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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 8
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Original Articles

Synthesis of a New Carbon-11–Labeled Sulfamate Derivative as a Potential PET Tracer for Imaging of Breast Cancer Aromatase and Steroid Sulfatase Expression

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Pages 1127-1140 | Received 05 Dec 2009, Published online: 21 Mar 2011

REFERENCES

  • Woo , L. W. ; Bubert , C. ; Sutcliffe , O. B. ; Smith , A. ; Chander , S. K. ; Mahon , M. F. ; Purohit , A. ; Reed , M. J. ; Potter , B. V. Dual aromatase–steroid sulfatase inhibitors . J. Med. Chem. 2007 , 50 , 3540 – 3560 .
  • Wang , M. ; Mickens , J. ; Gao , M. ; Miller , K. D. ; Sledge , G. W. ; Hutchins , G. D. ; Zheng , Q.-H. Design and synthesis of carbon-11-labeled dual aromatase–steroid sulfatase inhibitors as new potential PET agents for imaging of aromatase and steroid sulfatase expression in breast cancer . Steroids 2009 , 74 , 896 – 905 .
  • Wang , M. ; Lacy , G. ; Gao , M. ; Miller , K. D. ; Sledge , G. W. ; Zheng , Q.-H. Synthesis of carbon-11 labeled sulfonanilide analogues as new potential PET agents for imaging of aromatase in breast cancer. Bioorg. Med. Chem. Lett. 2007, 17, 332–336.
  • Gao , M. ; Wang , M. ; Mock , B. H. ; Miller , K. D. ; Sledge , G. W. ; Hutchins , G. D. ; Zheng , Q.-H. Synthesis of new carbon-11 labeled cyclofenil derivatives for PET imaging of breast cancer estrogen receptors . Appl. Radiat. Isot. 2008 , 66 , 523 – 529 .
  • Gao , M. ; Wang , M. ; Miller , K. D. ; Sledge , G. W. ; Zheng , Q.-H. Synthesis and preliminary biological evaluation of new carbon-11 labeled tetrahydroisoquinoline derivatives as SERM radioligands for PET imaging of ER expression in breast cancer . Eur. J. Med. Chem. 2008 , 43 , 2211 – 2219 .
  • Kaiser , C. ; Colella , D. F. ; Pavloff , A. M. ; Wardell Jr. , J. R. Adrenergic agents, 2: Synthesis and potential β-adrenergic agonist activity of some ring-chlorinated relatives of isoproterenol . J. Med. Chem. 1974 , 17 , 1071 – 1075 .
  • Okada , M. ; Yoden , T. ; Kawaminami , E. ; Shimada , Y. ; Kudoh , M. ; Isomura , Y. ; Shikama , H. ; Fujikura , T. Studies on aromatase inhibitors, I: Synthesis and biological evaluation of 4-amino-4H-1,2,4-triazole derivatives . Chem. Pharm. Bull. 1996 , 44 , 1871 – 1879 .
  • Wang , M. ; Gao , M. ; Miller , K. D. ; Sledge , G. W. ; Hutchins , G. D. ; Zheng , Q.-H. Synthesis of carbon-11 labeled 7-aroyl-aminoindoline-1-sulfonamides as potential PET agents for imaging of tubulin polymerization in cancers . J. Label. Compd. Radiopharm. 2008 , 51 , 6 – 11 .
  • Hua , D. H. ; Huang , X. ; Chen , Y. ; Battina , S. K. ; Tamura , M. ; Noh , S. K. ; Koo , S. I. ; Namatame , I. ; Tomoda , H. ; Perchellet , E. M. ; Perchellet , J. P. Total syntheses of (+)-chloropuupehenone and (+)-chloropuupehenol and their analogues and evaluation of their bioactivities . J. Org. Chem. 2004 , 69 , 6065 – 6078 .
  • Masuno , M. N. ; Pessah , I. S. ; Olmstead , M. M. ; Molinski , T. F. Simplified cyclic analogues of bastadin-5: Structure–activity relationships for modulation of the RyR1/FKBP12 Ca2+ channel complex . J. Med. Chem. 2006 , 49 , 4497 – 4511 .
  • Plourde , G. L. ; Spaetzel , R. R. Regioselective protection of the 4-hydroxyl of 3,4-dihydroxy-benzadehyde . Molecules 2002 , 7 , 697 – 705 .
  • Yamazaki , T. ; Oniki , T. ; Kitazume , T. 1,2- and 1,3-O,O-Silyl migration reactions of fluorine-containing monosilylated diols . Tetrahedron 1996 , 52 , 11753 – 11762 .
  • O'Reilly , J. M. ; Li , N. ; Duax , W. L. ; Brueggemeier , R. W. Synthesis, structure elucidation, and biochemical evaluation of 7α- and 7β-arylaliphatic-substituted androst-4-ene-3,17-diones as inhibitors of aromatase . J. Med. Chem. 1995 , 38 , 2842 – 2850 .
  • Jewett , D. M. A simple synthesis of [11C]methyl triflate . Int. J. Rad. Appl. Instrum. A 1992 , 43 , 1383 – 1385 .
  • Mock , B. H. ; Mulholland , G. K. ; Vavrek , M. T. Convenient gas phase bromination of [11C]methane and production of [11C]methyl triflate . Nucl. Med. Biol. 1999 , 26 , 467 – 471 .
  • Mock , B. H. ; Zheng , Q.-H. ; DeGrado , T. R. A multi-purpose 11C-radio-synthesis system . J. Label. Compd. Radiopharm. 2005 , 48 , S225 .
  • Mock , B. H. ; Glick-Wilson , B. E. ; Zheng , Q.-H. ; DeGrado , T. R. Automated measurement of specific activity of radiolabeled ligands during synthesis . J. Label. Compd. Radiopharm. 2005 , 48 , S224 .
  • Zheng , Q.-H. ; Mock , B. H. Purification of carbon-11 PET radiotracers from unlabeled precursors by preparative HPLC and SPE . Biomed. Chromatogr. 2005 , 19 , 671 – 676 .
  • Leese , M. P. ; Leblond , B. ; Smith , A. ; Newman , S. P. ; Di Fiore , A. ; De Simone , G. ; Supuran , C. T. ; Purohit , A. ; Reed , M. J. ; Potter , B. V. L. 2-Substituted estradiol bis-sulfamates, multitargeted antitumor agents: Synthesis, in vitro SAR, protein crystallography, and in vivo activity . J. Med. Chem. 2006 , 49 , 7683 – 7696 .

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