Synthesis and binding affinities of 2β-(3-iodoallyloxycarbonyl)-3β-(4-substituted-aryl)tropane analogues as ligands for the dopamine transporter studies
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Section snippets
Chemistry
The structures of compounds selected for the synthesis and binding data on the dopamine transporter are shown in Table 1. All compounds described herein were prepared from natural (R)-cocaine, and therefore they have the same absolute configuration as (R)-cocaine. Compound 5 were prepared from cocaine based on the previous reports.8 According with Carroll's modification9 of the original procedure of Clarke et al.,10 the 3β-intermediate WIN analogues 6a–d were synthesized in 52% yield with
Discussion
Recently, the goals of research and the summary of results regarding C2 modification of cocaine were well described.2a There are several reports that for the basic nitrogen and a hydrogen bond of 2β-carbomethoxy ester function of cocaine are not essential for potent activity. The major putative interaction of cocaine with DAT, however, would be (1) the ionic interaction of the protonated nitrogen and carboxylate of its receptor, (2) the hydrogen bond of 2β-carbomethoxy ester, and (3) lipophilic
Acknowledgements
We are grateful for the support of this work through a grant from the Korea Science and Engineering Foundation (No. 97-03-01-01-5-L).
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Development and validation of high-performance liquid chromatography method for analysis of β-CCT and its related substances
2022, Arabian Journal of ChemistryCitation Excerpt :Up till now, most DAT imaging agents are based on tropane derivatives structure labelled with radioactive nuclides (Booth et al., 2015; Jeon et al., 2020; Haseli et al., 2021), such as 99mTc-TRODAT-1 (Shinto et al., 2014) for SPECT, [18F]FECNT (van der Zande et al., 2016) and [18F]FECNT-d4 (Cao et al., 2021) for PET and so on (Naumiec et al., 2015). Compound 2β-carbomethoxy-3β-(4-chlorophenyl)tropane (β-CCT, Fig. 1) is a key synthetic intermediate for the above-mentioned DAT imaging agents (Meegalla et al., 1997; Xing et al., 2000; Chung et al., 2001; Pijarowska-Kruszyna et al., 2014; Naumiec et al., 2015). In the pharmaceutical industry, it is very essential to control the purity of key intermediates to ensure the quality of the final medicine products (Xiao et al., 2007).
An extended study of dimeric phenyl tropanes
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2004, Synthetic Communications