Abstract
13α-Steroid-ferrocene derivatives were synthesized via two reaction pathways starting from an unnatural 16-keto-18-nor-13α-steroid. The unnatural steroid was converted to ferrocene derivatives via copper-catalyzed azide-alkyne cycloaddition or palladium-catalyzed aminocarbonylation. 16-Azido- and 16-N-(prop-2-ynyl)-carboxamido-steroids were synthesized as starting materials for azide-alkyne cycloaddition with the appropriate ferrocene derivatives. Based on our earlier work, aminocarbonylation of 16-iodo-16-ene and 16-iodo-15-ene derivatives was studied with ferrocenylmethylamine. The new products were obtained in moderate to good yields and were characterized by 1H and 13C NMR, IR and MS. The solid state structure of the starting material 13α-18-norandrostan-16-one and two carboxamide products were determined by X-ray crystallography. Evidences were provided that the N-propargyl-carboxamide compound as well as its ferrocenylmethyltriazole derivative are able to decrease the activation of TRPV1 receptor on TRG neurons.
Original language | English |
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Pages (from-to) | 284-293 |
Number of pages | 10 |
Journal | Steroids |
Volume | 104 |
DOIs | |
Publication status | Published - 1 Dec 2015 |
Keywords
- 13α-18-nor-Steroid
- Aminocarbonylation
- Copper
- Cycloaddition
- Ferrocene
- Palladium
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Dive into the research topics of 'Synthesis of novel 13α-18-norandrostane-ferrocene conjugates via homogeneous catalytic methods and their investigation on TRPV1 receptor activation'. Together they form a unique fingerprint.Equipment
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Physical Chemistry and characterization(PC2)
Johan Wouters (Manager) & Carmela Aprile (Manager)
Technological Platform Physical Chemistry and characterizationFacility/equipment: Technological Platform
Datasets
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CCDC 1054250: Experimental Crystal Structure Determination
Gömöry, Á. (Contributor), Helyes, Z. (Contributor), Kollár, L. (Contributor), Sághy, É. (Contributor), Skoda-Földes, R. (Contributor), Szánti-Pintér, E. (Contributor), Szőke, É. (Contributor) & Wouters, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2015
DOI: 10.5517/cc14d12n, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc14d12n&sid=DataCite
Dataset
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CCDC 1054252: Experimental Crystal Structure Determination
Gömöry, Á. (Contributor), Helyes, Z. (Contributor), Kollár, L. (Contributor), Sághy, É. (Contributor), Skoda-Földes, R. (Contributor), Szánti-Pintér, E. (Contributor), Szőke, É. (Contributor) & Wouters, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2016
DOI: 10.5517/ccdc.csd.cc14d14q, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc14d14q&sid=DataCite
Dataset
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CCDC 1054251: Experimental Crystal Structure Determination
Gömöry, Á. (Contributor), Helyes, Z. (Contributor), Kollár, L. (Contributor), Sághy, É. (Contributor), Skoda-Földes, R. (Contributor), Szánti-Pintér, E. (Contributor), Szőke, É. (Contributor) & Wouters, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2016
DOI: 10.5517/ccdc.csd.cc14d13p, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc14d13p&sid=DataCite
Dataset