Regio- and stereoselective cleavage of steroidal 22-oxo-23-spiroketals catalyzed by BF3·Et2O

Dı́az-Lanza, Ana Marı́a; Merinos, J. Pablo Garcia; López, Yliana; Campos, Janett Betzabe González; Río, Rosa E. del; Santillán, Rosa; Farfán, Norberto; Morzycki, Jacek W.

doi:10.1016/j.steroids.2015.04.004

Cited by 8 publications

(3 citation statements)

References 37 publications

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“…In this study, the method described in [ 24 ] for carrying out ring-opening and fluoridation reactions of steroidal epoxide were used. The literature describes the reaction of 3α-acetoxy-4α,5-epoxy-cholestane ( I ) with BF 3 -etherate in benzene, yielding 3α-acetoxy-5a-cholestan-4-one ( II ), along with a rearranged product of 3α acetoxy-4 α-hydroxyl–compound ( III ) Scheme 1 [ 25 ].…”

Section: Introductionmentioning

confidence: 99%

Fabrication of Chitosan Nanofibers Containing Some Steroidal Compounds as a Drug Delivery System

et al. 2022

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A novel drug delivery system based on chitosan nanofibers containing some steroidal derivatives was developed using an electrospinning process. Oxazolines and aziridines from the cholestane series of steroidal epoxides were successfully synthesized and characterized by elemental analysis, Fourier transforms infrared spectroscopy (FTIR), proton nuclear magnetic resonance (1HNMR), and mass spectroscopy (MS). Steroidal-compound-loaded chitosan (ST-CH) nanofibers were fabricated using the electrospinning technique in the presence of polyvinylpyrrolidone (CH/PVP). The electrospun nanofibers were characterized by scanning electron microscopy (SEM). The swelling degree of the electrospun nanofibers and their steroidal compound release performance were studied as well. Furthermore, their antibacterial activity against gram-positive (Staphylococcus aurous) and gram-negative bacteria (Escherichia coli) was evaluated. The experimental data revealed that identical and bead-free nanofiber mats loaded with 10 Wt. % of synthesized steroidal derivatives had been obtained. The FTIR spectrum proved that no change occurred in the chitosan structure during the electrospinning process. The synthesized nanofiber mats showed a high swelling degree and a burst release of steroidal compounds after 2 h doping in phosphate buffer saline. In addition, the electrospun nanofibers containing 3β-chloro-N-amido-5α-cholestano-aziridine and those containing 3β-acetoxy-N-amido-5α-cholestano-aziridine were the most active, with activity indices of 91 and 104% in the case of S. aureus and 52% and 61% in the case of E. coli, respectively. The release mechanism by CH/PVP of the drug samples was studied based on the charge density and diffusion controlled factors. The oxazoline derivatives release mechanism from CH/PVP was evaluated by applying the suppositions of the Ritger-Peppas kinetic model and by estimating the transport exponent; the latter revealed the involvement of the solvent diffusion and chain relaxation processes. Tailored steroidal loaded-chitosan (ST-CH) nanofibers are expected to be feasible and efficient drug delivery systems.

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Section: Introductionmentioning

confidence: 99%

Fabrication of Chitosan Nanofibers Containing Some Steroidal Compounds as a Drug Delivery System

et al. 2022

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“…The derivatives showed good anti‐tumor activities inhibited cell proliferation [15] . Other studies on the F‐ring modification were performed by the stereoselective opening of the F ring and yielded highly active target derivatives [16] . The introduction of the heteroatom in the diosgenin scaffold affects the chemical properties and modifies the biological activity.…”

Section: Introductionmentioning

confidence: 99%

“…[15] Other studies on the F-ring modification were performed by the stereoselective opening of the F ring and yielded highly active target derivatives. [16] The introduction of the heteroatom in the diosgenin scaffold affects the chemical properties and modifies the biological activity. A study of nitrogen-containing diosgenin derivatives reported that in vitro assays of the steroidal oximes showed significant antiproliferative activity compared to the one observed for diosgenin.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structural Analysis and Antiproliferative Activity of Nitrogen‐Containing Hetero Spirostan Derivatives: Oximes, Heterocyclic Ring‐Fused and Furostanes

Erdagi

Yıldız

2022

ChemistrySelect

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The present study focuses on the synthesis of spirostan derivatives as potential drug candidates for biological applications. Recently, spirostan derivatives containing the hetero‐atom have attracted great scientific attention due to their anti‐cancer, anti‐diabetes, and anti‐inflammatory properties. In this study, nitrogen‐containing novel spirostan derivatives with substituted oxime, nitrile, pyrazole, isoxazole structures in ring‐A and F were designed and synthesized starting from diosgenin. The intermediates and target derivatives’ chemical structures were characterized by FTIR, HRMS, 1HNMR, 13CNMR, elemental analysis, and HPLC techniques. The target compounds were evaluated for their cytotoxicities in two human cancer cell lines (MCF‐7 and A549). The tested compounds exhibited potent anticancer activity against human breast adenocarcinoma (MCF‐7) and lung adenocarcinoma (A549). On the other hand, the toxicity of the tested compounds against human healthy fetal lung fibroblasts (MCR‐5) indicated that compounds were non‐toxic for the human body. The results showed that compounds may be used as a promising agents for anticancer agents with improved efficacy.

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Rationally designed hecogenin thiosemicarbazone analogs as novel MEK inhibitors for the control of breast malignancies

Elsayed

Ebrahim

Haggag

et al. 2017

Bioorganic & Medicinal Chemistry

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Regio- and stereoselective cleavage of steroidal 22-oxo-23-spiroketals catalyzed by BF3·Et2O

Cited by 8 publications

References 37 publications

Fabrication of Chitosan Nanofibers Containing Some Steroidal Compounds as a Drug Delivery System

Fabrication of Chitosan Nanofibers Containing Some Steroidal Compounds as a Drug Delivery System

Synthesis, Structural Analysis and Antiproliferative Activity of Nitrogen‐Containing Hetero Spirostan Derivatives: Oximes, Heterocyclic Ring‐Fused and Furostanes

Rationally designed hecogenin thiosemicarbazone analogs as novel MEK inhibitors for the control of breast malignancies

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