20098-16-2Relevant articles and documents
A new one-step method for oxaadamantane synthesis
Krasutsky, Pavel A.,Kolomitsin, Igor V.,Carlson, Robert M.,Jones Jr., Maitland
, p. 5673 - 5674 (1996)
Oxidation of 2-methyl-2-hydroxyadamantane by trifluoroperacetic acid in trifluoroacetic acid gives oxaadamantane and exo-2-oxaadamantane-4-ol in a good yield. Other 2-hydroxyadamantane derivatives do not undergo this transformation. An oxidative cleavage and subsequent cyclization mechanism is proposed.
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 (2013/10/22)
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.
CARBAMATE AND UREA INHIBITORS OF 11BETA-HYDROXYSTEROID DEHYDROGENASE 1
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Page/Page column 61, (2010/12/29)
This invention relates to novel compounds of the invention pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful for the therapeutic treatment of diseases associated with the modulation or inhibition of 11β-HSD1 in mammals. The invention further relates to pharmaceutical compositions of the novel compounds and methods for their use in the reduction or control of the production of cortisol in a cell or the inhibition of the conversion of cortisone to cortisol in a cell.
Synthetic approach to preparation of polycyclic compounds possessing physiological activity: I. Synthesis of 1,4-disubstituted adamantanes with amino acid fragment
Zefirova,Selyunina,Averina,Zyk,Zefirov
, p. 1125 - 1129 (2007/10/03)
In the present publication various synthetic procedures are reported for previously unknown 1,4-disubstituted adamantanes, containing in particular in position 1 an amino acid fragment (N-benzoyl-β-alanyloxy group). The procedures developed for modification of functional groups in the adamantane skeleton provide a possibility of synthesis of compounds with potential anticancer activity.
