12689-26-8

Usage

Uses

Used in Pharmaceutical Industry:
Ilicicolin H is used as an antifungal agent for its potent and broad-spectrum activity against various fungal infections. Its ability to inhibit the mitochondrial cytochrome bc1 reductase makes it a promising candidate for the development of new antifungal drugs to combat resistant strains and improve treatment outcomes.

References

1) Singh et al. (2013), Structure-activity relationship of cytochrome bc1 reductase inhibitor broad spectrum antifungal ilicicolin H; Bioorg. Med. Chem., 23 3018 2) Singh et al. (2012), Antifungal spectrum, in vivo efficacy, and structure-activity relationship of ilicicolin h; ACS Med. Chem. Lett., 3 814

Upstream product

• 97012-63-0 1-Benzyloxy-5-(4-benzyloxy-phenyl)-3-((2E,4E,10E,12E)-4,8-dimethyl-tetradeca-2,4,10,12-tetraenoyl)-4-hydroxy-1H-pyridin-2-one 
• 97012-74-3 Sulfuric acid mono-[(2E,4E,10E)-12-(tert-butyl-dimethyl-silanyloxy)-7,11-dimethyl-dodeca-2,4,10-trienyl] ester 
• 97012-64-1 Acetic acid (E)-8-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-oct-6-enyl ester 
• 97012-73-2 (2E,4E,10E)-12-(tert-Butyl-dimethyl-silanyloxy)-7,11-dimethyl-dodeca-2,4,10-trien-1-ol 
• 97012-67-4 tert-Butyl-((2E,8E,10E)-2,6-dimethyl-dodeca-2,8,10-trienyloxy)-dimethyl-silane 
• 150-84-5 citronellyl-acetate 
• 97012-71-0 5-(4-Benzyloxy-phenyl)-3-[(1S,2R,4aR,7R,8aS)-4,7-dimethyl-1-((E)-propenyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbonyl]-4-hydroxy-1H-pyridin-2-one 
• 97012-66-3 (2E,4E,10E)-12-(tert-Butyl-dimethyl-silanyloxy)-7,11-dimethyl-dodeca-2,4,10-trienoic acid ethyl ester 
• 97012-65-2 (E)-8-(tert-Butyl-dimethyl-silanyloxy)-3,7-dimethyl-oct-6-enal 
• 95576-02-6 8-acetoxy-2,6-dimethyloct-2E-en-1-ol 
• 97012-68-5 (2E,8E,10E)-2,6-Dimethyl-dodeca-2,8,10-trienal 

Downstream Products

• 1395854-86-0 C₂₇H₃₀N₂O₃ 
• 1432134-44-5 C₃₄H₃₅BrN₂O₅ 
• 1432134-37-6 C₃₂H₃₃NO₅S 
• 1432134-35-4 C₃₂H₄₀N₂O₅ 
• 1432134-32-1 C₃₇H₄₈N₂O₇ 
• 1432134-30-9 C₃₆H₄₆N₂O₇ 
• 1432134-25-2 C₃₅H₃₇NO₅ 
• 1432134-23-0 C₃₄H₃₅NO₅ 
• 1432134-21-8 C₃₄H₄₁NO₅ 
• 1432134-20-7 C₃₃H₃₉NO₅ 
• 1432134-17-2 C₃₂H₃₇NO₅ 
• 1432134-16-1 C₃₁H₃₅NO₅ 
• 1432134-15-0 C₃₀H₃₅NO₅ 
• 1432134-11-6 C₃₃H₄₄N₂O₄ 

Related news

Differential efficacy of inhibition of mitochondrial and bacterial cytochrome bc1 complexes by center N inhibitors antimycin, ilicicolin H (cas 12689-26-8) and funiculosin08/25/2019

We have compared the efficacy of inhibition of the cytochrome bc1 complexes from yeast and bovine heart mitochondria and Paracoccus denitrificans by antimycin, ilicicolin H, and funiculosin, three inhibitors that act at the quinone reduction site at center N of the enzyme. Although the three inh...detailed

Relevant academic research and scientific papers

Enzyme-Catalyzed Inverse-Electron Demand Diels-Alder Reaction in the Biosynthesis of Antifungal Ilicicolin H

The pericyclases are a growing superfamily of enzymes that catalyze pericyclic reactions. We report a pericyclase IccD catalyzing an inverse-electron demand Diels-Alder (IEDDA) reaction with a rate acceleration of 3 × 105-fold in the biosynthesis of fungal natural product ilicicolin H. We demonstrate IccD is highly periselective toward the IEDDA cycloaddition over a competing normal electron demand Diels-Alder (NEDDA) reaction from an ambimodal transition state. A predicted flavoenzyme IccE was identified to epimerize the IEDDA product 8-epi-ilicicolin H to ilicicolin H, a step that is critical for the observed antifungal activity of ilicicolin H. Our results reveal the ilicicolin H biosynthetic pathway and add to the collection of pericyclic reactions that are catalyzed by pericyclases.

Total Synthesis of (+/-)-Ilicicolin H

The first total synthesis of ilicicolin H (1) is described.An intramolecular Diels-Alder strategy provides high regio- and stereoselectivity.