Synthesis and Pharmacological Properties of Silicon-Containing 1,4-Dihydropyridine Derivatives: Calcium Channel Antagonists and α1 Adrenoceptor Antagonists of the Sila-niguldipine Type
1
Institut für Anorganische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany, and Amedis Pharmaceuticals Ltd., 162 Cambridge Science Park, Milton Road, Cambridge CB4 0GP, U.K.
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Publication type: Journal Article
Publication date: 2003-12-24
scimago Q2
wos Q1
SJR: 0.676
CiteScore: 5.1
Impact factor: 2.9
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
Racemic 3-(4,4-diphenyl-4-silapiperidin-1-yl)propyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (rac-sila-niguldipine, rac-1b), a sila analogue of the calcium antagonist rac-niguldipine (rac-1a), and the sila-niguldipine derivatives rac-2b−rac-4b were synthesized in multistep syntheses, starting from dichlorodiphenylsilane. The silicon compounds rac-1b−rac-4b contain a 4,4-diphenyl-4-silapiperidin-1-yl group instead of the 4,4-diphenylpiperidin-1-yl moiety in the parent carbon compound rac-1a. rac-Sila-niguldipine and the precursor 3-(4,4-diphenyl-4-silapiperidin-1-yl)propanol (11) were structurally characterized by single-crystal X-ray diffraction. The pharmacological profiles of rac-1b−rac-4b were compared with that of rac-1a across a range of receptor binding assays (radioligand binding studies at α1A and α2 adrenoceptors, the L-type Ca2+ channel, and the serotonin 5-HT receptor). The silicon compounds rac-2b−rac-4b exhibit a profile similar to that of SNAP 5089 and ther...
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Heinrich T. et al. Synthesis and Pharmacological Properties of Silicon-Containing 1,4-Dihydropyridine Derivatives: Calcium Channel Antagonists and α1 Adrenoceptor Antagonists of the Sila-niguldipine Type // Organometallics. 2003. Vol. 23. No. 3. pp. 361-366.
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Heinrich T., Burschka C., Warneck J., Tacke R. Synthesis and Pharmacological Properties of Silicon-Containing 1,4-Dihydropyridine Derivatives: Calcium Channel Antagonists and α1 Adrenoceptor Antagonists of the Sila-niguldipine Type // Organometallics. 2003. Vol. 23. No. 3. pp. 361-366.
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TY - JOUR
DO - 10.1021/om0305622
UR - https://doi.org/10.1021/om0305622
TI - Synthesis and Pharmacological Properties of Silicon-Containing 1,4-Dihydropyridine Derivatives: Calcium Channel Antagonists and α1 Adrenoceptor Antagonists of the Sila-niguldipine Type
T2 - Organometallics
AU - Heinrich, Tilman
AU - Burschka, Christian
AU - Warneck, Julie
AU - Tacke, Reinhold
PY - 2003
DA - 2003/12/24
PB - American Chemical Society (ACS)
SP - 361-366
IS - 3
VL - 23
SN - 0276-7333
SN - 1520-6041
ER -
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BibTex (up to 50 authors)
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@article{2003_Heinrich,
author = {Tilman Heinrich and Christian Burschka and Julie Warneck and Reinhold Tacke},
title = {Synthesis and Pharmacological Properties of Silicon-Containing 1,4-Dihydropyridine Derivatives: Calcium Channel Antagonists and α1 Adrenoceptor Antagonists of the Sila-niguldipine Type},
journal = {Organometallics},
year = {2003},
volume = {23},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/om0305622},
number = {3},
pages = {361--366},
doi = {10.1021/om0305622}
}
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Heinrich, Tilman, et al. “Synthesis and Pharmacological Properties of Silicon-Containing 1,4-Dihydropyridine Derivatives: Calcium Channel Antagonists and α1 Adrenoceptor Antagonists of the Sila-niguldipine Type.” Organometallics, vol. 23, no. 3, Dec. 2003, pp. 361-366. https://doi.org/10.1021/om0305622.