Synthesis of novel 13α-18-norandrostane-ferrocene conjugates via homogeneous catalytic methods and their investigation on TRPV1 receptor activation

Eszter Szánti-Pintér, Johan Wouters, A. Gömöry, Éva Sághy, E. Szöke, Z. Helyes, L. Kollár, R. Skoda-Földes

Research output: Contribution to journalArticle

4 Citations (Scopus)

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 languageEnglish
Pages (from-to)284-293
Number of pages10
JournalSteroids
Volume104
DOIs
Publication statusPublished - Dec 1 2015

Fingerprint

Norandrostanes
Chemical activation
Steroids
Derivatives
Alkynes
Azides
Cycloaddition Reaction
Cycloaddition
X Ray Crystallography
Palladium
X ray crystallography
Copper
Neurons
Nuclear magnetic resonance
TRPV1 receptor
ferrocene

Keywords

  • 13α-18-nor-Steroid
  • Aminocarbonylation
  • Copper
  • Cycloaddition
  • Ferrocene
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Endocrinology
  • Molecular Biology
  • Organic Chemistry
  • Pharmacology

Cite this

@article{13e71c5e505944bc985f29190123efb7,
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 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.",
keywords = "13α-18-nor-Steroid, Aminocarbonylation, Copper, Cycloaddition, Ferrocene, Palladium",
author = "Eszter Sz{\'a}nti-Pint{\'e}r and Johan Wouters and A. G{\"o}m{\"o}ry and {\'E}va S{\'a}ghy and E. Sz{\"o}ke and Z. Helyes and L. Koll{\'a}r and R. Skoda-F{\"o}ldes",
year = "2015",
month = "12",
day = "1",
doi = "10.1016/j.steroids.2015.10.016",
language = "English",
volume = "104",
pages = "284--293",
journal = "Steroids",
issn = "0039-128X",
publisher = "Elsevier Inc.",

}

TY - JOUR

T1 - Synthesis of novel 13α-18-norandrostane-ferrocene conjugates via homogeneous catalytic methods and their investigation on TRPV1 receptor activation

AU - Szánti-Pintér, Eszter

AU - Wouters, Johan

AU - Gömöry, A.

AU - Sághy, Éva

AU - Szöke, E.

AU - Helyes, Z.

AU - Kollár, L.

AU - Skoda-Földes, R.

PY - 2015/12/1

Y1 - 2015/12/1

N2 - 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.

AB - 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.

KW - 13α-18-nor-Steroid

KW - Aminocarbonylation

KW - Copper

KW - Cycloaddition

KW - Ferrocene

KW - Palladium

UR - http://www.scopus.com/inward/record.url?scp=84947934347&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84947934347&partnerID=8YFLogxK

U2 - 10.1016/j.steroids.2015.10.016

DO - 10.1016/j.steroids.2015.10.016

M3 - Article

C2 - 26519768

AN - SCOPUS:84947934347

VL - 104

SP - 284

EP - 293

JO - Steroids

JF - Steroids

SN - 0039-128X

ER -