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Anthony Barrett

Summary

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.

Anthony Gerard Martin Barrett
FRS FMedSci
Born
Anthony Gerard Martin Barrett

(1952-03-02) 2 March 1952 (age 72)
England, U.K
NationalityBritish, US
Alma materImperial College London
Scientific career
InstitutionsNorthwestern University, Colorado State University, Imperial College London
Doctoral advisorDerek Barton
Doctoral studentsMatthew Fuchter
Websitewww.imperial.ac.uk/people/agm.barrett

Education edit

Barrett was educated at Heles Grammar School in Exeter. He attended Imperial College, London (1st Class Honours BSc in 1973 and DIC and PhD in 1975). He carried out his Ph.D. working under the direction of Sir Derek Barton, Nobel Laureate.

Career and Research edit

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 edit

Barrett has received numerous awards for his contributions to research from the Royal Society of Chemistry (1980 Meldola Medal,[29] 1982 Harrison Medal [1], 1986 Corday-Morgan Medal [2], 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 [3]), Imperial College (1981 Armstrong Medal), the Camille and Henry Dreyfus Foundation (1987 Teacher Scholar Award [4]), 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 [5] (with Simak Ali, R. Charles Coombes and Matthew Fuchter).

References edit

  1. ^ "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. (1 May 2002). "Unified Route to the Palmarumycin and Preussomerin Natural Products. Enantioselective Synthesis of (−)-Preussomerin G". The Journal of Organic Chemistry. 67 (9): 2735–2750. doi:10.1021/jo0110247. ISSN 0022-3263. PMID 11975523.
  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 (1 November 2001). "Applications of crotyldiisopinocampheylboranes in synthesis: a formal total synthesis of (+)-calyculin A". Canadian Journal of Chemistry. 79 (11): 1562–1592. doi:10.1139/v01-133. ISSN 0008-4042.
  5. ^ Barrett, Anthony G. M.; Doubleday, Wendel W.; Hamprecht, Dieter; Kasdorf, Krista; Tustin, Gary J.; White, Andrew J. P.; Williams, David J. (1997). "Assembly of the antifungal agent FR-900848 and the CETP inhibitor U-106305: studies on remarkable multicyclopropane natural products". Chemical Communications (18): 1693–1700. doi:10.1039/A700487G.
  6. ^ Navarro, Ismael; Basset, Jean-François; Hebbe, Séverine; Major, Sarah M.; Werner, Thomas; Howsham, Catherine; Bräckow, Jan; Barrett, Anthony G. M. (1 August 2008). "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. 130 (31): 10293–10298. doi:10.1021/ja803445u. ISSN 0002-7863. PMID 18611011.
  7. ^ Calo, Frederick; Richardson, Jeffery; Barrett, Anthony G. M. (5 November 2009). "Total Synthesis of Aigialomycin D using a One-Pot Ketene Generation−Trapping−Aromatization Sequence". Organic Letters. 11 (21): 4910–4913. doi:10.1021/ol901979x. ISSN 1523-7060. PMID 19799447.
  8. ^ Miyatake-Ondozabal, Hideki; Barrett, Anthony G. M. (3 December 2010). "Total Synthesis of TAK-Kinase Inhibitor LL-Z1640-2 via Consecutive Macrocyclization and Transannular Aromatization". Organic Letters. 12 (23): 5573–5575. doi:10.1021/ol102468k. ISSN 1523-7060. PMID 21067221.
  9. ^ Fouché, Marianne; Rooney, Lisa; Barrett, Anthony G. M. (15 March 2012). "Biomimetic Total Synthesis of Cruentaren A via Aromatization of Diketodioxinones". The Journal of Organic Chemistry. 77 (7): 3060–3070. doi:10.1021/jo300225z. PMID 22401367.
  10. ^ Cordes, Jens; Calo, Frederick; Anderson, Katie; Pfaffeneder, Toni; Laclef, Sylvain; White, Andrew J. P.; Barrett, Anthony G. M. (6 January 2012). "Total Syntheses of Angelicoin A, Hericenone J, and Hericenol A via Migratory Prenyl- and Geranylation–Aromatization Sequences". The Journal of Organic Chemistry. 77 (1): 652–657. doi:10.1021/jo202354j. ISSN 0022-3263. PMID 22106838.
  11. ^ Cordes, Jens; Barrett, Anthony G. M. (March 2013). "Synthesis of Macrosporin and Related 9,10-Anthraquinones by Biomimetic Polyketide Aromatization and Cyclization of 6-Benzylresorcylates". European Journal of Organic Chemistry. 2013 (7): 1318–1326. doi:10.1002/ejoc.201201480.
  12. ^ Ma, Tsz-Kan; White, Andrew J.P.; Barrett, Anthony G.M. (July 2017). "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. 58 (28): 2765–2767. doi:10.1016/j.tetlet.2017.05.096. hdl:10044/1/48867. S2CID 98955569.
  13. ^ Ma, Tsz-Kan; Elliott, Daniel C.; Reid, Stephanie; White, Andrew J. P.; Parsons, Philip J.; Barrett, Anthony G. M. (2 November 2018). "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. 83 (21): 13276–13286. doi:10.1021/acs.joc.8b02095. ISSN 0022-3263. PMC 6303087. PMID 30346765.
  14. ^ Ma, Tsz-Kan; Parsons, Philip J.; Barrett, Anthony G. M. (2019-04-02). "Meroterpenoid Synthesis via Sequential Polyketide Aromatization and Radical Anion Cascade Triene Cyclization: Biomimetic Total Syntheses of Austalide Natural Products". The Journal of Organic Chemistry. 84 (9). American Chemical Society (ACS): 4961–4970. doi:10.1021/acs.joc.9b00142. hdl:10044/1/69726. ISSN 0022-3263. PMC 7007238. PMID 30938997.
  15. ^ Michel, Sarah L. J.; Hoffman, Brian M.; Baum, Sven M.; Barrett, Anthony G. M. (2002). "Peripherally Functionalized Porphyrazines: Novel Metallomacrocycles with Broad, Untapped Potential". Progress in Inorganic Chemistry. John Wiley & Sons, Ltd: 473–590. doi:10.1002/0471227110.ch8. ISBN 9780471435105.
  16. ^ Barrett, Anthony G. M.; Hoffman, Brian M.; Zong, Hong; Zhong, Chang; Fuchter, Matthew J. (19 May 2008). "Porphyrazines: Designer Macrocycles by Peripheral Substituent Change". Australian Journal of Chemistry. 61 (4): 235–255. doi:10.1071/CH07445. ISSN 1445-0038.
  17. ^ Hoffman, Brian M.; Meade, Thomas J.; Barrett, Anthony G. M.; Sloane, Bonnie F.; Moin, Kamiar; Podgorski, Izabela; Olive, Mary B.; Harney, Allison S.; Trivedi, Evan R. (26 January 2010). "Chiral porphyrazine near-IR optical imaging agent exhibiting preferential tumor accumulation". Proceedings of the National Academy of Sciences. 107 (4): 1284–1288. Bibcode:2010PNAS..107.1284T. doi:10.1073/pnas.0912811107. ISSN 0027-8424. PMC 2824358. PMID 20080563.
  18. ^ Trivedi, Evan R.; Vesper, Benjamin J.; Weitman, Hana; Ehrenberg, Benjamin; Barrett, Anthony G. M.; Radosevich, James A.; Hoffman, Brian M. (2010). "Chiral bis-Acetal Porphyrazines as Near-infrared Optical Agents for Detection and Treatment of Cancer". Photochemistry and Photobiology. 86 (2): 410–417. doi:10.1111/j.1751-1097.2009.00681.x. ISSN 1751-1097. PMID 20074089. S2CID 39590233.
  19. ^ Trivedi, Evan R.; Ma, Zhidong; Waters, Emily A.; Macrenaris, Keith W.; Subramanian, Rohit; Barrett, Anthony G. M.; Meade, Thomas J.; Hoffman, Brian M. (July 2014). "Synthesis and characterization of a porphyrazine-Gd(III) MRI contrast agent and imaging of a breast cancer xenograft model". Contrast Media & Molecular Imaging. 9 (4): 313–322. doi:10.1002/cmmi.1577. PMC 4327828. PMID 24706615.
  20. ^ Kandela, Irawati K.; McAuliffe, Katherine J.; Cochran, Lauren E.; Barrett, Anthony G. M.; Hoffman, Brian M.; Mazar, Andrew P.; Trivedi, Evan R. (13 July 2017). "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. 8 (7): 705–709. doi:10.1021/acsmedchemlett.7b00063. PMC 5512131. PMID 28740602.
  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 (June 2018). "ICEC0942, an Orally Bioavailable Selective Inhibitor of CDK7 for Cancer Treatment". Molecular Cancer Therapeutics. 17 (6): 1156–1166. doi:10.1158/1535-7163.MCT-16-0847. PMC 5985928. PMID 29545334.
  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 (23 December 2010). "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. 53 (24): 8508–8522. doi:10.1021/jm100732t. ISSN 0022-2623. PMID 21080703.
  23. ^ Coombes, R. Charles; Barrett, Anthony G. M.; Aboagye, Eric O.; 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 (1 August 2009). "The Development of a Selective Cyclin-Dependent Kinase Inhibitor That Shows Antitumor Activity". Cancer Research. 69 (15): 6208–6215. doi:10.1158/0008-5472.CAN-09-0301. ISSN 0008-5472. PMC 2875168. PMID 19638587.
  24. ^ Barrett, Anthony (1981). "Dissolving metal reduction of esters to alkanes. A method for the deoxygenation of alcohols". Journal of the Chemical Society. Perkin Transactions (1): 1501. doi:10.1039/p19810001501.
  25. ^ Kuchenmeister, Mark E.; Dye, James L. (1989). "Synthesis and structures of two thermally stable sodides with the macrocyclic complexant hexamethyl hexacyclen". Journal of the American Chemical Society. 111 (3): 935–938. doi:10.1021/ja00185a024.
  26. ^ Redko, M. Y.; Vlassa, M.; Jackson, J. E.; Misiolek, A. W.; Huang, R. H.; Dye, J. L. (2002). ""Inverse sodium hydride": A crystalline salt that contains H(+) and Na(-)". Journal of the American Chemical Society. 124 (21): 5928–5929. doi:10.1021/ja025655+. PMID 12022811.
  27. ^ Redko, Mikhail Y.; Jackson, James E.; Huang, Rui H.; Dye, James L. (2005). "Design and Synthesis of a Thermally Stable Organic Electride". Journal of the American Chemical Society. 127 (35): 12416–12422. doi:10.1021/ja053216f. PMID 16131224.
  28. ^ 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. (2021). "Superalkali–Alkalide Interactions and Ion Pairing in Low-Polarity Solvents". Journal of the American Chemical Society. 143 (10): 3934–3943. doi:10.1021/jacs.1c00115. PMC 8028040. PMID 33660507.
  29. ^ "RSC Harrison-Meldola Prize". Royal Society of Chemistry.
  30. ^ "Tilden Prize Previous Winners". Royal Society of Chemistry.
  31. ^ "Pedler Award Previous Winners". Royal Society of Chemistry.
  32. ^ "Simonsen Award Previous Winners". Royal Society of Chemistry.
  33. ^ "Charles Rees Award 2010 Winner". Royal Society of Chemistry.

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