- Empirical Guidelines for the Development of Remote Directing Templates through Quantitative and Experimental Analyses
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The ability to differentiate and selectively activate remote C-H bonds represents a perennial challenge in the field of C-H activation. Since its first report in 2012, a now-established "directing template"(DT) approach remains demonstrably effective for the functionalization of remote C-H bonds. As selectivity is hypothesized to be principally determined by the optimal positioning of the reactive catalyst to a target C-H bond, a DT's spatial factors are particularly important toward achieving high selectivity, though a systematic study on its requisite factors remain unelucidated. Through an in-depth analysis of 119 structurally unique published remote DTs, this report summarizes the key factors that are central toward achieving high selectivity at defined aryl positions, which are experimentally corroborated through the development of new aliphatic meta and para-selective DTs for electronically unbiased arenes. These empirical rules, which summarize key distance and geometric factors, are expected to be useful tools for the future development of site-selective arene C-H activation as well as other reactions that rely on covalent/noncovalent DT-mediated remote regioselection.
- Fan, Zhoulong,Lam, Nelson Y. S.,Park, Han Seul,Shim, Su Yong,Strassfeld, Daniel A.,Wu, Kevin,Yu, Jin-Quan
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p. 2793 - 2803
(2022/02/16)
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- Sulfonyl fluoride inhibitors of fatty acid amide hydrolase
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Sulfonyl fluorides are known to inhibit esterases. Early work from our laboratory has identified hexadecyl sulfonylfluoride (AM374) as a potent in vitro and in vivo inhibitor of fatty acid amide hydrolase (FAAH). We now report on later generation sulfonyl
- Alapafuja, Shakiru O.,Nikas, Spyros P.,Bharathan, Indu T.,Shukla, Vidyanand G.,Nasr, Mahmoud L.,Bowman, Anna L.,Zvonok, Nikolai,Li, Jing,Shi, Xiaomeng,Engen, John R.,Makriyannis, Alexandros
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p. 10074 - 10089
(2013/01/16)
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- MONOACYLGLYCEROL LIPASE INHIBITORS FOR MODULATION OF CANNABINOID ACTIVITY
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Disclosed are compounds and compositions that inhibit the action of monoacylglycerol lipase (MGL) and fatty acid amide hydrolase (FAAH), methods of inhibiting MGL and FAAH, methods of modulating cannabinoid receptors, and methods of treating various disorders related to the modulation of cannabinoid receptors.
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Page/Page column 65-66
(2009/05/28)
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- FATTY ACID AMIDE HYDROLASE INHIBITORS
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Disclosed are compounds of formula R-X-Y that may be used to inhibit the action of fatty acid amide hydrolase (FAAH). Inhibition of fatty acid amide hydrolase (FAAH) will slow the normal degradation and inactivation of endogenous cannabinoid ligands by FAAH hydrolysis and allow higher levels of those endogenous cannabinergic ligands to remain present. These higher levels of endocannabinoid ligands provide increased stimulation of the cannabinoid CBl and CB2 receptors and produce physiological effects related to the activation of the cannabinoid receptors. They will also enhance the effects of other exogenous cannabinergic ligands and allow them to produce their effects at lower concentrations as compared to systems in which fatty acid amide hydrolase (FAAH) action is hot inhibited. Thus, a compound that inhibits the inactivation of endogenous cannabinoid ligands by fatty acid amide hydrolase (FAAH) may increase the levels of endocannabinoids and, thus, enhance the activation of cannabinoid receptors. Thus, the compound may not directly modulate the cannabinoid receptors but has the effect of indirectly stimulating the cannabinoid receptors by increasing the levels of endocannabinoid ligands. It may also enhance the effects and duration of action of other exogenous cannabinergic ligands that are administered in order to elicit a cannabinergic response.
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Page/Page column 29-30
(2008/06/13)
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- One-pot, one- and multi-carbon homologation of alkyl halides; reaction of Grignard reagents with chloroiodomethane
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Reaction of a Grignard reagent (RMgX) with chloroiodomethane affords the corresponding iodide (RI) and, depending on R, solvent and temperature, iodides which are one-carbon and multicarbon homologs of RX. Allyl iodide but not allyl bromide can be monohomologated by the combined action of chloroiodomethane and isopropyl Grignard.
- Hahn,Tompkins
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p. 937 - 940
(2007/10/02)
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