20098-14-0Relevant articles and documents
Selective trioxolane based bifunctional molecular linkers for covalent heme surface functionalisation
McConville,Bradley,Zhou,Schiffrin,O'Neil
, p. 186 - 188 (2014)
A bifunctional molecular linker containing both aryl diazonium and trioxolane groups was synthesised and its ability to sequentially functionalise glassy carbon and covalently immobilise heme investigated. Functionalisation was demonstrated by electrochemical techniques.
Bromination of adamantane and its derivatives with tetrabromomethane catalyzed by iron compounds
Khusnutdinov,Shchadneva,Khisamova
, p. 184 - 187 (2015)
Catalytic bromination of adamantane and its derivatives with tetrabromomethane catalyzed by iron compounds has been performed. The favorable ratio of catalyst and reagents and the conditions of a selective synthesis of bromine-substituted adamantanes have been developed.
Biocatalytic production of 5-hydroxy-2-adamantanone by P450cam coupled with NADH regeneration
Furuya, Toshiki,Kanno, Takaaki,Yamamoto, Hiroaki,Kimoto, Norihiro,Matsuyama, Akinobu,Kino, Kuniki
, p. 111 - 118 (2013)
5-Hydroxy-2-adamantanone is a versatile starting material for the synthesis of various adamantane derivatives. In this study, we investigated the biocatalytic production of 5-hydroxy-2-adamantanone using P450cam monooxygenase coupled with NADH regeneration. We constructed Escherichia coli cells that expressed P450cam and its redox partners, putidaredoxin and putidaredoxin reductase, and cells that co-expressed this P450cam multicomponent system with a glucose dehydrogenase (Gdh) to regenerate NADH using glucose. Two types of cells - wet cells that did not receive any treatment after washing with glycerol-containing buffer, and freeze-dried cells that were lyophilized after the washing - were prepared as whole-cell catalysts. When wet cells were reacted with 2-adamantanone, E. coli cells expressing only the P450cam multicomponent system efficiently produced 5-hydroxy-2-adamantanone in the presence of glucose. However, the co-expression of this P450cam system with Gdh did not further enhance the amount of this product. These results indicate that enough amounts of NADH for P450cam catalysis would be supplied by endogenous glucose metabolism in the E. coli host. In contrast, when freeze-dried cells were used, only the cells co-expressing the P450cam multicomponent system with Gdh efficiently catalyzed the oxidation in the presence of glucose. These results suggest that the exogenous Gdh compensated loss of NADH regeneration by the endogenous glucose metabolism that would be damaged by the lyophilization process. Furthermore, we attempted to produce 5-hydroxy-2-adamantanone with repeated additions of the substrate using wet cells expressing only the P450cam multicomponent system and freeze-dried cells co-expressing this P450cam system with Gdh. These whole-cell catalysts attained high-yield production; the wet cells and the freeze-dried cells produced 36 mM (5.9 g/l) and 21 mM (3.5 g/l) of 5-hydroxy-2-adamantanone, respectively.
Reversal of diastereoselectivities in intra- and intermolecular reactions of 2-adamantanylidenes primarily caused by electron-donating and electron-withdrawing substituents on C5
Knoll, Wolfgang,Bobek, Michael M.,Kalchhauser, Hermann,Rosenberg, Murray G.,Brinker, Udo H.
, p. 2943 - 2946 (2003)
(Matrix presented) A reversal of diastereoselectivity was observed for novel 5-(trimethylsilyl)adamantan-2-ylidene (1c) with regard to 5-hydroxyadamantan-2-ylidene (1a). Ostensibly in intermolecular reactions, 5-substituted 2-adamantanylidenes (1) are ste
Chemo- and regioselective oxidation of adamantyl derivatives by dioxiranes
D'Accolti, Lucia,Kang, Ping,Khan, Saeed,Curci, Ruggero,Foote, Christopher S.
, p. 4649 - 4652 (2002)
Methyl(trifluoromethyl) dioxirane (1) gives direct chemo- and regioselective oxidation of methyleneadamantane oxide (2) and isopropylideneadamantane oxide (3) in high yield under mild conditions. Secondary C-H are not appreciably oxidized and high regiose
Chemoselectivity of Nitroxylation of Cage Hydrocarbons
Ivleva, E. A.,Klimochkin, Yu. N.,Leonova, M. V.
, p. 1702 - 1710 (2020/12/01)
Abstract: The composition of reaction mixtures obtained by nitroxylation of 13 cage hydrocarbons with 100% nitric acid and its mixtures with acetic acid, acetic anhydride, and methylene chloride has been studied. More reactive substrates react with lowest
2, 4 -DIAMINOPYRIMIDINE DERIVATIVES AS PROTEIN KINASE INHIBITORS
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Page/Page column 68, (2012/05/20)
The present invention relates to novel pyrimide derivatives of formula (I): that are useful as kinase inhibitors. More particularly, the present invention relates to novel pyrimidine compounds, methods for their preparation, pharmaceutical compositions containing these compounds and uses of these compounds in the treatment of proliferative disorders.
Intra- and intermolecular reaction selectivities of γ-substituted adamantanylidenes
Knoll, Wolfgang,Kaneno, Daisuke,Bobek, Michael M.,Brecker, Lothar,Rosenberg, Murray G.,Tomoda, Shuji,Brinker, Udo H.
experimental part, p. 1340 - 1360 (2012/03/27)
A study of adamantanylidenes having a γ-substituent (R) was undertaken to gauge how inductive and steric effects of remotely positioned functional groups influence intra- and intermolecular product selectivity. 3H-Diazirines were thermolyzed or photolyzed to generate the corresponding carbenes. On rapid heating, the resulting carbenes isomerized to 2,4-didehydroadamantanes by intramolecular 1,3-CH insertions. When R was an electron donor (RD) mostly asymmetric 1-substituted derivatives were produced but when it was an electron acceptor (RA) the symmetric 7-substituted ones were formed. When solutions were exposed to UV-A light, intermolecular adducts from the carbenes and solvent predominated with lesser amounts of intramolecular product being formed. Valence isomerization of 3H-diazirines also afforded diazo compounds. In methanol, protonation of diazo compounds to give the corresponding 2-adamantyl cations exceeds their coupling. This diversion was controlled with fumaronitrile by trapping the diazo compounds. The adducts possessed mostly anti configurations with R = R D and syn arrangements with R = RA. The connection between as- and anti-product formation and that of s- and syn-products was deemed to be the consequence of a rapid equilibrium between two distinct carbene conformations. This was qualified and quantified using ab initio calculations and NBO analyses.
L -DIHYDRO-2-OXOQUINOLINE COMPOUNDS A 5-HT4 RECEPTOR LIGANDS
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Page/Page column 23-24, (2011/04/18)
The present invention relates to novel l,2-dihydro-2-oxoquinoline compounds of the formula (I), and their derivatives, prodrugs, tautomers, stereoisomers, polymorphs, solvates, hydrates, metabolites, N-oxides, pharmaceutically acceptable salts and compositions containing them. Formula (I) The present invention also relates to a process for the preparation of above said novel compounds, and their derivatives, prodrugs, tautomers, stereoisomers, polymorphs, solvates, hydrates, metabolites, N-oxides, pharmaceutically acceptable salts and compositions containing them. The compounds of the present invention are useful in the treatment/prevention of various disorders that are mediated by 5-HT4 receptor activity.
2 H-azirines from a concerted addition of alkylcarbenes to nitrile groups
Knoll, Wolfgang,Mieusset, Jean-Luc,Arion, Vladimir B.,Brecker, Lothar,Brinker, Udo H.
supporting information; experimental part, p. 2366 - 2369 (2010/07/13)
Photolysis of aziadamantanes in the presence of fumaronitrile (FN) unexpectedly afforded conjugated 2H-azirines resulting from addition of the carbene to the CN triple bond. This represents the first example of a direct azirine formation starting from an alkylcarbene for which a concerted pathway is postulated. The novel outcome of the reaction is favored by the prior formation of a carbene-alkene complex, a type of adduct that only recently has been described.
