5672-30-0

Usage

Uses

Used in Pharmaceutical Industry:
(5Z)-5-(2-nitrobenzylidene)-2-thioxo-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one is used as a potential pharmaceutical agent for [application reason] due to its thiazolidine and nitro groups, which are known for their biological activity and medicinal properties.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (5Z)-5-(2-nitrobenzylidene)-2-thioxo-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one serves as a compound of interest for further research and experimentation. Its unique structure and functional groups may lead to the discovery of new therapeutic applications and effects.

Upstream product

• 4860-15-5 (25R)-3β,N-diacetoxysolasod-5-ene 
• 1181-87-9 N,O-diacetylsolasodine 
• 64-19-7 acetic acid 
• 126-17-0 solasodine 
• 108-24-7 acetic anhydride 
• 63342-06-3 3β-Acetoxy-26-acetylamino-16,22-secofurost-5-ene-16,22-dione 
• 4860-15-5 solasodine N,O-diacetate 

Relevant academic research and scientific papers

A one-pot efficient process for 16-dehydropregnenolone acetate

A one-pot eco-friendly and efficient transformation of steroidal sapogenin diosgenin (1) and solasodine (2) to a commercially very important drug intermediate 16-dehydropregnenolone acetate (16-DPA, 9) was developed with an overall yield of 75%. This process can easily be exploited for industrial production.

Some observations on solasodine reactivity

This article presents new transformations of solasodine – a representative steroid alkaloid sapogenin from the Solanum family. Oxidation of N,O-diacetylated solasodine with either NaNO2/BF3·Et2O or t-BuONO/BF3·Et2O resulted in partial degradation of the side chain to (20S)-3β-acetoxypregn-5-ene-20,16β-carbolactone (vespertilin acetate). The same starting compound when treated with TMSOTf afforded the corresponding pseudosapogenin after aqueous work-up. However, when the crude reaction mixture was directly subjected to purification on a silica gel column, efficient autoxidation to pregna-5,16-dien-3β-ol-20-one acetate was observed. One-step synthesis of this important drug intermediate from spirosolan alkaloids may be potentially exploited for large-scale production of steroid hormones.

NMR Spectra and Stereochemistry of N-Acetyl and N-Benzoyl Derivatives of Solasodine

N-Acetylation of solasodine gives only one rotameric N-acetyl derivative compared with N-acetyl-3-methylpiperidine, which exists in solution as two equally populated rotamers.The 1H and 13C NMR spectra (CDCl3) of O,N-diacetyl- and O-acetyl-N-benzoylsolasodine indicate significant deviations from F-ring chair geometry.Opening of the F ring of these derivatives in CDCl3 solution at 25 deg C, to give the corresponding furosta-5,20(22)-diene derivatives, was ascertained by NMR spectroscopy.Key Words: Solasodine O,N-Diacetylsolasodine O-Acetyl-N-benzoylsolasodine 3β-Acetoxy-26-acetamidofurosta-5,20(22)-diene 3β-Acetoxy-26-benzamidofurosta-5,20(22)-diene

Solanum Alkaloids. XVIII. Utilization of Solasodine for the Preparation of Nitrogen Analogues of Ecdysones

Solasodine (spirosol-5-en-3β-ol) (1) has been converted into (20S,22R,25R)-26-acetylamino-2β,3β,14α-trihydroxy-5β-furost-7-en-6-one (41), a compound bearing ecdysone functionality in the steroidal nucleus aud retaining the N-atom in the side chain.The rou