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Search for "androstanes" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

Isolation and characterisation of irinans, androstane-type withanolides from Physalis peruviana L.

  • Annika Stein,
  • Dave Compera,
  • Bianka Karge,
  • Mark Brönstrup and
  • Jakob Franke

Beilstein J. Org. Chem. 2019, 15, 2003–2012, doi:10.3762/bjoc.15.196

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  • lower than those of 4ß-hydroxywithanolide E. Our work establishes androwithanolides as a new subclass of withanolides. Keywords: androstanes; Physalis peruviana; steroids; structure elucidation; withanolides; Introduction Traditional medicine has long been a source of inspiration for modern drug
  • ). Irinans represent highly unusual withanolide derivatives, as they lack the side-chain lactone ring that is a common structural feature of virtually all known withanolides [3], but possess an androstane backbone instead. While androstanes such as androsterone (7) are well-known human sex hormones (Figure
  • characteristic of Physalis species. The biosynthesis of androstanes in mammals requires three enzymatic steps starting from cholesterol (9, Figure 3B) [27]. Cholesterol (9) is converted to pregnenolone (10) by the cytochrome P450 cholesterol side-chain cleavage enzyme (P450scc), which cleaves the C20–C22 bond
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Published 23 Aug 2019

Microwave-assisted synthesis of biologically relevant steroidal 17-exo-pyrazol-5'-ones from a norpregnene precursor by a side-chain elongation/heterocyclization sequence

  • Gergő Mótyán,
  • László Mérai,
  • Márton Attila Kiss,
  • Zsuzsanna Schelz,
  • Izabella Sinka,
  • István Zupkó and
  • Éva Frank

Beilstein J. Org. Chem. 2018, 14, 2589–2596, doi:10.3762/bjoc.14.236

Graphical Abstract
  • the reference compound, cisplatin. Keywords: antiproliferative activity; Knorr reaction; microwave; pyrazol-5-ones; steroids; Introduction 17-exo-Heterocyclic androstanes with five or six-membered heterocyclic rings connected directly to C-17 of the sterane core represent a remarkable subclass of
  • the sterane framework; (iii) a hydroxy or keto group at C-3 and (iv) the presence of a C16–C17 double bond, which facilitates the inhibitory effect but is not an essential requirement. Some 17-heterocycle-substituted androstanes, even those that lack the structural features described above, are also
  • the sterane skeleton have been published, but not to C-17 [10]. Nevertheless, this heterocyclic scaffold is also an important building block in many clinically relevant drugs, agrochemicals, dyes, pigments and chelating agents [11][12][13], and therefore its introduction to C-17 of androstanes may be
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Published 08 Oct 2018
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