4701-54-6

Usage

Uses

16-Deacetylfusidic Acid γ-Lactone is a metabolite of the drug Fusidic Acid (F865500). Fusidic acid is a bacteriostatic antibiotic. Fusidic Acid suppresses nitric oxide lysis of pancreatic islet cells. Inhibits protein synthesis in prokaryotes by inhibiting the ribosome-dependent activity of G factor and translocation of peptidyl-tRNA.

InChI:InChI=1/C29H44O4/c1-15(2)8-7-9-18-24-17(4)26(33-27(18)32)29(6)20-11-10-19-16(3)22(30)12-13-28(19,5)25(20)23(31)14-21(24)29/h8,16-17,19-23,25-26,30-31H,7,9-14H2,1-6H3/t16-,17?,19?,20-,21-,22+,23+,25-,26?,28-,29+/m0/s1

Upstream product

• 3482-49-3 fusidine 

Downstream Products

• 368859-51-2 3-O-TBDMS-21-O-diphenylmethylsilyl-16β-acetoxy-17S,20R-dihydrofusidin-3,11,16,21-tetrol 
• 335106-46-2 3-O-TBDMS-21-O-diphenylmethylsilyl-16β-acetoxy-17S,20S-dihydrofusidin-3,11,16,21-tetrol 
• 368859-50-1 3-O-TBDMS-21-O-diphenylmethylsilyl-17S,20R-dihydrofusidin-3,11,16,21-tetrol 
• 335106-44-0 3-O-TBDMS-21-O-diphenylmethylsilyl-17S,20S-dihydrofusidin-3,11,16,21-tetrol 
• 335106-26-8 17S,20S-dihydrofusidic acid lactone 
• 457889-92-8 C₅₁H₇₈O₅Si₂ 
• 457889-95-1 C₄₉H₇₆O₄Si₂ 
• 4701-60-4 17S,20R-dihydrofusidic acid lactone 

Relevant academic research and scientific papers

Synthesis and Biological Activity of Cyanoethyl Derivatives of Fusidic Acid

3,11-Dihydroxy and 3,11-dioxo triterpenoids of the fusidane series reacted with acrylonitrile in 1,4-dioxane in the presence of alkali and phase-transfer catalyst to give mono- and bis(2-cyanoethoxy) and 2-cyanoethyl derivatives. The reaction with 3,11-dioxo analog afforded 2,2-disubstituted derivative as a result of addition of two cyanoethyl groups to the α-position with respect to the C3=O carbonyl group. The isolated compounds were screened for antibacterial and antifungal activities.

17S,20S-Methanofusidic acid, a new potent semi-synthetic fusidane antibiotic.

A novel fusidic acid type antibiotic having the side chain linked to the tetracyclic ring system via a spiro-cyclopropane system is described. 17S,20S-Methanofusidic acid is obtained by an efficient synthetic route including cyclopropanation of the Delta17(20) bond with attack solely from the least hindered alpha-face. The spiro-cyclopropane system orients the side chain into a bioactive conformational space. The new 17S,20S-methanofusidic acid exerts antibacterial activity against several Gram-positive species with potency essentially equal to natural fusidic acid.

Synthesis and conformational analysis of fusidic acid side chain derivatives in relation to antibacterial activity

Novel fusidic acid type antibiotics having flexible side chains are described. Saturation of the double bond between C-17 and C-20 of fusidic acid produces four stereoisomers differing in the configuration at C-17 and C-20. The structure-activity relation