74131-26-3

Upstream product

• 29799-07-3 4-adamantylphenol 
• 533-58-4 2-Iodophenol 
• 768-95-6 1-adamanthanol 

Downstream Products

• 1469268-18-5 2-(4-(adamantan-1-yl)-2-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenoxy)acetic acid 
• 1469268-17-4 ethyl 2-(4-(adamantan-1-yl)-2-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenoxy)acetate 
• 1469268-16-3 4-adamantan-1-yl-2-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenol 
• 1469268-15-2 3-(5-adamantan-1-yl-2-methoxyphenyl)-3-(trifluoromethyl)-3H-diazirine 
• 1469268-14-1 3-(5-adamantan-1-yl-2-methoxyphenyl)-3-(trifluoromethyl)diaziridine 
• 1469268-13-0 1-(5-adamantan-1y-l-2-methoxyphenyl)-2,2,2-trifluoroethanone O-tosyl oxime 
• 1469268-12-9 1-(5-adamantan-1-yl-2-methoxyphenyl)-2,2,2-trifluoroethanone oxime 
• 1469268-11-8 1-(5-adamantan-1-yl-2-methoxyphenyl)-2,2,2-trifluoroethan-1-one 
• 1469268-02-7 prop-2-ynyl 3-(2-(4-adamantan-1-yl-2-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenoxy)acetamido)-4-hydroxybenzoate 
• 1381804-79-0 4-adamantan-1-yl-2-iodo-1-methoxybenzene 

Relevant academic research and scientific papers

Synthesis and structure-activity relationship study of chemical probes as hypoxia induced factor-1α/malate dehydrogenase 2 inhibitors

A structure-activity relationship study of hypoxia inducible factor-1α inhibitor 3-aminobenzoic acid-based chemical probes, which were previously identified to bind to mitochondrial malate dehydrogenase 2, was performed to provide a better understanding of the pharmacological effects of LW6 and its relation to hypoxia inducible factor-1α (HIF-1α) and malate dehydrogenase 2 (MDH2). A variety of multifunctional probes including the benzophenone or the trifluoromethyl diazirine for photoaffinity labeling and click reaction were prepared and evaluated for their biological activity using a cell-based HRE-luciferase assay as well as a MDH2 assay in human colorectal cancer HCT116 cells. Among them, the diazirine probe 4a showed strong inhibitory activity against both HIF-1α and MDH2. Significantly, the inhibitory effect of the probes on HIF-1α activity was consistent with that of the MDH2 enzyme assay, which was further confirmed by the effect on in vitro binding activity to recombinant human MDH2, oxygen consumption, ATP production, and AMP activated protein kinase (AMPK) activation. Competitive binding modes of LW6 and probe 4a to MDH2 were also demonstrated.

Identification of malate dehydrogenase 2 as a target protein of the HIF-1 inhibitor LW6 using chemical probes

Tracking the target: To identify a protein that binds directly to the HIF-1α inhibitor LW6, a series of new chemical probes were synthesized with a clickable tag and/or a photoactivatable moiety. LW6 was found to be localized to the mitochondria (see picture) and MDH2 was identified as a target protein of LW6. These results indicate that the HIF-1α inhibitory activity of LW6 is a consequence of MDH2 suppression. Copyright

New rearrangement in the adamantylation reaction of 4-iodophenol and 4-iodoanisole

A reaction of 2-iodophenol and 2-iodoanisole with 1-adamantanol in trifluoroacetic acid gives the corresponding 4-(1-adamantyl) derivatives. Similar adamantylation of 4-iodophenol and 4-iodoanisole is accompanied by migration of the iodine atom from para- to ortho-position, giving 4,6-di(1-adamantyl)-2-iodophenol and 4-(1-adamantyl)-2-iodoanisole, respectively, as the reaction products.