15897-81-1Relevant articles and documents
Schleyer et al.
, p. 5246 (1970)
N-Hydroxyphthalimide-Catalyzed Carboxylation of Polycyclic Alkanes with Carbon Monoxide in the Presence of Dioxygen
Kato, Susumu,Iwahama, Takahiro,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 222 - 223 (1998)
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Discovery and metabolic stabilization of potent and selective 2-amino-N-(adamant-2-yl) acetamide 11β-hydroxysteroid dehydrogenase type 1 inhibitors
Rohde, Jeffrey J.,Pliushchev, Marina A.,Sorensen, Bryan K.,Wodka, Dariusz,Shuai, Qi,Wang, Jiahong,Fung, Steven,Monzon, Katina M.,Chiou, William J.,Pan, Liping,Deng, Xiaoqing,Chovan, Linda E.,Ramaiya, Atul,Mullally, Mark,Henry, Rodger F.,Stolarik, DeAnne F.,Imade, Hovis M.,Marsh, Kennan C.,Beno, David W. A.,Fey, Thomas A.,Droz, Brian A.,Brune, Michael E.,Camp, Heidi S.,Sham, Hing L.,Frevert, Ernst Uli,Jacobson, Peer B.,Link
, p. 149 - 164 (2007)
Starting from a rapidly metabolized adamantane 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor 22a, a series of E-5-hydroxy-2-adamantamine inhibitors, exemplified by 22d and (±)-22f, was discovered. Many of these compounds are potent inhibitors of 11β-HSD1 and are selective over 11β-HSD2 for multiple species (human, mouse, and rat), unlike other reported species-selective series. These compounds have good cellular potency and improved microsomal stability. Pharmacokinetic profiling in rodents indicated moderate to large volumes of distribution, short half-lives, and a pharmacokinetic species difference with the greatest exposure measured in rat with 22d. One hour postdose liver, adipose, and brain tissue 11β-HSD1 inhibition was confirmed with (±)-22f in a murine ex vivo assay. Although 5,7-disubstitued-2-adamantamines provided greater stability, a single, E-5-position, polar functional group afforded inhibitors with the best combination of stability, potency, and selectivity. These results indicate that adamantane metabolic stabilization sufficient to obtain short-acting, potent, and selective 11β-HSD1 inhibitors has been discovered.
New chemical agents based on adamantane-monoterpene conjugates against orthopoxvirus infections
Agafonov, Alexander P.,Bormotov, Nikolay I.,Korchagina, Dina V.,Maksyutov, Rinat A.,Mozhaytsev, Evgenii S.,Salakhutdinov, Nariman F.,Serova, Olga A.,Shishkina, Larisa N.,Suslov, Evgenii V.,Volcho, Konstantin P.,Yarovaya, Olga I.
, p. 1185 - 1195 (2020/11/03)
Currently, the spectrum of agents against orthopoxviruses, in particular smallpox, is very narrow. Despite the fact that smallpox is well controlled, there is, for many reasons, a real threat of epidemics associated with this or a similar virus. In order to search for new low molecular weight orthopoxvirus inhibitors, a series of amides combining adamantane and monoterpene moieties were synthesized using 1- and 2-adamantanecarboxylic acids as well as myrtenic, citronellic and camphorsulfonic acids as acid components. The produced compounds exhibited high activity against the vaccinia virus (an enveloped virus belonging to the poxvirus family), which was combined with low cytotoxicity. Some compounds had a selectivity index higher than that of the reference drug cidofovir; the highest SI = 1123 was exhibited by 1-adamantanecarboxylic acid amide containing the (-)-10-amino-2-pinene moiety. The produced compounds demonstrated inhibitory activity against other orthopoxviruses: cowpox virus (SI = 30-406) and ectromelia virus (mousepox virus, SI = 39-707). This journal is
Ring-fused compound, pharmaceutical composition containing same and application of compound
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, (2018/04/01)
The invention discloses a ring-fused compound, a preparation method thereof, pharmaceutical composition containing the compound and an application of the compound. A polycyclic compound (I) as well asan isomer, a prodrug, a stable isotopic derivative or pharmacologically acceptable salt of the compound (I) has the following structure. The polycyclic compound has good IDO1 and/or TDO2 inhibition functions, can effectively treat, relieve and/or prevent various diseases which are related with IDO1 and/or TDO2, such as cancer, virus infection, autoimmune diseases or the like.
