Oxo-analogues of 20-hydroxyecdysone in the synthesis of novel fluorinated ecdysteroid derivatives

Author:

Savchenko Rimma G.11,Apaeva Anastasia V.11,Kostyleva Svetlana A.11,Mozgovoj Oleg S.11,Odinokov Victor N.11,Parfenova Lyudmila V.11

Affiliation:

1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences prosp. Oktyabrya 141, 450075 Ufa, Russian Federation.

Abstract

Novel side chain ω-fluorinated ecdysteroid analogues were obtained starting from ω-functionalized ecdysteroids. Thus, the reaction of diacetonides of 25RS-hydroxy- and 24-hydroxy 27-nor- and 25,26,27-tris-nor-20-hydroxyecdysone derivatives with diethylaminosulfur trifluoride (DAST) involves replacement of the terminal hydroxyl group and dehydration at the 14-position to give 25RS-fluoro- and 24-fluoro-14-anhydro analogues of ecdysteroids.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Reference19 articles.

1. Dinan, L. In Studies in International Products Chemistry; Atta-ur-Raman, Ed.; Elsevier: Amsterdam, 2003; pp. 3–71.

2. Cymborowski, B. In Ecdysone, from Chemistry to Mode of Action; Koolman, J., Ed.; Georg Thieme: Stuttgart, 1989; pp. 144–149.

3. Synthesis of 25-fluoroponasterone A, a fluorinated analogue of 20-hdyroxyecdysone.

4. Practical uses for ecdysteroids in mammals including humans: and update

5. Phytoecdysteroids and Anabolic-Androgenic Steroids - Structure and Effects on Humans

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