کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
2027729 1542704 2015 10 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis of novel 13α-18-norandrostane–ferrocene conjugates via homogeneous catalytic methods and their investigation on TRPV1 receptor activation
موضوعات مرتبط
علوم زیستی و بیوفناوری بیوشیمی، ژنتیک و زیست شناسی مولکولی زیست شیمی
پیش نمایش صفحه اول مقاله
Synthesis of novel 13α-18-norandrostane–ferrocene conjugates via homogeneous catalytic methods and their investigation on TRPV1 receptor activation
چکیده انگلیسی


• New 13α-18-norandrostane–ferrocene conjugates were synthesized.
• Ferrocene containing triazoles were obtained via azide–alkyne cycloaddition.
• Pd-catalyzed aminocarbonylation was investigated with ferrocenylmethylamine.
• X-ray structures of three compounds were determined.
• An effect on the activation of TRPV1 receptor on TRG neurons was observed.

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.

Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Steroids - Volume 104, December 2015, Pages 284–293
نویسندگان
, , , , , , , ,