74572-09-1Relevant articles and documents
Surprising unreactivity of cholesterol-5,6-epoxides towards nucleophiles
Paillasse, Michael R.,Saffon, Nathalie,Gornitzka, Heinz,Silvente-Poirot, Sandrine,Poirot, Marc,De Medina, Philippe
experimental part, p. 718 - 725 (2012/06/18)
We recently established that drugs used for the treatment and the prophylaxis of breast cancers, such as tamoxifen, were potent inhibitors of cholesterol-5,6-epoxide hydrolase (ChEH), which led to the accumulation of 5,6α-epoxy-cholesterol (5,6α-EC) and 5,6β-epoxy-cholesterol (5,6β-EC). This could be considered a paradox because epoxides are known as alkylating agents with putative carcinogenic properties. We report here that, as opposed to the carcinogen styrene-oxide, neither of the ECs reacted spontaneously with nucleophiles. Under catalytic conditions, 5,6β-EC remains unreactive whereas 5,6α-EC gives cholestan-3β,5 α-diol-6β-substituted compounds. These data showed that 5,6-ECs are stable epoxides and unreactive toward nucleophiles in the absence of a catalyst, which contrasts with the well-known reactivity of aromatic and aliphatic epoxides. These data rule out 5,6-EC acting as spontaneous alkylating agents. In addition, these data support the existence of a stereoselective metabolism of 5,6α-EC. Copyright
POLYCYCLIC COMPOUNDS WHICH MODULATE THE CB2 RECEPTOR
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Page/Page column 10-11, (2008/12/05)
Compounds of formula (I) are disclosed. Compounds according to the invention are agonists, antagonists or inverse agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treati
COMPOUNDS WHICH MODULATE THE CB2 RECEPTOR
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Page/Page column 18, (2008/06/13)
Compounds are provided which bind to and are agonists, antagonists or inverse agonists of the CB2 receptor, the compounds having the general formula (I) wherein, R1, R2, A, Y, X, Ar1 and Ar2 have the meanings given in the specification, and the preparation and use thereof. The compounds are valuable CB2 receptor modulators.