29844-80-2Relevant academic research and scientific papers
Preparative Flash Vacuum Thermolysis. Formation of 3-Noradamantylacetylene via Adamantylidenecarbene
Scharp, Jan,Wiersum, Ulfert E.
, p. 629 - 630 (1983)
3-Ethynyltricyclo3,7>nonane is conveniently prepared from adamantanone, via an anomalous alkylidenecarbene rearrangement, by flash vacuum thermolysis of 5-adamantylidene-2,2-dimethyl-1,3-dioxane-4,6-dione.
Synthesis of Adamantanoid Ketones from Bridgehead Alcohols by the Hypoiodite Thermolysis-Cyclization Sequence
Janjatovic, Jelena,Majerski, Zdenko
, p. 4892 - 4898 (1980)
Thermolysis of tertiary polycyclic hypoiodites followed by base-promoted C-alkylation of the resulting iodoketones appears to be an excellent synthetic route to a number of adamantaniod ketones.The hypoiodites can be prepared readily from the corresponding alcohols by the action of Pb(OAc)4 and iodine and thermolyzed in a single operation. 6-Protoadamantanol yielded 70 percent of a 3:2 mixture of 4-homobrendan-4-one (tricyclo3,8>decan-4-one) and 2-homobrendan-2'-one (tricyclo4,8>decan-3-one); 3-noradamantanol produced 30 percent of a 2:1 mixture of tricyclo2,7>nonan-3-one and 1-hydroxy-2-oxaadamantane, while 4-homoisotwistan-3-ol gave exclusively the elimination product, 8-methylenebicyclodecan-2-one.This route has been successfully used also in the preparation of protoadamantan-4-one, 10-homoprotoadamantan-4-one (tricyclo3,8>undecan-4-one) and 4-homoprotoadamantan-4-one (tricyclo3,9>undecan-4-one).The direction of α-CC bond scission in the thermolysis of polycyclic hypoiodites appears to be controlled by the relative thermodynamic stabilities of the intermediary carbonylalkyl free radicals.In most cases this can be approximated simply by combination of the relative strain energies of the corresponding hydrocarbons and the relative stabilities of the free-radical centers.The course of intramolecular C-alkylation of polycyclic ketones is controlled by the balance of at least three factors: preferential enolization, the size of the smallest ring to be formed, and the degree of distortion of the prefered collinear arrangement of the enolate α-carbon atom and the carbon-leaving group bond.
Discovery of adamantane based highly potent HDAC inhibitors
Gopalan, Balasubramanian,Ponpandian, Thanasekaran,Kachhadia, Virendra,Bharathimohan, Kuppusamy,Vignesh, Radhakrishnan,Sivasudar, Velaiah,Narayanan, Shridhar,Mandar, Bhonde,Praveen, Rajendran,Saranya, Nithyanandan,Rajagopal, Sriram,Rajagopal, Sridharan
, p. 2532 - 2537 (2013/06/27)
Herein, we report the development of highly potent HDAC inhibitors for the treatment of cancer. A series of adamantane and nor-adamantane based HDAC inhibitors were designed, synthesized and screened for the inhibitory activity of HDAC. A number of compounds exhibited GI50 of 10-100 nM in human HCT116, NCI-H460 and U251 cancer cells, in vitro. Compound 32 displays efficacy in human tumour animal xenograft model.
Enantioselective borohydride reduction of aliphatic ketones catalyzed by ketoiminatocobalt(iii) complex with 1-chlorovinyl axial ligand
Tsubo, Tatsuyuki,Chen, Hsiu-Hui,Yokomori, Minako,Fukui, Kosuke,Kikuchi, Satoshi,Yamada, Tohru
supporting information; experimental part, p. 780 - 782 (2012/09/22)
For the enantioselective borohydride reduction of aliphatic ketones, the optically active ketoiminatocobalt(II) catalysts was successfully designed based on their axial ligand. Instead of chloroform for the aryl ketone reduction, various axial ligand precursors were examined for the aliphatic ketone. Consequently, 1, 1, 1-trichloroethane was found to be the most effective activator of the cobalt(II) complexes to generate the corresponding 1-chlorovinyl cobalt(III) derivatives as the reactive intermediate. Several aliphatic ketones were successfully reduced to afford the corresponding secondary alcohols with high enantioselectivities.
HISTONE DEACETYLASE INHIBITORS FOR THE TREATMENT OF FUNGAL INFECTIONS
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Page/Page column 28, (2011/06/16)
Described are bridged compounds of the formula (I), their analogs, tautomeric forms, stereoisomers, geometrical isomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts, pharmaceutical compositions, metabolites and prodrugs thereof. The invention relates to compositions and methods to treat fungal infection. These compounds are selective HDAC inhibitors that act as inherent antifungal compounds or enhance the activity of other antifungal compounds such as azoles.
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: Effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and inhibition of Src homology 2 domain-containing protein tyrosine phosphatase-2 activity
Dawson, Marcia I.,Xia, Zebin,Jiang, Tao,Ye, Mao,Fontana, Joseph A.,Farhana, Lulu,Patel, Bhaumik,Li, Ping Xue,Bhuiyan, Mohammad,Pellicciari, Roberto,Macchiarulo, Antonio,Nuti, Roberto,Zhang, Xiao-Kun,Han, Young-Hoon,Tautz, Lutz,Hobbs, Peter D.,Jong, Ling,Waleh, Nahid,Chao, Wan-Ru,Feng, Gen-Sheng,Pang, Yuhong,Su, Ying
supporting information; experimental part, p. 5650 - 5662 (2009/08/09)
(E)-4-[3-(1-Adamantyl)-4′-hydroxyphenyl]-3-chlorocinnamic acid (3-Cl-AHPC) induces the cell-cycle arrest and apoptosis of leukemia and cancer cells. Studies demonstrated that 3-Cl-AHPC bound to the atypical orphan nuclear receptor small heterodimer partner (SHP). Although missing a DNA-binding domain, SHP heterodimerizes with the ligand-binding domains of other nuclear receptors to repress their abilities to induce or inhibit gene expression. 3-Cl-AHPC analogues having the 1-adamantyl and phenolic hydroxyl pharmacophoric elements replaced with isosteric groups were designed, synthesized, and evaluated for their inhibition of proliferation and induction of human cancer cell apoptosis. Structure-anticancer activity relationship studies indicated the importance of both groups to apoptotic activity. Docking of 3-Cl-AHPC and its analogues to an SHP computational model that was based on the crystal structure of ultraspiracle complexed with 1-stearoyl-2-palmitoylglycero-3-phosphoethanolamine suggested why these 3-Cl-AHPC groups could influence SHP activity. Inhibitory activity against Src homology 2 domain-containing protein tyrosine phosphatase 2 (Shp-2) was also assessed. The most active Shp-2 inhibitor was found to be the 3′-(3,3-dimethylbutynyl) analogue of 3-Cl-AHPC.
