74131-26-3

Basic information

• Product Name: 4-adamantan-1-yl-2-iodophenol
• Synonyms: 4-adamantan-1-yl-2-iodophenol
• CAS NO: 74131-26-3
• Molecular Weight: 354.231
• Mol File: 74131-26-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-adamantan-1-yl-2-iodophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-adamantan-1-yl-2-iodophenol(74131-26-3)
• EPA Substance Registry System: 4-adamantan-1-yl-2-iodophenol(74131-26-3)

Safety Data

• Hazardous Substances Data: 74131-26-3(Hazardous Substances Data)

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 articles and documents

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.

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.