5874-17-9Relevant academic research and scientific papers
Synthesis of diosgenin derivatives by A and B ring modifications and low-valent titanium (Ti0)-catalysed McMurry coupling reactions and designing to create novel biological agents
Ilkar Erdagi, Sevinc,Yildiz, Ufuk
, (2022/02/07)
Diosgenin is a steroidal sapogenin ((25R)-spirost-5-en-3β-ol) occurs abundantly in therapeutic herbs such as Dioscorea alata, Smilax China, and Trigonella foenum graecum. It demonstrates a wide range of pharmacological activities and medicinal properties in a large of experimental and theoretical studies. It also constitutes an important class of compounds for new drug development. In the current study, diosgenin derivatives were synthesized and designed, aiming to discover new steroid-based biological agents. In this work, new diosgenin derivatives were synthesized through low-valent titanium (Ti0)-catalyzed McMurry coupling reaction and structural modifications to the A- and B- rings in the diosgenin. McMurry reaction gave the A-nor and B-nor derivatives in by the intramolecular reductive dimerization of carbonyl compounds in the presence of low-valent titanium agents, in moderate yields (46–47%). The modification reactions on the A and B rings of diosgenin were accomplished by using efficient reagents to give three different series, in moderate to high yields (55–97%). The structures of all novel derivatives were confirmed by FTIR, 1H NMR, 13C NMR, and HRMS methods.
In vitro neuroprotective and anti-inflammatory activities of natural and semi-synthetic spirosteroid analogues
García-Pupo, Laura,Zaldo-Castro, Armando,Exarchou, Vassiliki,Tacoronte-Morales, Juan Enrique,Pieters, Luc,Berghe, Wim Vanden,Nu?ez-Figueredo, Yanier,Delgado-Hernández, René
, (2016/08/12)
Two spirosteroid analogues were synthesized and evaluated for their in vitro neuroprotective activities in PC12 cells, against glutamate-induced excitotoxicity and mitochondrial damage in glucose deprivation conditions, as well as their anti-inflammatory potential in LPS/IFNγ-stimulated microglia primary cultures. We also evaluated the in vitro anti-excitotoxic and anti-inflammatory activities of natural and endogenous steroids. Our results show that the plant-derived steroid solasodine decreased PC12 glutamate-induced excitotoxicity, but not the cell death induced by mitochondrial damage and glucose deprivation. Among the two synthetic spirosteroid analogues, only the (25R)-5α-spirostan-3,6-one (S15) protected PC12 against ischemia-related in vitro models and inhibited NO production, as well as the release of IL-1β by stimulated primary microglia. These findings provide further insights into the role of specific modifications of the A and B rings of sapogenins for their neuroprotective potential.
A rapid and simple one-pot procedure for the synthesis of 3β-acetoxy-5α-hydroxy-6-oxo steroids
Rosado-Abon, Anielka,Romero-Avila, Margarita,Iglesias-Arteaga, Martin A.
experimental part, p. 110 - 115 (2011/01/12)
A fast one-pot procedure for the synthesis of 5α-hydroxy-6-oxo steroids is described. Epoxidation of 3β-hydoxy-Δ5 steroids followed by oxidative cleavage of the resulting epoxide with aqueous CrO3 lead to the desired compounds without affection of labile side chains. ARKAT USA, Inc.
Synthesis of peptidomimetic-spirostane hybrids via Ugi reaction: a versatile approach for the formation of peptide-steroid conjugates
Rivera, Daniel G.,Pando, Orlando,Coll, Francisco
, p. 8327 - 8334 (2007/10/03)
A general approach towards the preparation of peptide-steroid conjugates has been addressed. Utilizing the Ugi reaction, five peptidomimetic-steroid hybrids were achieved in good to excellent yields from carboxy- and amino-spirostanes and mono-protected α-amino acids. Diverse synthetic routes, specially focused on the formation of secosteroids, were implemented to introduce Ugi-type functionalities at different positions of the steroidal nucleus. This versatile approach is suitable for the formation of stable conjugates of steroids with other biologically relevant molecules.
Schmidt Reaction of 3β-Acetoxy-5α-hydroxy-22β-spirostan-6-one and Beckmann Rearrangement of Corresponding Ketoxime
Siddiqui, Abdul Hameed,Rajeshwar, K.,Baig, M. H.,Siddiqui, A. H. U.
, p. 276 - 277 (2007/10/02)
3β-Acetoxy-5α-hydroxy-22β-spirostan-6-one (2), obtainable from diosgenin acetate, undergoes second order Schmidt reaction to form 3β-acetoxy-5-oxo-22β-spirostan-7-nitrile (3); the same nitrile is also obtained by the Beckmann rearrangement of the ketoxime
