- Synthesis, Radiolabeling, and Biological Evaluation of the cis Stereoisomers of 1-Amino-3-Fluoro-4-(fluoro-18F)Cyclopentane-1-Carboxylic Acid as PET Imaging Agents
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The non-natural cyclic amino acids (1S,3R,4S)-1-amino-3-fluoro-4-(fluoro-18F)cyclopentane-1-carboxylic acid ([18F]9) and (1S,3S,4R)-1-amino-3-fluoro-4-(fluoro-18F)cyclopentane-1-carboxylic acid ([18F]28) have been prepared in 10 and 1.7% decay corrected radiochemical yield, respectively, and in greater than 99% radiochemical purity. Cell assays in rat 9L gliosarcoma, human U87 ΔEGFR glioblastoma, and human DU145 androgen-independent prostate carcinoma tumor cells indicated that both compounds are substrates for amino acid transport primarily by system L, with some transport taking place via system ASC. In rats with 9L gliosarcoma, [18F]9 and [18F]28 provided high tumor to normal brain tissue ratios, with maximal ratios of 3.5 and 4.1, respectively. Biodistribution studies in healthy rats confirmed that both compounds are BBB permeable and that bladder accumulation is low until at least 5 min post injection.
- Pickel, Thomas C.,Voll, Ronald J.,Yu, Weiping,Wang, Zhaobin,Nye, Jonathon A,Bacsa, John,Olson, Jeffrey J.,Liebeskind, Lanny S.,Goodman, Mark M.
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- Complete facial selectivity in the Diels-Alder reaction of a 5-amino-5-carboxycyclopentadiene derivative
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5-tert-Butoxycarbonylamino-5-carbethoxy-2-tert-butyldimethylsilyloxy- cyclopentadiene undergoes a Diels-Alder reaction exclusively from the face syn to the nitrogen functionality. Complete reversal of facial bias may be achieved, but at the cost of dimini
- Kim, Simon,Ciufolini, Marco A.
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supporting information; scheme or table
p. 3274 - 3277
(2011/08/05)
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- Regio- and diastereoselective synthesis of cyclic amino esters
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Several cyclic amino esters have been prepared regio- and diastereoselectively depending on the electrophile (cis or trans alkene) and its leaving group.
- Park, Kyung-Ho,Kurth, Thomas M.,Olmstead, Marilyn M.,Kurth, Mark J.
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p. 991 - 992
(2007/10/03)
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