- A visible-light mediated ring opening reaction of alkylidenecyclopropanes for the generation of homopropargyl radicals
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Classical cyclopropylcarbinyl radical clock reactions have been widely applied to conduct mechanistic studies for probing radical processes for a long time; however, alkylidenecyclopropanes, which have a similar molecular structure to methylcyclopropanes, surprisingly have not yet attracted researcher's attention for similar ring opening radical clock processes. In recent years, photocatalytic NHPI ester activation chemistry has witnessed significant blooming developments and provided new synthetic routes for cross-coupling reactions. Herein, we wish to report a non-classical ring opening radical clock reaction using innovative NHPI esters bearing alkylidenecyclopropanes upon photoredox catalysis, providing a brand-new synthetic approach for the direct preparation of a variety of alkynyl derivatives. The potential synthetic utility of this protocol is demonstrated in the diverse transformations and facile synthesis of bioactive molecules or their derivatives and medicinal substances.
- Mao, Ben,Ning, Chao,Shi, Min,Wei, Yin,Zhang, Xiao-Yu
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p. 9088 - 9095
(2021/07/12)
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- Ketide compounds, method for manufacturing, and use for treating diabetes thereof
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The present invention relates to ketide compounds, as well as ketide compounds. The present invention relates to a method for preparing a ketide compound, and a use thereof, in which various anti-diabetic TMPA derivative designs can be induced, and is effective in comparison with existing multi-stage synthesis. In addition, the ketide compounds according to the present invention have strong AMPMPK activity and are expected to be useful as a therapeutic agent for diabetes. (by machine translation)
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Paragraph 0078; 0178-0181; 0251-0253
(2019/08/27)
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- Enantioselective synthesis of (-)-CP-55940 via ruthenium-catalyzed asymmetric hydrogenation of ketones
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A new and efficient catalytic asymmetric synthesis of the potent cannabinoid receptor agonist (-)-CP-55940 has been developed by using ruthenium-catalyzed asymmetric hydrogenation of racemic α-aryl ketones via dynamic kinetic resolution (DKR) as a key step. With RuCl2-SDPs/ diamine [SDPs=7,7'-bis(diarylphophino)-1,1'-spirobiindane] catalysts the asymmetric hydrogenation of racemic α-arylcyclohexanones via DKR provided the corresponding cis-β-arylcyclohexanols in high yields with up to 99.3% ee and >99:1 cis-selectivities. Both ethylene ketal group at the cyclohexane ring and ortho-methoxy group at the phenyl ring of the substrates 6 have little effect on the selectivity and reactivity of the hydrogenations. Based on this highly efficient asymmetric ketone hydrogenation, (-)-CP-55940 was synthesized in 13 steps (the longest linear steps) in 14.6% overall yield starting from commercially available 3-methoxybenzaldehyde and 1,4-cyclohexenedione monoethylene acetal. Copyright
- Cheng, Li-Jie,Xie, Jian-Hua,Wang, Li-Xin,Zhou, Qi-Lin
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p. 1105 - 1113
(2012/05/21)
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- MODULATOR
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The present invention relates to a compound of formula I, or a pharmaceutically acceptable salt thereof. Formula (I), wherein R1 and R2 are each independently H or alkyl; Y is an alkyl group. CONR3R4, COOR5SO2NR16R17, NHSO2R18 or CN; X is an aryl or heteroaryl group, each of which may be optionally substituted with one or more substituents selected from (CH2)mZ where Z is halogen, OH, CN, alkyl, alkoxy, NO2, CF3, CONR6R7, CN, NR8R9, COOR10 or NHCOR11 and m is 0 to 3; R3 to R11 are each independently H, alkyl or aryl, wherein said alkyl and aryl groups are optionally substituted by one or more substituents selected from halogen, OH, CN, alkyl, alkoxy, NO2, CF3, CONR12R13, CN, NH2, COOR14, NHCOR15, and CN; R12 to R18 are each independently H or alkyl, more preferably H or Me; n is 1 to 6; wherein the compound is other than 3′,5′-dimethyl-4-(1,1-dimethylheptyl)-1,1′-biphenyl-2-ol. Further aspects of the invention related to the use of such compounds in the preparation of a medicament for the treatment of a muscular disorder, a gastrointestinal disorder, or for controlling spasticity or tremors.
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Page/Page column 14
(2008/12/04)
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- Novel, potent THC/anandamide (hybrid) analogs
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The structure-activity relationship (SAR) of the end pentyl chain in anandamide (AEA) has been established to be very similar to that of Δ9-tetrahydrocannabinol (Δ9-THC). In order to broaden our understanding of the structural similarities between AEA and THC, hybrid structures 1-3 were designed. In these hybrids the aromatic ring of THC-DMH was linked to the AEA moiety through an ether linkage with the oxygen of the phenol of THC. Hybrid 1 (O-2220) was found to have very high binding affinity to CB1 receptors (Ki = 8.5 nM), and it is interesting to note that the orientation of the side chain with respect to the oxygen in the phenol is the same as in THCs. To further explore the SAR in this series the terminal carbon of the side chain was modified by adding different substituents. Several such analogs were synthesized and tested for their CB1 and CB2 binding affinities and in vivo activity (tetrad tests). The details of the synthesis and the biological activity of these compounds are described.
- Bourne, Caryl,Roy, Sucharita,Wiley, Jenny L.,Martin, Billy R.,Thomas, Brian F.,Mahadevan, Anu,Razdan, Raj K.
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p. 7850 - 7864
(2008/04/12)
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