Abstract
In our search for novel therapeutic agents useful in the treatment of cocaine abuse, we have studied the synthesis and biological activity of 2β- butyl-3-phenyltropane derivatives with the phenyl ring in α- or β- configuration and bearing different substituents at the 6- and 7-positions of the tropane ring. All of the compounds synthesized showed micromolar or submicromolar affinity for the DAT in the rat striatum. In particular, among all the compounds described in this paper, the 7α-fluoro-3α-phenyltropane derivative 12 was found to be the most potent, inhibiting mazindol binding with a K(i) of 0.20 μM and dopamine reuptake with a K(i) of 0.49 μM.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 43-58 |
| Number of pages | 16 |
| Journal | Medicinal Chemistry Research |
| Volume | 8 |
| Issue number | 1-2 |
| State | Published - 1998 |
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ASJC Scopus subject areas
- Organic Chemistry
- Drug Discovery
Cite this
Synthesis and biological activity of new 6- and 7-substituted 2β- butyl-3-phenyltropanes as ligands for the dopamine transporter. / Prakash, K. R C; Araldi, Gian Luca; Smith, Miles P.; Zhang, Mai; Johnson, Kenneth M.; Kozikowski, Alan P.
In: Medicinal Chemistry Research, Vol. 8, No. 1-2, 1998, p. 43-58.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis and biological activity of new 6- and 7-substituted 2β- butyl-3-phenyltropanes as ligands for the dopamine transporter
AU - Prakash, K. R C
AU - Araldi, Gian Luca
AU - Smith, Miles P.
AU - Zhang, Mai
AU - Johnson, Kenneth M.
AU - Kozikowski, Alan P.
PY - 1998
Y1 - 1998
N2 - In our search for novel therapeutic agents useful in the treatment of cocaine abuse, we have studied the synthesis and biological activity of 2β- butyl-3-phenyltropane derivatives with the phenyl ring in α- or β- configuration and bearing different substituents at the 6- and 7-positions of the tropane ring. All of the compounds synthesized showed micromolar or submicromolar affinity for the DAT in the rat striatum. In particular, among all the compounds described in this paper, the 7α-fluoro-3α-phenyltropane derivative 12 was found to be the most potent, inhibiting mazindol binding with a K(i) of 0.20 μM and dopamine reuptake with a K(i) of 0.49 μM.
AB - In our search for novel therapeutic agents useful in the treatment of cocaine abuse, we have studied the synthesis and biological activity of 2β- butyl-3-phenyltropane derivatives with the phenyl ring in α- or β- configuration and bearing different substituents at the 6- and 7-positions of the tropane ring. All of the compounds synthesized showed micromolar or submicromolar affinity for the DAT in the rat striatum. In particular, among all the compounds described in this paper, the 7α-fluoro-3α-phenyltropane derivative 12 was found to be the most potent, inhibiting mazindol binding with a K(i) of 0.20 μM and dopamine reuptake with a K(i) of 0.49 μM.
UR - http://www.scopus.com/inward/record.url?scp=0031861199&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0031861199&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0031861199
VL - 8
SP - 43
EP - 58
JO - Medicinal Chemistry Research
JF - Medicinal Chemistry Research
SN - 1054-2523
IS - 1-2
ER -