90554-82-8Relevant articles and documents
Synthesis of sorbicillinoid analogues with anti-inflammation activities
Zhang, Meng,Wang, Fangfang,Ding, Wenjuan,Xu, Zhipeng,Li, Xiaosan,Tian, Danmei,Zhang, Youwei,Tang, Jinshan
, (2022/01/06)
Recently, we demonstrated potential anti-inflammatory effects of sorbicillinoids isolated from marine fungi. Here, we report the synthesis of a series of new sorbicillinoid analogues and assessed their anti-inflammatory activities. Our results reveal that side chain substitution with (E)-2-butenoyl, (E)-3-(4-fluorophenyl)-2-propenoyl, and (E)-3-(3,4,5-trimethoxyphenyl)-2-propenoyl significantly enhanced the inhibitory effects of the derivatives on nitric oxide (NO) production and inducible NO synthesis (iNOS) expression stimulated by lipopolysaccharides (LPS) in mouse macrophage. Further chemical derivatization shows that the monomethylresorcinol skeleton worked better than the dimethylresorcinol skeleton in inhibiting LPS-induced inflammatory response in cultured cells. Among the 29 synthesized sorbicillinoid analogues, compounds 4b and 12b exhibited the strongest anti-inflammatory activities, holding the promise of being developed into lead compounds that can be explored as potent anti-inflammation agents.
Asymmetric total synthesis of sperabillins B and D via lithium amide conjugate addition
Davies, Stephen G.,Haggitt, Jane R.,Ichihara, Osamu,Kelly, Richard J.,Leech, Michael A.,Mortimer, Anne J. Price,Roberts, Paul M.,Smith, Andrew D.
, p. 2630 - 2649 (2007/10/03)
Diastereoselective conjugate addition of homochiral lithium (R)-N-allyl-N-α-methylbenzylamide to methyl (2E,5E)-hepatadienoate, followed by protecting group manipulation and subsequent iodocyclocarbamation allows a concise route to the core fragment, methyl (3R,5R,6R)-3,6-diamino-5- hydroxyheptanoate, of sperabillins B and D. Differentiation between the C-3 and C-6 primary amino groups of this core amino acid was readily achieved by treatment with acetone, giving the 5,6-isopropylidene and C-3-imine protected diamine, with subsequent regioselective acylation of the C-6-nitrogen facilitating the total synthesis of sperabillin D in 10.8% overall yield, and the first asymmetric synthesis of sperabillin B in 5.8% overall yield.
Conjugate addition reactions of α-aminoalkylcuprates with α,β-alkenyl-, α,β-alkynyl-, α,β-allenyl-, and α,β-γ,δ-dienyl carboxylic acid derivatives, nitriles, and sulfoxides
Dieter,Lu,Velu
, p. 8715 - 8724 (2007/10/03)
α-Aminoalkylcuprates prepared from α-lithio carbamates and CuCN·2LiCl participate in 1,4-addition reactions with α,β-unsaturated esters, thiol esters, imides, and nitriles in poor to excellent yields depending upon the electron-withdrawing substituent and the substitution pattern of the unsaturated substrate. These reagents also undergo conjugate addition reactions with α,β-alkynyl esters, sulfoxides, and nitriles and with α,β-β,γ-unsaturated allenyl esters. Excellent stereocontrol is achieved in the conjugate additions of α-aminoalkylcuprates to the allenyl esters, while poor stereoselectivity results in the conjugate additions to the alkynyl derivatives. Deprotection and cyclization of the alkynyl adducts affords pyrrolin-2-ones, while similar treatment of the allenyl adducts affords 4-alkylidine- pyrrolidin-2-ones and pyrrolizidinones.
