Anthony Barrett Explained

Anthony Gerard Martin Barrett
Birth Name:Anthony Gerard Martin Barrett
Birth Date:1952 3, df=y
Birth Place:England, U.K
Nationality:British, US
Alma Mater:Imperial College London
Workplaces:Northwestern University, Colorado State University, Imperial College London
Doctoral Advisor:Derek Barton
Doctoral Students:Matthew Fuchter

Anthony Gerard Martin Barrett FRS, FMedSci is a British chemist, and Sir Derek Barton Professor of Synthesis, Glaxo Professor of Organic Chemistry at Imperial College London. He is Director of the Wolfson Centre for Organic Chemistry in Medical Science.[1] He was elected a fellow of the Royal Society in 1999[2] and Academy of Medical Sciences in 2003. He obtained a BSc as well as PhD from Imperial College London in 1973 and 1975 respectively.

Education

Barrett was educated at Heles Grammar School in Exeter. He attended Imperial College, London (1st Class Honours BSc in 1973 and DIC and PhD in1975). He carried out his Ph.D. working under the direction of Sir Derek Barton, Nobel Laureate.

Career and Research

Barrett was appointed lecturer in organic chemistry (1975) at IC and senior lecturer (1982). In 1983, he was appointed full professor of Chemistry at Northwestern University in Evanston, Illinois, and in 1990 moved to Colorado State University. After ten years research in the US, he returned to IC as Glaxo Professor of Organihttps://en.wikipedia.org/wiki/Wikipedia:Biographies_of_living_persons/Helpc Chemistry, Director of the Wolfson Centre for Organic Chemistry in Medical Science and Head of the Organic Section. He was appointed the Sir Derek Barton Professor of Synthetic Chemistry in 1999. Barrett has invented many reactions including novel glycosidations, atom-economic aromatic substitution reactions, metal-catalyzed oxidations and hydroaminations, reactions using ROMP-gel supported reagents and multi-component benzyne coupling reactions. He has contributed extensively to the synthesis of β-lactams using alkenyl anions, ynolates, novel isocyanates, iron vinylidines, heteroatom functionalized nitroalkenes, and ring closing alkene and enyne metathesis reactions. He has completed the total synthesis of diverse bioactive natural products including papulacandin D, papuamine, showdomycin, milbemycin β3, the palmarumycins and preussomerin G,[3] (+)-calyculin A[4] and the multiple cyclopropane CETP inhibitor U-106305 and structurally related cyclopropane nucleoside FR-900848[5] and coronanes. He has also published highly flexible methods for the biomimetic total syntheses of resorcylate and meroterpenoid natural products including 15G256β,[6] aigialomycin D,[7] LL-Z1640-2,[8] cruentaren A,[9] hericenone J[10] and macrosporin,[11] amorphastilbol,[12] (+)-hongoquercin A and B,[13] and austalides.[14] Barrett, in collaboration with Brian Hoffman at Northwestern University, has published pioneering work on the synthesis of diverse porphyrazines bearing 8, 6, 4, and 2 thiols, amines or alcohols as peripheral macrocyclic ring substituents and the conversion of these polydentate ligands by the complexation of metal ions both within the macrocyclic cavity and at the periphery to produce diverse multimetallic complexes.[15] [16] Several such complexes are imaging agents for the highly selective detection of cancers in both cells and in vivo and as PDT agents.[17] [18] [19] [20] Additionally, Barrett in collaboration with Simak Ali and R. Charles Coombes in Medicine at Imperial College and Dennis Liotta and James P. Snyder in Emory University has made pioneering contributions to addressing unmet medical need with the invention of highly selective and bioavailable inhibitors of the Cyclin Dependent Kinases including CDK-7 inhibitor ICEC0942 (CT7001), which have been licensed by Carrick Therapeutics for clinical trials to treat Tamoxifen-resistant and other cancers.[21] [22] [23]
Barrett was the first to demonstrate the increased stability of per-alkylated aza crown ether analogues under dissolving metal reduction conditions.[24] This not only triggered the development of thermally stable solid alkalides[25] [26] and electrides[27]), but also led him and his doctoral student René Riedel, in a multidisciplinary approach and in collaboration with Peter Edwards, to provide compelling experimental evidence for the predominant formation of alkalide ion pairs in solution for the first time.[28]

Awards and honors

Barrett has received numerous awards for his contributions to research from the Royal Society of Chemistry (1980 Meldola Medal,[29] 1982 Harrison Medal https://www.rsc.org/ScienceAndTechnology/Awards/HarrisonMeldolaMemorialPrizes/, 1986 Corday-Morgan Medal https://www.rsc.org/ScienceAndTechnology/Awards/CordayMorganPrizes/, 1994 Tilden Lectureship,[30] 1996 Award in Synthetic Organic Chemistry, 2001 Award in Natural Products Chemistry, 2004 Pedler Lectureship,[31] 2005 Simonsen Lectureship,[32] 2010 Charles Rees Award[33]), the American Chemical Society (1986 Cope Scholar Award), the Royal Society (2002 Royal Society Wolfson Research Merit Award https://royalsociety.org/grants-schemes-awards/grants/wolfson-research-merit/), Imperial College (1981 Armstrong Medal), the Camille and Henry Dreyfus Foundation (1987 Teacher Scholar Award https://www.dreyfus.org/camille-dreyfus-teacher-scholar/), Glaxo GlaxoSmithKline Wellcome (2000 Award for Innovative Chemistry), Institute of Applied Catalysis (2001 Award for Innovation in Applied Catalysis), and the Specialised Organic Sector Association (2000 Innovation Award). In 2017 he received the Imperial College President's Medal for Excellence in Research: Excellence in Innovation and Entrepreneurship https://www.imperial.ac.uk/staff/college-staff-recognition-awards/research-excellence (with Simak Ali, R. Charles Coombes and Matthew Fuchter).

Notes and References

  1. Web site: AGM Barrett Webpage. Imperial College London.
  2. "Fellows of the Royal Society")
  3. Barrett . Anthony G. M. . Blaney . Frank . Campbell . Andrew D. . Hamprecht . Dieter . Meyer . Thorsten . White . Andrew J. P. . Witty . David . Williams . David J. . Unified Route to the Palmarumycin and Preussomerin Natural Products. Enantioselective Synthesis of (−)-Preussomerin G . The Journal of Organic Chemistry . 1 May 2002 . 67 . 9 . 2735–2750 . 10.1021/jo0110247 . 11975523 . 0022-3263.
  4. Anderson . Oren P . Barrett . Anthony GM . Edmunds . Jeremy J . Hachiya . Shun-Ichiro . Hendrix . James A . Horita . Kiyoshi . Malecha . James W . Parkinson . Christopher J . VanSickle . Andrew . Applications of crotyldiisopinocampheylboranes in synthesis: a formal total synthesis of (+)-calyculin A . Canadian Journal of Chemistry . 1 November 2001 . 79 . 11 . 1562–1592 . 10.1139/v01-133 . 0008-4042.
  5. Barrett . Anthony G. M. . Doubleday . Wendel W. . Hamprecht . Dieter . Kasdorf . Krista . Tustin . Gary J. . White . Andrew J. P. . Williams . David J. . Assembly of the antifungal agent FR-900848 and the CETP inhibitor U-106305: studies on remarkable multicyclopropane natural products . Chemical Communications . 1997 . 18 . 1693–1700 . 10.1039/A700487G.
  6. Navarro . Ismael . Basset . Jean-François . Hebbe . Séverine . Major . Sarah M. . Werner . Thomas . Howsham . Catherine . Bräckow . Jan . Barrett . Anthony G. M. . Biomimetic Synthesis of Resorcylate Natural Products Utilizing Late Stage Aromatization: Concise Total Syntheses of the Marine Antifungal Agents 15G256ι and 15G256β . Journal of the American Chemical Society . 1 August 2008 . 130 . 31 . 10293–10298 . 10.1021/ja803445u . 18611011 . 0002-7863.
  7. Calo . Frederick . Richardson . Jeffery . Barrett . Anthony G. M. . Total Synthesis of Aigialomycin D using a One-Pot Ketene Generation−Trapping−Aromatization Sequence . Organic Letters . 5 November 2009 . 11 . 21 . 4910–4913 . 10.1021/ol901979x . 19799447 . 1523-7060.
  8. Miyatake-Ondozabal . Hideki . Barrett . Anthony G. M. . Total Synthesis of TAK-Kinase Inhibitor LL-Z1640-2 via Consecutive Macrocyclization and Transannular Aromatization . Organic Letters . 3 December 2010 . 12 . 23 . 5573–5575 . 10.1021/ol102468k . 21067221 . 1523-7060.
  9. Fouché . Marianne . Rooney . Lisa . Barrett . Anthony G. M. . Biomimetic Total Synthesis of Cruentaren A via Aromatization of Diketodioxinones . The Journal of Organic Chemistry . 15 March 2012 . 77 . 7 . 3060–3070 . 10.1021/jo300225z. 22401367 .
  10. Cordes . Jens . Calo . Frederick . Anderson . Katie . Pfaffeneder . Toni . Laclef . Sylvain . White . Andrew J. P. . Barrett . Anthony G. M. . Total Syntheses of Angelicoin A, Hericenone J, and Hericenol A via Migratory Prenyl- and Geranylation–Aromatization Sequences . The Journal of Organic Chemistry . 6 January 2012 . 77 . 1 . 652–657 . 10.1021/jo202354j . 22106838 . 0022-3263.
  11. Cordes . Jens . Barrett . Anthony G. M. . Synthesis of Macrosporin and Related 9,10-Anthraquinones by Biomimetic Polyketide Aromatization and Cyclization of 6-Benzylresorcylates . European Journal of Organic Chemistry . March 2013 . 2013 . 7 . 1318–1326 . 10.1002/ejoc.201201480.
  12. Ma . Tsz-Kan . White . Andrew J.P. . Barrett . Anthony G.M. . Meroterpenoid total synthesis: Conversion of geraniol and farnesol into amorphastilbol, grifolin and grifolic acid by dioxinone- β -keto-acylation, palladium catalyzed decarboxylative allylic rearrangement and aromatization . Tetrahedron Letters . July 2017 . 58 . 28 . 2765–2767 . 10.1016/j.tetlet.2017.05.096. 10044/1/48867 . 98955569 . free .
  13. Ma . Tsz-Kan . Elliott . Daniel C. . Reid . Stephanie . White . Andrew J. P. . Parsons . Philip J. . Barrett . Anthony G. M. . Meroterpenoid Synthesis via Sequential Polyketide Aromatization and Cationic Polyene Cyclization: Total Syntheses of (+)-Hongoquercin A and B and Related Meroterpenoids . The Journal of Organic Chemistry . 2 November 2018 . 83 . 21 . 13276–13286 . 10.1021/acs.joc.8b02095 . 30346765 . 0022-3263. 6303087 .
  14. Ma . Tsz-Kan . Parsons . Philip J. . Barrett . Anthony G. M. . Meroterpenoid Synthesis via Sequential Polyketide Aromatization and Radical Anion Cascade Triene Cyclization: Biomimetic Total Syntheses of Austalide Natural Products . The Journal of Organic Chemistry . American Chemical Society (ACS) . 84 . 9 . 2019-04-02 . 0022-3263 . 10.1021/acs.joc.9b00142 . 30938997 . 4961–4970 . 7007238 . 10044/1/69726 . free .
  15. Michel . Sarah L. J. . Hoffman . Brian M. . Baum . Sven M. . Barrett . Anthony G. M. . Peripherally Functionalized Porphyrazines: Novel Metallomacrocycles with Broad, Untapped Potential . Progress in Inorganic Chemistry . 2002 . 473–590 . 10.1002/0471227110.ch8 . John Wiley & Sons, Ltd . en. 9780471435105 .
  16. Barrett . Anthony G. M. . Hoffman . Brian M. . Zong . Hong . Zhong . Chang . Fuchter . Matthew J. . Porphyrazines: Designer Macrocycles by Peripheral Substituent Change . Australian Journal of Chemistry . 19 May 2008 . 61 . 4 . 235–255 . 10.1071/CH07445 . en . 1445-0038.
  17. Hoffman . Brian M. . Meade . Thomas J. . Barrett . Anthony G. M. . Sloane . Bonnie F. . Bonnie Sloane. Moin . Kamiar . Podgorski . Izabela . Olive . Mary B. . Harney . Allison S. . Trivedi . Evan R. . Chiral porphyrazine near-IR optical imaging agent exhibiting preferential tumor accumulation . Proceedings of the National Academy of Sciences . 26 January 2010 . 107 . 4 . 1284–1288 . 10.1073/pnas.0912811107 . 20080563 . en . 0027-8424. 2824358 . 2010PNAS..107.1284T . free .
  18. Trivedi . Evan R. . Vesper . Benjamin J. . Weitman . Hana . Ehrenberg . Benjamin . Barrett . Anthony G. M. . Radosevich . James A. . Hoffman . Brian M. . Chiral bis-Acetal Porphyrazines as Near-infrared Optical Agents for Detection and Treatment of Cancer . Photochemistry and Photobiology . 2010 . 86 . 2 . 410–417 . 10.1111/j.1751-1097.2009.00681.x . 20074089 . 39590233 . en . 1751-1097.
  19. Trivedi . Evan R. . Ma . Zhidong . Waters . Emily A. . Macrenaris . Keith W. . Subramanian . Rohit . Barrett . Anthony G. M. . Meade . Thomas J. . Hoffman . Brian M. . Synthesis and characterization of a porphyrazine-Gd(III) MRI contrast agent and imaging of a breast cancer xenograft model . Contrast Media & Molecular Imaging . July 2014 . 9 . 4 . 313–322 . 10.1002/cmmi.1577 . 24706615 . 4327828 .
  20. Kandela . Irawati K. . McAuliffe . Katherine J. . Cochran . Lauren E. . Barrett . Anthony G. M. . Hoffman . Brian M. . Mazar . Andrew P. . Trivedi . Evan R. . Discovery of the Antitumor Effects of a Porphyrazine Diol (Pz 285) in MDA-MB-231 Breast Tumor Xenograft Models in Mice . ACS Medicinal Chemistry Letters . 13 July 2017 . 8 . 7 . 705–709 . 10.1021/acsmedchemlett.7b00063 . 28740602 . 5512131 .
  21. Patel . Hetal . Periyasamy . Manikandan . Sava . Georgina P. . Bondke . Alexander . Slafer . Brian W. . Kroll . Sebastian H. B. . Barbazanges . Marion . Starkey . Richard . Ottaviani . Silvia . Harrod . Alison . Aboagye . Eric O. . Buluwela . Laki . Fuchter . Matthew J. . Barrett . Anthony G. M. . Coombes . R. Charles . Ali . Simak . ICEC0942, an Orally Bioavailable Selective Inhibitor of CDK7 for Cancer Treatment . Molecular Cancer Therapeutics . June 2018 . 17 . 6 . 1156–1166 . 10.1158/1535-7163.MCT-16-0847. 29545334 . 5985928 .
  22. Heathcote . Dean A. . Patel . Hetal . Kroll . Sebastian H. B. . Hazel . Pascale . Periyasamy . Manikandan . Alikian . Mary . Kanneganti . Seshu K. . Jogalekar . Ashutosh S. . Scheiper . Bodo . Barbazanges . Marion . Blum . Andreas . Brackow . Jan . Siwicka . Alekasandra . Pace . Robert D. M. . Fuchter . Matthew J. . Snyder . James P. . Liotta . Dennis C. . Freemont . Paul. S. . Aboagye . Eric O. . Coombes . R. Charles . Barrett . Anthony G. M. . Ali . Simak . A Novel Pyrazolo[1,5-a]pyrimidine Is a Potent Inhibitor of Cyclin-Dependent Protein Kinases 1, 2, and 9, Which Demonstrates Antitumor Effects in Human Tumor Xenografts Following Oral Administration . Journal of Medicinal Chemistry . 23 December 2010 . 53 . 24 . 8508–8522 . 10.1021/jm100732t . 21080703 . 0022-2623.
  23. Coombes . R. Charles . Barrett . Anthony G. M. . Aboagye . Eric O. . Eric Aboagye. Liotta . Dennis C. . Snyder . James P. . Kanneganti . Seshu K. . Tolhurst . Robert S. . Periyasamy . Manikandan . Fuchter . Matthew J. . Siwicka . Alekasandra . Brackow . Jan . Patel . Hetal . Scheiper . Bodo . Jogalekar . Ashutosh S. . Kroll . Sebastian H. B. . Heathcote . Dean A. . Ali . Simak . The Development of a Selective Cyclin-Dependent Kinase Inhibitor That Shows Antitumor Activity . Cancer Research . 1 August 2009 . 69 . 15 . 6208–6215 . 10.1158/0008-5472.CAN-09-0301 . 19638587 . 2875168 . en . 0008-5472. free .
  24. Barrett . Anthony . Dissolving metal reduction of esters to alkanes. A method for the deoxygenation of alcohols . Journal of the Chemical Society . 1981 . Perkin Transactions . 1 . 1501 . 10.1039/p19810001501 .
  25. Synthesis and structures of two thermally stable sodides with the macrocyclic complexant hexamethyl hexacyclen. 10.1021/ja00185a024. 1989. Kuchenmeister. Mark E.. Dye. James L.. Journal of the American Chemical Society. 111. 3. 935–938.
  26. "Inverse sodium hydride": A crystalline salt that contains H(+) and Na(-). 10.1021/ja025655+. 12022811. 2002. Redko. M. Y.. Vlassa. M.. Jackson. J. E.. Misiolek. A. W.. Huang. R. H.. Dye. J. L.. Journal of the American Chemical Society. 124. 21. 5928–5929.
  27. Design and Synthesis of a Thermally Stable Organic Electride. 10.1021/ja053216f. 2005. Redko. Mikhail Y.. Jackson. James E.. Huang. Rui H.. Dye. James L.. Journal of the American Chemical Society. 127. 35. 12416–12422. 16131224.
  28. 10.1021/jacs.1c00115. Superalkali–Alkalide Interactions and Ion Pairing in Low-Polarity Solvents. 2021. Riedel. René. Seel. Andrew G.. Malko. Daniel. Miller. Daniel P.. Sperling. Brendan T.. Choi. Heungjae. Headen. Thomas F.. Zurek. Eva. Porch. Adrian. Kucernak. Anthony. Pyper. Nicholas C.. Edwards. Peter P.. Barrett. Anthony G. M.. Journal of the American Chemical Society. 143. 10. 3934–3943. 33660507. 8028040.
  29. Web site: RSC Harrison-Meldola Prize. Royal Society of Chemistry.
  30. Web site: Tilden Prize Previous Winners. Royal Society of Chemistry.
  31. Web site: Pedler Award Previous Winners. Royal Society of Chemistry.
  32. Web site: Simonsen Award Previous Winners. Royal Society of Chemistry.
  33. Web site: Charles Rees Award 2010 Winner. Royal Society of Chemistry.

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