Synthesis of new symmetrical bis-steroidal pyrazine analogues from diosgenin

Shawakfeh, Khaled Q.; Al-Said, Naim H.

doi:10.1016/j.steroids.2010.10.002

Cited by 17 publications

(16 citation statements)

References 25 publications

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“…In order to identify previous published information, concerning the chemical structures of the obtained compounds, an extensive search was done in the SciFinder database [40]. The previously-reported carbon NMR data for Compounds S9 [41] and S15 [42] are in concordance with the carbon spectroscopic data we obtained (Figures S4 and S5).…”

Section: Resultsmentioning

confidence: 55%

In Vitro Neuroprotective and Anti-Inflammatory Activities of Natural and Semi-Synthetic Spirosteroid Analogues

et al. 2016

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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.

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Section: Resultsmentioning

confidence: 55%

In Vitro Neuroprotective and Anti-Inflammatory Activities of Natural and Semi-Synthetic Spirosteroid Analogues

et al. 2016

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“…The reaction with (25 R )-5α,6α-epoxyspirostan-3β-ol acetate [36] (3, 85 mg, 0.2 mmol) was carried out (reaction time 6 h). Silica gel column chromatography gave pure compound 4 as a white solid (70 mg; 62%) eluted with ethyl acetate/hexane 5:95.…”

Section: Methodsmentioning

confidence: 99%

PhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activity

Jastrzębska

Mellea

Salerno

et al. 2019

IJMS

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We report here the reaction of in situ prepared PhSeZnCl with steroid derivatives having an epoxide as an electrophilic functionalization. The corresponding ring-opening reaction resulted to be regio- and stereoselective affording to novel phenylselenium-substituted steroids. Assessment of their antibacterial properties against multidrug-resistant bacteria, such as Pseudomonas aeruginosa Xen 5 strain, indicates an interesting bactericidal activity and their ability to prevent bacterial biofilm formation.

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“…Ring A-ring A connection through various spacer groups is one of the most preferred routes for the synthesis of steroid dimers or bissteroids from monomeric steroidal units. The synthesis of bis-steroidal pyrazines is well documented and generally involves reduction of 2-azido-3-oxo monomeric steroid [4]. In the synthesis of several of such steroid dimers, 3-oxo-11,21-dihydroxy-pregna-4,17 (20)-diene (2) was employed as the starting material for the synthesis of diacetate pyrazine dimer 3 (77%) in five-steps (Scheme 1).…”

Section: Dimers Via Ring A-ring a Connectionmentioning

confidence: 99%

“…(Scheme 5) [4,6]. The steroidal pyrazine dimers 12-14 were obtained by classical condensation of -amino ketones, which is considered the most efficient method of pyrazine ring formation [4].…”

Section: Dimers Via Ring A-ring a Connectionmentioning

confidence: 99%