含新型频哪醇硼酸酯的康普他汀“抗有丝分裂剂”类似物的设计与合成
Design and synthesis of novel pinacolylboronate containing combretastatin 'antimitotic agent' analogues.
作者信息
Das Bhaskar C, Mahalingam Sakkarapalayam M, Evans Todd
机构信息
Department of Nuclear Medicine, Albert Einstein College of Medicine, Bronx, NY 10461, USA.
出版信息
Tetrahedron Lett. 2009 Jun 24;50(25):3031-3034. doi: 10.1016/j.tetlet.2009.04.003.
Abstract
We developed a procedure to synthesize pinacolyl boronate containing stilbene derivatives and used this procedure to synthesize boron-containing combretastatin analogues. The key step involves the Wittig reaction of the ylide 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide 11 with 3,4,5-trimethoxy benzaldehyde in the presence of (t)BuONa in DMF, providing 88% yield. We are now in a position to evaluate the biological activity of these derivatives as modulators of TGF-beta signaling pathways.
摘要
我们开发了一种合成含茋衍生物的频哪醇硼酸酯的方法，并使用该方法合成了含硼的康普他汀类似物。关键步骤涉及在DMF中，在叔丁醇钠存在下，叶立德4-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷苯基)-甲基三苯基溴化鏻11与3,4,5-三甲氧基苯甲醛的维蒂希反应，产率为88%。我们现在能够评估这些衍生物作为TGF-β信号通路调节剂的生物活性。
相似文献
1
Design and synthesis of novel pinacolylboronate containing combretastatin 'antimitotic agent' analogues.
Tetrahedron Lett. 2009 Jun 24;50(25):3031-3034. doi: 10.1016/j.tetlet.2009.04.003.
2
Design, synthesis and biological study of pinacolyl boronate-substituted stilbenes as novel lipogenic inhibitors.
Bioorg Med Chem Lett. 2011 Sep 15;21(18):5638-41. doi: 10.1016/j.bmcl.2011.05.124. Epub 2011 Jun 28.
3
Combretastatin A-4 analogues with benzoxazolone scaffold: Synthesis, structure and biological activity.
Eur J Med Chem. 2016 Sep 14;120:121-33. doi: 10.1016/j.ejmech.2016.05.012. Epub 2016 May 6.
4
Design and synthesis of 3,5-disubstituted boron-containing 1,2,4-oxadiazoles as potential combretastatin A-4 (CA-4) analogs.
Tetrahedron Lett. 2012 Aug 1;53(31):3947-3950. doi: 10.1016/j.tetlet.2012.02.110.
5
Recent advancement in discovery and development of natural product combretastatin-inspired anticancer agents.
Anticancer Agents Med Chem. 2015;15(8):955-69. doi: 10.2174/1871520615666150526141259.
6
Interactions of tubulin with potent natural and synthetic analogs of the antimitotic agent combretastatin: a structure-activity study.
Mol Pharmacol. 1988 Aug;34(2):200-8.
7
Naphthalene combretastatin analogues: synthesis, cytotoxicity and antitubulin activity.
J Enzyme Inhib Med Chem. 2004 Dec;19(6):521-40. doi: 10.1080/14756360412331280473.
8
Synthesis and Antiproliferative Evaluation of 3-Chloroazetidin-2-ones with Antimitotic Activity: Heterocyclic Bridged Analogues of Combretastatin A-4.
Pharmaceuticals (Basel). 2021 Oct 31;14(11):1119. doi: 10.3390/ph14111119.
9
Synthesis and Evaluation of 2-Naphthaleno trans-Stilbenes and Cyanostilbenes as Anticancer Agents.
Anticancer Agents Med Chem. 2018;18(4):556-564. doi: 10.2174/1871521409666170412115703.
10
Development of water soluble derivatives of cis-3, 4', 5-trimethoxy-3'-aminostilbene for optimization and use in cancer therapy.
Invest New Drugs. 2009 Feb;27(1):41-52. doi: 10.1007/s10637-008-9139-y. Epub 2008 May 31.
引用本文的文献
1
Synthesis of a boron-containing amidoxime reagent and its application to synthesize functionalized oxadiazole and quinazolinone derivatives.
Tetrahedron Lett. 2022 Mar 2;92. doi: 10.1016/j.tetlet.2022.153657. Epub 2022 Jan 25.
2
Boronate-Based Probes for Biological Oxidants: A Novel Class of Molecular Tools for Redox Biology.
Front Chem. 2020 Sep 25;8:580899. doi: 10.3389/fchem.2020.580899. eCollection 2020.
3
Small molecules targeting LapB protein prevent Listeria attachment to catfish muscle.
PLoS One. 2017 Dec 18;12(12):e0189809. doi: 10.1371/journal.pone.0189809. eCollection 2017.
4
Design and synthesis of 3,5-disubstituted boron-containing 1,2,4-oxadiazoles as potential combretastatin A-4 (CA-4) analogs.
Tetrahedron Lett. 2012 Aug 1;53(31):3947-3950. doi: 10.1016/j.tetlet.2012.02.110.
5
Design and synthesis of boron containing potential pan-RAR inverse agonists.
Tetrahedron Lett. 2012 Mar 14;53(11):1316-1318. doi: 10.1016/j.tetlet.2011.12.118. Epub 2012 Jan 3.
6
Intraoperative fluorescence imaging of peripheral and central nerves through a myelin-selective contrast agent.
Mol Imaging Biol. 2012 Dec;14(6):708-17. doi: 10.1007/s11307-012-0555-1.
7
Design, synthesis and biological study of pinacolyl boronate-substituted stilbenes as novel lipogenic inhibitors.
Bioorg Med Chem Lett. 2011 Sep 15;21(18):5638-41. doi: 10.1016/j.bmcl.2011.05.124. Epub 2011 Jun 28.
8
Design and Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazole Containing Retinoids from a Retinoic Acid Receptor Agonist.
Tetrahedron Lett. 2011 May 11;52(19):2433-2435. doi: 10.1016/j.tetlet.2011.03.011.
本文引用的文献
1
Wavelength-ratiometric probes for saccharides based on donor-acceptor diphenylpolyenes.
J Photochem Photobiol A Chem. 2001 Oct 1;143(1):39-47. doi: 10.1016/S1010-6030(01)00471-3. Epub 2001 Sep 5.
2
Synthesis of 2-substituted 2H-chromenes using potassium vinyltrifluoroborates.
Tetrahedron Lett. 2008 Mar 3;49(10):1578-1581. doi: 10.1016/j.tetlet.2008.01.008.
3
A forward chemical screen using zebrafish embryos with novel 2-substituted 2H-chromene derivatives.
Chem Biol Drug Des. 2009 Mar;73(3):339-45. doi: 10.1111/j.1747-0285.2009.00782.x.
4
Nitro-substituted stilbeneboronate pinacol esters and their fluoro-adducts. Fluoride ion induced polarity enhancement of arylboronate esters.
J Org Chem. 2007 Jun 8;72(12):4328-39. doi: 10.1021/jo070084v. Epub 2007 May 18.
5
Resveratrol: a review of preclinical studies for human cancer prevention.
Toxicol Appl Pharmacol. 2007 Nov 1;224(3):274-83. doi: 10.1016/j.taap.2006.12.025. Epub 2007 Jan 3.
6
Synthesis of unsaturated organotrifluoroborates via Wittig and Horner-Wadsworth-Emmons olefination.
J Org Chem. 2006 Aug 4;71(16):6135-40. doi: 10.1021/jo060863w.
7
Medicinal chemistry of combretastatin A4: present and future directions.
J Med Chem. 2006 Jun 1;49(11):3033-44. doi: 10.1021/jm0512903.
8
An improved synthesis of resveratrol.
Nat Prod Res. 2006 Mar;20(3):247-52. doi: 10.1080/14786410500059532.
9
Amphidinolide B: asymmetric synthesis of a C7-C20 synthon.
Org Lett. 2006 Jan 5;8(1):7-10. doi: 10.1021/ol051861l.
10
Synthesis and evaluation of new omega-borono-alpha-amino acids as rat liver arginase inhibitors.
Bioorg Med Chem. 2005 Apr 1;13(7):2373-9. doi: 10.1016/j.bmc.2005.01.053.
Zotero 插件