484-93-5Relevant articles and documents
COMPOUNDS AND METHODS FOR PREVENTING OR TREATING SENSORY HAIR CELL DEATH
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Paragraph 0301; 0302, (2016/09/06)
Disclosed herein are compounds, and pharmaceutical compositions that include such compounds, for preventing or treating hearing loss. The compounds and pharmaceutical compositions described herein prevent or treat hair cell death. In addition, the compounds and pharmaceutical compositions described herein protect against kidney damage in an individual receiving an aminoglycoside antibiotic. Methods of using the compounds, alone or in combination with other therapeutic agents, are also disclosed.
Synthesis of novel halo and tosyloxy nortropane derivatives as efficient precursors for the one-step synthesis of the dopamine transporter PET ligand [18F]FECNT
Pijarowska-Kruszyna,Jaron,Kachniarz,Kasprzak,Kowalska,Malkowski,Demphel,Dolle,Mikolajczak
, p. 148 - 157 (2014/04/03)
The fluorine-18 labeled nortropane derivative 2β-carbomethoxy-3β- (4-chlorophenyl)-8-(2-fluoroethyl)-nortropane (FECNT) is a dopamine transporter (DAT) ligand. Currently, it is considered as reference for positron emission tomography imaging. Herein, the synthesis of novel precursors (N-tosyloxy-, chloro-, and bromo- analogues) for one-step radiosynthesis of [ 18F]FECNT is reported. Using the N-mesyloxy- precursor in a one-step radiosynthesis, the crude [18F]FECNT was obtained with the radiolabeling yield of 45 ± 10%, confirming the practical efficiency of this approach in the design of novel precursors for labeling. Copyright
[11C]PR04.MZ, a promising DAT ligand for low concentration imaging: Synthesis, efficient 11C-O-methylation and initial small animal PET studies
Riss, Patrick J.,Hooker, Jacob M.,Alexoff, David,Kim, Sung-Won,Fowler, Joanna S.,Roesch, Frank
body text, p. 4343 - 4345 (2010/04/25)
PR04.MZ was designed as a highly selective dopamine transporter inhibitor, derived from natural cocaine. Its binding profile indicates that [11C]PR04.MZ may be suited as a PET radioligand for the non-invasive exploration of striatal and extrastriatal DAT populations. As a key feature, its structural design facilitates both, labelling with fluorine-18 at its terminally fluorinated butynyl moiety and carbon-11 at its methyl ester function. The present report concerns the efficient [11C]MeI mediated synthesis of [11C]PR04.MZ from an O-desmethyl precursor trifluoroacetic acid salt with Rb2CO3 in DMF in up to 95 ± 5% labelling yield. A preliminary μPET-experiment demonstrates the reversible, highly specific binding of [11C]PR04.MZ in the brain of a male Sprague-Dawley rat.
Synthesis and 11C-Radiolabelling of a Tropane Derivative Lacking the 2β Ester Group: A Potential PET-Tracer for the Dopamine Transporter
Schoenbaechler, Roland,Ametamey, Simon M.,Schubiger, Pius A.
, p. 447 - 456 (2007/10/03)
The synthesis and 11C-radiolabelling of a new tropane analogue, 3β-(4'-chlorophenyl)-2β-(3'-phenylisoxazol-5'-yl)tropane (β-CPPIT), an inhibitor of the dopamine transporter, is reported. The desmethyl compound, 3β-(4'-chlorophenyl)-2β-(3'-phenylisoxazol-5'-yl)nortropane (5) was prepared via a six-step reaction sequence starting from cocaine. [11C]-β-CPPIT was labelled by N-methylation using [11C]-methyl iodide obtained from the gas phase reaction of [11C]-methane with iodine in 60 +/- 10 percent radiochemical yield (decay corrected from [11C]-methyl iodide). The overall synthesis time was on average 60 minutes at EOB (end of bombardment). The final product had a specific activity of 2000 - 2700 Ci/mmol (74 - 100 TBq/mmol) at EOS (end of synthesis) and the radiochemical purity was greater than 99 percent. [11C]-β-CPPIT showed a logP value of 2.1 indicating that a free diffusion through the blood-brain-barrier should be possible.
Fmoc-protected tropane-based amino acids for peptide structure-function studies
Thompson, Philip E.,Hearn, Milton T. W.
, p. 2907 - 2910 (2007/10/03)
Cyclic amino acids derived from the tropane alkaloid nucleus have been prepared and incorporated into synthetic peptides. These conformationally constrained β-amino acids hold considerable potential for use in the development of novel, synthetic analogues of biologically active peptides.
Substituted 3-Phenyltropane Analogs of Cocaine: Synthesis, Inhibition of Binding at Cocaine Recognition Sites, and Positron Emission Tomography Imaging
Meltzer, P. C.,Liang, A. Y.,Brownell, A.-L.,Elmaleh, D. R.,Madras, B. K.
, p. 855 - 862 (2007/10/02)
It is now accepted that (-)-cocaine binds to specific recognition sites associated with monoamine transporters in the mammalian brain. In this study, several analogs of 3β-phenyltropane-2β-carboxylic acid methyl ester were prepared and their potency for inhibiting the binding of -3β-(4-fluorophenyl)tropane-2β-carboxylic acid methyl ester to primate caudate-putamen was evaluated. The synthesis and binding affinity of 3β-(3,4-dichlorophenyl)tropane-2β-carboxylic acid methyl ester, one of the most potent cocaine congeners yet reported, is presented. The feasibility of synthesizing high-affinity ligands for cocaine recognition sites and their suitability as PET imaging ligands for cocaine receptors in vivo is demonstrated.
