Characterization of the binding site of the histamine H3 receptor. 1. Various approaches to the synthesis of 2-(1H-imidazol-4-yl)cyclopropylamine and histaminergic activity of (1R,2R)-and (1S,2S)-2-(1H-imidazol-4-yl)-cyclopropylamine.

I.J.P. de Esch; R.C. Vollinga; K. Goubitz; H. Schenk; U. Appelberg; U. Hacksel; S. Lemstra; M. Hoffmann; R. Leurs; W.M.P.B. Menge; H. Timmerman; O.P. Zuiderveld

doi:10.1021/jm9810912

Characterization of the binding site of the histamine H3 receptor. 1. Various approaches to the synthesis of 2-(1H-imidazol-4-yl)cyclopropylamine and histaminergic activity of (1R,2R)-and (1S,2S)-2-(1H-imidazol-4-yl)-cyclopropylamine.

I.J.P. de Esch, R.C. Vollinga, K. Goubitz, H. Schenk, U. Appelberg, U. Hacksel, S. Lemstra, M. Hoffmann, R. Leurs, W.M.P.B. Menge, H. Timmerman, O.P. Zuiderveld

Medicinal chemistry

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Abstract

Various approaches to the synthesis of all four stereoisomers of 2-(1H- imidazol-4-yl)cyclopropylamine (cyclopropylhistamine) are described. The rapid and convenient synthesis and resolution of trans-cyclopropylhistamine is reported. The absolute configuration of its enantiomers was determined by single-crystal X-ray crystallographic analysis. The distinct transcyclopropylhistamine enantiomers were tested for their activity and affinity on the histamine H

Original language	English
Pages (from-to)	1115-1122
Journal	Journal of Medicinal Chemistry
Volume	43
DOIs	https://doi.org/10.1021/jm9810912
Publication status	Published - 1999

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de Esch, I. J. P., Vollinga, R. C., Goubitz, K., Schenk, H., Appelberg, U., Hacksel, U., Lemstra, S., Hoffmann, M., Leurs, R., Menge, W. M. P. B., Timmerman, H., & Zuiderveld, O. P. (1999). Characterization of the binding site of the histamine H3 receptor. 1. Various approaches to the synthesis of 2-(1H-imidazol-4-yl)cyclopropylamine and histaminergic activity of (1R,2R)-and (1S,2S)-2-(1H-imidazol-4-yl)-cyclopropylamine. Journal of Medicinal Chemistry, 43, 1115-1122. https://doi.org/10.1021/jm9810912

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title = "Characterization of the binding site of the histamine H3 receptor. 1. Various approaches to the synthesis of 2-(1H-imidazol-4-yl)cyclopropylamine and histaminergic activity of (1R,2R)-and (1S,2S)-2-(1H-imidazol-4-yl)-cyclopropylamine.",

abstract = "Various approaches to the synthesis of all four stereoisomers of 2-(1H- imidazol-4-yl)cyclopropylamine (cyclopropylhistamine) are described. The rapid and convenient synthesis and resolution of trans-cyclopropylhistamine is reported. The absolute configuration of its enantiomers was determined by single-crystal X-ray crystallographic analysis. The distinct transcyclopropylhistamine enantiomers were tested for their activity and affinity on the histamine H",

author = "{de Esch}, I.J.P. and R.C. Vollinga and K. Goubitz and H. Schenk and U. Appelberg and U. Hacksel and S. Lemstra and M. Hoffmann and R. Leurs and W.M.P.B. Menge and H. Timmerman and O.P. Zuiderveld",

year = "1999",

doi = "10.1021/jm9810912",

language = "English",

volume = "43",

pages = "1115--1122",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

publisher = "American Chemical Society",

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de Esch, IJP, Vollinga, RC, Goubitz, K, Schenk, H, Appelberg, U, Hacksel, U, Lemstra, S, Hoffmann, M, Leurs, R, Menge, WMPB, Timmerman, H & Zuiderveld, OP 1999, 'Characterization of the binding site of the histamine H3 receptor. 1. Various approaches to the synthesis of 2-(1H-imidazol-4-yl)cyclopropylamine and histaminergic activity of (1R,2R)-and (1S,2S)-2-(1H-imidazol-4-yl)-cyclopropylamine.', Journal of Medicinal Chemistry, vol. 43, pp. 1115-1122. https://doi.org/10.1021/jm9810912

Characterization of the binding site of the histamine H3 receptor. 1. Various approaches to the synthesis of 2-(1H-imidazol-4-yl)cyclopropylamine and histaminergic activity of (1R,2R)-and (1S,2S)-2-(1H-imidazol-4-yl)-cyclopropylamine. / de Esch, I.J.P.; Vollinga, R.C.; Goubitz, K. et al.
In: Journal of Medicinal Chemistry, Vol. 43, 1999, p. 1115-1122.

Research output: Contribution to Journal › Article › Academic › peer-review

TY - JOUR

T1 - Characterization of the binding site of the histamine H3 receptor. 1. Various approaches to the synthesis of 2-(1H-imidazol-4-yl)cyclopropylamine and histaminergic activity of (1R,2R)-and (1S,2S)-2-(1H-imidazol-4-yl)-cyclopropylamine.

AU - de Esch, I.J.P.

AU - Vollinga, R.C.

AU - Goubitz, K.

AU - Schenk, H.

AU - Appelberg, U.

AU - Hacksel, U.

AU - Lemstra, S.

AU - Hoffmann, M.

AU - Leurs, R.

AU - Menge, W.M.P.B.

AU - Timmerman, H.

AU - Zuiderveld, O.P.

PY - 1999

Y1 - 1999

N2 - Various approaches to the synthesis of all four stereoisomers of 2-(1H- imidazol-4-yl)cyclopropylamine (cyclopropylhistamine) are described. The rapid and convenient synthesis and resolution of trans-cyclopropylhistamine is reported. The absolute configuration of its enantiomers was determined by single-crystal X-ray crystallographic analysis. The distinct transcyclopropylhistamine enantiomers were tested for their activity and affinity on the histamine H

AB - Various approaches to the synthesis of all four stereoisomers of 2-(1H- imidazol-4-yl)cyclopropylamine (cyclopropylhistamine) are described. The rapid and convenient synthesis and resolution of trans-cyclopropylhistamine is reported. The absolute configuration of its enantiomers was determined by single-crystal X-ray crystallographic analysis. The distinct transcyclopropylhistamine enantiomers were tested for their activity and affinity on the histamine H

U2 - 10.1021/jm9810912

DO - 10.1021/jm9810912

M3 - Article

SN - 0022-2623

VL - 43

SP - 1115

EP - 1122

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

ER -

de Esch IJP, Vollinga RC, Goubitz K, Schenk H, Appelberg U, Hacksel U et al. Characterization of the binding site of the histamine H3 receptor. 1. Various approaches to the synthesis of 2-(1H-imidazol-4-yl)cyclopropylamine and histaminergic activity of (1R,2R)-and (1S,2S)-2-(1H-imidazol-4-yl)-cyclopropylamine. Journal of Medicinal Chemistry. 1999;43:1115-1122. doi: 10.1021/jm9810912