Synthesis and structure-activity relationship studies of conformationally flexible tetrahydroisoquinolinyl triazole carboxamide and triazole substituted benzamide analogues as σ2 receptor ligands

Suping Bai; Shihong Li; Jinbin Xu; Xin Peng; Kiran Sai; Wenhua Chu; Zhude Tu; Chenbo Zeng; Robert H. Mach

doi:10.1021/jm5001453

Synthesis and structure-activity relationship studies of conformationally flexible tetrahydroisoquinolinyl triazole carboxamide and triazole substituted benzamide analogues as σ₂ receptor ligands

Suping Bai, Shihong Li, Jinbin Xu, Xin Peng, Kiran Sai, Wenhua Chu, Zhude Tu, Chenbo Zeng, Robert H. Mach

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

32 Scopus citations

Abstract

Two novel classes of compounds targeting the sigma-2 (σ₂) receptor were synthesized, and their bioactivities to binding σ₁ and σ₂ receptors were measured. Four novel triazole carboxamide analogues, 24d, 24e, 24f, and 39c, demonstrated high affinity and selectivity for the σ₂ receptor. These data suggest ¹¹C-labeled versions of these compounds may be potential σ₂-selective radiotracers for imaging the proliferative status of solid tumors.

Original language	English
Pages (from-to)	4239-4251
Number of pages	13
Journal	Journal of Medicinal Chemistry
Volume	57
Issue number	10
DOIs	https://doi.org/10.1021/jm5001453
State	Published - May 22 2014

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10.1021/jm5001453

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Bai, S., Li, S., Xu, J., Peng, X., Sai, K., Chu, W., Tu, Z., Zeng, C., & Mach, R. H. (2014). Synthesis and structure-activity relationship studies of conformationally flexible tetrahydroisoquinolinyl triazole carboxamide and triazole substituted benzamide analogues as σ₂ receptor ligands. Journal of Medicinal Chemistry, 57(10), 4239-4251. https://doi.org/10.1021/jm5001453

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title = "Synthesis and structure-activity relationship studies of conformationally flexible tetrahydroisoquinolinyl triazole carboxamide and triazole substituted benzamide analogues as σ2 receptor ligands",

abstract = "Two novel classes of compounds targeting the sigma-2 (σ2) receptor were synthesized, and their bioactivities to binding σ1 and σ2 receptors were measured. Four novel triazole carboxamide analogues, 24d, 24e, 24f, and 39c, demonstrated high affinity and selectivity for the σ2 receptor. These data suggest 11C-labeled versions of these compounds may be potential σ2-selective radiotracers for imaging the proliferative status of solid tumors.",

author = "Suping Bai and Shihong Li and Jinbin Xu and Xin Peng and Kiran Sai and Wenhua Chu and Zhude Tu and Chenbo Zeng and Mach, {Robert H.}",

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Bai, S, Li, S, Xu, J, Peng, X, Sai, K, Chu, W , Tu, Z, Zeng, C & Mach, RH 2014, 'Synthesis and structure-activity relationship studies of conformationally flexible tetrahydroisoquinolinyl triazole carboxamide and triazole substituted benzamide analogues as σ₂ receptor ligands', Journal of Medicinal Chemistry, vol. 57, no. 10, pp. 4239-4251. https://doi.org/10.1021/jm5001453

Synthesis and structure-activity relationship studies of conformationally flexible tetrahydroisoquinolinyl triazole carboxamide and triazole substituted benzamide analogues as σ₂ receptor ligands. / Bai, Suping; Li, Shihong; Xu, Jinbin et al.
In: Journal of Medicinal Chemistry, Vol. 57, No. 10, 22.05.2014, p. 4239-4251.

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

TY - JOUR

T1 - Synthesis and structure-activity relationship studies of conformationally flexible tetrahydroisoquinolinyl triazole carboxamide and triazole substituted benzamide analogues as σ2 receptor ligands

AU - Bai, Suping

AU - Li, Shihong

AU - Xu, Jinbin

AU - Peng, Xin

AU - Sai, Kiran

AU - Chu, Wenhua

AU - Tu, Zhude

AU - Zeng, Chenbo

AU - Mach, Robert H.

PY - 2014/5/22

Y1 - 2014/5/22

N2 - Two novel classes of compounds targeting the sigma-2 (σ2) receptor were synthesized, and their bioactivities to binding σ1 and σ2 receptors were measured. Four novel triazole carboxamide analogues, 24d, 24e, 24f, and 39c, demonstrated high affinity and selectivity for the σ2 receptor. These data suggest 11C-labeled versions of these compounds may be potential σ2-selective radiotracers for imaging the proliferative status of solid tumors.

AB - Two novel classes of compounds targeting the sigma-2 (σ2) receptor were synthesized, and their bioactivities to binding σ1 and σ2 receptors were measured. Four novel triazole carboxamide analogues, 24d, 24e, 24f, and 39c, demonstrated high affinity and selectivity for the σ2 receptor. These data suggest 11C-labeled versions of these compounds may be potential σ2-selective radiotracers for imaging the proliferative status of solid tumors.

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IS - 10

ER -

Synthesis and structure-activity relationship studies of conformationally flexible tetrahydroisoquinolinyl triazole carboxamide and triazole substituted benzamide analogues as σ₂ receptor ligands

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