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| Synthesis and GTPγS Binding Activity of Novel 2-Bromo-benzamides Small Molecule CCR5 Antagonists |
| CHENG De-jun, HUANG Bin, Yang Guo |
| College of Materials and Chemical Engineering， Sichuan University of Science and Engineering， Zigong 643000, China |
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Abstract 5-Bromo-1-［(4-chlorobenzyl)oxy］-2-bromotoluene(3) was obtained by substitution reaction, reduction and NBS bromination from 5-bromo-2-hydroxybenzaldehyde. N-allyl-2-bromo-N-(4-piperidinyl)benzamide(7) was prepared by protection, reduction and condensation reaction from 4-piperidone-hydrochlorid. A novel non-peptide small molecule compound, N-allyl-2-bromo-N-【1-{2-［(4-chlorobenz)oxyyl］-5-bromobenz}-4-piperidin】 benzamide(8) with total yield of 32.5%, was synthesized by substitution reaction of 3 with 7. The structure was characterized by 1H NMR， 13C NMR， IR and ESI-MS. The biological activity of 8 was detected by the SPA GTPγS assay. The results indicated that the biological binding activity of 8 approach to TD0232 with IC50 of (8.12±0.3) nmol·L-1.
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Received: 28 October 2015
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2016, Vol. 24 
