Herstellung von ungesättigten Lactonen der Steroidreihe, VII. Synthese von 4(5)‐Dehydro‐bufadienoliden

Stache, Ulrich; Radscheit, Kurt; Fritsch, Werner; Haede, Werner; Köhl, H.; Ruschig, Heinrich

doi:10.1002/jlac.19717500117

Cited by 18 publications

(1 citation statement)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A series of 65 CDs was employed in this study; they were obtained from Digitalis lanata leaves [40,41] or from commercial suppliers (Extrasynthèse, Genay, France; Merck, Darmstadt, Germany; Boehringer, Mannheim, Germany; Carl Roth, Karlsruhe, Germany) or by fungi biotransformation [42] or by semisynthesis [43–45] . The purity of the tested compounds was checked by HPLC and NMR analyses (at least 95 % purity; data not shown).…”

Section: Methodsmentioning

confidence: 99%

Effects of Lipophilicity and Structural Features on the Antiherpes Activity of Digitalis Cardenolides and Derivatives

Pádua

Kratz

Munkert

et al. 2022

Chemistry & Biodiversity

View full text Add to dashboard Cite

There is growing interest in exploring Digitalis cardenolides as potential antiviral agents. Hence, we herein investigated the influence of structural features and lipophilicity on the antiherpes activity of 65 natural and semisynthetic cardenolides assayed in vitro against HSV-1. The presence of an α,β-unsaturated lactone ring at C-17, a β-hydroxy group at C-14 and C-3β-OR substituents were considered essential requirements for this biological activity. Glycosides were more active than their genins, especially monoglycosides containing a rhamnose residue. The activity enhanced in derivatives bearing an aldehyde group at C-19 instead of a methyl group, whereas inserting a C-5β-OH improved the antiherpes effect significantly. The cardenolides lipophilicity was accessed by measuring experimentally their log P values (n-octanol-water partition coefficient) and disclosed a range of lipophilicity (log P 0.75 � 0.25) associated with the optimal antiherpes activity. In silico studies were carried out and resulted in the establishment of two predictive models potentially useful to identify and/or optimize novel antiherpes cardenolides. The effectiveness of the models was confirmed by retrospective analysis of the studied compounds. This is the first SAR study addressing the antiherpes activity of cardenolides. The developed computational models were able to predict the active cardenolides and their log P values.

show abstract

Section: Methodsmentioning

confidence: 99%