits translation at levels equal to or greater than rocaglamide however it has a cytostatic effect on leukemia cells in contrast to the cytotoxic effects of rocaglamide. Temsirolimus also does not synergize with anti-cancer compounds to the same degree as rocaglamide. These results suggest that rocaglamide's ability to modulate several key pathways in addition to inhibiting translation are critical to the activity of rocagalmaide and may suggest ways to improve the efficacy of translational inhibitors currently used in the clinic. These studies along with preliminary in vivo pharmacodynamic and pharmacokinetic experiments indicate that rocaglamide may be a promising candidate for the development of a new class of compounds for the treatment of leukemia and for increasing the efficacy of treatments designed to specifically target AML cells. Disclosures: No relevant conflicts of interest to declare.

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Arai, Midori A., Yuuki Kofuji, Yuuki Tanaka, Natsuki Yanase, Kazuki Yamaku, Rolly G. Fuentes, Utpal Kumar Karmakar, and Masami Ishibashi. "Synthesis of rocaglamide derivatives and evaluation of their Wnt signal inhibitory activities." Organic & Biomolecular Chemistry 14, no. 11 (2016): 3061–68. http://dx.doi.org/10.1039/c5ob02537k.

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4

Bruce, Ian, Nigel G. Cooke, Louis J. Diorazio, Roger G. Hall, and Ed Irving. "Synthesis of the carbocyclic analogue of (±)-Rocaglamide." Tetrahedron Letters 40, no. 22 (May 1999): 4279–82. http://dx.doi.org/10.1016/s0040-4039(99)00706-6.

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Dobler, Markus R., Ian Bruce, Fredrik Cederbaum, Nigel G. Cooke, Louis J. Diorazio, Roger G. Hall, and Ed Irving. "Total synthesis of (±)-rocaglamide and some aryl analogues." Tetrahedron Letters 42, no. 47 (November 2001): 8281–84. http://dx.doi.org/10.1016/s0040-4039(01)01807-x.

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6

Zhou, Zhe, Darryl D. Dixon, Anais Jolit, and Marcus A. Tius. "The Evolution of the Total Synthesis of Rocaglamide." Chemistry - A European Journal 22, no. 44 (September 15, 2016): 15929–36. http://dx.doi.org/10.1002/chem.201603312.

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7

Malona, John A., Kevin Cariou, William T. Spencer, and Alison J. Frontier. "Total Synthesis of (±)-Rocaglamide via Oxidation-Initiated Nazarov Cyclization." Journal of Organic Chemistry 77, no. 4 (January 26, 2012): 1891–908. http://dx.doi.org/10.1021/jo202366c.

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8

Schoop, Andreas, Helmut Greiving, and Axel Göhrt. "A new analogue of rocaglamide by an oxidative dihydrofuran synthesis." Tetrahedron Letters 41, no. 12 (March 2000): 1913–16. http://dx.doi.org/10.1016/s0040-4039(00)00021-6.

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9

Davey, Andrew E., Marcel J. Schaeffer, and Richard J. K. Taylor. "Synthesis of the novel anti-leukaemic tetrahydrocyclopenta[b]benzofuran, rocaglamide." Journal of the Chemical Society, Chemical Communications, no. 16 (1991): 1137. http://dx.doi.org/10.1039/c39910001137.

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Bruce, Ian, Nigel G. Cooke, Louis J. Diorazio, Roger G. Hall, and Ed Irving. "ChemInform Abstract: Synthesis of the Carbocyclic Analogue (X) of (.+-.)-Rocaglamide (XII)." ChemInform 30, no. 32 (June 14, 2010): no. http://dx.doi.org/10.1002/chin.199932247.

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Dissertations / Theses on the topic "Rocaglamide synthesis"

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Davey, A. E. "Synthetic approaches to rocaglamide." Thesis, University of East Anglia, 1987. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.378903.

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Havenhand, M. "Synthetic studies towards the antileukaemic rocaglamide." Thesis, University of Cambridge, 1986. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.383802.

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Staubitz, Anne. "Towards the asymmetric synthesis of (-)-rocaglamide and Optimisation of the Mizoroki-Heck reaction using design of experiment." Thesis, University of Bristol, 2007. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.440140.

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Freund, Wesley Allen. "Studies on the total synthesis of (±)-rocaglamide." Thesis, 2009. http://hdl.handle.net/2152/ETD-UT-2009-08-258.

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The use of a Nazarov cyclization for the diastereoselective synthesis of rocaglamide was studied. Chapter 1 discusses the biological activity of the rocaglamide family of natural products and details the previous synthetic work on these compounds. Chapter 2 discusses the approaches taken in the Magnus group for the total synthesis of rocaglamide. Several approaches to the natural product were undertaken. Using a novel acid bromide induced Nazarov cyclization, construction of the C-ring of the natural product was achieved. Attempts to construct the remainder of rocaglamide were ultimately unsuccessful.
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Moorhead, Eric J. "Synthesis of (±)-methyl rocaglate using an unprecedented acetyl bromide mediated Nazarov reaction." Thesis, 2012. http://hdl.handle.net/2152/ETD-UT-2012-05-5777.

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To date, the Nazarov cyclization of a pentadienone has not been a proven methodology towards the construction of the core of the rocaglate natural products. It has been found that this conversion can be achieved using acetylbromide in excellent yield. This represents the first time acetylbromide has been employed in this manner. This methadology provides a very effective and direct route to the core structures of this class of molecules.
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Rainey, Trevor James. "Studies directed towards the synthesis of irroratin A and studies directed towards the synthesis of rocaglamide and silvestrol." Thesis, 2006. http://hdl.handle.net/2152/2797.

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Books on the topic "Rocaglamide synthesis"

1

Davey, A. E. Synthetic approaches to rocaglamide. Norwich: University of East Anglia, 1987.

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Book chapters on the topic "Rocaglamide synthesis"

1

Porco, John A., and Baudouin Gerard. "Chapter 6 A biomimetic approach to the rocaglamides employing photogeneration of oxidopyryliums derived from 3-hydroxyflavones." In Strategies and Tactics in Organic Synthesis, 219—VIII. Elsevier, 2008. http://dx.doi.org/10.1016/s1874-6004(08)80010-x.

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Conference papers on the topic "Rocaglamide synthesis"

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Nalli, Ancy D., Lauren E. Brown, Cheryl L. Thomas, Thomas J. Sayers, John A. Porco, and Curtis J. Henrich. "Abstract 3903: Rocaglamide A and synthetic analogues sensitize resistant renal carcinoma cells to TRAIL-induced apoptosis and inhibit cell proliferation." In Proceedings: AACR Annual Meeting 2018; April 14-18, 2018; Chicago, IL. American Association for Cancer Research, 2018. http://dx.doi.org/10.1158/1538-7445.am2018-3903.

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