The synthesis of tricyclic cocaine analogs via the 1,3-dipolar cycloaddition of oxidopyridinium betaines

Miles P. Smith; Clifford George; Alan P. Kozikowski

doi:10.1016/S0040-4039(97)10524-X

The synthesis of tricyclic cocaine analogs via the 1,3-dipolar cycloaddition of oxidopyridinium betaines

Miles P. Smith, Clifford George, Alan P. Kozikowski

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

Abstract

Tricyclic cocaine analogs with a spatially fixed nitrogen lone pair were synthesized as structural probes of the dopamine transporter. A tandem cycloaddition/radical cyclization protocol was used to gain access to analog 12 with a two carbon linker between C-2 and N-8. On the other hand, the intramolecular dipolar cycloaddition reaction of betaine 13 was used to procure cocaine analog 18 and its C-3 epimer 19 in which an extra ring links N-8 to C-6. Binding studies reveal 12c and 18 to be potent DAT ligands.

Original language	English (US)
Pages (from-to)	197-200
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	3-4
DOIs	https://doi.org/10.1016/S0040-4039(97)10524-X
State	Published - Jan 15 1998
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(97)10524-X

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title = "The synthesis of tricyclic cocaine analogs via the 1,3-dipolar cycloaddition of oxidopyridinium betaines",

abstract = "Tricyclic cocaine analogs with a spatially fixed nitrogen lone pair were synthesized as structural probes of the dopamine transporter. A tandem cycloaddition/radical cyclization protocol was used to gain access to analog 12 with a two carbon linker between C-2 and N-8. On the other hand, the intramolecular dipolar cycloaddition reaction of betaine 13 was used to procure cocaine analog 18 and its C-3 epimer 19 in which an extra ring links N-8 to C-6. Binding studies reveal 12c and 18 to be potent DAT ligands.",

author = "Smith, {Miles P.} and Clifford George and Kozikowski, {Alan P.}",

note = "Funding Information: Acknowledgments. We are indebted to the NIH, National Institute on Drug Abuse (DA10458) for support of this work.",

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AU - George, Clifford

AU - Kozikowski, Alan P.

N1 - Funding Information: Acknowledgments. We are indebted to the NIH, National Institute on Drug Abuse (DA10458) for support of this work.

PY - 1998/1/15

Y1 - 1998/1/15

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AB - Tricyclic cocaine analogs with a spatially fixed nitrogen lone pair were synthesized as structural probes of the dopamine transporter. A tandem cycloaddition/radical cyclization protocol was used to gain access to analog 12 with a two carbon linker between C-2 and N-8. On the other hand, the intramolecular dipolar cycloaddition reaction of betaine 13 was used to procure cocaine analog 18 and its C-3 epimer 19 in which an extra ring links N-8 to C-6. Binding studies reveal 12c and 18 to be potent DAT ligands.

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The synthesis of tricyclic cocaine analogs via the 1,3-dipolar cycloaddition of oxidopyridinium betaines

Abstract

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