Synthesis of N-substituted 9-azabicyclo[3.3.1]nonan-3α-yl carbamate analogs as σ2 receptor ligands

Suwanna Vangveravong; Jinbin Xu; Chenbo Zeng; Robert H. Mach

doi:10.1016/j.bmc.2006.06.028

Synthesis of N-substituted 9-azabicyclo[3.3.1]nonan-3α-yl carbamate analogs as σ₂ receptor ligands

Suwanna Vangveravong
, Jinbin Xu
, Chenbo Zeng
, Robert H. Mach

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

46 Scopus citations

Abstract

A series of N-substituted 9-azabicyclo[3.3.1]nonan-3α-yl phenylcarbamate analogs was prepared and their affinities for sigma (σ₁ and σ₂) receptors were measured in vitro. The results of their structure-activity relationship study identified two new compounds, N-(9-(4-aminobutyl)-9-azabicyclo[3.3.1]nonan-3α-yl)-N′-(2-methoxy-5-methylphenyl)carbamate and N-(9-(6-aminohexyl)-9-azabicyclo[3.3.1]nonan-3α-yl)-N′-(2-methoxy-5-methylphenyl)carbamate, having a high affinity and selectivity for σ₂ versus σ₁ receptors. These compounds were also used in the preparation of biotinylated and fluorescent probes of the σ₂ receptor.

Original language	English
Pages (from-to)	6988-6997
Number of pages	10
Journal	Bioorganic and Medicinal Chemistry
Volume	14
Issue number	20
DOIs	https://doi.org/10.1016/j.bmc.2006.06.028
State	Published - Oct 15 2006

Keywords

Fluorescent probe
Two-photon microscopy
σ Receptors

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10.1016/j.bmc.2006.06.028

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@article{e4a2a8743a754f6c8a0c584cf0b1f211,

title = "Synthesis of N-substituted 9-azabicyclo[3.3.1]nonan-3α-yl carbamate analogs as σ2 receptor ligands",

abstract = "A series of N-substituted 9-azabicyclo[3.3.1]nonan-3α-yl phenylcarbamate analogs was prepared and their affinities for sigma (σ1 and σ2) receptors were measured in vitro. The results of their structure-activity relationship study identified two new compounds, N-(9-(4-aminobutyl)-9-azabicyclo[3.3.1]nonan-3α-yl)-N′-(2-methoxy-5-methylphenyl)carbamate and N-(9-(6-aminohexyl)-9-azabicyclo[3.3.1]nonan-3α-yl)-N′-(2-methoxy-5-methylphenyl)carbamate, having a high affinity and selectivity for σ2 versus σ1 receptors. These compounds were also used in the preparation of biotinylated and fluorescent probes of the σ2 receptor.",

keywords = "Fluorescent probe, Two-photon microscopy, σ Receptors",

author = "Suwanna Vangveravong and Jinbin Xu and Chenbo Zeng and Mach, \{Robert H.\}",

note = "Funding Information: This research was funded by NIH Grant CA 102869 and the U.S. Army Medical Research and Material Command under DAMD 17-01-1-0446.",

year = "2006",

month = oct,

day = "15",

doi = "10.1016/j.bmc.2006.06.028",

language = "English",

volume = "14",

pages = "6988--6997",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

number = "20",

}

TY - JOUR

T1 - Synthesis of N-substituted 9-azabicyclo[3.3.1]nonan-3α-yl carbamate analogs as σ2 receptor ligands

AU - Vangveravong, Suwanna

AU - Xu, Jinbin

AU - Zeng, Chenbo

AU - Mach, Robert H.

N1 - Funding Information: This research was funded by NIH Grant CA 102869 and the U.S. Army Medical Research and Material Command under DAMD 17-01-1-0446.

PY - 2006/10/15

Y1 - 2006/10/15

N2 - A series of N-substituted 9-azabicyclo[3.3.1]nonan-3α-yl phenylcarbamate analogs was prepared and their affinities for sigma (σ1 and σ2) receptors were measured in vitro. The results of their structure-activity relationship study identified two new compounds, N-(9-(4-aminobutyl)-9-azabicyclo[3.3.1]nonan-3α-yl)-N′-(2-methoxy-5-methylphenyl)carbamate and N-(9-(6-aminohexyl)-9-azabicyclo[3.3.1]nonan-3α-yl)-N′-(2-methoxy-5-methylphenyl)carbamate, having a high affinity and selectivity for σ2 versus σ1 receptors. These compounds were also used in the preparation of biotinylated and fluorescent probes of the σ2 receptor.

AB - A series of N-substituted 9-azabicyclo[3.3.1]nonan-3α-yl phenylcarbamate analogs was prepared and their affinities for sigma (σ1 and σ2) receptors were measured in vitro. The results of their structure-activity relationship study identified two new compounds, N-(9-(4-aminobutyl)-9-azabicyclo[3.3.1]nonan-3α-yl)-N′-(2-methoxy-5-methylphenyl)carbamate and N-(9-(6-aminohexyl)-9-azabicyclo[3.3.1]nonan-3α-yl)-N′-(2-methoxy-5-methylphenyl)carbamate, having a high affinity and selectivity for σ2 versus σ1 receptors. These compounds were also used in the preparation of biotinylated and fluorescent probes of the σ2 receptor.

KW - Fluorescent probe

KW - Two-photon microscopy

KW - σ Receptors

UR - https://www.scopus.com/pages/publications/33748102817

U2 - 10.1016/j.bmc.2006.06.028

DO - 10.1016/j.bmc.2006.06.028

M3 - Article

C2 - 16837201

AN - SCOPUS:33748102817

SN - 0968-0896

VL - 14

SP - 6988

EP - 6997

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 20

ER -

Synthesis of N-substituted 9-azabicyclo[3.3.1]nonan-3α-yl carbamate analogs as σ₂ receptor ligands

Abstract

Keywords

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