56531-56-7Relevant articles and documents
Enantioselective Desymmetrization of 1,3-Disubstituted Adamantane Derivatives via Rhodium-Catalyzed C?H Bond Amination: Access to Optically Active Amino Acids Containing Adamantane Core
Yasue, Risa,Yoshida, Kazuhiro
, p. 1662 - 1671 (2021)
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.).
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
-
, (2015/11/09)
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.
A novel class of highly potent multidrug resistance reversal agents: Disubstituted adamantyl derivatives
Min, Kyung Hoon,Xia, Yan,Kim, Eun Kyung,Jin, Yinglan,Kaur, Navneet,Kim, Eun Seon,Kim, Dae Kyong,Jung, Hwa Young,Choi, Yongseok,Park, Mi-Kyung,Min, Yong Ki,Lee, Kiho,Lee, Kyeong
scheme or table, p. 5376 - 5379 (2010/05/19)
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.