56531-56-7

Usage

InChI:InChI=1/C18H22O3/c1-21-15-4-2-14(3-5-15)17-7-12-6-13(8-17)10-18(9-12,11-17)16(19)20/h2-5,12-13H,6-11H2,1H3,(H,19,20)/p-1/t12-,13+,17?,18?

Upstream product

• 21816-08-0 3-bromoadamantane-1-carboxylic acid 
• 100-66-3 methoxybenzene 
• 828-51-3 1-Adamantanecarboxylic acid 

Downstream Products

• 1192322-52-3 3-(4-carboxymethoxyphenyl)adamantane-1-carboxylic acid benzylester 
• 1192322-53-4 3-(4-[(3-methoxycarbonylphenylcarbamoyl)methoxy]phenyl)adamantane-1-carboxylic acid benzylester 
• 1192322-49-8 3-(4-ethoxycarbonylmethoxyphenyl)adamantane-1-carboxylic acid benzylester 
• 1192322-46-5 3-(4-Hydroxyphenyl)-adamantane-1-carboxylic acid benzyl ester 
• 61065-71-2 1-Brom-3-<4-methoxy-phenyl>-adamantan 
• 61065-70-1 1-Brom-3-<4-hydroxy-phenyl>-adamantan 
• 117077-70-0 3-(4-Methoxyphenyl)-1-adamantanemethylamine 
• 61051-24-9 3-(4-Methoxyphenyl)-1-adamantanecarboxamide 
• 341496-73-9 3-(4-Methoxy-phenyl)-adamantane-1-carbonyl chloride 
• 61065-69-8 3-(p-Methoxyphenyl)-1-adamantanol 
• 56531-55-6 3-(4-hydroxyphenyl)adamantane-1-carboxylic acid 

Relevant academic research and scientific papers

Enantioselective Desymmetrization of 1,3-Disubstituted Adamantane Derivatives via Rhodium-Catalyzed C?H Bond Amination: Access to Optically Active Amino Acids Containing Adamantane Core

In order to synthesize optically active amino acids containing the adamantane core, an enantioselective desymmetrization of adamantanes via rhodium-catalyzed C?H bond amination was examined. After investigating various conditions, it was found that the coupling reaction between disubstituted adamantane and aryloxysulfonamide was catalyzed by Rh2(S-TCPTTL)4 to furnish the desired products having up to 85% ee (e.r.=92.4: 7.6) (>99% ee after recrystallization). The synthetic utility of the enantioenriched products as chiral building blocks was demonstrated by transforming one of them into a dipeptide derivative and a Schiff-base ligand. The absolute configuration of one of the amino acid derivatives was determined unambiguously by X-ray single-crystal structure analysis. (Figure presented.).

Disubstituted adamantyl derivative or pharmaceutically acceptable salt thereof, and pharmaceutical composition and kit for inhibiting the growth of cancer containing the same as an active ingredient

The present invention relates to: a disubstituted adamantyl derivative or a pharmaceutically acceptable salt thereof, and an anticancer pharmaceutical composition and a kit containing same as an active ingredient. The disubstituted adamantyl derivative according to the present invention suppresses the growth of cancer cells by targeting mitochondria ETC complex I and damaging the metabolism of cancer cells, and thus can be useful as an anticancer pharmaceutical composition that is a powerful therapeutic agent for cancer dependent on oxidative phosphorylation for producing ATP.

NOVEL DISUBSTITUTED ADAMANTYL DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PRODUCTION METHOD FOR SAME, AND PHARMACEUTICAL COMPOSITION FOR SUPPRESSING CANCER METASTASIS COMPRISING SAME AS ACTIVE INGREDIENT

The present invention relates to a novel disubstituted adamantyl derivative or the pharmaceutically acceptable salts thereof, a method for preparing the same, and a pharmaceutical anticancer or antimetastasis composition comprising the same as an active ingredient. The disubstituted adamantyl derivative of the present invention suppressed accumulation of HIF-1α, inhibiting the expression of the metastasis related protein Twist dose-dependently. Thus, the disubstituted adamantyl derivative of the invention is effective in inhibiting the expressions of the metastasis related proteins, β-catenin and RohA, and the EMT related genes such as MMP2 and MMP9, without cytotoxicity. Therefore, the disubstituted adamantyl derivative or the pharmaceutically acceptable salts thereof of the invention can be efficiently used as a pharmaceutical anticancer or antimetastasis composition.

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.

A novel class of highly potent multidrug resistance reversal agents: Disubstituted adamantyl derivatives

Novel disubstituted adamantyl derivatives were synthesized and evaluated in a P-glycoprotein dependent multidrug resistance cancer cell line. The hit to lead optimization provided potent MDR reversal agents. Some potent adamantyl derivatives were more than 10-fold more potent than verapamil without considerable intrinsic cytotoxicity. The 3-trifluorophenyl derivative 14f did not affect the metabolism of CYP450 3A4, whereas most of MDR revertants had a weak inhibitory effect.