title: Synthesis of novel 13α-18-norandrostane-ferrocene conjugates via homogeneous catalytic methods and their investigation on TRPV1 receptor activation.
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 (1)H and (13)C 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.
authors.affiliation: University of Pannonia, Institute of Chemistry, Department of Organic Chemistry, Egyetem u. 10 (P.O. Box 158), H-8200 Veszprém, Hungary.
authors.forename: Eszter
authors.initials: E
authors.lastname: Szánti-Pintér
authors.affiliation: University of Namur, Department of Chemistry, Rue de Bruxelles 61, B-5000 Namur, Belgium.
authors.forename: Johan
authors.initials: J
authors.lastname: Wouters
authors.affiliation: Hungarian Academy of Sciences, Research Centre for Natural Sciences, Magyar tudósok körútja 2, H-1117 Budapest, Hungary.
authors.forename: Ágnes
authors.initials: Á
authors.lastname: Gömöry
authors.affiliation: Department of Pharmacology and Pharmacotherapy, Szentágothai Research Center, MTA-PTE Chronic Pain Research Group, University of Pécs, Ifjúság u. 6 (P.O. Box 266), H-7624 Pécs, Hungary.
authors.forename: Éva
authors.initials: É
authors.lastname: Sághy
authors.affiliation: Department of Pharmacology and Pharmacotherapy, Szentágothai Research Center, MTA-PTE Chronic Pain Research Group, University of Pécs, Ifjúság u. 6 (P.O. Box 266), H-7624 Pécs, Hungary.
authors.forename: Éva
authors.initials: É
authors.lastname: Szőke
authors.affiliation: Department of Pharmacology and Pharmacotherapy, Szentágothai Research Center, MTA-PTE Chronic Pain Research Group, University of Pécs, Ifjúság u. 6 (P.O. Box 266), H-7624 Pécs, Hungary.
authors.forename: Zsuzsanna
authors.initials: Z
authors.lastname: Helyes
authors.affiliation: University of Pécs, Department of Inorganic Chemistry and MTA-PTE Research Group for Selective Chemical Syntheses, Ifjúság u. 6 (P.O. Box 266), H-7624 Pécs, Hungary.
authors.forename: László
authors.initials: L
authors.lastname: Kollár
authors.affiliation: University of Pannonia, Institute of Chemistry, Department of Organic Chemistry, Egyetem u. 10 (P.O. Box 158), H-8200 Veszprém, Hungary. Electronic address: skodane@almos.uni-pannon.hu.
authors.forename: Rita
authors.initials: R
authors.lastname: Skoda-Földes
mesh_terms: D000818:Animals; D002384:Catalysis; D002478:Cells, Cultured; D003300:Copper / Q000737:chemistry; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D005296:Ferrous Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000075163:Metallocenes; D008958:Models, Molecular; D015394:Molecular Structure; D009474:Neurons / Q000166:cytology / Q000187:drug effects; D009635:Norandrostanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010165:Palladium / Q000737:chemistry; D051381:Rats; D017208:Rats, Wistar; D013329:Structure-Activity Relationship; D050916:TRPV Cation Channels / Q000378:metabolism*; D012668:Trigeminal Ganglion / Q000166:cytology / Q000187:drug effects
chemical_list: D005296:Ferrous Compounds; D000075163:Metallocenes; D009635:Norandrostanes; D050916:TRPV Cation Channels; C493922:Trpv1 protein, rat; D010165:Palladium; D003300:Copper; C004998:ferrocene
keywords: 13α-18-nor-Steroid; Aminocarbonylation; Copper; Cycloaddition; Ferrocene; Palladium